# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Montis, Riccardo' _publ_contact_author_email riccardo.montis@gmail.com loop_ _publ_author_name R.Montis M.Hursthouse # Attachment '4-aminopyridinium-6-fluorosalicylate.cif' data_4-aminopyridinium_6-fluorosalicylate _database_code_depnum_ccdc_archive 'CCDC 888884' #TrackingRef '4-aminopyridinium-6-fluorosalicylate.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 4-aminopyridinium_6-fluorosalicylate ; _chemical_name_common 4-aminopyridinium_6-fluorosalicylate _chemical_melting_point ? _chemical_formula_moiety 'C7 H4 F O3, C5 H7 N2' _chemical_formula_sum 'C12 H11 F N2 O3' _chemical_formula_weight 250.23 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' F F 0.0171 0.0103 '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 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' '-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 11.655(1) _cell_length_b 11.6654(3) _cell_length_c 16.9859(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2309.4(2) _cell_formula_units_Z 8 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 68667 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.439 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1040 _exptl_absorpt_coefficient_mu 0.115 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9795 _exptl_absorpt_correction_T_max 0.9886 _exptl_absorpt_process_details 'SADABS 2007/2 (Sheldrick, G.M., 2007)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius Roper CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 49936 _diffrn_reflns_av_R_equivalents 0.0825 _diffrn_reflns_av_sigmaI/netI 0.0309 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.97 _diffrn_reflns_theta_max 27.50 _reflns_number_total 2648 _reflns_number_gt 2208 _reflns_threshold_expression >2\s(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' #Although determined using DirAx, the cell is refined in the HKL #package during data reduction _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^ > 2\s(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^)+(0.0566P)^2^+1.1138P] 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 2648 _refine_ls_number_parameters 167 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0635 _refine_ls_R_factor_gt 0.0496 _refine_ls_wR_factor_ref 0.1250 _refine_ls_wR_factor_gt 0.1160 _refine_ls_goodness_of_fit_ref 1.080 _refine_ls_restrained_S_all 1.080 _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 C11 C 0.56062(13) 0.47182(13) 0.33800(9) 0.0253(3) Uani 1 1 d . . . C12 C 0.61500(14) 0.54443(14) 0.28353(10) 0.0285(4) Uani 1 1 d . . . C13 C 0.70975(15) 0.51507(15) 0.24021(10) 0.0330(4) Uani 1 1 d . . . H13 H 0.7438 0.5679 0.2046 0.040 Uiso 1 1 calc R . . C14 C 0.75473(15) 0.40493(15) 0.25013(11) 0.0344(4) Uani 1 1 d . . . H14 H 0.8207 0.3826 0.2212 0.041 Uiso 1 1 calc R . . C15 C 0.70454(15) 0.32849(15) 0.30138(10) 0.0330(4) Uani 1 1 d . . . H15 H 0.7354 0.2535 0.3070 0.040 Uiso 1 1 calc R . . C16 C 0.60880(14) 0.36067(14) 0.34503(10) 0.0287(4) Uani 1 1 d . . . C17 C 0.45773(14) 0.50595(13) 0.38602(9) 0.0261(3) Uani 1 1 d . . . O12 O 0.41198(10) 0.42592(10) 0.42744(7) 0.0336(3) Uani 1 1 d . . . O11 O 0.42001(10) 0.60547(10) 0.38489(8) 0.0335(3) Uani 1 1 d . . . O13 O 0.56424(11) 0.28282(10) 0.39510(8) 0.0358(3) Uani 1 1 d . . . F11 F 0.57172(9) 0.65131(8) 0.27148(6) 0.0381(3) Uani 1 1 d . . . H13A H 0.504(2) 0.315(2) 0.4147(14) 0.064(8) Uiso 1 1 d . . . C21 C 0.20210(15) 0.64076(14) 0.49564(10) 0.0310(4) Uani 1 1 d . . . H21A H 0.2459 0.6887 0.4619 0.037 Uiso 1 1 calc R . . C22 C 0.11481(14) 0.68688(13) 0.53745(10) 0.0285(4) Uani 1 1 d . . . H22 H 0.0977 0.7662 0.5330 0.034 Uiso 1 1 calc R . . C23 C 0.04874(14) 0.61560(14) 0.58818(10) 0.0276(4) Uani 1 1 d . . . C24 C 0.07771(15) 0.49772(13) 0.59110(10) 0.0285(4) Uani 1 1 d . . . H24 H 0.0351 0.4466 0.6234 0.034 Uiso 1 1 calc R . . C25 C 0.16683(15) 0.45840(14) 0.54732(10) 0.0313(4) Uani 1 1 d . . . H25 H 0.1861 0.3794 0.5497 0.038 Uiso 1 1 calc R . . N21 N 0.22855(12) 0.52824(12) 0.50071(8) 0.0318(3) Uani 1 1 d . . . H21 H 0.2864 0.5005 0.4734 0.038 Uiso 1 1 calc R . . N22 N -0.03681(13) 0.65871(12) 0.63024(9) 0.0369(4) Uani 1 1 d . . . H22A H -0.0775 0.6138 0.6611 0.044 Uiso 1 1 calc R . . H22B H -0.0529 0.7323 0.6273 0.044 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 C11 0.0245(7) 0.0222(7) 0.0293(8) -0.0006(6) -0.0036(6) -0.0027(6) C12 0.0316(8) 0.0207(8) 0.0333(8) 0.0009(6) -0.0044(7) -0.0042(6) C13 0.0316(9) 0.0349(9) 0.0323(9) 0.0001(7) 0.0014(7) -0.0094(7) C14 0.0261(8) 0.0422(10) 0.0349(9) -0.0051(8) 0.0004(7) 0.0013(7) C15 0.0328(9) 0.0308(9) 0.0353(9) -0.0016(7) -0.0023(7) 0.0059(7) C16 0.0306(8) 0.0239(8) 0.0315(9) 0.0004(7) -0.0024(7) -0.0008(6) C17 0.0262(8) 0.0211(7) 0.0309(8) -0.0003(6) -0.0040(6) -0.0028(6) O12 0.0357(6) 0.0229(6) 0.0422(7) 0.0050(5) 0.0099(5) 0.0009(5) O11 0.0337(6) 0.0191(6) 0.0477(7) 0.0001(5) 0.0029(5) 0.0007(5) O13 0.0398(7) 0.0228(6) 0.0448(7) 0.0079(5) 0.0098(6) 0.0060(5) F11 0.0436(6) 0.0218(5) 0.0488(6) 0.0081(4) 0.0061(5) -0.0014(4) C21 0.0333(9) 0.0270(8) 0.0326(8) 0.0021(7) -0.0014(7) -0.0047(7) C22 0.0324(8) 0.0189(7) 0.0342(8) 0.0029(6) -0.0033(7) -0.0008(6) C23 0.0285(8) 0.0223(8) 0.0321(9) -0.0009(6) -0.0033(7) -0.0006(6) C24 0.0325(8) 0.0193(7) 0.0336(9) 0.0027(6) -0.0016(7) -0.0022(6) C25 0.0345(9) 0.0245(8) 0.0349(9) -0.0003(7) -0.0035(7) -0.0011(7) N21 0.0308(7) 0.0288(8) 0.0358(7) -0.0034(6) 0.0022(6) 0.0021(6) N22 0.0400(8) 0.0226(7) 0.0480(9) 0.0034(6) 0.0119(7) 0.0009(6) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 C11 C12 1.405(2) . ? C11 C16 1.418(2) . ? C11 C17 1.504(2) . ? C12 F11 1.3604(19) . ? C12 C13 1.370(2) . ? C13 C14 1.398(2) . ? C13 H13 0.9500 . ? C14 C15 1.377(3) . ? C14 H14 0.9500 . ? C15 C16 1.391(2) . ? C15 H15 0.9500 . ? C16 O13 1.348(2) . ? C17 O11 1.2416(19) . ? C17 O12 1.2848(19) . ? O13 H13A 0.86(3) . ? C21 N21 1.351(2) . ? C21 C22 1.352(2) . ? C21 H21A 0.9500 . ? C22 C23 1.424(2) . ? C22 H22 0.9500 . ? C23 N22 1.326(2) . ? C23 C24 1.417(2) . ? C24 C25 1.357(2) . ? C24 H24 0.9500 . ? C25 N21 1.345(2) . ? C25 H25 0.9500 . ? N21 H21 0.8800 . ? N22 H22A 0.8800 . ? N22 H22B 0.8800 . ? 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 C12 C11 C16 115.34(15) . . ? C12 C11 C17 123.85(14) . . ? C16 C11 C17 120.81(14) . . ? F11 C12 C13 116.56(15) . . ? F11 C12 C11 118.96(15) . . ? C13 C12 C11 124.48(16) . . ? C12 C13 C14 117.85(16) . . ? C12 C13 H13 121.1 . . ? C14 C13 H13 121.1 . . ? C15 C14 C13 120.82(16) . . ? C15 C14 H14 119.6 . . ? C13 C14 H14 119.6 . . ? C14 C15 C16 120.20(16) . . ? C14 C15 H15 119.9 . . ? C16 C15 H15 119.9 . . ? O13 C16 C15 117.61(15) . . ? O13 C16 C11 121.09(15) . . ? C15 C16 C11 121.29(15) . . ? O11 C17 O12 122.74(15) . . ? O11 C17 C11 121.43(14) . . ? O12 C17 C11 115.82(13) . . ? C16 O13 H13A 104.9(17) . . ? N21 C21 C22 121.65(16) . . ? N21 C21 H21A 119.2 . . ? C22 C21 H21A 119.2 . . ? C21 C22 C23 119.50(15) . . ? C21 C22 H22 120.3 . . ? C23 C22 H22 120.3 . . ? N22 C23 C24 121.91(16) . . ? N22 C23 C22 120.76(15) . . ? C24 C23 C22 117.33(15) . . ? C25 C24 C23 119.42(16) . . ? C25 C24 H24 120.3 . . ? C23 C24 H24 120.3 . . ? N21 C25 C24 121.82(16) . . ? N21 C25 H25 119.1 . . ? C24 C25 H25 119.1 . . ? C25 N21 C21 120.27(15) . . ? C25 N21 H21 119.9 . . ? C21 N21 H21 119.9 . . ? C23 N22 H22A 120.0 . . ? C23 N22 H22B 120.0 . . ? H22A N22 H22B 120.0 . . ? 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 N22 H22B O11 0.88 1.93 2.8083(19) 175.9 4_466 N22 H22B F11 0.88 2.63 3.0493(19) 110.4 4_466 O13 H13A O12 0.86(3) 1.69(3) 2.4976(17) 154(2) . N21 H21 O12 0.88 1.87 2.7466(19) 171.5 . N21 H21 O11 0.88 2.49 3.1083(19) 128.2 . _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.267 _refine_diff_density_min -0.263 _refine_diff_density_rms 0.073 # Attachment '4-aminopyridinium-5-bromosalicylate-hydrate.cif' data_4-aminopyridium_5-bromosalicylate_monohydrate _database_code_depnum_ccdc_archive 'CCDC 888885' #TrackingRef '4-aminopyridinium-5-bromosalicylate-hydrate.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 4-aminopyridium_5-bromosalicylate_monohydrate ; _chemical_name_common 4-aminopyridium_5-bromosalicylate_monohydrate _chemical_melting_point ? _chemical_formula_moiety 'C7 H4 Br O3, C5 H7 N2, H2 O' _chemical_formula_sum 'C12 H13 Br N2 O4' _chemical_formula_weight 329.15 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pca21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y, z' '-x+1/2, y, z+1/2' _cell_length_a 17.1666(5) _cell_length_b 3.85010(10) _cell_length_c 19.5610(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1292.85(6) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 4787 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.691 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 664 _exptl_absorpt_coefficient_mu 3.192 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4685 _exptl_absorpt_correction_T_max 0.7007 _exptl_absorpt_process_details 'SADABS 2007/2 (Sheldrick, G.M., 2007)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator '10cm confocal mirrors' _diffrn_measurement_device_type 'Bruker-Nonius APEX II CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean '4096x4096pixels / 62x62mm' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10855 _diffrn_reflns_av_R_equivalents 0.0389 _diffrn_reflns_av_sigmaI/netI 0.0502 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -4 _diffrn_reflns_limit_k_max 4 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 3.16 _diffrn_reflns_theta_max 27.49 _reflns_number_total 2881 _reflns_number_gt 2415 _reflns_threshold_expression >2\s(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' #Although determined using DirAx, the cell is refined in the HKL #package during data reduction _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^ > 2\s(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^)+(0.0022P)^2^+0.4217P] 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 0.025(10) _refine_ls_number_reflns 2881 _refine_ls_number_parameters 181 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0384 _refine_ls_R_factor_gt 0.0282 _refine_ls_wR_factor_ref 0.0629 _refine_ls_wR_factor_gt 0.0584 _refine_ls_goodness_of_fit_ref 1.089 _refine_ls_restrained_S_all 1.089 _refine_ls_shift/su_max 0.003 _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 C11 C 0.23223(17) 0.1363(8) 0.25037(15) 0.0138(6) Uani 1 1 d . . . C12 C 0.26967(15) 0.1364(8) 0.18688(15) 0.0148(6) Uani 1 1 d . . . C13 C 0.23037(17) 0.2467(8) 0.12859(17) 0.0186(7) Uani 1 1 d . . . H13 H 0.2561 0.2477 0.0856 0.022 Uiso 1 1 calc R . . C14 C 0.15380(18) 0.3548(8) 0.13331(15) 0.0165(6) Uani 1 1 d . . . H14 H 0.1270 0.4319 0.0936 0.020 Uiso 1 1 calc R . . C15 C 0.11627(13) 0.3507(7) 0.19582(17) 0.0150(5) Uani 1 1 d . . . C16 C 0.15457(16) 0.2445(8) 0.25430(15) 0.0149(6) Uani 1 1 d . . . H16 H 0.1283 0.2451 0.2970 0.018 Uiso 1 1 calc R . . C17 C 0.27355(17) 0.0221(7) 0.31390(16) 0.0160(6) Uani 1 1 d . . . O11 O 0.23890(12) 0.0425(6) 0.37013(12) 0.0220(5) Uani 1 1 d . . . O12 O 0.34319(12) -0.0946(6) 0.30666(11) 0.0227(5) Uani 1 1 d . . . O13 O 0.34485(11) 0.0280(5) 0.17958(10) 0.0202(5) Uani 1 1 d . . . H13A H 0.3629 -0.0277 0.2180 0.030 Uiso 1 1 calc R . . Br11 Br 0.010296(12) 0.49680(7) 0.20068(4) 0.01882(9) Uani 1 1 d . . . C21 C 0.50790(17) 0.1514(10) 0.38536(17) 0.0191(8) Uani 1 1 d . . . H21 H 0.5105 0.2023 0.3379 0.023 Uiso 1 1 calc R . . C22 C 0.56962(18) 0.2326(8) 0.42618(15) 0.0199(7) Uani 1 1 d . . . H22 H 0.6146 0.3391 0.4072 0.024 Uiso 1 1 calc R . . C23 C 0.56638(17) 0.1573(8) 0.49709(15) 0.0162(7) Uani 1 1 d . . . C24 C 0.49754(18) 0.0008(7) 0.5219(2) 0.0155(8) Uani 1 1 d . . . H24 H 0.4928 -0.0522 0.5692 0.019 Uiso 1 1 calc R . . C25 C 0.43780(18) -0.0748(8) 0.47845(16) 0.0192(7) Uani 1 1 d . . . H25 H 0.3919 -0.1811 0.4957 0.023 Uiso 1 1 calc R . . N21 N 0.44331(16) 0.0005(6) 0.41089(14) 0.0200(6) Uani 1 1 d . . . H21A H 0.4043 -0.0497 0.3834 0.024 Uiso 1 1 calc R . . N22 N 0.62591(13) 0.2327(7) 0.53816(12) 0.0208(6) Uani 1 1 d . . . H22A H 0.6230 0.1850 0.5821 0.025 Uiso 1 1 calc R . . H22B H 0.6681 0.3303 0.5214 0.025 Uiso 1 1 calc R . . O31 O 0.26760(13) 0.5520(6) 0.46697(12) 0.0221(5) Uani 1 1 d D . . H31A H 0.2636(19) 0.724(6) 0.4404(15) 0.027(11) Uiso 1 1 d D . . H31B H 0.260(3) 0.376(6) 0.440(2) 0.077(17) Uiso 1 1 d 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 C11 0.0175(16) 0.0124(15) 0.0115(15) 0.0013(13) -0.0017(12) -0.0017(13) C12 0.0127(13) 0.0149(14) 0.0167(18) -0.0015(12) 0.0003(11) -0.0023(11) C13 0.0177(16) 0.0247(18) 0.0135(15) 0.0025(14) 0.0016(12) -0.0017(13) C14 0.0174(16) 0.0176(16) 0.0145(15) 0.0016(13) -0.0028(12) -0.0028(13) C15 0.0130(12) 0.0134(13) 0.0186(14) -0.0019(14) -0.0043(15) -0.0001(10) C16 0.0153(15) 0.0150(16) 0.0146(15) -0.0005(12) 0.0031(13) -0.0034(12) C17 0.0176(15) 0.0169(16) 0.0136(16) 0.0008(13) -0.0020(12) -0.0050(12) O11 0.0256(12) 0.0291(14) 0.0114(12) 0.0028(9) 0.0010(9) -0.0002(9) O12 0.0173(11) 0.0345(13) 0.0161(11) 0.0017(10) -0.0042(9) 0.0063(10) O13 0.0127(10) 0.0333(14) 0.0146(12) 0.0008(10) -0.0012(7) 0.0022(9) Br11 0.01426(13) 0.01968(15) 0.02251(15) -0.00130(13) -0.0014(3) 0.00297(12) C21 0.0215(18) 0.022(2) 0.0135(17) 0.0051(16) 0.0015(13) 0.0035(15) C22 0.0182(17) 0.0250(18) 0.0164(15) 0.0010(14) 0.0014(12) -0.0001(14) C23 0.0149(16) 0.0164(17) 0.0172(15) 0.0018(13) 0.0015(12) 0.0036(14) C24 0.0168(16) 0.016(2) 0.0139(18) -0.0007(12) 0.0002(12) 0.0042(12) C25 0.0158(16) 0.0245(17) 0.0175(17) 0.0020(13) 0.0030(12) 0.0020(13) N21 0.0139(14) 0.0269(17) 0.0192(14) -0.0006(10) -0.0079(11) 0.0018(11) N22 0.0168(13) 0.0315(15) 0.0142(14) 0.0036(12) -0.0011(10) -0.0018(11) O31 0.0232(14) 0.0287(15) 0.0145(13) 0.0046(11) -0.0002(9) 0.0007(10) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 C11 C12 1.398(4) . ? C11 C16 1.399(4) . ? C11 C17 1.497(4) . ? C12 O13 1.364(3) . ? C12 C13 1.391(4) . ? C13 C14 1.382(4) . ? C13 H13 0.9500 . ? C14 C15 1.382(4) . ? C14 H14 0.9500 . ? C15 C16 1.381(4) . ? C15 Br11 1.907(2) . ? C16 H16 0.9500 . ? C17 O11 1.253(4) . ? C17 O12 1.285(4) . ? O13 H13A 0.8400 . ? C21 N21 1.348(4) . ? C21 C22 1.363(4) . ? C21 H21 0.9500 . ? C22 C23 1.418(4) . ? C22 H22 0.9500 . ? C23 N22 1.332(4) . ? C23 C24 1.413(4) . ? C24 C25 1.363(5) . ? C24 H24 0.9500 . ? C25 N21 1.356(4) . ? C25 H25 0.9500 . ? N21 H21A 0.8800 . ? N22 H22A 0.8800 . ? N22 H22B 0.8800 . ? O31 H31A 0.845(18) . ? O31 H31B 0.871(19) . ? 