# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Huili Chen' _publ_contact_author_email huilichen@sxu.edu.cn _publ_section_title ; A Highly Selective OFF-ON Fluorescent Sensor for Zinc in Aqueous Solution and Living Cell ; loop_ _publ_author_name 'Huili Chen.' 'Wei Gao.' 'Miaoli Zhu.' 'Jingfang Xue.' 'Xiaokai Li.' # Attachment 'C1.cif.txt' data_chl-g-14 _database_code_depnum_ccdc_archive 'CCDC 772010' #TrackingRef 'C1.cif.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H20 N4 O5 Se' _chemical_formula_weight 475.36 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M ? 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 18.708(2) _cell_length_b 14.3200(10) _cell_length_c 7.349(3) _cell_angle_alpha 90.00 _cell_angle_beta 92.890(10) _cell_angle_gamma 90.00 _cell_volume 1966.3(8) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.39 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.606 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 968 _exptl_absorpt_coefficient_mu 1.952 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.5166 _exptl_absorpt_correction_T_max 0.8755 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10891 _diffrn_reflns_av_R_equivalents 0.0460 _diffrn_reflns_av_sigmaI/netI 0.0519 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 2.60 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3462 _reflns_number_gt 2203 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0574P)^2^+1.6038P] 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 3462 _refine_ls_number_parameters 273 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0895 _refine_ls_R_factor_gt 0.0489 _refine_ls_wR_factor_ref 0.1305 _refine_ls_wR_factor_gt 0.1100 _refine_ls_goodness_of_fit_ref 1.018 _refine_ls_restrained_S_all 1.018 _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 Se1 Se 0.84062(3) 0.37409(4) 0.46007(8) 0.0597(2) Uani 1 1 d . . . O1 O 0.90248(17) 0.4563(2) 0.4442(5) 0.0660(10) Uani 1 1 d . . . O2 O 0.8257(3) 0.3330(3) 0.2534(7) 0.1067(15) Uani 1 1 d . . . O3 O 0.8951(3) 0.2931(4) 0.5701(10) 0.142(3) Uani 1 1 d . . . H3 H 0.8825 0.2859 0.6745 0.212 Uiso 1 1 calc R . . C1 C 0.9358(2) 0.6758(3) 0.5103(6) 0.0470(12) Uani 1 1 d . . . H1 H 0.9738 0.6371 0.5468 0.056 Uiso 1 1 calc R . . C2 C 0.9436(2) 0.7708(3) 0.5241(6) 0.0476(12) Uani 1 1 d . . . H2 H 0.9864 0.7963 0.5708 0.057 Uiso 1 1 calc R . . C3 C 0.8882(2) 0.8276(3) 0.4689(6) 0.0417(11) Uani 1 1 d . . . H3A H 0.8935 0.8920 0.4786 0.050 