# Supplementary Material (ESI) for New Journal of Chemistry # This journal is (c) The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2006 data_global _journal_name_full 'New J.Chem.(Nouv.J.Chim.)' _journal_coden_Cambridge 0440 _publ_contact_author_name 'Dr Chun-ying Duan' _publ_contact_author_address ; School of Chemistry and Chemistry Engineering Coordination Chemistry Institute State Key Laboratory of Coordinatio Nanjing 210093 CHINA ; _publ_contact_author_email DUANCY@NJU.EDU.CN _publ_section_title ; A Highly Selective Fluorescent Sensor for Fluoride through ESPT Signaling Transduction ; loop_ _publ_author_name 'Duan Chun-ying' 'Zhi-hua Lin' 'Qing-Jin Meng' 'Bing-guang Zhang' ; Yong-gang Zhao ; # Attachment 'NP2.cif' data_compound_NP2 _database_code_depnum_ccdc_archive 'CCDC 291364' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H22 N4 O4' _chemical_formula_weight 502.52 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)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 15.323(3) _cell_length_b 9.3464(15) _cell_length_c 17.451(3) _cell_angle_alpha 90.00 _cell_angle_beta 104.854(3) _cell_angle_gamma 90.00 _cell_volume 2415.6(7) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 670 _cell_measurement_theta_min 2.40 _cell_measurement_theta_max 20.36 _exptl_crystal_description prism _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.382 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1048 _exptl_absorpt_coefficient_mu 0.094 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_reflns_number 11705 _diffrn_reflns_av_R_equivalents 0.0611 _diffrn_reflns_av_sigmaI/netI 0.0794 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.41 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4249 _reflns_number_gt 2314 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _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^)+(0.0000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4249 _refine_ls_number_parameters 343 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1129 _refine_ls_R_factor_gt 0.0505 _refine_ls_wR_factor_ref 0.0760 _refine_ls_wR_factor_gt 0.0659 _refine_ls_goodness_of_fit_ref 0.958 _refine_ls_restrained_S_all 0.958 _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 0.79141(10) 0.01918(18) 0.78898(9) 0.0772(6) Uani 1 1 d . . . H1A H 0.7591 0.0903 0.7792 0.116 Uiso 1 1 calc R . . O2 O 0.69545(10) 0.41263(16) 0.80209(9) 0.0643(5) Uani 1 1 d . . . O3 O 0.40794(10) 