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 C12 C11 C16 119.1(3) . . ? C12 C11 C17 121.3(2) . . ? C16 C11 C17 119.6(3) . . ? O13 C12 C13 117.8(2) . . ? O13 C12 C11 121.9(2) . . ? C13 C12 C11 120.3(2) . . ? C14 C13 C12 119.9(3) . . ? C14 C13 H13 120.1 . . ? C12 C13 H13 120.1 . . ? C13 C14 C15 119.9(3) . . ? C13 C14 H14 120.0 . . ? C15 C14 H14 120.0 . . ? C16 C15 C14 120.9(2) . . ? C16 C15 Br11 120.0(2) . . ? C14 C15 Br11 119.0(2) . . ? C15 C16 C11 119.8(3) . . ? C15 C16 H16 120.1 . . ? C11 C16 H16 120.1 . . ? O11 C17 O12 124.1(3) . . ? O11 C17 C11 119.0(3) . . ? O12 C17 C11 116.9(3) . . ? C12 O13 H13A 109.5 . . ? N21 C21 C22 121.4(3) . . ? N21 C21 H21 119.3 . . ? C22 C21 H21 119.3 . . ? C21 C22 C23 119.7(3) . . ? C21 C22 H22 120.1 . . ? C23 C22 H22 120.1 . . ? N22 C23 C24 121.8(3) . . ? N22 C23 C22 121.0(3) . . ? C24 C23 C22 117.1(3) . . ? C25 C24 C23 120.4(4) . . ? C25 C24 H24 119.8 . . ? C23 C24 H24 119.8 . . ? N21 C25 C24 120.6(3) . . ? N21 C25 H25 119.7 . . ? C24 C25 H25 119.7 . . ? C21 N21 C25 120.7(3) . . ? C21 N21 H21A 119.6 . . ? C25 N21 H21A 119.6 . . ? C23 N22 H22A 120.0 . . ? C23 N22 H22B 120.0 . . ? H22A N22 H22B 120.0 . . ? H31A O31 H31B 103(3) . . ? 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 O13 H13A Br11 0.84 3.13 3.5099(19) 110.4 3 N22 H22B O31 0.88 2.06 2.923(3) 165.5 3_565 N22 H22A O13 0.88 2.15 2.985(3) 158.7 2_655 O31 H31A O11 0.845(18) 1.89(2) 2.720(3) 167(3) 1_565 O13 H13A O12 0.84 1.79 2.530(3) 146.6 . N21 H21A O12 0.88 1.84 2.692(3) 162.3 . O31 H31B O11 0.871(19) 1.91(2) 2.771(3) 171(4) . _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.265 _refine_diff_density_min -0.564 _refine_diff_density_rms 0.080 # Attachment '4-aminopyridinium-5-iodosalicylate-hydrate.cif' data_4-aminopyridinium_5-iodosalicylate_monohydrate _database_code_depnum_ccdc_archive 'CCDC 888886' #TrackingRef '4-aminopyridinium-5-iodosalicylate-hydrate.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 4-aminopyridinium 5-iodosalicylate monohydrate ; _chemical_name_common '4-aminopyridinium 5-iodosalicylate monohydrate' _chemical_melting_point ? _chemical_formula_moiety 'C7 H4 I O3, C5 H7 N2, H2 O' _chemical_formula_sum 'C12 H13 I N2 O4' _chemical_formula_weight 376.14 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' I I -0.4742 1.8119 '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 P21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 4.400(5) _cell_length_b 18.068(5) _cell_length_c 8.581(5) _cell_angle_alpha 90.00 _cell_angle_beta 96.077(5) _cell_angle_gamma 90.00 _cell_volume 678.3(9) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 9176 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description Plate _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.842 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 368 _exptl_absorpt_coefficient_mu 2.372 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7639 _exptl_absorpt_correction_T_max 0.8708 _exptl_absorpt_process_details 'SADABS 2007/2 (Sheldrick, G.M., 2007)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator '10cm confocal mirrors' _diffrn_measurement_device_type 'Bruker-Nonius APEX II CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean '4096x4096pixels / 62x62mm' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7757 _diffrn_reflns_av_R_equivalents 0.0274 _diffrn_reflns_av_sigmaI/netI 0.0358 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 3.28 _diffrn_reflns_theta_max 27.48 _reflns_number_total 3041 _reflns_number_gt 3008 _reflns_threshold_expression >2\s(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' #Although determined using DirAx, the cell is refined in the HKL #package during data reduction _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _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^ > 2\s(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^+0.0718P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.027(13) _refine_ls_number_reflns 3041 _refine_ls_number_parameters 173 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0165 _refine_ls_R_factor_gt 0.0162 _refine_ls_wR_factor_ref 0.0388 _refine_ls_wR_factor_gt 0.0386 _refine_ls_goodness_of_fit_ref 1.066 _refine_ls_restrained_S_all 1.065 _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 I11 I 0.41256(2) 0.270135(16) 0.159318(11) 0.01949(5) Uani 1 1 d . . . O11 O 1.2009(4) 0.09105(9) 0.54318(19) 0.0240(3) Uani 1 1 d . . . O12 O 1.4148(4) 0.15695(9) 0.74567(17) 0.0241(3) Uani 1 1 d . . . O13 O 1.2678(4) 0.29042(8) 0.78338(16) 0.0246(4) Uani 1 1 d . . . H13 H 1.3644 0.2507 0.8015 0.037 Uiso 1 1 d R . . C11 C 1.0476(5) 0.21614(12) 0.5675(3) 0.0152(4) Uani 1 1 d . . . C12 C 1.0764(5) 0.28352(13) 0.6482(2) 0.0177(5) Uani 1 1 d . . . C13 C 0.9137(6) 0.34511(13) 0.5915(3) 0.0231(5) Uani 1 1 d . . . H13A H 0.9372 0.3906 0.6471 0.028 Uiso 1 1 calc R . . C14 C 0.7183(5) 0.34126(13) 0.4557(3) 0.0220(5) Uani 1 1 d . . . H14 H 0.6059 0.3836 0.4176 0.026 Uiso 1 1 calc R . . C15 C 0.6875(4) 0.2744(2) 0.37486(19) 0.0174(4) Uani 1 1 d . . . C16 C 0.8471(5) 0.21275(12) 0.4288(2) 0.0165(4) Uani 1 1 d . . . H16 H 0.8222 0.1676 0.3722 0.020 Uiso 1 1 calc R . . C17 C 1.2314(5) 0.14966(12) 0.6210(2) 0.0182(4) Uani 1 1 d . . . N21 N -0.1752(5) 0.06102(12) -0.1141(2) 0.0209(4) Uani 1 1 d . . . H21A H -0.3151 0.0856 -0.1742 0.025 Uiso 1 1 calc R . . N22 N 0.4783(5) -0.05301(12) 0.1670(2) 0.0212(4) Uani 1 1 d . . . H22A H 0.5619 -0.0327 0.2544 0.025 Uiso 1 1 calc R . . H22B H 0.5356 -0.0974 0.1398 0.025 Uiso 1 1 calc R . . C21 C -0.0888(6) -0.00712(14) -0.1568(3) 0.0219(5) Uani 1 1 d . . . H21 H -0.1799 -0.0277 -0.2524 0.026 Uiso 1 1 calc R . . C22 C 0.1244(6) -0.04694(14) -0.0670(3) 0.0205(5) Uani 1 1 d . . . H22 H 0.1801 -0.0950 -0.0990 0.025 Uiso 1 1 calc R . . C23 C 0.2635(6) -0.01620(13) 0.0750(3) 0.0168(5) Uani 1 1 d . . . C24 C 0.1689(5) 0.05508(14) 0.1166(3) 0.0191(5) Uani 1 1 d . . . H24 H 0.2554 0.0776 0.2111 0.023 Uiso 1 1 calc R . . C25 C -0.0476(6) 0.09125(14) 0.0202(3) 0.0203(5) Uani 1 1 d . . . H25 H -0.1103 0.1393 0.0486 0.024 Uiso 1 1 calc R . . O31 O 0.6761(4) 0.00891(9) 0.46402(18) 0.0260(4) Uani 1 1 d . . . H31A H 0.8246 0.0330 0.4789 0.039 Uiso 1 1 d R . . H31B H 0.5626 0.0300 0.4989 0.039 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 I11 0.01828(7) 0.02074(7) 0.01839(7) 0.00281(7) -0.00306(5) -0.00078(7) O11 0.0222(8) 0.0186(8) 0.0300(9) -0.0001(7) -0.0024(7) 0.0028(6) O12 0.0227(9) 0.0258(8) 0.0221(8) 0.0047(6) -0.0057(7) -0.0001(7) O13 0.0291(9) 0.0256(10) 0.0170(7) -0.0016(6) -0.0079(6) -0.0004(6) C11 0.0123(10) 0.0179(11) 0.0157(10) 0.0026(8) 0.0022(8) -0.0016(8) C12 0.0152(9) 0.0219(17) 0.0159(8) -0.0026(9) 0.0011(7) -0.0046(8) C13 0.0272(13) 0.0190(11) 0.0231(12) -0.0038(9) 0.0023(9) 0.0009(10) C14 0.0218(12) 0.0195(11) 0.0241(12) -0.0009(9) -0.0001(9) 0.0053(10) C15 0.0156(8) 0.0223(10) 0.0144(7) 0.0035(14) 0.0015(6) 0.0050(14) C16 0.0180(12) 0.0174(11) 0.0138(10) 0.0000(8) 0.0007(9) -0.0036(9) C17 0.0139(11) 0.0204(11) 0.0201(10) 0.0037(9) 0.0009(8) -0.0001(8) N21 0.0196(11) 0.0227(11) 0.0193(10) 0.0048(8) -0.0028(8) -0.0018(8) N22 0.0232(10) 0.0195(10) 0.0201(10) -0.0009(7) -0.0015(7) 0.0027(8) C21 0.0222(13) 0.0222(12) 0.0206(12) -0.0004(10) -0.0013(9) -0.0047(10) C22 0.0228(13) 0.0180(11) 0.0207(12) -0.0034(9) 0.0021(10) -0.0003(9) C23 0.0161(11) 0.0162(11) 0.0181(11) 0.0047(9) 0.0027(9) -0.0020(9) C24 0.0183(12) 0.0183(11) 0.0203(12) -0.0026(10) 0.0006(9) -0.0032(9) C25 0.0203(12) 0.0168(11) 0.0237(13) -0.0004(9) 0.0016(10) 0.0006(9) O31 0.0231(9) 0.0265(9) 0.0275(9) -0.0083(7) -0.0015(7) 0.0013(7) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 I11 C15 2.102(2) . ? O11 C17 1.252(3) . ? O12 C17 1.277(3) . ? O13 C12 1.365(2) . ? O13 H13 0.8401 . ? C11 C12 1.399(3) . ? C11 C16 1.406(3) . ? C11 C17 1.493(3) . ? C12 C13 1.383(3) . ? C13 C14 1.375(3) . ? C13 H13A 0.9500 . ? C14 C15 1.393(4) . ? C14 H14 0.9500 . ? C15 C16 1.371(4) . ? C16 H16 0.9500 . ? N21 C25 1.343(3) . ? N21 C21 1.351(4) . ? N21 H21A 0.8800 . ? N22 C23 1.342(3) . ? N22 H22A 0.8800 . ? N22 H22B 0.8800 . ? C21 C22 1.356(4) . ? C21 H21 0.9500 . ? C22 C23 1.418(4) . ? C22 H22 0.9500 . ? C23 C24 1.411(4) . ? C24 C25 1.361(4) . ? C24 H24 0.9500 . ? C25 H25 0.9500 . ? O31 H31A 0.7841 . ? O31 H31B 0.7182 . ? 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 C12 O13 H13 109.5 . . ? C12 C11 C16 118.2(2) . . ? C12 C11 C17 122.01(19) . . ? C16 C11 C17 119.7(2) . . ? O13 C12 C13 118.3(2) . . ? O13 C12 C11 121.0(2) . . ? C13 C12 C11 120.64(19) . . ? C14 C13 C12 120.7(2) . . ? C14 C13 H13A 119.6 . . ? C12 C13 H13A 119.6 . . ? C13 C14 C15 119.0(2) . . ? C13 C14 H14 120.5 . . ? C15 C14 H14 120.5 . . ? C16 C15 C14 121.14(18) . . ? C16 C15 I11 119.6(2) . . ? C14 C15 I11 119.1(2) . . ? C15 C16 C11 120.2(2) . . ? C15 C16 H16 119.9 . . ? C11 C16 H16 119.9 . . ? O11 C17 O12 123.84(19) . . ? O11 C17 C11 119.52(19) . . ? O12 C17 C11 116.64(19) . . ? C25 N21 C21 120.0(2) . . ? C25 N21 H21A 120.0 . . ? C21 N21 H21A 120.0 . . ? C23 N22 H22A 120.0 . . ? C23 N22 H22B 120.0 . . ? H22A N22 H22B 120.0 . . ? N21 C21 C22 121.8(2) . . ? N21 C21 H21 119.1 . . ? C22 C21 H21 119.1 . . ? C21 C22 C23 119.4(2) . . ? C21 C22 H22 120.3 . . ? C23 C22 H22 120.3 . . ? N22 C23 C24 120.8(2) . . ? N22 C23 C22 121.6(2) . . ? C24 C23 C22 117.6(2) . . ? C25 C24 C23 119.4(2) . . ? C25 C24 H24 120.3 . . ? C23 C24 H24 120.3 . . ? N21 C25 C24 121.9(2) . . ? N21 C25 H25 119.0 . . ? C24 C25 H25 119.0 . . ? H31A O31 H31B 104.0 . . ? 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 C16 C11 C12 O13 -179.87(18) . . . . ? C17 C11 C12 O13 -2.4(3) . . . . ? C16 C11 C12 C13 -0.6(3) . . . . ? C17 C11 C12 C13 176.89(19) . . . . ? O13 C12 C13 C14 179.9(2) . . . . ? C11 C12 C13 C14 0.6(4) . . . . ? C12 C13 C14 C15 -0.4(4) . . . . ? C13 C14 C15 C16 0.3(4) . . . . ? C13 C14 C15 I11 -175.81(17) . . . . ? C14 C15 C16 C11 -0.3(3) . . . . ? I11 C15 C16 C11 175.77(15) . . . . ? C12 C11 C16 C15 0.5(3) . . . . ? C17 C11 C16 C15 -177.1(2) . . . . ? C12 C11 C17 O11 -178.8(2) . . . . ? C16 C11 C17 O11 -1.3(3) . . . . ? C12 C11 C17 O12 0.8(3) . . . . ? C16 C11 C17 O12 178.26(18) . . . . ? C25 N21 C21 C22 0.4(4) . . . . ? N21 C21 C22 C23 -0.6(4) . . . . ? C21 C22 C23 N22 -179.2(2) . . . . ? C21 C22 C23 C24 0.6(4) . . . . ? N22 C23 C24 C25 179.4(2) . . . . ? C22 C23 C24 C25 -0.3(3) . . . . ? C21 N21 C25 C24 -0.1(4) . . . . ? C23 C24 C25 N21 0.1(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 N21 H21A O12 0.88 1.84 2.692(3) 163.3 1_354 N22 H22B O13 0.88 2.27 3.055(3) 147.9 2_746 O31 H31B O11 0.72 2.01 2.709(3) 166.3 1_455 O13 H13 O12 0.84 1.78 2.526(2) 146.9 . N22 H22A O31 0.88 1.97 2.835(3) 169.5 . O31 H31A O11 0.78 1.99 2.768(3) 173.3 . _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.319 _refine_diff_density_min -0.321 _refine_diff_density_rms 0.058 data_4-aminopyridinium_3-nitrosalicylate _database_code_depnum_ccdc_archive 'CCDC 888887' #TrackingRef '4-aminopyridinium-3-nitrosalicylate.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '4-aminopyridinium 3-nitrosalicylate' _chemical_melting_point ? _chemical_formula_moiety 'C7 H4 N O5, C5 H7 N2' _chemical_formula_sum 'C12 H11 N3 O5' _chemical_formula_weight 277.24 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0110 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 10.9737(5) _cell_length_b 4.5752(2) _cell_length_c 11.9808(5) _cell_angle_alpha 90.00 _cell_angle_beta 96.809(3) _cell_angle_gamma 90.00 _cell_volume 597.28(5) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 7798 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description Block _exptl_crystal_colour Gold _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.02 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.542 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 288 _exptl_absorpt_coefficient_mu 0.123 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9412 _exptl_absorpt_correction_T_max 0.9988 _exptl_absorpt_process_details 'SADABS 2007/2 (Sheldrick, G.M., 2007)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator '10cm confocal mirrors' _diffrn_measurement_device_type 'Bruker-Nonius APEX II CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean '4096x4096pixels / 62x62mm' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7769 _diffrn_reflns_av_R_equivalents 0.0669 _diffrn_reflns_av_sigmaI/netI 0.0515 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.43 _diffrn_reflns_theta_max 27.50 _reflns_number_total 1532 _reflns_number_gt 1247 _reflns_threshold_expression >2\s(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' #Although determined using DirAx, the cell is refined in the HKL #package during data reduction _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^ > 2\s(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^+0.9339P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_number_reflns 1532 _refine_ls_number_parameters 181 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0819 _refine_ls_R_factor_gt 0.0587 _refine_ls_wR_factor_ref 0.1219 _refine_ls_wR_factor_gt 0.1093 _refine_ls_goodness_of_fit_ref 1.119 _refine_ls_restrained_S_all 1.119 _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 O11 O 1.0288(2) 0.2113(8) 0.1871(2) 0.0238(7) Uani 1 1 d . . . O12 O 0.9131(3) 0.2138(8) 0.3291(2) 0.0247(7) Uani 1 1 d . . . O13 O 0.7316(3) 0.5223(7) 0.3225(2) 0.0261(7) Uani 1 1 d . . . H13 H 0.7877 0.4057 0.3468 0.039 Uiso 1 1 d R . . O14 O 0.5688(3) 0.9506(8) 0.3090(2) 0.0293(8) Uani 1 1 d . . . O15 O 0.4844(3) 1.0472(12) 0.1416(3) 0.0581(14) Uani 1 1 d . . . N11 N 0.5693(3) 0.9488(9) 0.2062(3) 0.0272(9) Uani 1 1 d . . . C11 C 0.8512(4) 0.5120(10) 0.1703(3) 0.0177(8) Uani 1 1 d . . . C12 C 0.7515(4) 0.6187(10) 0.2213(3) 0.0183(9) Uani 1 1 d . . . C13 C 0.6722(3) 0.8192(10) 0.1591(3) 0.0197(9) Uani 1 1 d . . . C14 C 0.6900(4) 0.9038(10) 0.0508(3) 0.0231(10) Uani 1 1 d . . . H14 H 0.6341 1.0349 0.0101 0.028 Uiso 1 1 calc R . . C15 C 0.7896(4) 0.7961(11) 0.0021(3) 0.0250(10) Uani 1 1 d . . . H15 H 0.8031 0.8542 -0.0715 0.030 Uiso 1 1 calc R . . C16 C 0.8695(3) 0.6014(10) 0.0632(3) 0.0193(9) Uani 1 1 d . . . H16 H 0.9382 0.5284 0.0305 0.023 Uiso 1 1 calc R . . C17 C 0.9380(4) 0.2964(10) 0.2314(3) 0.0193(9) Uani 1 1 d . . . N21 N 0.1604(3) 0.8129(8) 0.3079(3) 0.0218(8) Uani 1 1 d . . . H21A H 0.0980 0.9470 0.2650 0.026 Uiso 1 1 d R . . N22 N 0.3865(3) 0.1846(9) 0.4656(3) 0.0231(8) Uani 1 1 d . . . H22A H 0.3720 0.1120 0.5269 0.028 Uiso 1 1 d R . . H22B H 0.4470 0.0950 0.4279 0.028 Uiso 1 1 d R . . C21 C 0.2559(4) 0.7082(11) 0.2584(3) 0.0236(9) Uani 1 1 d . . . H21 H 0.2699 0.7823 0.1870 0.028 Uiso 1 1 calc R . . C22 C 0.3324(4) 0.5003(10) 0.3079(3) 0.0201(9) Uani 1 1 d . . . H22 H 0.3990 0.4301 0.2715 0.024 Uiso 1 1 calc R . . C23 C 0.3121(4) 0.3904(10) 0.4134(3) 0.0198(9) Uani 1 1 d . . . C24 C 0.2116(4) 0.5008(10) 0.4639(3) 0.0215(9) Uani 1 1 d . . . H24 H 0.1953 0.4313 0.5354 0.026 Uiso 1 1 calc R . . C25 C 0.1383(4) 0.7086(11) 0.4087(3) 0.0225(9) Uani 1 1 d . . . H25 H 0.0701 0.7814 0.4421 0.027 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 O11 0.0201(14) 0.0284(17) 0.0239(14) 0.0051(15) 0.0072(11) 0.0069(14) O12 0.0265(15) 0.0288(18) 0.0197(14) 0.0045(15) 0.0072(11) 0.0044(15) O13 0.0291(16) 0.0303(19) 0.0200(14) 