Uiso 1 1 calc R . . C4 C 0.8236(2) 0.7904(3) 0.3979(5) 0.0344(10) Uani 1 1 d . . . C5 C 0.8171(2) 0.6909(3) 0.3879(5) 0.0358(10) Uani 1 1 d . . . C6 C 0.7516(2) 0.6456(3) 0.3186(5) 0.0362(10) Uani 1 1 d . . . C7 C 0.6929(2) 0.7002(3) 0.2540(5) 0.0342(10) Uani 1 1 d . . . C8 C 0.6320(2) 0.6530(3) 0.1844(6) 0.0414(11) Uani 1 1 d . . . H8 H 0.5924 0.6865 0.1385 0.050 Uiso 1 1 calc R . . C9 C 0.6307(3) 0.5576(3) 0.1843(7) 0.0504(12) Uani 1 1 d . . . H9 H 0.5903 0.5255 0.1400 0.060 Uiso 1 1 calc R . . C10 C 0.6911(2) 0.5093(3) 0.2518(7) 0.0508(12) Uani 1 1 d . . . H10 H 0.6897 0.4444 0.2494 0.061 Uiso 1 1 calc R . . C11 C 0.7624(2) 0.8419(3) 0.3313(6) 0.0345(10) Uani 1 1 d . . . C12 C 0.6998(2) 0.8003(3) 0.2613(5) 0.0336(10) Uani 1 1 d . . . C13 C 0.6818(2) 0.9483(3) 0.2489(6) 0.0367(10) Uani 1 1 d . . . C14 C 0.6484(2) 1.0405(3) 0.2218(6) 0.0367(10) Uani 1 1 d . . . C15 C 0.5774(2) 1.0468(3) 0.1544(6) 0.0446(11) Uani 1 1 d . . . H15 H 0.5519 0.9926 0.1262 0.053 Uiso 1 1 calc R . . C16 C 0.5444(2) 1.1328(3) 0.1291(6) 0.0448(11) Uani 1 1 d . . . H16 H 0.4972 1.1351 0.0835 0.054 Uiso 1 1 calc R . . C17 C 0.5804(2) 1.2160(3) 0.1704(6) 0.0396(11) Uani 1 1 d . . . C18 C 0.6515(2) 1.2089(3) 0.2374(7) 0.0504(12) Uani 1 1 d . . . H18 H 0.6773 1.2631 0.2644 0.060 Uiso 1 1 calc R . . C19 C 0.6845(2) 1.1233(3) 0.2646(7) 0.0478(11) Uani 1 1 d . . . H19 H 0.7314 1.1209 0.3122 0.057 Uiso 1 1 calc R . . C20 C 0.5441(3) 1.3096(3) 0.1460(7) 0.0530(12) Uani 1 1 d . . . H20A H 0.5509 1.3324 0.0253 0.079 Uiso 1 1 calc R . . H20B H 0.5645 1.3529 0.2337 0.079 Uiso 1 1 calc R . . H20C H 0.4939 1.3029 0.1636 0.079 Uiso 1 1 calc R . . N1 N 0.87439(19) 0.6382(2) 0.4451(5) 0.0405(9) Uani 1 1 d . . . H1A H 0.8709 0.5784 0.4391 0.049 Uiso 1 1 calc R . . N2 N 0.75055(18) 0.5499(2) 0.3192(5) 0.0421(9) Uani 1 1 d . . . N3 N 0.75011(17) 0.9360(2) 0.3214(5) 0.0376(8) Uani 1 1 d . . . H3B H 0.7798 0.9794 0.3545 0.045 Uiso 1 1 calc R . . N4 N 0.64966(17) 0.8670(2) 0.2098(5) 0.0374(8) Uani 1 1 d . . . O4 O 0.85438(19) 0.0636(3) 0.4431(6) 0.0865(13) Uani 1 1 d . . . H4A H 0.8543 0.1073 0.5214 0.130 Uiso 1 1 d R . . H4B H 0.8839 0.0764 0.3625 0.130 Uiso 1 1 d R . . O5 O 0.9949(2) 0.4846(3) 0.8086(6) 0.1006(15) Uani 1 1 d . . . H5A H 1.0306 0.5201 0.8002 0.151 Uiso 1 1 d R . . H5B H 0.9675 0.4905 0.7144 0.151 Uiso 1 1 d 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 Se1 0.0520(3) 0.0513(4) 0.0765(4) 0.0079(3) 0.0092(3) -0.0031(3) O1 0.0455(19) 