# 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_coden_Cambridge 440 _publ_requested_journal 'New Journal of Chemistry' loop_ _publ_author_name 'Anunay Samanta' 'Bismillah Ansari' 'Sandip Banthia' 'Aditi Patil' 'Moloy Sarkar' _publ_contact_author_name 'Anunay Samanta' _publ_contact_author_address ; School of Chemistry University of Hyderabad Gachi Bowli Hyderabad 500046 INDIA ; _publ_contact_author_email ASSC@UOHYD.ERNET.IN _publ_section_title ; pH-Regulated 'Off-On' Fluorescence Signaling of d-block Metal Ions in Aqueous Media and Realization of Molecular IMP Logic Function ; # Attachment 'B607642D_cpd1.cif' data_1 _database_code_depnum_ccdc_archive 'CCDC 615587' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H11 N5 O3' _chemical_formula_weight 285.26 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0030 0.0020 '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 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0110 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 Pbca _symmetry_space_group_name_Hall '-P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' _cell_length_a 13.560(11) _cell_length_b 7.385(6) _cell_length_c 26.06(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2609(4) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1237 _cell_measurement_theta_min 2.17 _cell_measurement_theta_max 19.44 _exptl_crystal_description 'tiny plate' _exptl_crystal_colour 'orange yellow' _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.452 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1184 _exptl_absorpt_coefficient_mu 0.108 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min .809 _exptl_absorpt_correction_T_max .998 _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_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 23234 _diffrn_reflns_av_R_equivalents 0.1549 _diffrn_reflns_av_sigmaI/netI 0.0723 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 1.56 _diffrn_reflns_theta_max 25.10 _reflns_number_total 2322 _reflns_number_gt 1221 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _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^)+(0.0730P)^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 2322 _refine_ls_number_parameters 193 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1312 _refine_ls_R_factor_gt 0.0567 _refine_ls_wR_factor_ref 0.1495 _refine_ls_wR_factor_gt 0.1164 _refine_ls_goodness_of_fit_ref 0.950 _refine_ls_restrained_S_all 0.950 _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 N1 N 0.1812(3) 0.3270(4) 0.56102(11) 0.0567(9) Uani 1 1 d . . . N2 N 0.0391(2) 0.1991(4) 0.47752(12) 0.0515(8) Uani 1 1 d . . . N3 N 0.0916(2) 0.0837(4) 0.40022(11) 0.0455(8) Uani 1 1 d . . . N4 N 0.29377(19) 0.0322(4) 0.36979(10) 0.0390(7) Uani 1 1 d . . . H4A H 0.247(2) -0.010(4) 0.3481(13) 0.059 Uiso 1 1 d . . . N5 N 0.3306(2) 0.3676(4) 0.28650(10) 0.0461(8) Uani 1 1 d . . . O1 O 0.01186(17) 0.1292(3) 0.42999(10) 0.0554(7) Uani 1 1 d . . . O2 O 0.0939(2) 0.3527(5) 0.56965(11) 0.0891(10) Uani 1 1 d . . . O3 O 0.2471(2) 0.3702(4) 0.59078(10) 0.0778(9) Uani 1 1 d . . . C1 C 0.1678(2) 0.1237(4) 0.42853(12) 0.0330(8) Uani 1 1 d . . . C2 C 0.1360(2) 0.1952(4) 0.47668(13) 0.0357(8) Uani 1 1 d . . . C3 C 0.2082(2) 0.2489(4) 0.51283(12) 0.0397(8) Uani 1 1 d . . . C4 C 0.3045(2) 0.2278(4) 0.49980(13) 0.0409(9) Uani 1 1 d . . . H4 H 0.3521 0.2620 0.5236 0.049 Uiso 1 1 calc R . . C5 C 0.3364(2) 0.1581(4) 0.45284(13) 0.0391(8) Uani 1 1 d . . . H5 H 0.4037 0.1488 0.4465 0.047 Uiso 1 1 calc R . . C6 C 0.2706(2) 0.1025(4) 0.41544(12) 0.0350(8) Uani 1 1 d . . . C7 C 0.3949(2) 0.0070(4) 0.35302(12) 0.0425(9) Uani 1 1 d . . . H7A H 0.3959 -0.0822 0.3257 0.051 Uiso 1 1 calc R . . H7B H 0.4330 -0.0413 0.3814 0.051 Uiso 1 1 calc R . . C8 C 0.4447(2) 0.1795(4) 0.33386(13) 0.0423(9) Uani 1 1 d . . . H8A H 0.4373 0.2733 0.3596 0.051 Uiso 1 1 calc R . . H8B H 0.5147 0.1565 0.3297 0.051 Uiso 1 1 calc R . . C9 C 0.4040(2) 0.2470(4) 0.28417(12) 0.0361(8) Uani 1 1 d . . . C10 C 0.4395(3) 0.1844(5) 0.23776(14) 0.0503(10) Uani 1 1 d . . . H10 H 0.4912 0.1018 0.2370 0.060 Uiso 1 1 calc R . . C11 C 0.3982(3) 0.2440(6) 0.19293(15) 0.0611(11) Uani 1 1 d . . . H11 H 0.4208 0.2008 0.1615 0.073 Uiso 1 1 calc R . . C12 C 0.3244(3) 0.3664(6) 0.19478(15) 0.0654(12) Uani 1 1 d . . . H12 H 0.2952 0.4095 0.1649 0.079 Uiso 1 1 calc R . . C13 C 0.2938(3) 0.4253(5) 0.24209(15) 0.0606(11) Uani 1 1 d . . . H13 H 0.2438 0.5115 0.2432 0.073 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 N1 0.059(2) 0.072(2) 0.038(2) -0.0025(17) 0.0053(18) 0.0034(19) N2 0.0396(19) 0.063(2) 0.052(2) -0.0020(17) 0.0036(15) 0.0003(15) N3 0.0378(17) 0.0492(18) 0.0497(18) 0.0006(14) -0.0002(16) 0.0012(15) N4 0.0357(17) 0.0443(18) 0.0371(17) -0.0019(14) 0.0015(14) -0.0017(13) N5 0.0486(19) 0.0519(19) 0.0378(17) 0.0031(15) 0.0006(15) 0.0088(15) O1 0.0350(14) 0.0685(18) 0.0627(18) -0.0023(14) -0.0015(14) -0.0025(13) O2 0.058(2) 0.140(3) 0.070(2) -0.0254(19) 0.0238(16) 0.0054(19) O3 0.079(2) 0.108(2) 0.0461(17) -0.0208(16) -0.0055(16) 0.0072(18) C1 0.0325(19) 0.0298(18) 0.037(2) 0.0047(15) -0.0026(16) 0.0013(15) C2 0.0295(19) 0.038(2) 0.040(2) 0.0079(16) 0.0086(16) -0.0003(15) C3 0.043(2) 0.045(2) 0.0308(19) 0.0006(17) 0.0028(17) 0.0005(17) C4 0.039(2) 0.046(2) 0.038(2) 0.0031(17) -0.0050(17) -0.0020(16) C5 0.030(2) 0.047(2) 0.040(2) 0.0040(17) -0.0006(16) 0.0024(16) C6 0.039(2) 0.0302(18) 0.036(2) 