0.0041(15) 0.0075(12) 0.0056(15) O14 0.0319(17) 0.032(2) 0.0256(16) -0.0016(15) 0.0102(13) 0.0044(16) O15 0.041(2) 0.100(4) 0.0346(18) 0.014(2) 0.0102(15) 0.045(3) N11 0.0238(18) 0.032(2) 0.0269(19) 0.0043(19) 0.0061(15) 0.0074(18) C11 0.0198(19) 0.014(2) 0.0190(18) 0.0010(18) 0.0029(15) 0.0039(18) C12 0.0197(18) 0.020(2) 0.0155(18) -0.0010(17) 0.0039(15) -0.0021(17) C13 0.0151(18) 0.023(2) 0.0215(19) -0.0013(19) 0.0024(15) -0.0004(19) C14 0.025(2) 0.024(2) 0.020(2) 0.004(2) 0.0030(16) 0.0036(19) C15 0.027(2) 0.031(3) 0.0174(19) 0.004(2) 0.0063(17) 0.004(2) C16 0.0168(19) 0.021(2) 0.0217(19) 0.0024(19) 0.0067(15) 0.0015(17) C17 0.0194(19) 0.019(2) 0.0192(19) 0.0000(18) 0.0001(16) -0.0021(18) N21 0.0208(17) 0.0204(19) 0.0235(17) -0.0037(16) -0.0004(14) 0.0006(16) N22 0.0236(17) 0.026(2) 0.0199(16) 0.0037(17) 0.0037(13) 0.0074(17) C21 0.030(2) 0.023(2) 0.0182(19) -0.003(2) 0.0042(16) -0.005(2) C22 0.022(2) 0.019(2) 0.0206(19) -0.002(2) 0.0047(15) 0.0019(19) C23 0.0188(19) 0.021(2) 0.019(2) -0.0052(18) 0.0012(16) -0.0034(18) C24 0.024(2) 0.020(2) 0.0212(19) -0.002(2) 0.0060(16) -0.002(2) C25 0.023(2) 0.020(2) 0.026(2) -0.004(2) 0.0073(16) 0.000(2) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 O11 C17 1.245(5) . ? O12 C17 1.289(5) . ? O13 C12 1.331(5) . ? O14 N11 1.232(4) . ? O15 N11 1.225(5) . ? N11 C13 1.448(5) . ? C11 C16 1.385(5) . ? C11 C12 1.403(5) . ? C11 C17 1.501(6) . ? C12 C13 1.415(6) . ? C13 C14 1.389(6) . ? C14 C15 1.389(6) . ? C15 C16 1.395(6) . ? N21 C25 1.346(5) . ? N21 C21 1.352(5) . ? N22 C23 1.350(6) . ? C21 C22 1.358(6) . ? C22 C23 1.403(5) . ? C23 C24 1.413(5) . ? C24 C25 1.365(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 O15 N11 O14 122.4(4) . . ? O15 N11 C13 118.3(4) . . ? O14 N11 C13 119.3(3) . . ? C16 C11 C12 120.5(4) . . ? C16 C11 C17 119.5(3) . . ? C12 C11 C17 120.0(3) . . ? O13 C12 C11 120.1(4) . . ? O13 C12 C13 122.5(4) . . ? C11 C12 C13 117.3(4) . . ? C14 C13 C12 121.8(4) . . ? C14 C13 N11 116.9(4) . . ? C12 C13 N11 121.2(3) . . ? C15 C14 C13 119.9(4) . . ? C14 C15 C16 118.9(4) . . ? C11 C16 C15 121.5(4) . . ? O11 C17 O12 124.1(4) . . ? O11 C17 C11 119.4(3) . . ? O12 C17 C11 116.4(3) . . ? C25 N21 C21 119.9(4) . . ? N21 C21 C22 121.9(4) . . ? C21 C22 C23 119.3(4) . . ? N22 C23 C22 121.0(4) . . ? N22 C23 C24 120.7(4) . . ? C22 C23 C24 118.2(4) . . ? C25 C24 C23 119.1(4) . . ? N21 C25 C24 121.6(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 N21 H21A O11 1.01 1.66 2.647(5) 164.9 1_465 N21 H21A O12 1.01 2.56 3.309(5) 130.4 1_465 N22 H22A O13 0.84 2.28 3.076(4) 158.2 2_646 N22 H22A O14 0.84 2.53 2.950(5) 112.4 2_646 N22 H22B O14 0.94 2.17 3.092(5) 166.8 1_545 _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.352 _refine_diff_density_min -0.296 _refine_diff_density_rms 0.068 # Attachment '4-aminopyridinium-5-acetylaminosalicylate.cif' data_4-aminopyridinium_5-acetylaminosalicylate _database_code_depnum_ccdc_archive 'CCDC 888888' #TrackingRef '4-aminopyridinium-5-acetylaminosalicylate.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 4-aminopyridinium_5-acetylaminosalicylate ; _chemical_name_common 4-aminopyridinium_5-acetylaminosalicylate _chemical_melting_point ? _chemical_formula_moiety 'C9 H8 N O4, C5 H7 N2' _chemical_formula_sum 'C14 H15 N3 O4' _chemical_formula_weight 289.29 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 P21/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 15.1705(7) _cell_length_b 4.6669(2) _cell_length_c 19.6506(8) _cell_angle_alpha 90.00 _cell_angle_beta 104.734(2) _cell_angle_gamma 90.00 _cell_volume 1345.50(10) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 19387 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.428 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 608 _exptl_absorpt_coefficient_mu 0.107 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9831 _exptl_absorpt_correction_T_max 0.9957 _exptl_absorpt_process_details 'SADABS 2007/2 (Sheldrick, G.M., 2007)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator '10cm confocal mirrors' _diffrn_measurement_device_type 'Bruker-Nonius APEX II CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean '4096x4096pixels / 62x62mm' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12624 _diffrn_reflns_av_R_equivalents 0.0486 _diffrn_reflns_av_sigmaI/netI 0.0459 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 3.05 _diffrn_reflns_theta_max 27.50 _reflns_number_total 3056 _reflns_number_gt 2443 _reflns_threshold_expression >2\s(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' #Although determined using DirAx, the cell is refined in the HKL #package during data reduction _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^ > 2\s(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^)+(0.0166P)^2^+1.9190P] 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 3056 _refine_ls_number_parameters 191 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0741 _refine_ls_R_factor_gt 0.0542 _refine_ls_wR_factor_ref 0.1212 _refine_ls_wR_factor_gt 0.1083 _refine_ls_goodness_of_fit_ref 1.062 _refine_ls_restrained_S_all 1.062 _refine_ls_shift/su_max 0.001 _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 O11 O -0.00670(8) 0.0014(3) 0.38514(6) 0.0245(3) Uani 1 1 d . . . O12 O -0.10080(8) -0.0194(3) 0.27716(6) 0.0251(3) Uani 1 1 d . . . O13 O -0.07588(8) 0.2840(3) 0.18041(6) 0.0278(3) Uani 1 1 d . . . H13A H -0.1021 0.1696 0.2018 0.042 Uiso 1 1 d R . . O14 O 0.29810(8) 0.2453(3) 0.41041(6) 0.0235(3) Uani 1 1 d . . . N11 N 0.24952(9) 0.6697(3) 0.35804(7) 0.0191(3) Uani 1 1 d . . . H11 H 0.2625 0.8528 0.3560 0.023 Uiso 1 1 d R . . C11 C 0.02931(10) 0.2782(3) 0.29441(8) 0.0181(3) Uani 1 1 d . . . C12 C 0.00160(11) 0.3813(4) 0.22497(8) 0.0207(4) Uani 1 1 d . . . C13 C 0.05447(11) 0.5856(4) 0.20178(8) 0.0242(4) Uani 1 1 d . . . H13 H 0.0349 0.6605 0.1554 0.029 Uiso 1 1 calc R . . C14 C 0.13526(11) 0.6791(4) 0.24619(8) 0.0219(4) Uani 1 1 d . . . H14 H 0.1709 0.8187 0.2302 0.026 Uiso 1 1 calc R . . C15 C 0.16495(10) 0.5702(3) 0.31439(8) 0.0181(3) Uani 1 1 d . . . C16 C 0.11088(10) 0.3734(3) 0.33814(8) 0.0174(3) Uani 1 1 d . . . H16 H 0.1300 0.3029 0.3849 0.021 Uiso 1 1 calc R . . C17 C -0.02949(11) 0.0713(4) 0.32108(8) 0.0196(3) Uani 1 1 d . . . C18 C 0.31079(10) 0.5030(4) 0.40202(8) 0.0187(3) Uani 1 1 d . . . C19 C 0.39863(11) 0.6441(4) 0.44013(9) 0.0262(4) Uani 1 1 d . . . H19A H 0.4127 0.5934 0.4901 0.039 Uiso 1 1 calc R . . H19B H 0.3924 0.8525 0.4350 0.039 Uiso 1 1 calc R . . H19C H 0.4480 0.5782 0.4201 0.039 Uiso 1 1 calc R . . N21 N 0.62543(9) 1.1176(3) 0.09062(7) 0.0217(3) Uani 1 1 d . . . H21A H 0.5891 1.2527 0.0989 0.026 Uiso 1 1 d R . . N22 N 0.79645(9) 0.4890(3) 0.05251(7) 0.0224(3) Uani 1 1 d . . . H22A H 0.8399 0.4219 0.0875 0.027 Uiso 1 1 d R . . H22B H 0.7901 0.4228 0.0096 0.027 Uiso 1 1 d R . . C21 C 0.61550(11) 1.0198(4) 0.02452(8) 0.0218(4) Uani 1 1 d . . . H21 H 0.5697 1.1004 -0.0127 0.026 Uiso 1 1 calc R . . C22 C 0.66976(11) 0.8077(4) 0.01002(8) 0.0203(4) Uani 1 1 d . . . H22 H 0.6605 0.7380 -0.0367 0.024 Uiso 1 1 calc R . . C23 C 0.73976(10) 0.6921(3) 0.06464(8) 0.0187(3) Uani 1 1 d . . . C24 C 0.74880(11) 0.8008(4) 0.13300(8) 0.0207(4) Uani 1 1 d . . . H24 H 0.7951 0.7293 0.1713 0.025 Uiso 1 1 calc R . . C25 C 0.69096(11) 1.0086(4) 0.14394(8) 0.0222(4) Uani 1 1 d . . . H25 H 0.6969 1.0786 0.1903 0.027 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 O11 0.0244(6) 0.0298(6) 0.0192(5) 0.0028(5) 0.0053(4) -0.0048(5) O12 0.0213(5) 0.0300(7) 0.0226(5) -0.0006(5) 0.0030(4) -0.0067(5) O13 0.0231(6) 0.0338(7) 0.0219(6) 0.0057(5) -0.0029(5) -0.0075(5) O14 0.0279(6) 0.0186(6) 0.0232(5) 0.0015(5) 0.0049(5) 0.0018(5) N11 0.0201(6) 0.0156(7) 0.0206(6) 0.0012(5) 0.0036(5) -0.0021(5) C11 0.0193(7) 0.0176(8) 0.0175(7) -0.0008(6) 0.0047(6) 0.0013(6) C12 0.0205(7) 0.0216(8) 0.0179(7) -0.0003(6) 0.0009(6) 0.0007(7) C13 0.0268(8) 0.0253(9) 0.0193(7) 0.0064(7) 0.0040(6) 0.0009(7) C14 0.0233(8) 0.0218(8) 0.0213(7) 0.0037(6) 0.0071(6) -0.0019(7) C15 0.0182(7) 0.0195(8) 0.0165(7) -0.0010(6) 0.0042(6) 0.0007(6) C16 0.0194(7) 0.0178(8) 0.0147(6) 0.0006(6) 0.0038(6) 0.0019(6) C17 0.0196(7) 0.0191(8) 0.0202(7) -0.0006(6) 0.0050(6) 0.0004(6) C18 0.0207(7) 0.0199(8) 0.0166(7) -0.0011(6) 0.0069(6) 0.0021(6) C19 0.0227(8) 0.0253(9) 0.0280(8) -0.0029(7) 0.0018(7) 0.0022(7) N21 0.0208(6) 0.0221(7) 0.0236(6) -0.0016(6) 0.0080(5) 0.0002(6) N22 0.0241(7) 0.0247(7) 0.0174(6) 0.0001(6) 0.0037(5) 0.0044(6) C21 0.0184(7) 0.0260(9) 0.0208(7) 0.0026(7) 0.0044(6) -0.0025(7) C22 0.0207(7) 0.0235(9) 0.0166(7) -0.0006(6) 0.0047(6) -0.0029(7) C23 0.0192(7) 0.0181(8) 0.0193(7) -0.0001(6) 0.0055(6) -0.0038(6) C24 0.0223(8) 0.0219(8) 0.0166(7) -0.0004(6) 0.0029(6) -0.0025(7) C25 0.0255(8) 0.0245(9) 0.0169(7) -0.0018(6) 0.0056(6) -0.0032(7) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 O11 C17 1.2606(19) . ? O12 C17 1.2725(18) . ? O13 C12 1.3530(19) . ? O13 H13A 0.8396 . ? O14 C18 1.236(2) . ? N11 C18 1.344(2) . ? N11 C15 1.4274(19) . ? N11 H11 0.8801 . ? C11 C16 1.388(2) . ? C11 C12 1.406(2) . ? C11 C17 1.497(2) . ? C12 C13 1.395(2) . ? C13 C14 1.382(2) . ? C13 H13 0.9500 . ? C14 C15 1.396(2) . ? C14 H14 0.9500 . ? C15 C16 1.389(2) . ? C16 H16 0.9500 . ? C18 C19 1.504(2) . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? N21 C25 1.347(2) . ? N21 C21 1.349(2) . ? N21 H21A 0.8794 . ? N22 C23 1.341(2) . ? N22 H22A 0.8802 . ? N22 H22B 0.8800 . ? C21 C22 1.363(2) . ? C21 H21 0.9500 . ? C22 C23 1.411(2) . ? C22 H22 0.9500 . ? C23 C24 1.410(2) . ? C24 C25 1.361(2) . ? C24 H24 0.9500 . ? C25 H25 0.9500 . ? 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 C12 O13 H13A 109.5 . . ? C18 N11 C15 124.54(14) . . ? C18 N11 H11 117.7 . . ? C15 N11 H11 117.8 . . ? C16 C11 C12 119.38(15) . . ? C16 C11 C17 120.44(13) . . ? C12 C11 C17 120.17(14) . . ? O13 C12 C13 119.65(14) . . ? O13 C12 C11 120.62(15) . . ? C13 C12 C11 119.72(14) . . ? C14 C13 C12 120.05(15) . . ? C14 C13 H13 120.0 . . ? C12 C13 H13 120.0 . . ? C13 C14 C15 120.59(16) . . ? C13 C14 H14 119.7 . . ? C15 C14 H14 119.7 . . ? C16 C15 C14 119.29(14) . . ? C16 C15 N11 122.04(13) . . ? C14 C15 N11 118.66(14) . . ? C11 C16 C15 120.89(14) . . ? C11 C16 H16 119.6 . . ? C15 C16 H16 119.6 . . ? O11 C17 O12 124.15(15) . . ? O11 C17 C11 118.67(14) . . ? O12 C17 C11 117.17(14) . . ? O14 C18 N11 122.91(14) . . ? O14 C18 C19 120.52(14) . . ? N11 C18 C19 116.55(15) . . ? C18 C19 H19A 109.5 . . ? C18 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C18 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C25 N21 C21 120.07(15) . . ? C25 N21 H21A 120.0 . . ? C21 N21 H21A 119.9 . . ? C23 N22 H22A 120.0 . . ? C23 N22 H22B 120.0 . . ? H22A N22 H22B 120.1 . . ? N21 C21 C22 121.44(15) . . ? N21 C21 H21 119.3 . . ? C22 C21 H21 119.3 . . ? C21 C22 C23 119.76(15) . . ? C21 C22 H22 120.1 . . ? C23 C22 H22 120.1 . . ? N22 C23 C24 120.81(14) . . ? N22 C23 C22 121.85(14) . . ? C24 C23 C22 117.34(15) . . ? C25 C24 C23 119.77(14) . . ? C25 C24 H24 120.1 . . ? C23 C24 H24 120.1 . . ? N21 C25 C24 121.60(15) . . ? N21 C25 H25 119.2 . . ? C24 C25 H25 119.2 . . ? 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 N11 H11 O14 0.88 2.12 2.9039(18) 147.9 1_565 N21 H21A O11 0.88 1.79 2.6678(19) 174.4 2_565 N22 H22A O13 0.88 2.05 2.9166(17) 169.0 1_655 N22 H22B O14 0.88 2.13 3.0048(18) 170.7 4_665 O13 H13A O12 0.84 1.72 2.4755(17) 148.7 . _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.299 _refine_diff_density_min -0.276 _refine_diff_density_rms 0.059 # Attachment '4-aminopyridinium-5-aminosalicylate-pyridine.cif' data_4-aminopyridium_5-aminosalicylate_pyridine _database_code_depnum_ccdc_archive 'CCDC 888889' #TrackingRef '4-aminopyridinium-5-aminosalicylate-pyridine.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 4-aminopyridium_5-aminosalicylate_pyridine ; _chemical_name_common 4-aminopyridium_5-aminosalicylate_pyridine _chemical_melting_point ? _chemical_formula_moiety 'C7 H6 N O3, C5 H7 N2, C5 H5 N' _chemical_formula_sum 'C17 H18 N4 O3' _chemical_formula_weight 326.35 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 23.3169(11) _cell_length_b 8.1015(4) _cell_length_c 18.0588(8) _cell_angle_alpha 90.00 _cell_angle_beta 110.986(2) _cell_angle_gamma 90.00 _cell_volume 3185.1(3) _cell_formula_units_Z 8 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 10400 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description Block _exptl_crystal_colour Bronze _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.361 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1376 _exptl_absorpt_coefficient_mu 0.096 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9886 _exptl_absorpt_correction_T_max 0.9962 _exptl_absorpt_process_details 'SADABS 2007/2 (Sheldrick, G.M., 2007)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator '10cm confocal mirrors' _diffrn_measurement_device_type 'Bruker-Nonius APEX II CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean '4096x4096pixels / 62x62mm' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13334 _diffrn_reflns_av_R_equivalents 0.0779 _diffrn_reflns_av_sigmaI/netI 0.0854 _diffrn_reflns_limit_h_min -30 _diffrn_reflns_limit_h_max 30 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 3.08 _diffrn_reflns_theta_max 27.50 _reflns_number_total 3649 _reflns_number_gt 2382 _reflns_threshold_expression >2\s(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' #Although determined using DirAx, the cell is refined in the HKL #package during data reduction _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^ > 2\s(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^+16.8821P] 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 3649 _refine_ls_number_parameters 241 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1426 _refine_ls_R_factor_gt 0.0879 _refine_ls_wR_factor_ref 0.1762 _refine_ls_wR_factor_gt 0.1487 _refine_ls_goodness_of_fit_ref 1.119 _refine_ls_restrained_S_all 1.119 _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 H11B H 0.736(2) 1.042(6) 0.777(3) 0.045(13) Uiso 1 1 d . . . H21A H 0.233(2) 1.026(6) 0.480(3) 0.052(13) Uiso 1 1 d . . . H22A H 0.423(2) 0.650(6) 0.448(3) 0.053(15) Uiso 1 1 d . . . H11A H 0.6914(19) 1.181(6) 0.768(2) 0.041(13) Uiso 1 1 d . . . H22B H 0.451(2) 0.662(7) 0.542(3) 0.077(18) Uiso 1 1 d . . . H13A H 0.526(3) 0.524(8) 0.653(3) 0.09(2) Uiso 1 1 d . . . O12 O 0.58499(11) 0.4084(3) 0.67073(14) 0.0235(6) Uani 1 1 d . . . O13 O 0.50704(11) 0.6313(3) 0.65501(14) 0.0248(6) Uani 1 1 d . . . O11 O 0.68452(11) 0.4520(3) 0.73988(14) 0.0227(6) Uani 1 1 d . . . N11 N 0.70055(15) 1.0767(4) 0.78133(17) 0.0213(7) Uani 1 1 d . . . C16 C 0.66345(15) 0.7973(4) 0.74295(18) 0.0170(7) Uani 1 1 d . . . H16 H 0.7048 0.7598 0.7613 0.020 Uiso 1 1 calc R . . N21 N 0.27072(13) 0.9560(4) 0.48297(17) 0.0231(7) Uani 1 1 d . . . C17 C 0.63043(15) 0.5012(4) 0.70824(19) 0.0178(7) Uani 1 