0.65293(16) 0.48809(9) 0.0590(5) Uani 1 1 d . . . O4 O 0.14382(10) 0.74024(18) 0.36006(9) 0.0715(6) Uani 1 1 d . . . H4B H 0.1856 0.7243 0.3991 0.107 Uiso 1 1 calc R . . N1 N 0.67864(13) 0.1934(2) 0.70074(12) 0.0592(6) Uani 1 1 d . . . N2 N 0.63819(12) 0.3243(2) 0.67929(11) 0.0604(6) Uani 1 1 d . . . H2B H 0.6063 0.3387 0.6317 0.073 Uiso 1 1 calc R . . N3 N 0.32981(12) 0.77936(19) 0.55892(11) 0.0547(6) Uani 1 1 d . . . H3B H 0.3285 0.8114 0.6048 0.066 Uiso 1 1 calc R . . N4 N 0.25690(13) 0.8019(2) 0.49422(11) 0.0511(6) Uani 1 1 d . . . C1 C 0.69230(16) -0.1391(3) 0.59282(15) 0.0529(7) Uani 1 1 d . . . C2 C 0.62663(16) -0.1199(3) 0.51985(15) 0.0620(8) Uani 1 1 d . . . H2A H 0.5906 -0.0384 0.5124 0.074 Uiso 1 1 calc R . . C3 C 0.61509(18) -0.2174(3) 0.46079(16) 0.0736(9) Uani 1 1 d . . . H3A H 0.5705 -0.2025 0.4141 0.088 Uiso 1 1 calc R . . C4 C 0.6685(2) -0.3392(3) 0.46843(18) 0.0822(10) Uani 1 1 d . . . H4A H 0.6617 -0.4036 0.4267 0.099 Uiso 1 1 calc R . . C5 C 0.73134(19) -0.3625(3) 0.53855(19) 0.0775(9) Uani 1 1 d . . . H5A H 0.7662 -0.4452 0.5448 0.093 Uiso 1 1 calc R . . C6 C 0.74434(17) -0.2646(3) 0.60118(16) 0.0611(8) Uani 1 1 d . . . C7 C 0.80903(17) -0.2904(3) 0.67255(17) 0.0726(9) Uani 1 1 d . . . H7A H 0.8432 -0.3737 0.6782 0.087 Uiso 1 1 calc R . . C8 C 0.82279(16) -0.1964(3) 0.73347(17) 0.0732(9) Uani 1 1 d . . . H8A H 0.8655 -0.2163 0.7807 0.088 Uiso 1 1 calc R . . C9 C 0.77264(17) -0.0687(3) 0.72568(16) 0.0595(8) Uani 1 1 d . . . C10 C 0.70870(15) -0.0379(3) 0.65592(15) 0.0512(7) Uani 1 1 d . . . C11 C 0.66406(15) 0.0984(3) 0.64617(15) 0.0564(8) Uani 1 1 d . . . H11A H 0.6228 0.1184 0.5982 0.068 Uiso 1 1 calc R . . C12 C 0.64922(15) 0.4290(3) 0.73368(15) 0.0522(7) Uani 1 1 d . . . C13 C 0.59806(15) 0.5635(3) 0.70822(13) 0.0473(7) Uani 1 1 d . . . C14 C 0.61830(15) 0.6792(3) 0.75869(13) 0.0549(7) Uani 1 1 d . . . H14A H 0.6647 0.6718 0.8048 0.066 Uiso 1 1 calc R . . C15 C 0.57135(15) 0.8046(3) 0.74222(13) 0.0580(7) Uani 1 1 d . . . H15A H 0.5871 0.8824 0.7762 0.070 Uiso 1 1 calc R . . C16 C 0.50057(14) 0.8157(3) 0.67513(13) 0.0516(7) Uani 1 1 d . . . H16A H 0.4679 0.9004 0.6643 0.062 Uiso 1 1 calc R . . C17 C 0.47840(14) 0.7007(3) 0.62404(13) 0.0443(6) Uani 1 1 d . . . C18 C 0.52866(14) 0.5763(2) 0.63915(13) 0.0484(7) Uani 1 1 d . . . H18A H 0.5161 0.5010 0.6031 0.058 Uiso 1 1 calc R . . C19 C 0.40274(16) 0.7073(2) 0.55001(14) 0.0456(7) Uani 1 1 d . . . C20 C 0.20329(15) 0.9016(3) 0.50352(14) 0.0507(7) Uani 