0.048(2) 0.104(3) 0.012(2) 0.0037(18) -0.0023(16) O2 0.127(4) 0.070(3) 0.122(4) -0.024(3) -0.001(3) 0.010(3) O3 0.076(3) 0.102(4) 0.248(7) 0.099(5) 0.017(4) 0.013(3) C1 0.034(3) 0.052(3) 0.054(3) 0.004(2) -0.004(2) 0.004(2) C2 0.035(2) 0.048(3) 0.059(3) -0.005(2) -0.003(2) -0.006(2) C3 0.038(3) 0.039(3) 0.048(3) -0.001(2) -0.001(2) -0.003(2) C4 0.036(2) 0.037(3) 0.031(2) -0.0009(19) 0.0055(18) -0.0009(19) C5 0.033(2) 0.043(3) 0.032(2) 0.003(2) 0.0045(18) 0.003(2) C6 0.038(2) 0.039(3) 0.032(2) -0.0028(19) 0.0067(18) -0.0071(19) C7 0.031(2) 0.040(3) 0.032(2) -0.002(2) 0.0028(18) 0.0008(19) C8 0.037(2) 0.039(3) 0.047(3) -0.004(2) -0.003(2) -0.003(2) C9 0.046(3) 0.042(3) 0.064(3) -0.004(2) -0.001(2) -0.007(2) C10 0.052(3) 0.035(3) 0.065(3) -0.001(2) 0.000(2) -0.007(2) C11 0.036(2) 0.032(2) 0.036(2) -0.0011(19) 0.0067(19) 0.0002(18) C12 0.034(2) 0.036(3) 0.031(2) -0.0020(19) 0.0024(18) -0.0023(19) C13 0.036(2) 0.040(3) 0.035(2) -0.001(2) 0.0031(19) 0.002(2) C14 0.040(2) 0.029(2) 0.041(3) 0.000(2) 0.0039(19) 0.0001(19) C15 0.045(3) 0.039(3) 0.049(3) -0.007(2) -0.002(2) -0.003(2) C16 0.041(2) 0.046(3) 0.047(3) -0.002(2) -0.003(2) 0.007(2) C17 0.045(3) 0.034(3) 0.040(3) 0.003(2) 0.006(2) 0.003(2) C18 0.044(3) 0.036(3) 0.071(3) 0.004(2) 0.001(2) -0.007(2) C19 0.037(2) 0.039(3) 0.067(3) 0.006(2) -0.004(2) 0.000(2) C20 0.061(3) 0.042(3) 0.055(3) 0.002(2) 0.002(2) 0.008(2) N1 0.043(2) 0.034(2) 0.045(2) 0.0021(17) 0.0030(16) 0.0031(17) N2 0.042(2) 0.033(2) 0.052(2) -0.0006(18) 0.0015(17) -0.0023(17) N3 0.034(2) 0.036(2) 0.043(2) -0.0039(17) 0.0002(16) -0.0028(16) N4 0.0360(19) 0.035(2) 0.041(2) -0.0007(17) 0.0013(15) 0.0019(17) O4 0.065(2) 0.061(3) 0.132(4) -0.016(2) -0.014(2) -0.012(2) O5 0.076(3) 0.118(4) 0.108(3) 0.027(3) 0.004(2) 0.008(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 Se1 O2 1.640(5) . ? Se1 O1 1.659(3) . ? Se1 O3 1.719(4) . ? O3 H3 0.8200 . ? C1 N1 1.336(5) . ? C1 C2 1.372(6) . ? C1 H1 0.9300 . ? C2 C3 1.363(6) . ? C2 H2 0.9300 . ? C3 C4 1.397(6) . ? C3 H3A 0.9300 . ? C4 C11 1.428(6) . ? C4 C5 1.432(6) . ? C5 N1 1.360(5) . ? C5 C6 1.456(6) . ? C6 N2 1.370(5) . ? C6 C7 1.409(6) . ? C7 C8 1.401(6) . ? C7 C12 1.439(6) . ? C8 C9 1.366(6) . ? C8 H8 0.9300 . ? C9 C10 1.395(6) . ? C9 H9 0.9300 . ? C10 N2 1.328(5) . ? C10 H10 0.9300 . ? C11 N3 1.368(5) . ? C11 C12 1.389(6) . ? C12 N4 1.379(5) . ? C13 N4 1.335(5) . ? C13 N3 1.370(5) . ? C13 C14 1.470(6) . ? C14 C19 1.392(6) . ? C14 C15 1.398(6) . ? C15 C16 1.386(6) . ? C15 H15 0.9300 . ? C16 C17 1.394(6) . ? C16 H16 0.9300 . ? C17 C18 1.400(6) . ? C17 C20 1.508(6) . ? C18 C19 1.382(6) . ? C18 H18 0.9300 . ? C19 H19 0.9300 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? N1 H1A 0.8600 . ? N3 H3B 0.8600 . ? O4 H4A 0.8500 . ? O4 H4B 0.8499 . ? O5 H5A 0.8449 . ? O5 H5B 0.8441 . ? 