1 d . . . C15 C 0.65209(15) 0.9642(4) 0.74654(18) 0.0176(7) Uani 1 1 d . . . C11 C 0.61610(15) 0.6819(4) 0.71321(18) 0.0165(7) Uani 1 1 d . . . C14 C 0.59081(16) 1.0168(4) 0.7200(2) 0.0222(8) Uani 1 1 d . . . H14 H 0.5817 1.1306 0.7223 0.027 Uiso 1 1 calc R . . C13 C 0.54341(15) 0.9040(4) 0.6906(2) 0.0217(8) Uani 1 1 d . . . H13 H 0.5021 0.9415 0.6728 0.026 Uiso 1 1 calc R . . C22 C 0.36303(15) 0.8234(4) 0.5599(2) 0.0227(8) Uani 1 1 d . . . H22 H 0.3922 0.7957 0.6105 0.027 Uiso 1 1 calc R . . C25 C 0.27678(16) 0.9038(4) 0.4150(2) 0.0241(8) Uani 1 1 d . . . H25 H 0.2466 0.9331 0.3654 0.029 Uiso 1 1 calc R . . N22 N 0.42125(15) 0.6824(4) 0.4930(2) 0.0291(8) Uani 1 1 d . . . C21 C 0.31290(16) 0.9163(5) 0.5541(2) 0.0257(8) Uani 1 1 d . . . H21 H 0.3076 0.9537 0.6011 0.031 Uiso 1 1 calc R . . C23 C 0.37146(16) 0.7683(4) 0.4900(2) 0.0213(7) Uani 1 1 d . . . C24 C 0.32560(16) 0.8099(4) 0.4169(2) 0.0225(8) Uani 1 1 d . . . H24 H 0.3288 0.7721 0.3687 0.027 Uiso 1 1 calc R . . C12 C 0.55536(15) 0.7371(4) 0.68685(19) 0.0194(7) Uani 1 1 d . . . N31 N 0.83406(14) 0.8603(4) 0.53149(18) 0.0267(7) Uani 1 1 d . . . C31 C 0.87884(18) 0.8504(5) 0.6032(2) 0.0308(9) Uani 1 1 d . . . H31 H 0.8717 0.8971 0.6474 0.037 Uiso 1 1 calc R . . C35 C 0.84569(17) 0.7927(5) 0.4704(2) 0.0286(8) Uani 1 1 d . . . H35 H 0.8149 0.7993 0.4190 0.034 Uiso 1 1 calc R . . C32 C 0.93462(18) 0.7759(5) 0.6157(2) 0.0333(9) Uani 1 1 d . . . H32 H 0.9652 0.7720 0.6673 0.040 Uiso 1 1 calc R . . C33 C 0.94536(17) 0.7073(5) 0.5523(2) 0.0339(10) Uani 1 1 d . . . H33 H 0.9836 0.6559 0.5593 0.041 Uiso 1 1 calc R . . C34 C 0.89997(18) 0.7143(5) 0.4787(2) 0.0310(9) Uani 1 1 d . . . H34 H 0.9059 0.6658 0.4341 0.037 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 O12 0.0215(13) 0.0181(12) 0.0281(13) -0.0039(11) 0.0053(11) -0.0029(10) O13 0.0177(12) 0.0241(13) 0.0279(13) -0.0017(11) 0.0024(10) -0.0004(11) O11 0.0226(13) 0.0187(12) 0.0240(13) -0.0002(10) 0.0048(10) 0.0034(10) N11 0.0243(17) 0.0170(16) 0.0216(15) 0.0008(13) 0.0070(13) 0.0016(13) C16 0.0168(16) 0.0176(16) 0.0143(15) 0.0014(13) 0.0030(13) 0.0020(14) N21 0.0199(15) 0.0250(16) 0.0244(15) -0.0030(13) 0.0078(13) 0.0016(13) C17 0.0195(17) 0.0171(17) 0.0152(16) 0.0009(13) 0.0044(14) -0.0006(14) C15 0.0235(17) 0.0178(16) 0.0110(15) -0.0006(13) 0.0054(13) -0.0023(14) C11 0.0218(17) 0.0151(16) 0.0145(15) 0.0024(13) 0.0089(13) 0.0027(14) C14 0.0268(19) 0.0145(17) 0.0287(19) 0.0014(15) 0.0143(16) 0.0042(14) C13 0.0178(17) 0.0222(18) 0.0251(18) 0.0006(15) 0.0077(15) 0.0025(14) C22 0.0207(18) 0.0260(19) 0.0174(17) 0.0011(15) 0.0019(14) -0.0028(15) C25 0.0242(19) 0.0245(19) 0.0207(17) -0.0010(15) 0.0045(15) 0.0008(15) N22 0.0253(17) 0.0336(19) 0.0280(18) -0.0005(16) 0.0090(15) 0.0052(15) C21 0.029(2) 0.027(2) 0.0217(18) -0.0023(16) 0.0101(16) -0.0052(16) C23 0.0218(18) 0.0175(17) 0.0227(17) 0.0008(14) 0.0056(15) -0.0012(14) C24 0.030(2) 0.0203(18) 0.0189(16) -0.0020(14) 0.0107(15) -0.0006(15) C12 0.0216(18) 0.0196(17) 0.0173(16) 0.0039(14) 0.0072(14) 0.0006(14) N31 0.0256(17) 0.0254(16) 0.0281(16) -0.0014(14) 0.0083(14) 0.0028(13) C31 0.034(2) 0.032(2) 0.027(2) -0.0041(17) 0.0120(17) -0.0006(18) C35 0.035(2) 0.028(2) 0.0223(18) 0.0042(16) 0.0099(17) 0.0000(17) C32 0.030(2) 0.035(2) 0.030(2) 0.0027(18) 0.0050(17) -0.0046(18) C33 0.025(2) 0.035(2) 0.047(2) 0.015(2) 0.0184(19) 0.0062(18) C34 0.043(2) 0.027(2) 0.031(2) 0.0080(17) 0.0226(19) 0.0083(18) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 O12 C17 1.278(4) . ? O13 C12 1.368(4) . ? O13 H13A 0.98(6) . ? O11 C17 1.249(4) . ? N11 C15 1.412(4) . ? N11 H11B 0.90(4) . ? N11 H11A 0.88(5) . ? C16 C15 1.384(5) . ? C16 C11 1.399(5) . ? C16 H16 0.9500 . ? N21 C21 1.347(4) . ? N21 C25 1.352(4) . ? N21 H21A 1.03(5) . ? C17 C11 1.511(4) . ? C15 C14 1.401(5) . ? C11 C12 1.396(4) . ? C14 C13 1.385(5) . ? C14 H14 0.9500 . ? C13 C12 1.387(5) . ? C13 H13 0.9500 . ? C22 C21 1.362(5) . ? C22 C23 1.417(5) . ? C22 H22 0.9500 . ? C25 C24 1.360(5) . ? C25 H25 0.9500 . ? N22 C23 1.338(5) . ? N22 H22A 0.88(5) . ? N22 H22B 0.92(6) . ? C21 H21 0.9500 . ? C23 C24 1.411(5) . ? C24 H24 0.9500 . ? N31 C31 1.343(5) . ? N31 C35 1.343(5) . ? C31 C32 1.377(5) . ? C31 H31 0.9500 . ? C35 C34 1.376(5) . ? C35 H35 0.9500 . ? C32 C33 1.374(6) . ? C32 H32 0.9500 . ? C33 C34 1.372(5) . ? C33 H33 0.9500 . ? C34 H34 0.9500 . ? 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 C12 O13 H13A 105(3) . . ? C15 N11 H11B 112(3) . . ? C15 N11 H11A 115(3) . . ? H11B N11 H11A 115(4) . . ? C15 C16 C11 122.2(3) . . ? C15 C16 H16 118.9 . . ? C11 C16 H16 118.9 . . ? C21 N21 C25 120.8(3) . . ? C21 N21 H21A 120(2) . . ? C25 N21 H21A 119(2) . . ? O11 C17 O12 124.4(3) . . ? O11 C17 C11 119.4(3) . . ? O12 C17 C11 116.2(3) . . ? C16 C15 C14 118.1(3) . . ? C16 C15 N11 121.0(3) . . ? C14 C15 N11 120.7(3) . . ? C12 C11 C16 118.8(3) . . ? C12 C11 C17 120.6(3) . . ? C16 C11 C17 120.6(3) . . ? C13 C14 C15 120.4(3) . . ? C13 C14 H14 119.8 . . ? C15 C14 H14 119.8 . . ? C14 C13 C12 121.0(3) . . ? C14 C13 H13 119.5 . . ? C12 C13 H13 119.5 . . ? C21 C22 C23 119.6(3) . . ? C21 C22 H22 120.2 . . ? C23 C22 H22 120.2 . . ? N21 C25 C24 120.8(3) . . ? N21 C25 H25 119.6 . . ? C24 C25 H25 119.6 . . ? C23 N22 H22A 117(3) . . ? C23 N22 H22B 118(3) . . ? H22A N22 H22B 125(4) . . ? N21 C21 C22 121.3(3) . . ? N21 C21 H21 119.4 . . ? C22 C21 H21 119.4 . . ? N22 C23 C24 121.2(3) . . ? N22 C23 C22 121.5(3) . . ? C24 C23 C22 117.3(3) . . ? C25 C24 C23 120.2(3) . . ? C25 C24 H24 119.9 . . ? C23 C24 H24 119.9 . . ? O13 C12 C13 118.8(3) . . ? O13 C12 C11 121.7(3) . . ? C13 C12 C11 119.5(3) . . ? C31 N31 C35 116.8(3) . . ? N31 C31 C32 123.1(4) . . ? N31 C31 H31 118.4 . . ? C32 C31 H31 118.4 . . ? N31 C35 C34 123.2(3) . . ? N31 C35 H35 118.4 . . ? C34 C35 H35 118.4 . . ? C33 C32 C31 118.9(4) . . ? C33 C32 H32 120.5 . . ? C31 C32 H32 120.5 . . ? C34 C33 C32 118.9(4) . . ? C34 C33 H33 120.6 . . ? C32 C33 H33 120.6 . . ? C33 C34 C35 119.0(4) . . ? C33 C34 H34 120.5 . . ? C35 C34 H34 120.5 . . ? 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 N21 H21A N31 1.03(5) 1.77(5) 2.792(4) 177(4) 5_676 N22 H22A O12 0.88(5) 2.13(5) 3.000(4) 172(4) 5_666 N11 H11A O11 0.88(5) 2.25(5) 3.122(4) 171(4) 1_565 N22 H22B O13 0.92(6) 2.01(6) 2.922(4) 172(5) . O13 H13A O12 0.98(6) 1.61(6) 2.505(3) 151(5) . _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.326 _refine_diff_density_min -0.330 _refine_diff_density_rms 0.079 # Attachment '4-aminopyridinium-5-chlorosalicylate.cif' data_4-aminopyridinium_5-chlorosalicylate _database_code_depnum_ccdc_archive 'CCDC 888890' #TrackingRef '4-aminopyridinium-5-chlorosalicylate.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 4-aminopyridinium_5-chlorosalicylate ; _chemical_name_common 4-aminopyridinium_5-chlorosalicylate _chemical_melting_point ? _chemical_formula_moiety 'C7 H4 Cl O3, C5 H7 N2' _chemical_formula_sum 'C12 H11 Cl N2 O3' _chemical_formula_weight 266.68 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/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 11.9815(5) _cell_length_b 7.9626(2) _cell_length_c 12.4836(5) _cell_angle_alpha 90.00 _cell_angle_beta 100.400(2) _cell_angle_gamma 90.00 _cell_volume 1171.42(7) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 14383 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.512 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 552 _exptl_absorpt_coefficient_mu 0.328 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9081 _exptl_absorpt_correction_T_max 0.9374 _exptl_absorpt_process_details 'SADABS 2007/2 (Sheldrick, G.M., 2007)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius Roper CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13949 _diffrn_reflns_av_R_equivalents 0.0412 _diffrn_reflns_av_sigmaI/netI 0.0342 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.05 _diffrn_reflns_theta_max 27.50 _reflns_number_total 2679 _reflns_number_gt 2312 _reflns_threshold_expression >2\s(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' #Although determined using DirAx, the cell is refined in the HKL #package during data reduction _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^ > 2\s(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^)+(0.0304P)^2^+1.4966P] 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 2679 _refine_ls_number_parameters 231 _refine_ls_number_restraints 15 _refine_ls_R_factor_all 0.0619 _refine_ls_R_factor_gt 0.0527 _refine_ls_wR_factor_ref 0.1191 _refine_ls_wR_factor_gt 0.1150 _refine_ls_goodness_of_fit_ref 1.103 _refine_ls_restrained_S_all 1.100 _refine_ls_shift/su_max 0.001 _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 N21 N 0.4557(2) 0.2058(3) 0.4537(2) 0.0197(7) Uani 0.636(4) 1 d PD A 1 H21 H 0.5009 0.2718 0.4986 0.024 Uiso 0.636(4) 1 calc PR A 1 N22 N 0.2394(3) -0.0881(4) 0.2401(3) 0.0267(8) Uani 0.636(4) 1 d PD A 1 H22A H 0.2490 -0.0960 0.1720 0.032 Uiso 0.636(4) 1 calc PR A 1 H22B H 0.1832 -0.1418 0.2616 0.032 Uiso 0.636(4) 1 calc PR A 1 C21 C 0.4715(4) 0.1895(7) 0.3505(5) 0.0193(10) Uani 0.636(4) 1 d PD A 1 H21A H 0.5327 0.2463 0.3274 0.023 Uiso 0.636(4) 1 calc PR A 1 C22 C 0.4013(11) 0.0935(19) 0.2794(8) 0.024(2) Uani 0.636(4) 1 d PD A 1 H22 H 0.4132 0.0846 0.2064 0.029 Uiso 0.636(4) 1 calc PR A 1 C23 C 0.3104(3) 0.0057(4) 0.3110(3) 0.0201(8) Uani 0.636(4) 1 d PD A 1 C24 C 0.2999(16) 0.022(3) 0.4219(14) 0.0204(19) Uani 0.636(4) 1 d PD A 1 H24 H 0.2424 -0.0387 0.4490 0.024 Uiso 0.636(4) 1 calc PR A 1 C25 C 0.3721(4) 0.1230(6) 0.4894(4) 0.0207(9) Uani 0.636(4) 1 d PD A 1 H25 H 0.3632 0.1354 0.5631 0.025 Uiso 0.636(4) 1 calc PR A 1 N31 N 0.3143(4) -0.0202(7) 0.2361(5) 0.0279(14) Uani 0.364(4) 1 d PD A 2 H31 H 0.2941 -0.0634 0.1706 0.033 Uiso 0.364(4) 1 calc PR A 2 N32 N 0.4128(5) 0.1721(7) 0.5430(5) 0.0224(12) Uani 0.364(4) 1 d PD A 2 H32A H 0.3731 0.1506 0.5942 0.027 Uiso 0.364(4) 1 calc PR A 2 H32B H 0.4741 0.2347 0.5577 0.027 Uiso 0.364(4) 1 calc PR A 2 C31 C 0.4054(16) 0.081(3) 0.2563(13) 0.016(3) Uani 0.364(4) 1 d PD A 2 H31A H 0.4461 0.1055 0.1996 0.019 Uiso 0.364(4) 1 calc PR A 2 C32 C 0.4399(7) 0.1469(13) 0.3562(9) 0.022(2) Uani 0.364(4) 1 d PD A 2 H32 H 0.5042 0.2187 0.3693 0.027 Uiso 0.364(4) 1 calc PR A 2 C33 C 0.3798(6) 0.1096(9) 0.4427(6) 0.0159(16) Uani 0.364(4) 1 d PD A 2 C34 C 0.281(3) 0.008(5) 0.414(2) 0.022(4) Uani 0.364(4) 1 d PD A 2 H34 H 0.2352 -0.0152 0.4669 0.027 Uiso 0.364(4) 1 calc PR A 2 C35 C 0.2534(6) -0.0566(9) 0.3131(6) 0.0280(15) Uani 0.364(4) 1 d PD A 2 H35 H 0.1896 -0.1289 0.2961 0.034 Uiso 0.364(4) 1 calc PR A 2 H13A H 0.651(3) 0.440(5) 0.734(3) 0.081(12) Uiso 1 1 d . . . Cl1 Cl 1.05152(5) 0.77625(8) 0.56462(5) 0.0405(2) Uani 1 1 d . . . O12 O 0.60344(12) 0.3822(2) 0.61333(12) 0.0278(4) Uani 1 1 d . . . O13 O 0.70083(13) 0.5069(2) 0.79052(13) 0.0302(4) Uani 1 1 d . . . O11 O 0.68091(13) 0.3965(2) 0.46437(12) 0.0307(4) Uani 1 1 d . . . C16 C 0.86211(17) 0.5942(3) 0.57387(16) 0.0220(4) Uani 1 1 d . . . H16 H 0.8618 0.5688 0.4995 0.026 Uiso 1 1 calc R . . C11 C 0.77708(16) 0.5299(2) 0.62560(15) 0.0194(4) Uani 1 1 d . . . C17 C 0.68096(17) 0.4288(3) 0.56184(17) 0.0217(4) Uani 1 1 d . . . C12 C 0.78046(17) 0.5665(3) 0.73622(16) 0.0229(4) Uani 1 1 d . . . C14 C 0.94969(18) 0.7318(3) 0.74023(18) 0.0274(5) Uani 1 1 d . . . H14 H 1.0079 0.8015 0.7785 0.033 Uiso 1 1 calc R . . C15 C 0.94679(17) 0.6948(3) 0.63084(18) 0.0247(4) Uani 1 1 d . . . C13 C 0.86764(18) 0.6666(3) 0.79268(17) 0.0277(5) Uani 1 1 d . . . H13 H 0.8703 0.6898 0.8677 0.033 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 N21 0.0179(13) 0.0208(14) 0.0192(14) -0.0006(10) 0.0002(10) -0.0002(11) N22 0.0243(17) 0.0302(16) 0.0237(18) -0.0036(13) -0.0012(13) -0.0073(13) C21 0.012(3) 0.023(3) 0.023(2) -0.0025(18) 0.0036(18) -0.0018(17) C22 0.027(3) 0.031(3) 0.015(4) 0.001(3) 0.006(3) 0.000(2) C23 0.0195(18) 0.0184(16) 0.021(2) 0.0017(14) -0.0004(14) 0.0021(14) C24 0.018(6) 0.024(4) 0.020(3) 0.001(3) 0.008(4) 0.002(3) C25 0.024(2) 0.023(2) 0.015(2) 0.002(2) 0.005(2) 0.0064(15) N31 0.026(3) 0.035(3) 0.020(3) -0.002(2) -0.005(2) 0.007(2) N32 0.024(3) 0.027(3) 0.017(3) 0.001(2) 0.005(2) -0.003(2) C31 0.012(4) 0.031(6) 0.005(5) 0.004(4) 0.001(3) 0.004(3) C32 0.008(4) 0.032(5) 0.026(4) 0.005(4) 0.002(3) -0.007(3) C33 0.018(3) 0.020(3) 0.009(3) 0.000(3) 0.000(3) 0.009(3) C34 0.014(8) 0.026(6) 0.025(7) 0.003(4) -0.002(5) -0.003(5) C35 0.022(3) 0.028(3) 0.032(4) -0.005(3) 0.000(3) -0.001(3) Cl1 0.0330(3) 0.0435(4) 0.0464(4) -0.0056(3) 0.0109(3) -0.0156(3) O12 0.0205(7) 0.0318(8) 0.0312(8) -0.0058(7) 0.0049(6) -0.0032(6) O13 0.0289(8) 0.0392(9) 0.0243(8) -0.0040(7) 0.0094(7) -0.0006(7) O11 0.0266(8) 0.0413(9) 0.0227(7) -0.0089(7) 0.0002(6) -0.0046(7) C16 0.0222(10) 0.0208(10) 0.0216(10) -0.0010(8) 0.0002(8) 0.0026(8) C11 0.0191(9) 0.0194(9) 0.0181(9) -0.0024(7) -0.0008(7) 0.0045(8) C17 0.0177(9) 0.0218(10) 0.0239(10) -0.0023(8) -0.0010(8) 0.0034(8) C12 0.0223(10) 0.0248(10) 0.0209(10) -0.0010(8) 0.0024(8) 0.0058(8) C14 0.0212(10) 0.0267(11) 0.0305(11) -0.0088(9) -0.0057(8) 0.0032(8) C15 0.0181(10) 0.0243(11) 0.0305(11) 0.0000(9) 0.0011(8) 0.0012(8) C13 0.0278(11) 0.0316(11) 0.0213(10) -0.0073(9) -0.0017(8) 0.0058(9) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 N21 C21 1.341(6) . ? N21 C25 1.342(5) . ? N21 H21 0.8800 . ? N22 C23 1.339(5) . ? N22 H22A 0.8800 . ? N22 H22B 0.8800 . ? C21 C22 1.345(8) . ? C21 H21A 0.9500 . ? C22 C23 1.409(10) . ? C22 H22 0.9500 . ? C23 C24 1.419(14) . ? C24 C25 1.360(18) . ? C24 H24 0.9500 . ? C25 H25 0.9500 . ? N31 C35 1.339(9) . ? N31 C31 1.341(15) . ? N31 H31 0.8800 . ? N32 C33 1.339(7) . ? N32 H32A 0.8800 . ? N32 H32B 0.8800 . ? C31 C32 1.349(13) . ? C31 H31A 0.9500 . ? C32 C33 1.433(11) . ? C32 H32 0.9500 . ? C33 C34 1.42(2) . ? C34 C35 1.35(3) . ? C34 H34 0.9500 . ? C35 H35 0.9500 . ? Cl1 C15 1.747(2) . ? O12 C17 1.276(3) . ? O13 C12 1.352(3) . ? O13 H13A 0.99(4) . ? O11 C17 1.243(3) . ? C16 C15 1.384(3) . ? C16 C11 1.398(3) . ? C16 H16 0.9500 . ? C11 C12 1.405(3) . ? C11 C17 1.509(3) . ? C12 C13 1.399(3) . ? C14 C13 1.377(3) . ? C14 C15 1.391(3) . ? C14 H14 0.9500 . ? C13 H13 0.9500 . ? 