1 1 d . . . H20A H 0.2144 0.9493 0.5518 0.061 Uiso 1 1 calc R . . C21 C 0.12547(15) 0.9418(3) 0.44015(13) 0.0458(6) Uani 1 1 d . . . C22 C 0.07468(15) 1.0671(3) 0.44756(14) 0.0486(7) Uani 1 1 d . . . C23 C 0.09437(16) 1.1578(3) 0.51399(15) 0.0602(8) Uani 1 1 d . . . H23A H 0.1432 1.1367 0.5565 0.072 Uiso 1 1 calc R . . C24 C 0.04388(19) 1.2755(3) 0.51760(17) 0.0757(9) Uani 1 1 d . . . H24A H 0.0584 1.3330 0.5626 0.091 Uiso 1 1 calc R . . C25 C -0.03000(19) 1.3118(3) 0.4545(2) 0.0820(10) Uani 1 1 d . . . H25A H -0.0640 1.3931 0.4572 0.098 Uiso 1 1 calc R . . C26 C -0.05074(18) 1.2277(3) 0.39026(18) 0.0745(9) Uani 1 1 d . . . H26A H -0.1002 1.2510 0.3487 0.089 Uiso 1 1 calc R . . C27 C 0.00003(16) 1.1054(3) 0.38393(16) 0.0562(7) Uani 1 1 d . . . C28 C -0.02073(16) 1.0184(3) 0.31574(15) 0.0666(8) Uani 1 1 d . . . H28A H -0.0692 1.0434 0.2737 0.080 Uiso 1 1 calc R . . C29 C 0.02690(16) 0.9008(3) 0.30941(15) 0.0642(8) Uani 1 1 d . . . H29A H 0.0114 0.8456 0.2636 0.077 Uiso 1 1 calc R . . C30 C 0.10026(16) 0.8612(3) 0.37209(15) 0.0532(7) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0736(14) 0.0833(15) 0.0594(13) 0.0014(11) -0.0105(10) 0.0072(10) O2 0.0529(12) 0.0949(14) 0.0368(10) 0.0116(9) -0.0034(9) 0.0026(9) O3 0.0672(12) 0.0692(13) 0.0351(10) -0.0035(9) 0.0034(9) 0.0093(9) O4 0.0567(12) 0.0886(15) 0.0597(12) -0.0177(10) -0.0025(10) 0.0047(10) N1 0.0561(15) 0.0660(17) 0.0509(14) 0.0106(13) 0.0052(11) 0.0095(12) N2 0.0569(14) 0.0720(17) 0.0440(14) 0.0081(13) -0.0024(11) 0.0140(12) N3 0.0478(14) 0.0741(16) 0.0368(12) -0.0009(11) 0.0009(11) 0.0055(11) N4 0.0398(13) 0.0649(16) 0.0410(13) 0.0021(11) -0.0038(11) 0.0003(11) C1 0.0396(16) 0.062(2) 0.0549(18) 0.0149(15) 0.0076(14) -0.0092(14) C2 0.0573(19) 0.070(2) 0.0557(19) 0.0106(16) 0.0086(15) -0.0077(15) C3 0.074(2) 0.080(2) 0.059(2) 0.0026(18) 0.0032(17) -0.0192(18) C4 0.089(3) 0.075(3) 0.079(2) -0.0047(19) 0.015(2) -0.0194(19) C5 0.076(2) 0.061(2) 0.090(2) 0.0068(19) 0.0133(19) -0.0094(17) C6 0.0513(18) 0.060(2) 0.068(2) 0.0070(17) 0.0072(16) -0.0106(15) C7 0.058(2) 0.067(2) 0.084(2) 0.0125(18) 0.0032(18) 0.0030(16) C8 0.0485(18) 0.079(2) 0.080(2) 0.0214(18) -0.0071(16) 0.0071(17) C9 0.0465(18) 0.067(2) 0.0588(19) 0.0076(16) 0.0011(15) -0.0037(15) C10 0.0389(16) 0.0579(19) 0.0529(18) 0.0154(15) 0.0049(13) -0.0010(14) C11 0.0466(17) 0.071(2) 0.0469(18) 0.0118(15) 0.0041(14) -0.0054(15) C12 0.0416(17) 0.073(2) 0.0405(17) 0.0063(16) 0.0084(13) -0.0042(14) C13 