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 Se1 O1 106.0(2) . . ? O2 Se1 O3 105.2(3) . . ? O1 Se1 O3 96.5(2) . . ? Se1 O3 H3 109.5 . . ? N1 C1 C2 120.8(4) . . ? N1 C1 H1 119.6 . . ? C2 C1 H1 119.6 . . ? C3 C2 C1 119.6(4) . . ? C3 C2 H2 120.2 . . ? C1 C2 H2 120.2 . . ? C2 C3 C4 120.9(4) . . ? C2 C3 H3A 119.5 . . ? C4 C3 H3A 119.5 . . ? C3 C4 C11 126.5(4) . . ? C3 C4 C5 117.9(4) . . ? C11 C4 C5 115.6(4) . . ? N1 C5 C4 118.2(4) . . ? N1 C5 C6 119.8(4) . . ? C4 C5 C6 122.0(4) . . ? N2 C6 C7 123.0(4) . . ? N2 C6 C5 117.1(4) . . ? C7 C6 C5 119.8(4) . . ? C8 C7 C6 117.4(4) . . ? C8 C7 C12 124.3(4) . . ? C6 C7 C12 118.2(4) . . ? C9 C8 C7 119.8(4) . . ? C9 C8 H8 120.1 . . ? C7 C8 H8 120.1 . . ? C8 C9 C10 118.8(4) . . ? C8 C9 H9 120.6 . . ? C10 C9 H9 120.6 . . ? N2 C10 C9 124.3(4) . . ? N2 C10 H10 117.9 . . ? C9 C10 H10 117.9 . . ? N3 C11 C12 105.5(4) . . ? N3 C11 C4 131.0(4) . . ? C12 C11 C4 123.5(4) . . ? N4 C12 C11 110.7(4) . . ? N4 C12 C7 128.4(4) . . ? C11 C12 C7 120.9(4) . . ? N4 C13 N3 111.9(4) . . ? N4 C13 C14 124.7(4) . . ? N3 C13 C14 123.4(4) . . ? C19 C14 C15 117.8(4) . . ? C19 C14 C13 122.4(4) . . ? C15 C14 C13 119.8(4) . . ? C16 C15 C14 120.9(4) . . ? C16 C15 H15 119.5 . . ? C14 C15 H15 119.5 . . ? C15 C16 C17 121.6(4) . . ? C15 C16 H16 119.2 . . ? C17 C16 H16 119.2 . . ? C16 C17 C18 117.0(4) . . ? C16 C17 C20 121.6(4) . . ? C18 C17 C20 121.4(4) . . ? C19 C18 C17 121.6(4) . . ? C19 C18 H18 119.2 . . ? C17 C18 H18 119.2 . . ? C18 C19 C14 121.0(4) . . ? C18 C19 H19 119.5 . . ? C14 C19 H19 119.5 . . ? C17 C20 H20A 109.5 . . ? C17 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C17 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C1 N1 C5 122.5(4) . . ? C1 N1 H1A 118.7 . . ? C5 N1 H1A 118.7 . . ? C10 N2 C6 116.6(4) . . ? C11 N3 C13 107.3(3) . . ? C11 N3 H3B 126.3 . . ? C13 N3 H3B 126.3 . . ? C13 N4 C12 104.6(3) . . ? H4A O4 H4B 109.7 . . ? H5A O5 H5B 109.2 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 C3 -0.7(7) . . . . ? C1 C2 C3 C4 -0.2(7) . . . . ? C2 C3 C4 C11 -178.4(4) . . . . ? C2 C3 C4 C5 1.0(6) . . . . ? C3 C4 C5 N1 -1.1(6) . . . . ? C11 C4 C5 N1 