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 C21 N21 C25 121.0(4) . . ? C21 N21 H21 119.5 . . ? C25 N21 H21 119.5 . . ? C23 N22 H22A 120.0 . . ? C23 N22 H22B 120.0 . . ? H22A N22 H22B 120.0 . . ? N21 C21 C22 120.6(6) . . ? N21 C21 H21A 119.7 . . ? C22 C21 H21A 119.7 . . ? C21 C22 C23 121.3(7) . . ? C21 C22 H22 119.3 . . ? C23 C22 H22 119.3 . . ? N22 C23 C22 121.5(5) . . ? N22 C23 C24 122.5(7) . . ? C22 C23 C24 116.0(7) . . ? C25 C24 C23 119.9(7) . . ? C25 C24 H24 120.0 . . ? C23 C24 H24 120.0 . . ? N21 C25 C24 121.1(6) . . ? N21 C25 H25 119.5 . . ? C24 C25 H25 119.5 . . ? C35 N31 C31 121.7(9) . . ? C35 N31 H31 119.2 . . ? C31 N31 H31 119.2 . . ? C33 N32 H32A 120.0 . . ? C33 N32 H32B 120.0 . . ? H32A N32 H32B 120.0 . . ? N31 C31 C32 120.7(13) . . ? N31 C31 H31A 119.6 . . ? C32 C31 H31A 119.6 . . ? C31 C32 C33 120.3(9) . . ? C31 C32 H32 119.9 . . ? C33 C32 H32 119.9 . . ? N32 C33 C34 122.4(11) . . ? N32 C33 C32 121.6(7) . . ? C34 C33 C32 115.9(11) . . ? C35 C34 C33 120.3(13) . . ? C35 C34 H34 119.8 . . ? C33 C34 H34 119.8 . . ? N31 C35 C34 121.0(10) . . ? N31 C35 H35 119.5 . . ? C34 C35 H35 119.5 . . ? C12 O13 H13A 103(2) . . ? C15 C16 C11 120.14(19) . . ? C15 C16 H16 119.9 . . ? C11 C16 H16 119.9 . . ? C16 C11 C12 118.94(18) . . ? C16 C11 C17 120.14(18) . . ? C12 C11 C17 120.87(19) . . ? O11 C17 O12 124.11(19) . . ? O11 C17 C11 119.46(19) . . ? O12 C17 C11 116.43(18) . . ? O13 C12 C13 118.54(19) . . ? O13 C12 C11 121.47(19) . . ? C13 C12 C11 120.0(2) . . ? C13 C14 C15 119.58(19) . . ? C13 C14 H14 120.2 . . ? C15 C14 H14 120.2 . . ? C16 C15 C14 120.8(2) . . ? C16 C15 Cl1 119.60(17) . . ? C14 C15 Cl1 119.55(16) . . ? C14 C13 C12 120.5(2) . . ? C14 C13 H13 119.8 . . ? C12 C13 H13 119.8 . . ? 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 N22 H22A O11 0.88 2.03 2.885(4) 163.2 2_645 N22 H22A O11 0.88 2.03 2.885(4) 163.2 2_645 N31 H31 O11 0.88 1.79 2.599(6) 151.4 2_645 N32 H32A O13 0.88 2.15 2.987(5) 158.7 2_646 N21 H21 O12 0.88 1.92 2.793(3) 169.9 . N21 H21 O11 0.88 2.48 3.078(3) 125.7 . N32 H32B O12 0.88 1.97 2.840(6) 170.6 . O13 H13A O12 0.99(4) 1.58(4) 2.512(2) 154(3) . _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.634 _refine_diff_density_min -0.797 _refine_diff_density_rms 0.057 # Attachment '4-aminopyridinium-5-chlorosalicylate-hydrate.cif' data_4-aminopyridinium_5-chlorosalicylate_hydrate _database_code_depnum_ccdc_archive 'CCDC 888891' #TrackingRef '4-aminopyridinium-5-chlorosalicylate-hydrate.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 4-aminopyridinium_5-chlorosalicylate_hydrate ; _chemical_name_common 4-aminopyridinium_5-chlorosalicylate_hydrate _chemical_melting_point ? _chemical_formula_moiety 'C7 H4 Cl O3, C5 H7 N2, H2 O' _chemical_formula_sum 'C12 H13 Cl N2 O4' _chemical_formula_weight 284.69 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 '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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 4.4573(5) _cell_length_b 17.317(2) _cell_length_c 8.4840(7) _cell_angle_alpha 90.00 _cell_angle_beta 97.333(7) _cell_angle_gamma 90.00 _cell_volume 649.51(12) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 10209 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.456 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 296 _exptl_absorpt_coefficient_mu 0.306 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9414 _exptl_absorpt_correction_T_max 0.9584 _exptl_absorpt_process_details 'SADABS 2007/2 (Sheldrick, G.M., 2007)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius Roper CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7981 _diffrn_reflns_av_R_equivalents 0.0779 _diffrn_reflns_av_sigmaI/netI 0.1070 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 4.28 _diffrn_reflns_theta_max 27.50 _reflns_number_total 2863 _reflns_number_gt 1942 _reflns_threshold_expression >2\s(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' #Although determined using DirAx, the cell is refined in the HKL #package during data reduction _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^ > 2\s(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^)+(0.0567P)^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 0.02(9) _refine_ls_number_reflns 2863 _refine_ls_number_parameters 176 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1020 _refine_ls_R_factor_gt 0.0578 _refine_ls_wR_factor_ref 0.1316 _refine_ls_wR_factor_gt 0.1126 _refine_ls_goodness_of_fit_ref 0.992 _refine_ls_restrained_S_all 0.992 _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 H31B H 0.379(14) 0.280(4) 0.528(7) 0.09(2) Uiso 1 1 d . . . O11 O -0.2911(6) 0.33111(16) 0.4837(3) 0.0332(7) Uani 1 1 d . . . O12 O -0.4543(6) 0.39733(16) 0.2629(3) 0.0329(7) Uani 1 1 d . . . O13 O -0.2068(6) 0.52210(16) 0.1967(3) 0.0353(7) Uani 1 1 d . . . H13A H -0.3246 0.4842 0.1831 0.053 Uiso 1 1 d R . . C11 C -0.0629(8) 0.4521(2) 0.4424(4) 0.0245(8) Uani 1 1 d . . . C12 C -0.0349(8) 0.5161(2) 0.3430(4) 0.0269(9) Uani 1 1 d . . . C13 C 0.1656(9) 0.5747(2) 0.3911(4) 0.0318(9) Uani 1 1 d . . . H13 H 0.1804 0.6181 0.3240 0.038 Uiso 1 1 calc R . . C14 C 0.3451(9) 0.5708(2) 0.5362(5) 0.0326(9) Uani 1 1 d . . . H14 H 0.4846 0.6110 0.5685 0.039 Uiso 1 1 calc R . . C15 C 0.3199(8) 0.5073(2) 0.6352(4) 0.0279(8) Uani 1 1 d . . . C16 C 0.1190(8) 0.4494(2) 0.5890(4) 0.0240(8) Uani 1 1 d . . . H16 H 0.1031 0.4067 0.6577 0.029 Uiso 1 1 calc R . . C17 C -0.2829(8) 0.3892(2) 0.3943(4) 0.0272(9) Uani 1 1 d . . . Cl11 Cl 0.5441(2) 0.50292(6) 0.81913(10) 0.0378(3) Uani 1 1 d . . . N21 N 1.1137(7) 0.30120(19) 0.1283(3) 0.0303(8) Uani 1 1 d . . . H21A H 1.2597 0.3262 0.1866 0.036 Uiso 1 1 d R . . N22 N 0.4374(7) 0.1839(2) -0.1469(3) 0.0293(8) Uani 1 1 d . . . H22A H 0.3455 0.2050 -0.2343 0.035 Uiso 1 1 calc R . . H22B H 0.3837 0.1376 -0.1179 0.035 Uiso 1 1 calc R . . C21 C 1.0292(9) 0.2303(3) 0.1733(4) 0.0326(9) Uani 1 1 d . . . H21 H 1.1256 0.2089 0.2698 0.039 Uiso 1 1 calc R . . C22 C 0.8112(9) 0.1892(2) 0.0848(4) 0.0308(9) Uani 1 1 d . . . H22 H 0.7594 0.1389 0.1170 0.037 Uiso 1 1 calc R . . C23 C 0.6602(9) 0.2223(2) -0.0575(4) 0.0269(9) Uani 1 1 d . . . C24 C 0.7514(8) 0.2961(2) -0.1003(4) 0.0268(9) Uani 1 1 d . . . H24 H 0.6576 0.3200 -0.1947 0.032 Uiso 1 1 calc R . . C25 C 0.9744(9) 0.3330(2) -0.0059(4) 0.0286(9) Uani 1 1 d . . . H25 H 1.0343 0.3830 -0.0355 0.034 Uiso 1 1 calc R . . O31 O 0.2390(6) 0.24459(18) 0.5511(3) 0.0332(7) Uani 1 1 d . . . H31A H 0.0765 0.2686 0.5358 0.050 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 O11 0.0269(16) 0.0324(17) 0.0408(15) 0.0044(14) 0.0056(12) -0.0025(13) O12 0.0319(15) 0.0339(17) 0.0319(14) -0.0004(12) 0.0002(12) 0.0021(13) O13 0.0398(16) 0.0384(19) 0.0270(13) 0.0050(12) 0.0013(11) 0.0022(13) C11 0.024(2) 0.026(2) 0.0242(17) 0.0018(15) 0.0070(15) 0.0010(16) C12 0.0269(19) 0.032(3) 0.0221(16) 0.0015(16) 0.0049(14) 0.0047(18) C13 0.033(2) 0.029(2) 0.035(2) 0.0006(18) 0.0093(19) -0.003(2) C14 0.030(2) 0.024(2) 0.045(2) -0.0051(19) 0.0071(19) -0.0018(19) C15 0.0236(18) 0.033(2) 0.0268(17) -0.0042(19) 0.0038(14) 0.006(2) C16 0.025(2) 0.024(2) 0.0251(19) 0.0000(16) 0.0102(16) 0.0013(17) C17 0.027(2) 0.032(3) 0.0244(18) -0.0004(17) 0.0087(16) 0.0053(18) Cl11 0.0382(5) 0.0410(6) 0.0321(5) -0.0064(5) -0.0035(4) 0.0060(5) N21 0.0268(18) 0.038(2) 0.0253(16) -0.0059(15) 0.0000(14) -0.0019(16) N22 0.0308(18) 0.031(2) 0.0260(16) 0.0008(15) 0.0034(14) -0.0044(16) C21 0.037(2) 0.036(3) 0.0241(19) 0.0029(18) 0.0011(17) 0.006(2) C22 0.041(2) 0.028(2) 0.0238(18) 0.0039(17) 0.0081(17) -0.0025(19) C23 0.0241(19) 0.032(2) 0.0256(19) -0.0049(16) 0.0059(15) 0.0029(18) C24 0.024(2) 0.030(2) 0.0273(19) -0.0005(16) 0.0073(16) 0.0020(17) C25 0.027(2) 0.028(2) 0.032(2) 0.0061(17) 0.0069(17) 0.0025(18) O31 0.0286(15) 0.0383(19) 0.0319(15) 0.0051(12) 0.0004(12) -0.0021(14) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 O11 C17 1.264(4) . ? O12 C17 1.276(4) . ? O13 C12 1.377(4) . ? O13 H13A 0.8398 . ? C11 C16 1.396(5) . ? C11 C12 1.409(5) . ? C11 C17 1.487(5) . ? C12 C13 1.379(5) . ? C13 C14 1.382(5) . ? C13 H13 0.9500 . ? C14 C15 1.396(6) . ? C14 H14 0.9500 . ? C15 C16 1.368(5) . ? C15 Cl11 1.744(3) . ? C16 H16 0.9500 . ? N21 C25 1.343(5) . ? N21 C21 1.353(5) . ? N21 H21A 0.8794 . ? N22 C23 1.345(5) . ? N22 H22A 0.8800 . ? N22 H22B 0.8800 . ? C21 C22 1.353(6) . ? C21 H21 0.9500 . ? C22 C23 1.425(5) . ? C22 H22 0.9500 . ? C23 C24 1.403(6) . ? C24 C25 1.355(5) . ? C24 H24 0.9500 . ? C25 H25 0.9500 . ? O31 H31B 0.92(7) . ? O31 H31A 0.8310 . ? 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 C12 O13 H13A 109.4 . . ? C16 C11 C12 118.3(4) . . ? C16 C11 C17 120.5(3) . . ? C12 C11 C17 121.2(3) . . ? O13 C12 C13 118.5(3) . . ? O13 C12 C11 121.2(3) . . ? C13 C12 C11 120.4(3) . . ? C12 C13 C14 120.5(4) . . ? C12 C13 H13 119.8 . . ? C14 C13 H13 119.8 . . ? C13 C14 C15 119.5(4) . . ? C13 C14 H14 120.2 . . ? C15 C14 H14 120.2 . . ? C16 C15 C14 120.3(3) . . ? C16 C15 Cl11 120.3(3) . . ? C14 C15 Cl11 119.5(3) . . ? C15 C16 C11 121.0(3) . . ? C15 C16 H16 119.5 . . ? C11 C16 H16 119.5 . . ? O11 C17 O12 123.5(4) . . ? O11 C17 C11 119.1(3) . . ? O12 C17 C11 117.4(3) . . ? C25 N21 C21 119.7(3) . . ? C25 N21 H21A 120.2 . . ? C21 N21 H21A 120.0 . . ? C23 N22 H22A 120.0 . . ? C23 N22 H22B 120.0 . . ? H22A N22 H22B 120.0 . . ? N21 C21 C22 121.8(3) . . ? N21 C21 H21 119.1 . . ? C22 C21 H21 119.1 . . ? C21 C22 C23 119.1(4) . . ? C21 C22 H22 120.4 . . ? C23 C22 H22 120.4 . . ? N22 C23 C24 121.4(3) . . ? N22 C23 C22 120.9(4) . . ? C24 C23 C22 117.7(3) . . ? C25 C24 C23 119.5(3) . . ? C25 C24 H24 120.3 . . ? C23 C24 H24 120.3 . . ? N21 C25 C24 122.2(4) . . ? N21 C25 H25 118.9 . . ? C24 C25 H25 118.9 . . ? H31B O31 H31A 103.4 . . ? 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 N21 H21A O12 0.88 1.83 2.688(4) 164.2 1_755 N22 H22A O31 0.88 1.95 2.806(4) 165.1 1_554 N22 H22B O13 0.88 2.22 2.996(4) 146.6 2_545 O13 H13A O12 0.84 1.78 2.522(4) 147.0 . O31 H31A O11 0.83 1.97 2.794(4) 174.5 . _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.288 _refine_diff_density_min -0.392 _refine_diff_density_rms 0.071 # Attachment '4-aminopyridinium-5-fluorosalicylate.cif' data_4-aminopyridinium_5-fluorosalicylate _database_code_depnum_ccdc_archive 'CCDC 888892' #TrackingRef '4-aminopyridinium-5-fluorosalicylate.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 4-aminopyridinium_5-fluorosalicylate ; _chemical_name_common 4-aminopyridinium_5-fluorosalicylate _chemical_melting_point ? _chemical_formula_moiety 'C7 H4 F O3, C5 H7 N2' _chemical_formula_sum 'C12 H11 F N2 O3' _chemical_formula_weight 250.23 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/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 10.7838(4) _cell_length_b 8.5407(2) _cell_length_c 12.1504(5) _cell_angle_alpha 90.00 _cell_angle_beta 95.099(2) _cell_angle_gamma 90.00 _cell_volume 1114.64(7) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 7360 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description Slab _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.491 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 520 _exptl_absorpt_coefficient_mu 0.120 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9765 _exptl_absorpt_correction_T_max 0.9905 _exptl_absorpt_process_details 'SADABS 2007/2 (Sheldrick, G.M., 2007)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius Roper CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13543 _diffrn_reflns_av_R_equivalents 0.0487 _diffrn_reflns_av_sigmaI/netI 0.0410 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.92 _diffrn_reflns_theta_max 27.50 _reflns_number_total 2544 _reflns_number_gt 1949 _reflns_threshold_expression >2\s(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' #Although determined using DirAx, the cell is refined in the HKL #package during data reduction _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^ > 2\s(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^)+(0.0580P)^2^+0.3248P] 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 2544 _refine_ls_number_parameters 164 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0629 _refine_ls_R_factor_gt 0.0437 _refine_ls_wR_factor_ref 0.1198 _refine_ls_wR_factor_gt 0.1079 _refine_ls_goodness_of_fit_ref 1.063 _refine_ls_restrained_S_all 1.063 _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 C11 C 0.19764(13) 0.45915(17) 0.57161(12) 0.0175(3) Uani 1 1 d . . . C12 C 0.17802(14) 0.46671(17) 0.68421(12) 0.0195(3) Uani 1 1 d . . . C13 C 0.08187(15) 0.38009(19) 0.72504(13) 0.0237(3) Uani 1 1 d . . . H13 H 0.0686 0.3863 0.8012 0.028 Uiso 1 1 calc R . . C14 C 0.00608(15) 0.28554(19) 0.65534(14) 0.0248(4) Uani 1 1 d . . . H14 H -0.0591 0.2260 0.6826 0.030 Uiso 1 1 calc R . . C15 C 0.02777(14) 0.28016(19) 0.54520(14) 0.0239(4) Uani 1 1 d . . . C16 C 0.11999(14) 0.36409(18) 0.50193(13) 0.0205(3) Uani 1 1 d . . . H16 H 0.1311 0.3578 0.4254 0.025 Uiso 1 1 calc R . . C17 C 0.30016(14) 0.55044(18) 0.52523(12) 0.0189(3) Uani 1 1 d . . . C21 C 0.61942(14) 0.87411(18) 0.52729(13) 0.0211(3) Uani 1 1 d . . . H21 H 0.6244 0.8752 0.6057 0.025 Uiso 1 1 calc R . . C22 C 0.69638(14) 0.96870(18) 0.47416(12) 0.0204(3) Uani 1 1 d . . . H22 H 0.7540 1.0352 0.5152 0.024 Uiso 1 1 calc R . . C23 C 0.68996(13) 0.96724(17) 0.35729(12) 0.0186(3) Uani 1 1 d . . . C24 C 0.59962(14) 0.86868(18) 0.30118(12) 0.0210(3) Uani 1 1 d . . . H24 H 0.5903 0.8664 0.2227 0.025 Uiso 1 1 calc R . . C25 C 0.52618(15) 0.77714(18) 0.36016(13) 0.0230(4) Uani 1 1 d . . . H25 H 0.4664 0.7104 0.3220 0.028 Uiso 1 1 calc R . . N21 N 0.53646(12) 0.77905(15) 0.47141(11) 0.0211(3) Uani 1 1 d . . . H21A H 0.4887 0.7178 0.5078 0.025 Uiso 1 1 calc R . . N22 N 0.76444(12) 1.05625(16) 0.30122(11) 0.0246(3) Uani 1 1 d . . . H22A H 0.8195 1.1181 0.3369 0.030 Uiso 1 1 calc R . . H22B H 0.7584 1.0530 0.2285 0.030 Uiso 1 1 calc R . . O12 O 0.37091(10) 0.63061(13) 0.59432(9) 0.0242(3) Uani 1 1 d . . . O11 O 0.31288(10) 0.54421(14) 0.42464(9) 0.0266(3) Uani 1 1 d . . . O13 O 0.24986(11) 0.55717(14) 0.75596(9) 0.0263(3) Uani 1 1 d . . . H13A H 0.3055 0.6006 0.7226 0.039 Uiso 1 1 calc R . . F11 F -0.04759(9) 0.18612(12) 0.47617(8) 0.0358(3) 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 C11 0.0159(7) 0.0187(8) 0.0181(7) 0.0011(6) 0.0028(6) 0.0012(5) C12 0.0192(7) 0.0208(8) 0.0185(7) -0.0001(6) 0.0021(6) 0.0016(6) C13 0.0258(8) 0.0263(8) 0.0201(8) 0.0011(6) 0.0089(6) 0.0012(7) C14 0.0199(8) 0.0233(8) 0.0324(9) 0.0011(6) 0.0089(7) -0.0019(6) C15 0.0188(8) 0.0232(8) 0.0295(9) -0.0061(6) 0.0014(6) -0.0036(6) C16 0.0200(7) 0.0226(8) 0.0191(7) -0.0024(6) 0.0027(6) 0.0013(6) C17 0.0175(7) 0.0218(8) 0.0175(7) 0.0007(6) 0.0026(6) 0.0010(6) C21 0.0223(8) 0.0227(8) 0.0187(7) 0.0018(6) 0.0039(6) 0.0030(6) C22 0.0198(7) 0.0217(8) 0.0196(8) -0.0005(6) 0.0012(6) -0.0007(6) C23 0.0165(7) 0.0192(8) 0.0205(8) 0.0015(6) 0.0039(6) 0.0019(6) C24 0.0223(8) 0.0229(8) 0.0179(7) -0.0012(6) 0.0012(6) 0.0000(6) C25 0.0209(8) 0.0237(8) 0.0240(8) -0.0015(6) 0.0003(6) -0.0011(6) N21 0.0181(6) 0.0221(7) 0.0237(7) 0.0034(5) 0.0054(5) -0.0016(5) N22 0.0267(7) 0.0286(8) 0.0188(7) 0.0011(6) 0.0031(6) -0.0081(6) O12 0.0230(6) 0.0306(6) 0.0192(5) -0.0011(5) 0.0029(4) -0.0080(5) O11 0.0260(6) 0.0367(7) 0.0176(6) 0.0004(5) 0.0055(5) -0.0055(5) O13 0.0286(6) 0.0333(7) 0.0175(6) -0.0016(5) 0.0043(5) -0.0098(5) F11 0.0294(5) 0.0410(6) 0.0374(6) -0.0130(5) 0.0045(4) -0.0168(4) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 C11 C16 1.397(2) . ? C11 C12 1.404(2) . ? C11 C17 1.503(2) . ? C12 O13 1.3553(18) . ? C12 C13 1.400(2) . ? C13 C14 1.384(2) . ? C13 H13 0.9500 . ? C14 C15 1.380(2) . ? C14 H14 0.9500 . ? C15 C16 1.368(2) . ? C15 F11 1.3739(17) . ? C16 H16 0.9500 . ? C17 O11 1.2431(18) . ? C17 O12 1.2812(18) . ? C21 N21 1.346(2) . ? C21 C22 1.361(2) . ? C21 H21 0.9500 . ? C22 C23 1.416(2) . ? C22 H22 0.9500 . ? C23 N22 1.3358(19) . ? C23 C24 1.416(2) . ? C24 C25 1.361(2) . ? C24 H24 0.9500 . ? C25 N21 1.346(2) . ? C25 H25 0.9500 . ? N21 H21A 0.8800 . ? N22 H22A 0.8800 . ? N22 H22B 0.8800 . ? O13 H13A 0.8400 . ? 