0.0440(16) 0.0656(19) 0.0314(14) 0.0024(14) 0.0081(12) -0.0010(14) C14 0.0425(16) 0.082(2) 0.0367(16) -0.0003(15) 0.0046(12) -0.0007(15) C15 0.0494(17) 0.074(2) 0.0473(17) -0.0144(15) 0.0060(14) -0.0066(15) C16 0.0452(16) 0.0625(19) 0.0464(16) -0.0022(14) 0.0107(13) -0.0026(13) C17 0.0371(15) 0.0591(18) 0.0350(15) 0.0025(13) 0.0059(12) -0.0013(13) C18 0.0446(16) 0.0618(19) 0.0366(15) -0.0012(13) 0.0067(12) -0.0066(13) C19 0.0463(17) 0.0500(18) 0.0387(16) 0.0038(13) 0.0077(13) -0.0041(13) C20 0.0458(17) 0.0614(19) 0.0426(16) 0.0000(13) 0.0068(13) -0.0054(13) C21 0.0386(16) 0.0561(18) 0.0389(15) 0.0010(13) 0.0028(12) -0.0083(13) C22 0.0418(16) 0.0552(18) 0.0470(16) 0.0060(14) 0.0083(13) -0.0099(13) C23 0.0571(18) 0.058(2) 0.0617(19) 0.0031(16) 0.0075(15) -0.0035(15) C24 0.089(2) 0.060(2) 0.080(2) -0.0010(17) 0.0236(19) -0.0003(17) C25 0.083(2) 0.059(2) 0.103(3) 0.017(2) 0.021(2) 0.0129(18) C26 0.063(2) 0.075(2) 0.081(2) 0.0224(18) 0.0093(18) 0.0056(18) C27 0.0453(17) 0.062(2) 0.0565(19) 0.0127(15) 0.0053(14) -0.0035(15) C28 0.0434(18) 0.086(2) 0.059(2) 0.0145(17) -0.0066(15) -0.0064(16) C29 0.0462(18) 0.084(2) 0.0510(18) -0.0035(16) -0.0079(14) -0.0056(15) C30 0.0378(16) 0.067(2) 0.0538(18) 0.0007(15) 0.0092(14) -0.0037(14) _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 C9 1.347(3) . ? O1 H1A 0.8200 . ? O2 C12 1.232(2) . ? O3 C19 1.215(2) . ? O4 C30 1.357(3) . ? O4 H4B 0.8200 . ? N1 C11 1.279(3) . ? N1 N2 1.379(2) . ? N2 C12 1.343(3) . ? N2 H2B 0.8600 . ? N3 C19 1.347(3) . ? N3 N4 1.386(2) . ? N3 H3B 0.8600 . ? N4 C20 1.280(3) . ? C1 C6 1.405(3) . ? C1 C2 1.417(3) . ? C1 C10 1.424(3) . ? C2 C3 1.353(3) . ? C2 H2A 0.9300 . ? C3 C4 1.389(3) . ? C3 H3A 0.9300 . ? C4 C5 1.366(3) . ? C4 H4A 0.9300 . ? C5 C6 1.400(3) . ? C5 H5A 0.9300 . ? C6 C7 1.400(3) . ? C7 C8 1.353(3) . ? C7 H7A 0.9300 . ? C8 C9 1.407(3) . ? C8 H8A 0.9300 . ? C9 C10 1.383(3) . ? C10 C11 1.435(3) . ? C11 H11A 0.9300 . ? C12 C13 1.488(3) . ? C13 C14 1.379(3) . ? C13 C18 1.393(2) . ? C14 C15 1.367(3) . ? C14 H14A 0.9300 . ? C15 C16 1.381(3) . ? C15 H15A 0.9300 . ? C16 C17 1.382(3) . ? C16 H16A 0.9300 . ? C17 C18 1.383(3) . ? C17 C19 1.500(3) . ? C18 H18A 0.9300 . ? C20 C21 1.452(3) . ? C20 H20A 0.9300 . ? C21 C30 1.375(3) . ? C21 C22 1.430(3) . ? C22 C23 1.405(3) . ? C22 C27 1.421(3) . ? C23 C24 1.355(3) . ? C23 H23A 0.9300 . ? C24 C25 1.404(3) . ? C24 H24A 0.9300 . ? C25 C26 1.339(3) . ? C25 H25A 0.9300 . ? C26 C27 1.403(3) . ? C26 H26A 0.9300 . ? C27 C28 1.409(3) . ? C28 C29 1.340(3) . ? C28 H28A 0.9300 . ? C29 C30 1.402(3) . ? C29 H29A 0.9300 . ? 