0.0063(16) 0.0001(16) 0.0030(15) C7 0.043(2) 0.043(2) 0.042(2) 0.0010(17) 0.0040(17) 0.0072(17) C8 0.0338(19) 0.045(2) 0.048(2) 0.0016(18) 0.0045(17) 0.0037(16) C9 0.0314(18) 0.0337(19) 0.043(2) 0.0001(16) 0.0069(16) -0.0057(16) C10 0.048(2) 0.055(2) 0.048(2) -0.002(2) 0.018(2) 0.0016(18) C11 0.069(3) 0.076(3) 0.039(2) -0.004(2) 0.022(2) -0.010(3) C12 0.078(3) 0.075(3) 0.043(2) 0.013(2) -0.007(2) -0.003(3) C13 0.068(3) 0.061(3) 0.053(3) 0.004(2) -0.001(2) 0.016(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 N1 O2 1.220(4) . ? N1 O3 1.226(4) . ? N1 C3 1.429(4) . ? N2 C2 1.314(4) . ? N2 O1 1.392(4) . ? N3 C1 1.304(4) . ? N3 O1 1.372(3) . ? N4 C6 1.335(4) . ? N4 C7 1.452(4) . ? N4 H4A 0.90(3) . ? N5 C13 1.330(4) . ? N5 C9 1.337(4) . ? C1 C2 1.428(4) . ? C1 C6 1.443(4) . ? C2 C3 1.415(4) . ? C3 C4 1.359(4) . ? C4 C5 1.396(4) . ? C4 H4 0.9300 . ? C5 C6 1.383(4) . ? C5 H5 0.9300 . ? C7 C8 1.525(4) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.493(4) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.381(5) . ? C10 C11 1.368(5) . ? C10 H10 0.9300 . ? C11 C12 1.349(5) . ? C11 H11 0.9300 . ? C12 C13 1.372(5) . ? C12 H12 0.9300 . ? C13 H13 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 O2 N1 O3 123.4(3) . . ? O2 N1 C3 118.2(3) . . ? O3 N1 C3 118.3(3) . . ? C2 N2 O1 104.1(3) . . ? C1 N3 O1 104.4(3) . . ? C6 N4 C7 122.7(3) . . ? C6 N4 H4A 122(2) . . ? C7 N4 H4A 115(2) . . ? C13 N5 C9 116.9(3) . . ? N3 O1 N2 112.6(2) . . ? N3 C1 C2 110.0(3) . . ? N3 C1 C6 127.4(3) . . ? C2 C1 C6 122.6(3) . . ? N2 C2 C3 132.4(3) . . ? N2 C2 C1 108.9(3) . . ? C3 C2 C1 118.7(3) . . ? C4 C3 C2 117.8(3) . . ? C4 C3 N1 120.8(3) . . ? C2 C3 N1 121.4(3) . . ? C3 C4 C5 124.0(3) . . ? C3 C4 H4 118.0 . . ? C5 C4 H4 118.0 . . ? C6 C5 C4 121.8(3) . . ? C6 C5 H5 119.1 . . ? C4 C5 H5 119.1 . . ? N4 C6 C5 126.2(3) . . ? N4 C6 C1 118.7(3) . . ? C5 C6 C1 115.1(3) . . ? N4 C7 C8 114.2(3) . . ? N4 C7 H7A 108.7 . . ? C8 C7 H7A 108.7 . . ? N4 C7 H7B 108.7 . . ? C8 C7 H7B 108.7 . . ? H7A C7 H7B 107.6 . . ? C9 C8 C7 113.5(3) . . ? C9 C8 H8A 108.9 . . ? C7 C8 H8A 108.9 . . ? C9 C8 H8B 108.9 . . ? C7 C8 H8B 108.9 . . ? H8A C8 H8B 107.7 . . ? N5 C9 C10 121.5(3) . . ? N5 C9 C8 117.3(3) . . ? C10 C9 C8 121.2(3) . . ? C11 C10 C9 119.8(4) . . ? C11 C10 H10 120.1 . . ? C9 C10 H10 120.1 . . ? C12 C11 C10 119.2(4) . . ? C12 C11 H11 120.4 . . ? C10 C11 H11 120.4 . . ? C11 C12 C13 118.0(4) . . ? C11 C12 H12 121.0 . . ? C13 C12 H12 121.0 . . ? N5 C13 C12 124.5(4) . . ? N5 C13 H13 117.7 . . ? C12 C13 H13 117.7 . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.10 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.169 _refine_diff_density_min -0.161 _refine_diff_density_rms 0.042