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 C16 C11 C12 118.89(13) . . ? C16 C11 C17 119.71(13) . . ? C12 C11 C17 121.39(13) . . ? O13 C12 C13 118.18(14) . . ? O13 C12 C11 121.73(13) . . ? C13 C12 C11 120.09(14) . . ? C14 C13 C12 120.49(15) . . ? C14 C13 H13 119.8 . . ? C12 C13 H13 119.8 . . ? C15 C14 C13 118.12(14) . . ? C15 C14 H14 120.9 . . ? C13 C14 H14 120.9 . . ? C16 C15 F11 118.84(14) . . ? C16 C15 C14 123.16(15) . . ? F11 C15 C14 118.00(14) . . ? C15 C16 C11 119.25(14) . . ? C15 C16 H16 120.4 . . ? C11 C16 H16 120.4 . . ? O11 C17 O12 123.76(14) . . ? O11 C17 C11 119.71(13) . . ? O12 C17 C11 116.53(13) . . ? N21 C21 C22 121.63(14) . . ? N21 C21 H21 119.2 . . ? C22 C21 H21 119.2 . . ? C21 C22 C23 119.53(14) . . ? C21 C22 H22 120.2 . . ? C23 C22 H22 120.2 . . ? N22 C23 C22 121.91(14) . . ? N22 C23 C24 120.79(14) . . ? C22 C23 C24 117.29(13) . . ? C25 C24 C23 119.71(14) . . ? C25 C24 H24 120.1 . . ? C23 C24 H24 120.1 . . ? N21 C25 C24 121.45(14) . . ? N21 C25 H25 119.3 . . ? C24 C25 H25 119.3 . . ? C21 N21 C25 120.35(13) . . ? C21 N21 H21A 119.8 . . ? C25 N21 H21A 119.8 . . ? C23 N22 H22A 120.0 . . ? C23 N22 H22B 120.0 . . ? H22A N22 H22B 120.0 . . ? C12 O13 H13A 109.5 . . ? 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 N22 H22A F11 0.88 2.20 3.0153(16) 154.7 1_665 N22 H22B O11 0.88 1.95 2.7982(17) 161.1 2_655 N21 H21A O12 0.88 1.87 2.7384(16) 167.0 . N21 H21A O11 0.88 2.54 3.1488(17) 126.6 . O13 H13A O12 0.84 1.79 2.5319(15) 147.1 . _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.188 _refine_diff_density_min -0.257 _refine_diff_density_rms 0.057 # Attachment '4-aminopyridinium-5-iodosalicylate.cif' data_4-aminopyridinium_5-iodosalicylate _database_code_depnum_ccdc_archive 'CCDC 888893' #TrackingRef '4-aminopyridinium-5-iodosalicylate.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 4-aminopyridinium_5-iodosalicylate ; _chemical_name_common 4-aminopyridinium_5-iodosalicylate _chemical_melting_point ? _chemical_formula_moiety 'C7 H4 I O3, C5 H7 N2' _chemical_formula_sum 'C12 H11 I N2 O3' _chemical_formula_weight 358.13 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' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/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 13.6431(3) _cell_length_b 8.1006(2) _cell_length_c 12.4428(2) _cell_angle_alpha 90.00 _cell_angle_beta 112.2790(10) _cell_angle_gamma 90.00 _cell_volume 1272.49(5) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 8857 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description Slab _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.869 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 696 _exptl_absorpt_coefficient_mu 2.518 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6328 _exptl_absorpt_correction_T_max 0.7520 _exptl_absorpt_process_details 'SADABS 2007/2 (Sheldrick, G.M., 2007)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator '10cm confocal mirrors' _diffrn_measurement_device_type 'Bruker-Nonius APEX II CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean '4096x4096pixels / 62x62mm' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14879 _diffrn_reflns_av_R_equivalents 0.0284 _diffrn_reflns_av_sigmaI/netI 0.0260 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.23 _diffrn_reflns_theta_max 27.48 _reflns_number_total 2909 _reflns_number_gt 2742 _reflns_threshold_expression >2\s(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' #Although determined using DirAx, the cell is refined in the HKL #package during data reduction _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^ > 2\s(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^)+(0.0113P)^2^+1.7719P] 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 2909 _refine_ls_number_parameters 164 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0258 _refine_ls_R_factor_gt 0.0235 _refine_ls_wR_factor_ref 0.0527 _refine_ls_wR_factor_gt 0.0515 _refine_ls_goodness_of_fit_ref 1.096 _refine_ls_restrained_S_all 1.096 _refine_ls_shift/su_max 0.001 _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 C11 C 0.24381(16) 0.5289(2) 0.49444(17) 0.0129(4) Uani 1 1 d . . . C12 C 0.24105(16) 0.5241(3) 0.60634(17) 0.0149(4) Uani 1 1 d . . . C13 C 0.15839(17) 0.6003(3) 0.62731(18) 0.0199(4) Uani 1 1 d . . . H13 H 0.1562 0.5953 0.7026 0.024 Uiso 1 1 calc R . . C14 C 0.07965(18) 0.6832(3) 0.5395(2) 0.0209(5) Uani 1 1 d . . . H14 H 0.0235 0.7349 0.5542 0.025 Uiso 1 1 calc R . . C15 C 0.08332(17) 0.6902(3) 0.42950(19) 0.0174(4) Uani 1 1 d . . . C16 C 0.16449(16) 0.6152(3) 0.40683(17) 0.0149(4) Uani 1 1 d . . . H16 H 0.1664 0.6223 0.3314 0.018 Uiso 1 1 calc R . . C17 C 0.33129(16) 0.4465(3) 0.46846(17) 0.0145(4) Uani 1 1 d . . . O12 O 0.40409(12) 0.37720(19) 0.55502(12) 0.0191(3) Uani 1 1 d . . . O11 O 0.32957(12) 0.4477(2) 0.36803(13) 0.0212(3) Uani 1 1 d . . . O13 O 0.31741(12) 0.4480(2) 0.69554(12) 0.0211(3) Uani 1 1 d . . . H13A H 0.3616 0.4051 0.6719 0.032 Uiso 1 1 calc R . . I1 I -0.035742(12) 0.81816(2) 0.296386(13) 0.02844(7) Uani 1 1 d . . . C21 C 0.61190(17) 0.1194(3) 0.55751(18) 0.0171(4) Uani 1 1 d . . . H21 H 0.6159 0.1182 0.6354 0.021 Uiso 1 1 calc R . . C22 C 0.67900(17) 0.0220(3) 0.52760(18) 0.0168(4) Uani 1 1 d . . . H22 H 0.7291 -0.0461 0.5841 0.020 Uiso 1 1 calc R . . C23 C 0.67345(16) 0.0231(3) 0.41170(18) 0.0153(4) Uani 1 1 d . . . C24 C 0.59564(17) 0.1252(3) 0.33135(18) 0.0165(4) Uani 1 1 d . . . H24 H 0.5882 0.1279 0.2523 0.020 Uiso 1 1 calc R . . C25 C 0.53136(17) 0.2196(3) 0.36787(18) 0.0176(4) Uani 1 1 d . . . H25 H 0.4795 0.2883 0.3138 0.021 Uiso 1 1 calc R . . N21 N 0.54026(14) 0.2169(2) 0.47939(15) 0.0165(4) Uani 1 1 d . . . H21A H 0.4986 0.2798 0.5013 0.020 Uiso 1 1 calc R . . N22 N 0.73785(15) -0.0682(2) 0.37781(16) 0.0225(4) Uani 1 1 d . . . H22A H 0.7857 -0.1318 0.4282 0.027 Uiso 1 1 calc R . . H22B H 0.7325 -0.0649 0.3051 0.027 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 C11 0.0124(9) 0.0123(9) 0.0152(9) -0.0019(7) 0.0066(8) -0.0008(8) C12 0.0154(10) 0.0149(10) 0.0142(9) -0.0016(8) 0.0052(8) -0.0005(8) C13 0.0215(11) 0.0251(11) 0.0172(10) -0.0004(8) 0.0119(9) 0.0028(9) C14 0.0190(11) 0.0246(12) 0.0243(11) 0.0010(9) 0.0142(9) 0.0050(9) C15 0.0141(10) 0.0189(10) 0.0196(10) 0.0044(8) 0.0067(9) 0.0033(8) C16 0.0143(9) 0.0166(10) 0.0155(9) -0.0011(8) 0.0075(8) -0.0032(8) C17 0.0132(9) 0.0147(9) 0.0172(10) -0.0033(8) 0.0077(8) -0.0020(8) O12 0.0169(7) 0.0224(8) 0.0180(7) -0.0003(6) 0.0068(6) 0.0058(6) O11 0.0218(8) 0.0287(9) 0.0164(7) -0.0004(6) 0.0110(6) 0.0040(7) O13 0.0209(8) 0.0278(8) 0.0145(7) 0.0003(6) 0.0069(6) 0.0087(7) I1 0.02330(10) 0.03749(11) 0.02862(10) 0.01447(6) 0.01448(7) 0.01596(6) C21 0.0198(10) 0.0170(10) 0.0163(10) -0.0028(8) 0.0089(8) -0.0032(8) C22 0.0176(10) 0.0166(10) 0.0151(9) 0.0002(8) 0.0050(8) 0.0002(8) C23 0.0146(10) 0.0146(9) 0.0188(10) -0.0032(8) 0.0085(8) -0.0039(8) C24 0.0184(10) 0.0176(10) 0.0139(9) 0.0002(8) 0.0067(8) -0.0023(8) C25 0.0166(10) 0.0176(10) 0.0167(10) -0.0013(8) 0.0042(8) -0.0021(8) N21 0.0154(9) 0.0163(8) 0.0203(9) -0.0037(7) 0.0096(7) -0.0001(7) N22 0.0237(10) 0.0259(10) 0.0207(9) -0.0002(8) 0.0116(8) 0.0067(8) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 C11 C16 1.398(3) . ? C11 C12 1.408(3) . ? C11 C17 1.505(3) . ? C12 O13 1.349(2) . ? C12 C13 1.394(3) . ? C13 C14 1.382(3) . ? C13 H13 0.9500 . ? C14 C15 1.389(3) . ? C14 H14 0.9500 . ? C15 C16 1.383(3) . ? C15 I1 2.101(2) . ? C16 H16 0.9500 . ? C17 O11 1.241(2) . ? C17 O12 1.285(3) . ? O13 H13A 0.8400 . ? C21 N21 1.343(3) . ? C21 C22 1.363(3) . ? C21 H21 0.9500 . ? C22 C23 1.415(3) . ? C22 H22 0.9500 . ? C23 N22 1.333(3) . ? C23 C24 1.416(3) . ? C24 C25 1.365(3) . ? C24 H24 0.9500 . ? C25 N21 1.346(3) . ? C25 H25 0.9500 . ? N21 H21A 0.8800 . ? N22 H22A 0.8800 . ? N22 H22B 0.8800 . ? 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 C16 C11 C12 118.81(18) . . ? C16 C11 C17 119.78(18) . . ? C12 C11 C17 121.39(18) . . ? O13 C12 C13 118.39(18) . . ? O13 C12 C11 121.63(18) . . ? C13 C12 C11 119.98(19) . . ? C14 C13 C12 120.6(2) . . ? C14 C13 H13 119.7 . . ? C12 C13 H13 119.7 . . ? C13 C14 C15 119.4(2) . . ? C13 C14 H14 120.3 . . ? C15 C14 H14 120.3 . . ? C16 C15 C14 120.9(2) . . ? C16 C15 I1 119.71(16) . . ? C14 C15 I1 119.40(16) . . ? C15 C16 C11 120.27(19) . . ? C15 C16 H16 119.9 . . ? C11 C16 H16 119.9 . . ? O11 C17 O12 124.14(19) . . ? O11 C17 C11 119.91(18) . . ? O12 C17 C11 115.95(17) . . ? C12 O13 H13A 109.5 . . ? N21 C21 C22 121.51(19) . . ? N21 C21 H21 119.2 . . ? C22 C21 H21 119.2 . . ? C21 C22 C23 119.5(2) . . ? C21 C22 H22 120.2 . . ? C23 C22 H22 120.2 . . ? N22 C23 C22 122.1(2) . . ? N22 C23 C24 120.54(19) . . ? C22 C23 C24 117.34(19) . . ? C25 C24 C23 119.76(19) . . ? C25 C24 H24 120.1 . . ? C23 C24 H24 120.1 . . ? N21 C25 C24 121.1(2) . . ? N21 C25 H25 119.5 . . ? C24 C25 H25 119.5 . . ? C21 N21 C25 120.79(19) . . ? C21 N21 H21A 119.6 . . ? C25 N21 H21A 119.6 . . ? C23 N22 H22A 120.0 . . ? C23 N22 H22B 120.0 . . ? H22A N22 H22B 120.0 . . ? 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 N22 H22B O11 0.88 2.00 2.844(2) 161.3 2_645 O13 H13A O12 0.84 1.77 2.520(2) 147.4 . N21 H21A O12 0.88 1.84 2.711(2) 170.0 . _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.757 _refine_diff_density_min -1.029 _refine_diff_density_rms 0.082 # Attachment '4-aminopyridinium-5-iodosalicylate-pyridine.cif' data_4-aminopyridium_5-iodosalicylate_pyridine _database_code_depnum_ccdc_archive 'CCDC 888894' #TrackingRef '4-aminopyridinium-5-iodosalicylate-pyridine.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 4-aminopyridium_5-iodosalicylate_pyridine ; _chemical_name_common 4-aminopyridium_5-iodosalicylate_pyridine _chemical_melting_point ? _chemical_formula_moiety 'C7 H4 I O3, C5 H7 N2, C5 H5 N' _chemical_formula_sum 'C17 H16 I N3 O3' _chemical_formula_weight 437.23 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' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/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 18.6570(10) _cell_length_b 8.6657(5) _cell_length_c 10.9293(5) _cell_angle_alpha 90.00 _cell_angle_beta 102.573(4) _cell_angle_gamma 90.00 _cell_volume 1724.63(16) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 10400 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description Block _exptl_crystal_colour Bronze _exptl_crystal_size_max 0.11 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.684 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 864 _exptl_absorpt_coefficient_mu 1.877 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8202 _exptl_absorpt_correction_T_max 0.9287 _exptl_absorpt_process_details 'SADABS 2007/2 (Sheldrick, G.M., 2007)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator '10cm confocal mirrors' _diffrn_measurement_device_type 'Bruker-Nonius APEX II CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean '4096x4096pixels / 62x62mm' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15986 _diffrn_reflns_av_R_equivalents 0.0415 _diffrn_reflns_av_sigmaI/netI 0.0420 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.03 _diffrn_reflns_theta_max 27.49 _reflns_number_total 3922 _reflns_number_gt 3270 _reflns_threshold_expression >2\s(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' #Although determined using DirAx, the cell is refined in the HKL #package during data reduction _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^ > 2\s(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^+7.4563P] 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 3922 _refine_ls_number_parameters 218 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0579 _refine_ls_R_factor_gt 0.0433 _refine_ls_wR_factor_ref 0.0901 _refine_ls_wR_factor_gt 0.0817 _refine_ls_goodness_of_fit_ref 1.112 _refine_ls_restrained_S_all 1.112 _refine_ls_shift/su_max 0.001 _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 C11 C 0.2040(2) 1.0074(5) 1.1196(4) 0.0213(8) Uani 1 1 d . . . C12 C 0.2015(2) 1.1019(5) 1.2231(4) 0.0233(8) Uani 1 1 d . . . C13 C 0.2604(2) 1.1977(5) 1.2738(4) 0.0270(9) Uani 1 1 d . . . H13 H 0.2581 1.2622 1.3430 0.032 Uiso 1 1 calc R . . C14 C 0.3221(2) 1.1990(5) 1.2237(4) 0.0259(9) Uani 1 1 d . . . H14 H 0.3623 1.2643 1.2583 0.031 Uiso 1 1 calc R . . C15 C 0.3253(2) 1.1041(5) 1.1220(4) 0.0212(8) Uani 1 1 d . . . C16 C 0.2671(2) 1.0091(5) 1.0701(4) 0.0212(8) Uani 1 1 d . . . H16 H 0.2699 0.9450 1.0008 0.025 Uiso 1 1 calc R . . C17 C 0.1395(2) 0.9073(5) 1.0606(4) 0.0215(8) Uani 1 1 d . . . O11 O 0.14213(15) 0.8281(4) 0.9665(2) 0.0253(6) Uani 1 1 d . . . O12 O 0.08391(16) 0.9105(4) 1.1117(3) 0.0290(7) Uani 1 1 d . . . O13 O 0.14230(16) 1.1036(4) 1.2752(3) 0.0289(7) Uani 1 1 d . . . H13A H 0.1105 1.0421 1.2365 0.043 Uiso 1 1 calc R . . I1 I 0.420573(15) 1.10351(4) 1.04852(3) 0.02991(10) Uani 1 1 d . . . C21 C -0.0743(2) 0.6864(5) 0.9970(4) 0.0246(9) Uani 1 1 d . . . H21 H -0.0793 0.7367 1.0719 0.030 Uiso 1 1 calc R . . C22 C -0.1288(2) 0.5939(5) 0.9367(4) 0.0238(9) Uani 1 1 d . . . H22 H -0.1713 0.5790 0.9698 0.029 Uiso 1 1 calc R . . C23 C -0.1229(2) 0.5188(5) 0.8242(4) 0.0209(8) Uani 1 1 d . . . C24 C -0.0572(2) 0.5431(5) 0.7812(4) 0.0216(8) Uani 1 1 d . . . H24 H -0.0501 0.4934 0.7073 0.026 Uiso 1 1 calc R . . C25 C -0.0044(2) 0.6384(5) 0.8471(4) 0.0255(9) Uani 1 1 d . . . H25 H 0.0393 0.6554 0.8177 0.031 Uiso 1 1 calc R . . N21 N -0.01282(19) 0.7091(4) 0.9532(3) 0.0247(8) Uani 1 1 d . . . H21A H 0.0219 0.7704 0.9940 0.030 Uiso 1 1 calc R . . N22 N -0.17647(18) 0.4296(4) 0.7617(3) 0.0255(8) Uani 1 1 d . . . H22A H -0.2167 0.4162 0.7900 0.031 Uiso 1 1 calc R . . H22B H -0.1717 0.3840 0.6919 0.031 Uiso 1 1 calc R . . C31 C 0.2889(2) 0.6208(5) -0.0085(4) 0.0277(9) Uani 1 1 d . . . H31 H 0.2382 0.6226 -0.0473 0.033 Uiso 1 1 calc R . . C32 C 0.3397(3) 0.6334(5) -0.0835(4) 0.0296(10) Uani 1 1 d . . . H32 H 0.3238 0.6428 -0.1718 0.036 Uiso 1 1 calc R . . C33 C 0.4133(3) 0.6321(6) -0.0287(5) 0.0361(11) Uani 1 1 d . . . H33 H 0.4490 0.6422 -0.0782 0.043 Uiso 1 1 calc R . . C34 C 0.4344(3) 0.6159(6) 0.1003(5) 0.0373(11) Uani 1 1 d . . . H34 H 0.4849 0.6133 0.1412 0.045 Uiso 1 1 calc R . . C35 C 0.3801(3) 0.6038(5) 0.1677(4) 0.0317(10) Uani 1 1 d . . . H35 H 0.3947 0.5932 0.2562 0.038 Uiso 1 1 calc R . . N31 N 0.3082(2) 0.6060(5) 0.1164(4) 0.0314(8) 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 C11 0.0208(19) 0.024(2) 0.0195(19) 0.0053(16) 0.0042(15) 0.0023(17) C12 0.023(2) 0.027(2) 0.0202(19) 0.0029(17) 0.0054(15) 0.0070(18) C13 0.032(2) 0.027(2) 0.022(2) -0.0037(18) 