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 O1 H1A 109.5 . . ? C30 O4 H4B 109.5 . . ? C11 N1 N2 115.7(2) . . ? C12 N2 N1 119.2(2) . . ? C12 N2 H2B 120.4 . . ? N1 N2 H2B 120.4 . . ? C19 N3 N4 120.1(2) . . ? C19 N3 H3B 120.0 . . ? N4 N3 H3B 120.0 . . ? C20 N4 N3 114.7(2) . . ? C6 C1 C2 116.9(3) . . ? C6 C1 C10 119.4(2) . . ? C2 C1 C10 123.7(3) . . ? C3 C2 C1 121.6(3) . . ? C3 C2 H2A 119.2 . . ? C1 C2 H2A 119.2 . . ? C2 C3 C4 121.3(3) . . ? C2 C3 H3A 119.3 . . ? C4 C3 H3A 119.3 . . ? C5 C4 C3 118.6(3) . . ? C5 C4 H4A 120.7 . . ? C3 C4 H4A 120.7 . . ? C4 C5 C6 121.5(3) . . ? C4 C5 H5A 119.3 . . ? C6 C5 H5A 119.3 . . ? C7 C6 C5 120.6(3) . . ? C7 C6 C1 119.3(3) . . ? C5 C6 C1 120.1(3) . . ? C8 C7 C6 121.3(3) . . ? C8 C7 H7A 119.3 . . ? C6 C7 H7A 119.3 . . ? C7 C8 C9 120.2(3) . . ? C7 C8 H8A 119.9 . . ? C9 C8 H8A 119.9 . . ? O1 C9 C10 123.3(3) . . ? O1 C9 C8 116.2(2) . . ? C10 C9 C8 120.5(3) . . ? C9 C10 C1 119.2(2) . . ? C9 C10 C11 119.8(2) . . ? C1 C10 C11 120.9(2) . . ? N1 C11 C10 122.8(2) . . ? N1 C11 H11A 118.6 . . ? C10 C11 H11A 118.6 . . ? O2 C12 N2 122.1(2) . . ? O2 C12 C13 121.5(2) . . ? N2 C12 C13 116.3(2) . . ? C14 C13 C18 118.8(2) . . ? C14 C13 C12 117.2(2) . . ? C18 C13 C12 123.9(2) . . ? C15 C14 C13 121.2(2) . . ? C15 C14 H14A 119.4 . . ? C13 C14 H14A 119.4 . . ? C14 C15 C16 119.9(2) . . ? C14 C15 H15A 120.0 . . ? C16 C15 H15A 120.0 . . ? C15 C16 C17 119.9(2) . . ? C15 C16 H16A 120.0 . . ? C17 C16 H16A 120.0 . . ? C16 C17 C18 119.9(2) . . ? C16 C17 C19 122.1(2) . . ? C18 C17 C19 117.9(2) . . ? C17 C18 C13 120.1(2) . . ? C17 C18 H18A 119.9 . . ? C13 C18 H18A 119.9 . . ? O3 C19 N3 123.9(2) . . ? O3 C19 C17 122.4(2) . . ? N3 C19 C17 113.7(2) . . ? N4 C20 C21 121.3(2) . . ? N4 C20 H20A 119.3 . . ? C21 C20 H20A 119.3 . . ? C30 C21 C22 119.2(2) . . ? C30 C21 C20 120.7(2) . . ? C22 C21 C20 120.2(2) . . ? C23 C22 C27 116.9(2) . . ? C23 C22 C21 124.2(2) . . ? C27 C22 C21 118.9(2) . . ? C24 C23 C22 121.6(2) . . ? C24 C23 H23A 119.2 . . ? C22 C23 H23A 119.2 . . ? C23 C24 C25 121.0(3) . . ? C23 C24 H24A 119.5 . . ? C25 C24 H24A 119.5 . . ? C26 C25 C24 119.0(3) . . ? C26 C25 H25A 120.5 . . ? C24 C25 H25A 120.5 . . ? C25 C26 C27 121.8(3) . . ? C25 C26 H26A 119.1 . . ? C27 C26 H26A 119.1 . . ? C26 C27 C28 121.8(3) . . ? C26 C27 C22 119.7(3) . . ? C28 C27 C22 118.5(3) . . ? C29 C28 C27 