178.4(4) . . . . ? C3 C4 C5 C6 179.1(4) . . . . ? C11 C4 C5 C6 -1.5(6) . . . . ? N1 C5 C6 N2 1.7(6) . . . . ? C4 C5 C6 N2 -178.5(4) . . . . ? N1 C5 C6 C7 -178.0(4) . . . . ? C4 C5 C6 C7 1.8(6) . . . . ? N2 C6 C7 C8 -1.3(6) . . . . ? C5 C6 C7 C8 178.3(4) . . . . ? N2 C6 C7 C12 179.5(4) . . . . ? C5 C6 C7 C12 -0.8(6) . . . . ? C6 C7 C8 C9 1.1(6) . . . . ? C12 C7 C8 C9 -179.8(4) . . . . ? C7 C8 C9 C10 -0.9(7) . . . . ? C8 C9 C10 N2 0.8(7) . . . . ? C3 C4 C11 N3 -1.0(7) . . . . ? C5 C4 C11 N3 179.6(4) . . . . ? C3 C4 C11 C12 179.6(4) . . . . ? C5 C4 C11 C12 0.2(6) . . . . ? N3 C11 C12 N4 -0.3(5) . . . . ? C4 C11 C12 N4 179.3(4) . . . . ? N3 C11 C12 C7 -178.7(3) . . . . ? C4 C11 C12 C7 0.8(6) . . . . ? C8 C7 C12 N4 2.3(7) . . . . ? C6 C7 C12 N4 -178.6(4) . . . . ? C8 C7 C12 C11 -179.6(4) . . . . ? C6 C7 C12 C11 -0.5(6) . . . . ? N4 C13 C14 C19 -179.9(4) . . . . ? N3 C13 C14 C19 1.4(6) . . . . ? N4 C13 C14 C15 1.6(6) . . . . ? N3 C13 C14 C15 -177.2(4) . . . . ? C19 C14 C15 C16 0.8(6) . . . . ? C13 C14 C15 C16 179.4(4) . . . . ? C14 C15 C16 C17 -0.3(7) . . . . ? C15 C16 C17 C18 0.4(6) . . . . ? C15 C16 C17 C20 -178.9(4) . . . . ? C16 C17 C18 C19 -1.1(7) . . . . ? C20 C17 C18 C19 178.3(4) . . . . ? C17 C18 C19 C14 1.6(7) . . . . ? C15 C14 C19 C18 -1.4(7) . . . . ? C13 C14 C19 C18 180.0(4) . . . . ? C2 C1 N1 C5 0.6(7) . . . . ? C4 C5 N1 C1 0.3(6) . . . . ? C6 C5 N1 C1 -179.9(4) . . . . ? C9 C10 N2 C6 -0.9(7) . . . . ? C7 C6 N2 C10 1.2(6) . . . . ? C5 C6 N2 C10 -178.5(4) . . . . ? C12 C11 N3 C13 0.6(4) . . . . ? C4 C11 N3 C13 -178.9(4) . . . . ? N4 C13 N3 C11 -0.7(5) . . . . ? C14 C13 N3 C11 178.2(4) . . . . ? N3 C13 N4 C12 0.5(4) . . . . ? C14 C13 N4 C12 -178.4(4) . . . . ? C11 C12 N4 C13 -0.1(4) . . . . ? C7 C12 N4 C13 178.2(4) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag O5 H5B O1 0.84 2.33 3.139(6) 161.4 . . O5 H5A O1 0.84 2.27 2.866(5) 128.2 3_766 . N3 H3B O4 0.86 1.93 2.787(5) 172.3 1_565 . O4 H4B O5 0.85 2.30 2.936(6) 131.3 4_565 . O4 H4A O2 0.85 2.00 2.794(7) 154.1 4_566 . N1 H1A N2 0.86 2.41 2.758(5) 104.7 . . N1 H1A O1 0.86 1.85 2.657(5) 156.9 . . O3 H3 O2 0.82 2.10 2.633(6) 122.2 4_566 . C1 H1 O5 0.93 2.92 3.643(6) 135.3 . . C3 H3A O4 0.93 2.57 3.442(6) 155.6 1_565 . C19 H19 O4 0.93 2.58 3.484(6) 163.5 1_565 . C15 H15 N4 0.93 2.62 2.927(6) 100.2 . . C19 H19 O4 0.93 2.58 3.484(6) 163.5 1_565 . _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.622 _refine_diff_density_min -0.514 _refine_diff_density_rms 0.068