0.0069(17) 0.0027(19) C14 0.027(2) 0.026(2) 0.023(2) -0.0014(17) 0.0026(16) -0.0016(18) C15 0.0156(18) 0.027(2) 0.0218(19) 0.0015(17) 0.0050(15) -0.0026(17) C16 0.021(2) 0.021(2) 0.0216(19) 0.0029(16) 0.0057(15) 0.0020(16) C17 0.0164(18) 0.029(2) 0.0190(19) 0.0048(17) 0.0034(14) 0.0020(17) O11 0.0220(15) 0.0337(17) 0.0203(14) -0.0019(13) 0.0049(11) -0.0053(13) O12 0.0222(15) 0.0368(18) 0.0305(16) 0.0012(14) 0.0114(12) -0.0055(13) O13 0.0257(15) 0.0380(18) 0.0260(15) -0.0013(14) 0.0127(12) 0.0015(14) I1 0.01895(14) 0.04082(18) 0.03091(16) -0.00072(14) 0.00749(10) -0.00534(13) C21 0.027(2) 0.030(2) 0.0173(19) 0.0034(17) 0.0050(16) -0.0006(18) C22 0.0201(19) 0.032(2) 0.0196(19) 0.0034(17) 0.0043(15) 0.0019(18) C23 0.0176(19) 0.025(2) 0.0198(19) 0.0032(16) 0.0025(15) 0.0040(16) C24 0.0202(19) 0.025(2) 0.0194(19) 0.0020(16) 0.0037(15) 0.0019(16) C25 0.0150(19) 0.033(2) 0.030(2) 0.0068(18) 0.0082(16) 0.0062(17) N21 0.0232(18) 0.0237(19) 0.0255(18) -0.0032(15) 0.0017(14) -0.0055(15) N22 0.0182(17) 0.039(2) 0.0208(17) -0.0047(15) 0.0064(13) -0.0031(15) C31 0.025(2) 0.026(2) 0.033(2) 0.0026(19) 0.0093(18) -0.0033(18) C32 0.034(2) 0.027(2) 0.029(2) -0.0031(18) 0.0095(19) -0.0058(19) C33 0.028(2) 0.038(3) 0.045(3) -0.004(2) 0.015(2) -0.006(2) C34 0.022(2) 0.044(3) 0.045(3) -0.005(2) 0.0058(19) -0.004(2) C35 0.037(3) 0.027(2) 0.029(2) -0.004(2) 0.0036(19) 0.000(2) N31 0.029(2) 0.031(2) 0.036(2) 0.0028(18) 0.0116(16) 0.0018(17) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 C11 C16 1.398(5) . ? C11 C12 1.406(6) . ? C11 C17 1.510(6) . ? C12 O13 1.348(5) . ? C12 C13 1.392(6) . ? C13 C14 1.378(6) . ? C13 H13 0.9500 . ? C14 C15 1.394(6) . ? C14 H14 0.9500 . ? C15 C16 1.382(5) . ? C15 I1 2.104(4) . ? C16 H16 0.9500 . ? C17 O11 1.246(5) . ? C17 O12 1.281(5) . ? O13 H13A 0.8400 . ? C21 C22 1.349(6) . ? C21 N21 1.350(5) . ? C21 H21 0.9500 . ? C22 C23 1.415(6) . ? C22 H22 0.9500 . ? C23 N22 1.330(5) . ? C23 C24 1.420(5) . ? C24 C25 1.365(6) . ? C24 H24 0.9500 . ? C25 N21 1.351(5) . ? C25 H25 0.9500 . ? N21 H21A 0.8800 . ? N22 H22A 0.8800 . ? N22 H22B 0.8800 . ? C31 N31 1.340(6) . ? C31 C32 1.385(6) . ? C31 H31 0.9500 . ? C32 C33 1.374(6) . ? C32 H32 0.9500 . ? C33 C34 1.386(7) . ? C33 H33 0.9500 . ? C34 C35 1.381(7) . ? C34 H34 0.9500 . ? C35 N31 1.336(6) . ? C35 H35 0.9500 . ? 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 C16 C11 C12 118.9(4) . . ? C16 C11 C17 120.1(4) . . ? C12 C11 C17 121.0(4) . . ? O13 C12 C13 118.3(4) . . ? O13 C12 C11 121.4(4) . . ? C13 C12 C11 120.3(4) . . ? C14 C13 C12 120.2(4) . . ? C14 C13 H13 119.9 . . ? C12 C13 H13 119.9 . . ? C13 C14 C15 119.7(4) . . ? C13 C14 H14 120.1 . . ? C15 C14 H14 120.1 . . ? C16 C15 C14 120.8(4) . . ? C16 C15 I1 119.7(3) . . ? C14 C15 I1 119.5(3) . . ? C15 C16 C11 120.0(4) . . ? C15 C16 H16 120.0 . . ? C11 C16 H16 120.0 . . ? O11 C17 O12 123.6(4) . . ? O11 C17 C11 119.8(3) . . ? O12 C17 C11 116.6(4) . . ? C12 O13 H13A 109.5 . . ? C22 C21 N21 121.4(4) . . ? C22 C21 H21 119.3 . . ? N21 C21 H21 119.3 . . ? C21 C22 C23 120.3(4) . . ? C21 C22 H22 119.8 . . ? C23 C22 H22 119.8 . . ? N22 C23 C22 121.5(4) . . ? N22 C23 C24 121.5(4) . . ? C22 C23 C24 117.1(4) . . ? C25 C24 C23 119.4(4) . . ? C25 C24 H24 120.3 . . ? C23 C24 H24 120.3 . . ? N21 C25 C24 121.4(4) . . ? N21 C25 H25 119.3 . . ? C24 C25 H25 119.3 . . ? C25 N21 C21 120.3(4) . . ? C25 N21 H21A 119.8 . . ? C21 N21 H21A 119.8 . . ? C23 N22 H22A 120.0 . . ? C23 N22 H22B 120.0 . . ? H22A N22 H22B 120.0 . . ? N31 C31 C32 122.9(4) . . ? N31 C31 H31 118.5 . . ? C32 C31 H31 118.5 . . ? C33 C32 C31 119.3(4) . . ? C33 C32 H32 120.4 . . ? C31 C32 H32 120.4 . . ? C32 C33 C34 118.7(4) . . ? C32 C33 H33 120.6 . . ? C34 C33 H33 120.6 . . ? C35 C34 C33 118.1(4) . . ? C35 C34 H34 121.0 . . ? C33 C34 H34 121.0 . . ? N31 C35 C34 124.1(4) . . ? N31 C35 H35 117.9 . . ? C34 C35 H35 117.9 . . ? C35 N31 C31 116.9(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 N22 H22A N31 0.88 2.18 3.056(5) 172.5 3_566 N22 H22B O11 0.88 1.99 2.846(4) 164.4 2_546 O13 H13A O12 0.84 1.76 2.517(4) 148.1 . N21 H21A O12 0.88 1.95 2.818(5) 166.6 . N21 H21A O11 0.88 2.38 3.043(4) 132.3 . _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.669 _refine_diff_density_min -0.675 _refine_diff_density_rms 0.126 # Attachment '4-aminopyridinium-5-methoxysalicylate-monohydrate.cif' data_4-aminopyridinium_5-methoxysalicylate_hydrate _database_code_depnum_ccdc_archive 'CCDC 888895' #TrackingRef '4-aminopyridinium-5-methoxysalicylate-monohydrate.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 4-aminopyridinium_5-methoxysalicylate_monohydrate ; _chemical_name_common 4-aminopyridinium_5-methoxysalicylate_monohydrate _chemical_melting_point ? _chemical_formula_moiety 'C8 H7 O4, C5 H7 N2, H2 O' _chemical_formula_sum 'C13 H16 N2 O5' _chemical_formula_weight 280.28 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pna21 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' _cell_length_a 21.8619(15) _cell_length_b 15.0658(9) _cell_length_c 3.9918(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1314.77(16) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 17805 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description Lath _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.416 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 592 _exptl_absorpt_coefficient_mu 0.110 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9522 _exptl_absorpt_correction_T_max 0.9902 _exptl_absorpt_process_details 'SADABS 2007/2 (Sheldrick, G.M., 2007)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator '10cm confocal mirrors' _diffrn_measurement_device_type 'Bruker-Nonius APEX II CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean '4096x4096pixels / 62x62mm' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14780 _diffrn_reflns_av_R_equivalents 0.0864 _diffrn_reflns_av_sigmaI/netI 0.0551 _diffrn_reflns_limit_h_min -28 _diffrn_reflns_limit_h_max 28 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -5 _diffrn_reflns_limit_l_max 5 _diffrn_reflns_theta_min 3.11 _diffrn_reflns_theta_max 27.49 _reflns_number_total 1720 _reflns_number_gt 1319 _reflns_threshold_expression >2\s(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' #Although determined using DirAx, the cell is refined in the HKL #package during data reduction _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^ > 2\s(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^+0.2370P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_number_reflns 1720 _refine_ls_number_parameters 182 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0716 _refine_ls_R_factor_gt 0.0472 _refine_ls_wR_factor_ref 0.1128 _refine_ls_wR_factor_gt 0.1007 _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_restrained_S_all 1.041 _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 C11 C 0.08611(13) 0.28442(18) 0.7333(8) 0.0204(6) Uani 1 1 d . . . C12 C 0.02731(13) 0.30197(18) 0.6087(8) 0.0235(7) Uani 1 1 d . . . C13 C 0.01601(13) 0.38105(18) 0.4435(8) 0.0234(7) Uani 1 1 d . . . H13 H -0.0235 0.3920 0.3528 0.028 Uiso 1 1 calc R . . C14 C 0.06134(13) 0.44441(18) 0.4086(8) 0.0244(7) Uani 1 1 d . . . H14 H 0.0529 0.4984 0.2948 0.029 Uiso 1 1 calc R . . C15 C 0.11911(13) 0.42898(18) 0.5401(8) 0.0215(7) Uani 1 1 d . . . C16 C 0.13134(13) 0.34927(18) 0.6980(8) 0.0221(7) Uani 1 1 d . . . H16 H 0.1712 0.3384 0.7841 0.027 Uiso 1 1 calc R . . C17 C 0.09931(13) 0.19816(18) 0.9032(8) 0.0228(7) Uani 1 1 d . . . C18 C 0.15587(14) 0.5709(2) 0.3599(10) 0.0342(9) Uani 1 1 d . . . H18A H 0.1221 0.6017 0.4716 0.051 Uiso 1 1 calc R . . H18B H 0.1450 0.5597 0.1255 0.051 Uiso 1 1 calc R . . H18C H 0.1928 0.6078 0.3693 0.051 Uiso 1 1 calc R . . O11 O 0.15450(8) 0.17863(12) 0.9782(6) 0.0255(5) Uani 1 1 d . . . O12 O 0.05532(9) 0.14603(12) 0.9603(7) 0.0285(5) Uani 1 1 d . . . O13 O -0.01923(8) 0.24291(13) 0.6500(7) 0.0289(5) Uani 1 1 d . . . H13A H -0.0057 0.1964 0.7394 0.043 Uiso 1 1 d R . . O14 O 0.16717(9) 0.48859(12) 0.5246(6) 0.0303(6) Uani 1 1 d . . . C21 C 0.30107(13) 0.48114(18) -0.0673(9) 0.0249(7) Uani 1 1 d . . . H21 H 0.2634 0.5065 -0.1375 0.030 Uiso 1 1 calc R . . C22 C 0.30065(13) 0.40509(19) 0.1139(9) 0.0250(7) Uani 1 1 d . . . H22 H 0.2628 0.3782 0.1724 0.030 Uiso 1 1 calc R . . C23 C 0.35634(13) 0.36569(18) 0.2162(8) 0.0211(7) Uani 1 1 d . . . C24 C 0.41102(13) 0.41106(18) 0.1299(8) 0.0224(7) Uani 1 1 d . . . H24 H 0.4495 0.3885 0.2008 0.027 Uiso 1 1 calc R . . C25 C 0.40820(12) 0.48667(18) -0.0540(9) 0.0237(7) Uani 1 1 d . . . H25 H 0.4451 0.5157 -0.1165 0.028 Uiso 1 1 calc R . . N21 N 0.35419(11) 0.52140(16) -0.1498(7) 0.0249(6) Uani 1 1 d . . . H21A H 0.3535 0.5708 -0.2671 0.030 Uiso 1 1 d R . . N22 N 0.35757(11) 0.29014(15) 0.3879(7) 0.0259(6) Uani 1 1 d . . . H22A H 0.3231 0.2633 0.4409 0.031 Uiso 1 1 d R . . H22B H 0.3928 0.2669 0.4487 0.031 Uiso 1 1 d R . . O31 O 0.24161(8) 0.20418(12) 0.4717(7) 0.0293(5) Uani 1 1 d . . . H31A H 0.2141 0.1960 0.2869 0.044 Uiso 1 1 d R . . H31B H 0.2191 0.2080 0.6249 0.044 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 C11 0.0198(15) 0.0222(14) 0.0191(15) -0.0007(14) 0.0008(13) 0.0020(12) C12 0.0213(15) 0.0267(15) 0.0227(17) -0.0038(15) 0.0007(14) -0.0015(12) C13 0.0197(15) 0.0285(14) 0.0221(16) -0.0023(15) -0.0037(14) 0.0059(12) C14 0.0263(16) 0.0235(14) 0.0233(16) -0.0007(15) -0.0020(15) 0.0044(13) C15 0.0199(15) 0.0213(14) 0.0232(16) -0.0018(13) 0.0028(13) -0.0030(12) C16 0.0184(15) 0.0258(15) 0.0221(16) -0.0038(14) -0.0013(13) 0.0017(12) C17 0.0229(16) 0.0250(14) 0.0203(17) -0.0031(14) 0.0012(14) -0.0004(12) C18 0.0351(19) 0.0290(16) 0.038(2) 0.0057(17) 0.0015(17) -0.0040(14) O11 0.0190(10) 0.0287(10) 0.0287(12) 0.0066(11) -0.0026(10) 0.0007(8) O12 0.0214(11) 0.0272(10) 0.0369(13) 0.0031(12) 0.0026(12) -0.0039(9) O13 0.0185(11) 0.0266(10) 0.0415(14) 0.0059(11) -0.0039(11) -0.0041(9) O14 0.0249(11) 0.0239(10) 0.0421(15) 0.0058(11) -0.0020(11) -0.0045(8) C21 0.0218(15) 0.0285(14) 0.0244(17) -0.0001(16) 0.0002(15) 0.0019(12) C22 0.0187(15) 0.0271(15) 0.0292(17) -0.0022(15) 0.0013(15) -0.0005(12) C23 0.0205(16) 0.0227(14) 0.0201(16) -0.0009(14) -0.0009(13) -0.0006(12) C24 0.0174(15) 0.0251(14) 0.0247(16) -0.0022(13) -0.0014(14) 0.0017(12) C25 0.0176(14) 0.0278(15) 0.0256(16) -0.0002(15) 0.0025(14) -0.0023(12) N21 0.0292(15) 0.0220(12) 0.0235(15) 0.0018(12) -0.0004(12) 0.0002(11) N22 0.0190(13) 0.0261(13) 0.0325(17) 0.0070(13) -0.0015(12) 0.0002(10) O31 0.0203(10) 0.0367(11) 0.0310(12) 0.0013(12) 0.0000(11) -0.0021(8) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 C11 C16 1.397(4) . ? C11 C12 1.404(4) . ? C11 C17 1.494(4) . ? C12 O13 1.362(3) . ? C12 C13 1.384(4) . ? C13 C14 1.383(4) . ? C13 H13 0.9500 . ? C14 C15 1.387(4) . ? C14 H14 0.9500 . ? C15 C16 1.382(4) . ? C15 O14 1.384(3) . ? C16 H16 0.9500 . ? C17 O12 1.262(3) . ? C17 O11 1.277(3) . ? C18 O14 1.425(4) . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? O13 H13A 0.8402 . ? C21 N21 1.351(4) . ? C21 C22 1.355(4) . ? C21 H21 0.9500 . ? C22 C23 1.415(4) . ? C22 H22 0.9500 . ? C23 N22 1.329(4) . ? C23 C24 1.419(4) . ? C24 C25 1.357(4) . ? C24 H24 0.9500 . ? C25 N21 1.347(4) . ? C25 H25 0.9500 . ? N21 H21A 0.8793 . ? N22 H22A 0.8808 . ? N22 H22B 0.8804 . ? O31 H31A 0.9600 . ? O31 H31B 0.7873 . ? 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 C16 C11 C12 118.7(3) . . ? C16 C11 C17 121.2(3) . . ? C12 C11 C17 120.1(2) . . ? O13 C12 C13 119.1(3) . . ? O13 C12 C11 121.2(3) . . ? C13 C12 C11 119.6(3) . . ? C14 C13 C12 120.9(3) . . ? C14 C13 H13 119.5 . . ? C12 C13 H13 119.5 . . ? C13 C14 C15 119.9(3) . . ? C13 C14 H14 120.0 . . ? C15 C14 H14 120.0 . . ? C16 C15 O14 115.9(3) . . ? C16 C15 C14 119.6(3) . . ? O14 C15 C14 124.5(3) . . ? C15 C16 C11 121.1(3) . . ? C15 C16 H16 119.5 . . ? C11 C16 H16 119.5 . . ? O12 C17 O11 122.3(3) . . ? O12 C17 C11 118.4(2) . . ? O11 C17 C11 119.3(2) . . ? O14 C18 H18A 109.5 . . ? O14 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? O14 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C12 O13 H13A 109.5 . . ? C15 O14 C18 117.0(2) . . ? N21 C21 C22 121.0(3) . . ? N21 C21 H21 119.5 . . ? C22 C21 H21 119.5 . . ? C21 C22 C23 120.2(3) . . ? C21 C22 H22 119.9 . . ? C23 C22 H22 119.9 . . ? N22 C23 C22 121.7(3) . . ? N22 C23 C24 121.4(3) . . ? C22 C23 C24 116.9(3) . . ? C25 C24 C23 119.8(3) . . ? C25 C24 H24 120.1 . . ? C23 C24 H24 120.1 . . ? N21 C25 C24 121.3(3) . . ? N21 C25 H25 119.3 . . ? C24 C25 H25 119.3 . . ? C25 N21 C21 120.7(3) . . ? C25 N21 H21A 119.7 . . ? C21 N21 H21A 119.7 . . ? C23 N22 H22A 120.0 . . ? C23 N22 H22B 120.0 . . ? H22A N22 H22B 120.0 . . ? H31A O31 H31B 102.4 . . ? 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 N21 H21A O11 0.88 1.92 2.802(3) 175.8 4_553 N21 H21A O12 0.88 2.54 3.140(3) 126.4 4_553 N22 H22B O13 0.88 2.09 2.932(3) 160.0 3 O31 H31A O11 0.96 1.81 2.767(3) 172.6 1_554 O31 H31B O11 0.79 2.04 2.804(3) 162.2 . O31 H31B O11 0.79 2.04 2.804(3) 162.2 . _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.223 _refine_diff_density_min -0.287 _refine_diff_density_rms 0.058 # Attachment '4-aminopyridinium-5-methylsalicylate.cif' data_4-aminopyridinium_5-methylsalicylate _database_code_depnum_ccdc_archive 'CCDC 888896' #TrackingRef '4-aminopyridinium-5-methylsalicylate.