122.3(2) . . ? C29 C28 H28A 118.9 . . ? C27 C28 H28A 118.9 . . ? C28 C29 C30 119.8(3) . . ? C28 C29 H29A 120.1 . . ? C30 C29 H29A 120.1 . . ? O4 C30 C21 123.3(2) . . ? O4 C30 C29 115.3(2) . . ? C21 C30 C29 121.4(3) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.140 _refine_diff_density_min -0.160 _refine_diff_density_rms 0.031 data_compound_NP1 _database_code_depnum_ccdc_archive 'CCDC 291365' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C29 H21 N5 O4' _chemical_formula_weight 503.51 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 'C2/c ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 18.720(4) _cell_length_b 15.110(3) _cell_length_c 8.5745(18) _cell_angle_alpha 90.00 _cell_angle_beta 94.249(4) _cell_angle_gamma 90.00 _cell_volume 2418.7(9) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2213 _cell_measurement_theta_min 2.30 _cell_measurement_theta_max 22.08 _exptl_crystal_description prism _exptl_crystal_colour pale-yellow _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.383 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1048 _exptl_absorpt_coefficient_mu 0.095 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_reflns_number 5897 _diffrn_reflns_av_R_equivalents 0.1054 _diffrn_reflns_av_sigmaI/netI 0.0781 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 1.73 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2126 _reflns_number_gt 1782 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _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^)+(0.1000P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2126 _refine_ls_number_parameters 173 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0724 _refine_ls_R_factor_gt 0.0617 _refine_ls_wR_factor_ref 0.1688 _refine_ls_wR_factor_gt 0.1593 _refine_ls_goodness_of_fit_ref 1.103 _refine_ls_restrained_S_all 1.103 _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 -0.21564(8) 0.62169(11) -0.26307(17) 0.0700(5) Uani 1 1 d . . . H1A H -0.1916 0.5858 -0.2101 0.105 Uiso 1 1 calc R . . O2 O -0.09327(8) 0.39680(10) -0.11773(17) 0.0678(5) Uani 1 1 d . . . N1 N -0.12766(8) 0.56701(11) -0.03407(18) 0.0503(5) Uani 1 1 d . . . N2 N -0.09221(8) 0.50633(11) 0.06337(18) 0.0525(5) Uani 1 1 d . . . H2B H -0.0793 0.5212 0.1581 0.063 Uiso 1 1 calc R . . N3 N 0.0000 0.41543(13) 0.2500 0.0444(6) Uani 1 2 d S . . C1 C -0.20513(10) 0.70307(15) -0.2028(2) 0.0544(6) Uani 1 1 d . . . C2 C -0.24231(11) 0.77289(18) -0.2811(3) 0.0646(6) Uani 1 1 d . . . H2A H -0.2735 0.7611 -0.3682 0.077 Uiso 1 1 calc R . . C3 C -0.23282(12) 0.85656(17) -0.2304(3) 0.0683(7) Uani 1 1 d . . . H3A H -0.2578 0.9019 -0.2837 0.082 Uiso 1 1 calc R . . C4 C -0.18631(11) 0.87778(15) -0.0995(3) 0.0588(6) Uani 1 1 d . . . C5 C -0.17512(14) 0.96578(17) -0.0488(3) 0.0759(7) Uani 1 1 d . . . H5A H -0.1997 1.0113 -0.1025 0.091 Uiso 1 1 calc R . . C6 C -0.12974(15) 0.98553(17) 0.0754(4) 0.0832(8) Uani 1 1 d . . . H6A H -0.1220 1.0441 0.1053 0.100 Uiso 1 1 calc R . . C7 C -0.09451(14) 0.91737(17) 0.1588(3) 0.0814(8) Uani 1 1 d . . . H7A H -0.0641 0.9308 0.2463 0.098 Uiso 1 1 calc R . . C8 C -0.10387(12) 0.83161(16) 0.1145(3) 0.0661(6) Uani 1 1 d . . . H8A H -0.0794 0.7874 0.1720 0.079 Uiso 1 1 calc R . . C9 C -0.14987(10) 0.80793(14) -0.0168(2) 0.0519(5) Uani 1 1 d . . . C10 C -0.16071(9) 0.71871(14) -0.0699(2) 0.0486(5) Uani 1 1 d . . . C11 C -0.12569(10) 0.64654(13) 0.0165(2) 0.0498(5) Uani 1 1 d . . . H11A H -0.1009 0.6585 0.1122 0.060 Uiso 1 1 calc R . . C12 C -0.07735(10) 0.42490(13) 0.0143(2) 0.0495(5) Uani 1 1 d . . . C13 C -0.03698(9) 0.37044(12) 0.1374(2) 0.0467(5) Uani 1 1 d . . . C14 C -0.03785(10) 0.27917(14) 0.1311(3) 0.0579(6) Uani 1 1 d . . . H14A H -0.0631 0.2494 0.0495 0.069 Uiso 1 1 calc R . . C15 C 0.0000 0.2334(2) 0.2500 0.0644(8) Uani 1 2 d S . . H15A H 0.0000 0.1718 0.2500 0.077 Uiso 1 2 calc SR . . 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 0.0651(10) 0.0818(12) 0.0605(10) -0.0065(8) -0.0127(7) -0.0033(8) O2 0.0809(11) 0.0662(10) 0.0541(10) -0.0120(7) -0.0104(7) -0.0016(8) N1 0.0467(9) 0.0572(11) 0.0465(10) 0.0032(8) -0.0006(7) 0.0030(7) N2 0.0588(10) 0.0542(10) 0.0434(9) -0.0018(7) -0.0046(7) 0.0016(8) N3 0.0425(12) 0.0449(12) 0.0455(13) 0.000 0.0026(10) 0.000 C1 0.0433(10) 0.0715(14) 0.0484(12) 0.0003(10) 0.0021(8) -0.0035(9) C2 0.0503(12) 0.0935(18) 0.0492(13) 0.0167(12) -0.0020(9) 0.0029(11) C3 0.0592(13) 0.0802(17) 0.0659(15) 0.0263(13) 0.0077(11) 0.0145(12) C4 0.0504(12) 0.0660(14) 0.0612(13) 0.0144(10) 0.0119(10) 0.0074(10) C5 0.0773(16) 0.0626(15) 0.0900(19) 0.0139(13) 0.0202(14) 0.0150(12) C6 0.0851(18) 0.0607(15) 0.105(2) -0.0099(14) 0.0164(16) 0.0030(13) C7 0.0709(16) 0.0794(19) 0.0931(19) -0.0250(15) 0.0003(13) 0.0029(13) C8 0.0566(13) 0.0693(15) 0.0712(15) -0.0100(12) -0.0041(11) 0.0093(10) C9 0.0419(11) 0.0630(13) 0.0517(12) 0.0039(10) 0.0100(9) 0.0048(9) C10 0.0388(10) 0.0630(13) 0.0442(11) 0.0045(9) 0.0052(8) 0.0028(8) C11 0.0460(11) 0.0602(13) 0.0427(11) 0.0004(9) 0.0003(8) 0.0000(9) C12 0.0459(11) 0.0548(12) 0.0472(12) -0.0040(9) 0.0004(8) -0.0075(8) C13 0.0419(10) 0.0484(11) 0.0505(11) -0.0039(9) 0.0086(8) -0.0046(8) C14 0.0540(12) 0.0517(13) 0.0681(14) -0.0084(10) 0.0051(10) -0.0051(9) C15 0.0652(19) 0.0421(16) 0.087(2) 0.000 0.0101(17) 0.000 _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.343(3) . ? O1 H1A 0.8200 . ? O2 C12 1.225(2) . ? N1 C11 1.277(3) . ? N1 N2 1.377(2) . ? N2 C12 1.336(2) . ? N2 H2B 0.8600 . ? N3 C13 1.332(2) . ? N3 C13 1.332(2) 2 ? C1 C10 1.380(3) . ? C1 C2 1.407(3) . ? C2 C3 1.345(3) . ? C2 H2A 0.9300 . ? C3 C4 1.406(3) . ? C3 H3A 0.9300 . ? C4 C5 1.410(4) . ? C4 C9 1.418(3) . ? C5 C6 1.346(4) . ? C5 H5A 0.9300 . ? C6 C7 1.392(4) . ? C6 H6A 0.9300 . ? C7 C8 1.358(3) . ? C7 H7A 0.9300 . ? C8 C9 1.412(3) . ? C8 H8A 0.9300 . ? C9 C10 1.433(3) . ? C10 C11 1.448(3) . ? C11 H11A 0.9300 . ? C12 C13 1.498(3) . ? C13 C14 1.380(3) . ? C14 C15 1.384(3) . ? C14 H14A 0.9300 . ? C15 C14 1.384(3) 2 ? C15 H15A 0.9300 . ? 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 C1 O1 H1A 109.5 . . ? C11 N1 N2 114.82(16) . . ? C12 N2 N1 121.62(16) . . ? C12 N2 H2B 119.2 . . ? N1 N2 H2B 119.2 . . ? C13 N3 C13 118.6(2) . 2 ? O1 C1 C10 122.46(19) . . ? O1 C1 C2 116.72(19) . . ? C10 C1 C2 120.8(2) . . ? C3 C2 C1 120.1(2) . . ? C3 C2 H2A 119.9 . . ? C1 C2 H2A 119.9 . . ? C2 C3 C4 122.1(2) . . ? C2 C3 H3A 118.9 . . ? C4 C3 H3A 118.9 . . ? C3 C4 C5 122.0(2) . . ? C3 C4 C9 118.4(2) . . ? C5 C4 C9 119.5(2) . . ? C6 C5 C4 121.6(2) . . ? C6 C5 H5A 119.2 . . ? C4 C5 H5A 119.2 . . ? C5 C6 C7 119.3(2) . . ? C5 C6 H6A 120.3 . . ? C7 C6 H6A 120.3 . . ? C8 C7 C6 121.0(3) . . ? C8 C7 H7A 119.5 . . ? C6 C7 H7A 119.5 . . ? C7 C8 C9 121.6(2) . . ? C7 C8 H8A 119.2 . . ? C9 C8 H8A 119.2 . . ? C8 C9 C4 116.9(2) . . ? C8 C9 C10 123.75(19) . . ? C4 C9 C10 119.33(19) . . ? C1 C10 C9 119.08(18) . . ? C1 C10 C11 121.0(2) . . ? C9 C10 C11 119.87(18) . . ? N1 C11 C10 122.29(19) . . ? N1 C11 H11A 118.9 . . ? C10 C11 H11A 118.9 . . ? O2 C12 N2 124.60(18) . . ? O2 C12 C13 122.43(18) . . ? N2 C12 C13 112.96(16) . . ? N3 C13 C14 122.9(2) . . ? N3 C13 C12 115.99(17) . . ? C14 C13 C12 121.14(18) . . ? C13 C14 C15 117.8(2) . . ? C13 C14 H14A 121.1 . . ? C15 C14 H14A 121.1 . . ? C14 C15 C14 119.9(3) 2 . ? C14 C15 H15A 120.0 2 . ? C14 C15 H15A 120.0 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.249 _refine_diff_density_min -0.326 _refine_diff_density_rms 0.079