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 4-aminopyridinium_5-methylsalicylate ; _chemical_name_common 4-aminopyridinium_5-methylsalicylate _chemical_melting_point ? _chemical_formula_moiety 'C8 H7 O3, C5 H7 N2' _chemical_formula_sum 'C13 H14 N2 O3' _chemical_formula_weight 246.26 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 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 P21/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 13.5414(3) _cell_length_b 15.0598(2) _cell_length_c 13.0106(2) _cell_angle_alpha 90.00 _cell_angle_beta 108.6450(10) _cell_angle_gamma 90.00 _cell_volume 2514.01(8) _cell_formula_units_Z 8 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 16131 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.58 _exptl_crystal_size_mid 0.48 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.301 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1040 _exptl_absorpt_coefficient_mu 0.094 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9476 _exptl_absorpt_correction_T_max 0.9981 _exptl_absorpt_process_details 'SADABS 2007/2 (Sheldrick, G.M., 2007)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius Roper CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 35446 _diffrn_reflns_av_R_equivalents 0.0413 _diffrn_reflns_av_sigmaI/netI 0.0300 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.14 _diffrn_reflns_theta_max 27.50 _reflns_number_total 5742 _reflns_number_gt 4768 _reflns_threshold_expression >2\s(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' #Although determined using DirAx, the cell is refined in the HKL #package during data reduction _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^ > 2\s(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^)+(0.0438P)^2^+1.2805P] 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 5742 _refine_ls_number_parameters 328 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0553 _refine_ls_R_factor_gt 0.0432 _refine_ls_wR_factor_ref 0.1071 _refine_ls_wR_factor_gt 0.1003 _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_restrained_S_all 1.029 _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 C11 C 0.81467(10) 0.42613(8) 0.52684(10) 0.0169(3) Uani 1 1 d . . . C12 C 0.75248(11) 0.35886(9) 0.46404(11) 0.0213(3) Uani 1 1 d . . . C13 C 0.71744(12) 0.28954(10) 0.51461(12) 0.0269(3) Uani 1 1 d . . . H13 H 0.6746 0.2443 0.4719 0.032 Uiso 1 1 calc R . . C14 C 0.74468(11) 0.28621(10) 0.62645(12) 0.0246(3) Uani 1 1 d . . . H14 H 0.7206 0.2383 0.6597 0.030 Uiso 1 1 calc R . . C15 C 0.80705(11) 0.35210(9) 0.69149(11) 0.0215(3) Uani 1 1 d . . . C16 C 0.84025(10) 0.42128(9) 0.64006(10) 0.0185(3) Uani 1 1 d . . . H16 H 0.8818 0.4670 0.6831 0.022 Uiso 1 1 calc R . . C17 C 0.85365(10) 0.50210(8) 0.47588(10) 0.0174(3) Uani 1 1 d . . . C18 C 0.83743(13) 0.34730(10) 0.81356(11) 0.0295(3) Uani 1 1 d . . . H18A H 0.8490 0.2852 0.8368 0.044 Uiso 1 1 calc R . . H18B H 0.7814 0.3723 0.8372 0.044 Uiso 1 1 calc R . . H18C H 0.9016 0.3813 0.8460 0.044 Uiso 1 1 calc R . . O12 O 0.82934(8) 0.50264(6) 0.37186(7) 0.0209(2) Uani 1 1 d . . . O11 O 0.90590(8) 0.56284(6) 0.53351(8) 0.0229(2) Uani 1 1 d . . . O13 O 0.72482(9) 0.35762(7) 0.35385(8) 0.0302(3) Uani 1 1 d . . . H13A H 0.7497 0.4024 0.3325 0.045 Uiso 1 1 calc R . . C21 C 0.89209(12) 0.68994(10) 0.23814(14) 0.0290(3) Uani 1 1 d . . . H21A H 0.8458 0.6523 0.1861 0.035 Uiso 1 1 calc R . . C22 C 0.92469(11) 0.76685(9) 0.20532(12) 0.0231(3) Uani 1 1 d . . . H22 H 0.9000 0.7831 0.1309 0.028 Uiso 1 1 calc R . . C23 C 0.99542(10) 0.82321(9) 0.28138(11) 0.0181(3) Uani 1 1 d . . . C24 C 1.02824(11) 0.79625(9) 0.39134(11) 0.0233(3) Uani 1 1 d . . . H24 H 1.0755 0.8317 0.4455 0.028 Uiso 1 1 calc R . . C25 C 0.99081(12) 0.71794(11) 0.41868(13) 0.0301(4) Uani 1 1 d . . . H25 H 1.0122 0.6998 0.4925 0.036 Uiso 1 1 calc R . . N21 N 0.92423(10) 0.66637(8) 0.34281(12) 0.0317(3) Uani 1 1 d . . . H21 H 0.9016 0.6165 0.3625 0.038 Uiso 1 1 calc R . . N22 N 1.02905(9) 0.89809(8) 0.24982(10) 0.0231(3) Uani 1 1 d . . . H22A H 1.0730 0.9325 0.2979 0.028 Uiso 1 1 calc R . . H22B H 1.0074 0.9133 0.1809 0.028 Uiso 1 1 calc R . . C31 C 0.65899(10) 0.48656(8) -0.05447(10) 0.0170(3) Uani 1 1 d . . . C32 C 0.75831(11) 0.52133(9) -0.00193(11) 0.0204(3) Uani 1 1 d . . . C33 C 0.80996(12) 0.56907(10) -0.06125(14) 0.0296(3) Uani 1 1 d . . . H33 H 0.8771 0.5932 -0.0260 0.036 Uiso 1 1 calc R . . C34 C 0.76304(13) 0.58116(11) -0.17134(14) 0.0329(4) Uani 1 1 d . . . H34 H 0.7988 0.6141 -0.2108 0.040 Uiso 1 1 calc R . . C35 C 0.66451(13) 0.54641(10) -0.22659(12) 0.0282(3) Uani 1 1 d . . . C36 C 0.61402(11) 0.49960(9) -0.16597(11) 0.0212(3) Uani 1 1 d . . . H36 H 0.5468 0.4757 -0.2015 0.025 Uiso 1 1 calc R . . C37 C 0.60300(10) 0.43637(8) 0.00924(10) 0.0155(3) Uani 1 1 d . . . C38 C 0.61484(16) 0.55826(13) -0.34736(13) 0.0432(4) Uani 1 1 d . . . H38A H 0.6615 0.5928 -0.3761 0.065 Uiso 0.50 1 calc PR . . H38B H 0.5485 0.5898 -0.3618 0.065 Uiso 0.50 1 calc PR . . H38C H 0.6023 0.4999 -0.3825 0.065 Uiso 0.50 1 calc PR . . H38D H 0.5467 0.5289 -0.3709 0.065 Uiso 0.50 1 calc PR . . H38E H 0.6597 0.5319 -0.3852 0.065 Uiso 0.50 1 calc PR . . H38F H 0.6059 0.6217 -0.3645 0.065 Uiso 0.50 1 calc PR . . O32 O 0.64717(7) 0.42898(6) 0.11099(7) 0.0202(2) Uani 1 1 d . . . O31 O 0.51535(7) 0.40271(6) -0.04013(7) 0.0189(2) Uani 1 1 d . . . O33 O 0.80475(8) 0.50946(7) 0.10676(8) 0.0245(2) Uani 1 1 d . . . H33A H 0.7640 0.4819 0.1324 0.037 Uiso 1 1 calc R . . C41 C 0.50158(11) 0.28373(9) 0.19020(11) 0.0217(3) Uani 1 1 d . . . H41A H 0.5624 0.3179 0.2236 0.026 Uiso 1 1 calc R . . C42 C 0.47099(11) 0.22095(9) 0.24923(11) 0.0210(3) Uani 1 1 d . . . H42 H 0.5103 0.2118 0.3233 0.025 Uiso 1 1 calc R . . C43 C 0.38076(10) 0.16950(9) 0.20021(10) 0.0184(3) Uani 1 1 d . . . C44 C 0.32418(11) 0.18769(9) 0.09024(11) 0.0203(3) Uani 1 1 d . . . H44 H 0.2621 0.1559 0.0544 0.024 Uiso 1 1 calc R . . C45 C 0.35987(11) 0.25130(9) 0.03654(11) 0.0216(3) Uani 1 1 d . . . H45 H 0.3222 0.2630 -0.0374 0.026 Uiso 1 1 calc R . . N41 N 0.44683(9) 0.29805(7) 0.08517(9) 0.0203(2) Uani 1 1 d . . . H41 H 0.4682 0.3384 0.0481 0.024 Uiso 1 1 calc R . . N42 N 0.35027(9) 0.10623(8) 0.25631(9) 0.0222(3) Uani 1 1 d . . . H42A H 0.3866 0.0963 0.3246 0.027 Uiso 1 1 calc R . . H42B H 0.2940 0.0747 0.2248 0.027 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 C11 0.0161(6) 0.0160(6) 0.0180(6) 0.0008(5) 0.0047(5) 0.0029(5) C12 0.0203(7) 0.0212(7) 0.0186(6) 0.0006(5) 0.0007(5) 0.0010(5) C13 0.0244(7) 0.0226(7) 0.0288(7) 0.0004(6) 0.0015(6) -0.0067(6) C14 0.0225(7) 0.0228(7) 0.0297(7) 0.0056(6) 0.0100(6) -0.0016(6) C15 0.0239(7) 0.0208(7) 0.0224(7) 0.0030(5) 0.0111(6) 0.0048(5) C16 0.0205(7) 0.0172(6) 0.0180(6) -0.0016(5) 0.0066(5) 0.0008(5) C17 0.0172(6) 0.0176(6) 0.0178(6) 0.0023(5) 0.0061(5) 0.0047(5) C18 0.0438(9) 0.0265(8) 0.0227(7) 0.0039(6) 0.0170(7) 0.0025(7) O12 0.0247(5) 0.0219(5) 0.0159(4) 0.0028(4) 0.0062(4) 0.0033(4) O11 0.0269(5) 0.0188(5) 0.0212(5) 0.0005(4) 0.0053(4) -0.0041(4) O13 0.0407(7) 0.0258(5) 0.0165(5) 0.0006(4) -0.0016(4) -0.0077(5) C21 0.0234(7) 0.0214(7) 0.0447(9) -0.0039(6) 0.0144(7) -0.0018(6) C22 0.0208(7) 0.0222(7) 0.0271(7) -0.0040(6) 0.0085(6) -0.0009(5) C23 0.0163(6) 0.0179(6) 0.0219(6) 0.0005(5) 0.0085(5) 0.0019(5) C24 0.0244(7) 0.0250(7) 0.0216(7) 0.0017(5) 0.0089(6) 0.0054(6) C25 0.0314(8) 0.0338(8) 0.0330(8) 0.0153(7) 0.0212(7) 0.0171(7) N21 0.0274(7) 0.0191(6) 0.0563(9) 0.0084(6) 0.0241(6) 0.0016(5) N22 0.0240(6) 0.0209(6) 0.0219(6) 0.0028(5) 0.0035(5) -0.0046(5) C31 0.0183(6) 0.0141(6) 0.0203(6) 0.0006(5) 0.0084(5) 0.0019(5) C32 0.0188(7) 0.0166(6) 0.0267(7) -0.0015(5) 0.0083(5) 0.0016(5) C33 0.0239(8) 0.0248(7) 0.0437(9) -0.0008(6) 0.0158(7) -0.0052(6) C34 0.0359(9) 0.0280(8) 0.0444(9) 0.0088(7) 0.0261(8) -0.0011(7) C35 0.0344(8) 0.0279(8) 0.0282(7) 0.0090(6) 0.0181(7) 0.0056(6) C36 0.0218(7) 0.0214(7) 0.0215(6) 0.0031(5) 0.0085(5) 0.0009(5) C37 0.0172(6) 0.0130(6) 0.0162(6) -0.0001(5) 0.0053(5) 0.0019(5) C38 0.0542(12) 0.0521(11) 0.0289(8) 0.0174(8) 0.0214(8) 0.0079(9) O32 0.0219(5) 0.0217(5) 0.0151(4) 0.0020(4) 0.0033(4) 0.0006(4) O31 0.0193(5) 0.0195(5) 0.0171(4) -0.0001(4) 0.0049(4) -0.0041(4) O33 0.0188(5) 0.0265(5) 0.0252(5) -0.0028(4) 0.0027(4) -0.0020(4) C41 0.0193(7) 0.0223(7) 0.0226(6) -0.0005(5) 0.0055(5) -0.0039(5) C42 0.0192(7) 0.0233(7) 0.0185(6) 0.0019(5) 0.0029(5) -0.0022(5) C43 0.0170(6) 0.0179(6) 0.0201(6) 0.0016(5) 0.0059(5) 0.0004(5) C44 0.0174(6) 0.0215(7) 0.0192(6) 0.0007(5) 0.0020(5) -0.0040(5) C45 0.0229(7) 0.0219(7) 0.0180(6) 0.0027(5) 0.0036(5) -0.0008(5) N41 0.0219(6) 0.0186(5) 0.0211(5) 0.0033(4) 0.0079(5) -0.0029(5) N42 0.0183(6) 0.0252(6) 0.0197(5) 0.0067(5) 0.0015(4) -0.0062(5) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 C11 C12 1.4011(19) . ? C11 C16 1.4031(17) . ? C11 C17 1.5004(18) . ? C12 O13 1.3611(16) . ? C12 C13 1.395(2) . ? C13 C14 1.383(2) . ? C13 H13 0.9500 . ? C14 C15 1.399(2) . ? C14 H14 0.9500 . ? C15 C16 1.3885(19) . ? C15 C18 1.5096(18) . ? C16 H16 0.9500 . ? C17 O11 1.2491(16) . ? C17 O12 1.2866(15) . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? O13 H13A 0.8400 . ? C21 N21 1.338(2) . ? C21 C22 1.356(2) . ? C21 H21A 0.9500 . ? C22 C23 1.4181(19) . ? C22 H22 0.9500 . ? C23 N22 1.3294(17) . ? C23 C24 1.4151(18) . ? C24 C25 1.375(2) . ? C24 H24 0.9500 . ? C25 N21 1.350(2) . ? C25 H25 0.9500 . ? N21 H21 0.8800 . ? N22 H22A 0.8800 . ? N22 H22B 0.8800 . ? C31 C36 1.3961(18) . ? C31 C32 1.4009(19) . ? C31 C37 1.4950(17) . ? C32 O33 1.3632(16) . ? C32 C33 1.395(2) . ? C33 C34 1.381(2) . ? C33 H33 0.9500 . ? C34 C35 1.399(2) . ? C34 H34 0.9500 . ? C35 C36 1.3897(19) . ? C35 C38 1.509(2) . ? C36 H36 0.9500 . ? C37 O31 1.2613(16) . ? C37 O32 1.2714(15) . ? C38 H38A 0.9800 . ? C38 H38B 0.9800 . ? C38 H38C 0.9800 . ? C38 H38D 0.9800 . ? C38 H38E 0.9800 . ? C38 H38F 0.9800 . ? O33 H33A 0.8400 . ? C41 N41 1.3475(17) . ? C41 C42 1.3633(19) . ? C41 H41A 0.9500 . ? C42 C43 1.4148(19) . ? C42 H42 0.9500 . ? C43 N42 1.3432(17) . ? C43 C44 1.4171(18) . ? C44 C45 1.3622(19) . ? C44 H44 0.9500 . ? C45 N41 1.3440(18) . ? C45 H45 0.9500 . ? N41 H41 0.8800 . ? N42 H42A 0.8800 . ? N42 H42B 0.8800 . ? 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 C12 C11 C16 118.38(12) . . ? C12 C11 C17 121.63(11) . . ? C16 C11 C17 119.99(11) . . ? O13 C12 C13 117.76(12) . . ? O13 C12 C11 122.40(12) . . ? C13 C12 C11 119.83(12) . . ? C14 C13 C12 120.45(13) . . ? C14 C13 H13 119.8 . . ? C12 C13 H13 119.8 . . ? C13 C14 C15 121.13(13) . . ? C13 C14 H14 119.4 . . ? C15 C14 H14 119.4 . . ? C16 C15 C14 117.81(12) . . ? C16 C15 C18 121.44(13) . . ? C14 C15 C18 120.74(13) . . ? C15 C16 C11 122.39(12) . . ? C15 C16 H16 118.8 . . ? C11 C16 H16 118.8 . . ? O11 C17 O12 122.15(12) . . ? O11 C17 C11 120.33(11) . . ? O12 C17 C11 117.50(11) . . ? C15 C18 H18A 109.5 . . ? C15 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C15 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C12 O13 H13A 109.5 . . ? N21 C21 C22 120.95(15) . . ? N21 C21 H21A 119.5 . . ? C22 C21 H21A 119.5 . . ? C21 C22 C23 120.44(14) . . ? C21 C22 H22 119.8 . . ? C23 C22 H22 119.8 . . ? N22 C23 C24 121.85(13) . . ? N22 C23 C22 120.92(12) . . ? C24 C23 C22 117.23(12) . . ? C25 C24 C23 119.02(14) . . ? C25 C24 H24 120.5 . . ? C23 C24 H24 120.5 . . ? N21 C25 C24 121.32(14) . . ? N21 C25 H25 119.3 . . ? C24 C25 H25 119.3 . . ? C21 N21 C25 121.03(13) . . ? C21 N21 H21 119.5 . . ? C25 N21 H21 119.5 . . ? C23 N22 H22A 120.0 . . ? C23 N22 H22B 120.0 . . ? H22A N22 H22B 120.0 . . ? C36 C31 C32 119.09(12) . . ? C36 C31 C37 121.14(12) . . ? C32 C31 C37 119.77(12) . . ? O33 C32 C33 119.65(13) . . ? O33 C32 C31 120.64(12) . . ? C33 C32 C31 119.70(13) . . ? C34 C33 C32 119.73(14) . . ? C34 C33 H33 120.1 . . ? C32 C33 H33 120.1 . . ? C33 C34 C35 122.05(14) . . ? C33 C34 H34 119.0 . . ? C35 C34 H34 119.0 . . ? C36 C35 C34 117.36(14) . . ? C36 C35 C38 120.97(15) . . ? C34 C35 C38 121.68(14) . . ? C35 C36 C31 122.06(14) . . ? C35 C36 H36 119.0 . . ? C31 C36 H36 119.0 . . ? O31 C37 O32 123.23(12) . . ? O31 C37 C31 118.84(11) . . ? O32 C37 C31 117.92(11) . . ? C35 C38 H38A 109.5 . . ? C35 C38 H38B 109.5 . . ? H38A C38 H38B 109.5 . . ? C35 C38 H38C 109.5 . . ? H38A C38 H38C 109.5 . . ? H38B C38 H38C 109.5 . . ? C35 C38 H38D 109.5 . . ? H38A C38 H38D 141.1 . . ? H38B C38 H38D 56.3 . . ? H38C C38 H38D 56.3 . . ? C35 C38 H38E 109.5 . . ? H38A C38 H38E 56.3 . . ? H38B C38 H38E 141.1 . . ? H38C C38 H38E 56.3 . . ? H38D C38 H38E 109.5 . . ? C35 C38 H38F 109.5 . . ? H38A C38 H38F 56.3 . . ? H38B C38 H38F 56.3 . . ? H38C C38 H38F 141.1 . . ? H38D C38 H38F 109.5 . . ? H38E C38 H38F 109.5 . . ? C32 O33 H33A 109.5 . . ? N41 C41 C42 120.97(13) . . ? N41 C41 H41A 119.5 . . ? C42 C41 H41A 119.5 . . ? C41 C42 C43 120.00(12) . . ? C41 C42 H42 120.0 . . ? C43 C42 H42 120.0 . . ? N42 C43 C42 120.98(12) . . ? N42 C43 C44 121.66(12) . . ? C42 C43 C44 117.36(12) . . ? C45 C44 C43 119.19(12) . . ? C45 C44 H44 120.4 . . ? C43 C44 H44 120.4 . . ? N41 C45 C44 121.88(12) . . ? N41 C45 H45 119.1 . . ? C44 C45 H45 119.1 . . ? C45 N41 C41 120.58(12) . . ? C45 N41 H41 119.7 . . ? C41 N41 H41 119.7 . . ? C43 N42 H42A 120.0 . . ? C43 N42 H42B 120.0 . . ? H42A N42 H42B 120.0 . . ? 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 N22 H22A O33 0.88 2.08 2.9452(15) 169.0 2_755 N22 H22B O11 0.88 2.00 2.8368(15) 157.8 4_575 N42 H42A O31 0.88 2.04 2.8712(15) 156.3 4_566 N42 H42B O12 0.88 2.05 2.9217(15) 170.2 2_645 O13 H13A O12 0.84 1.83 2.5721(14) 146.3 . N21 H21 O12 0.88 2.00 2.8608(16) 166.9 . N21 H21 O11 0.88 2.35 3.0070(16) 131.5 . O33 H33A O32 0.84 1.71 2.4699(14) 148.7 . N41 H41 O31 0.88 1.77 2.6400(14) 169.5 . _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.255 _refine_diff_density_min -0.376 _refine_diff_density_rms 0.044 # Attachment '4-aminopyridinium-5-nitrosalicylate.cif' data_4-aminopyridinium_5-nitrosalicylate _database_code_depnum_ccdc_archive 'CCDC 888897' #TrackingRef '4-aminopyridinium-5-nitrosalicylate.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 4-aminopyridinium 5-nitrosalicylate ; _chemical_name_common '4-aminopyridinium 5-nitrosalicylate' _chemical_melting_point ? _chemical_formula_moiety 'C7 H4 N O5, C5 H7 N2' _chemical_formula_sum 'C12 H11 N3 O5' _chemical_formula_weight 277.24 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M P212121 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 3.77770(10) _cell_length_b 12.5991(5) _cell_length_c 25.0825(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1193.82(7) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 16932 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.542 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 576 _exptl_absorpt_coefficient_mu 0.123 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9583 _exptl_absorpt_correction_T_max 0.9903 _exptl_absorpt_process_details 'SADABS 2007/2 (Sheldrick, G.M., 2007)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator '10cm confocal mirrors' _diffrn_measurement_device_type 'Bruker-Nonius APEX II CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean '4096x4096pixels / 62x62mm' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9886 _diffrn_reflns_av_R_equivalents 0.0564 _diffrn_reflns_av_sigmaI/netI 0.0449 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_theta_min 2.92 _diffrn_reflns_theta_max 27.48 _reflns_number_total 1609 _reflns_number_gt 1336 _reflns_threshold_expression >2\s(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' #Although determined using DirAx, the cell is refined in the HKL #package during data reduction _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^ > 2\s(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^)+(0.0512P)^2^+0.6870P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_number_reflns 1609 _refine_ls_number_parameters 181 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0683 _refine_ls_R_factor_gt 0.0525 _refine_ls_wR_factor_ref 0.1218 _refine_ls_wR_factor_gt 0.1131 _refine_ls_goodness_of_fit_ref 1.109 _refine_ls_restrained_S_all 1.109 _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 C11 C 0.9455(8) 0.4511(2) 0.08900(11) 0.0164(6) Uani 1 1 d . . . C12 C 0.9401(9) 0.4491(2) 0.03269(12) 0.0191(6) Uani 1 1 d . . . C13 C 0.7949(9) 0.5354(2) 0.00461(12) 0.0219(7) Uani 1 1 d . . . H13 H 0.7966 0.5349 -0.0333 0.026 Uiso 1 1 calc R . . C14 C 0.6511(9) 0.6200(2) 0.03113(12) 0.0222(7) Uani 1 1 d . . . H14 H 0.5529 0.6780 0.0120 0.027 Uiso 1 1 calc R . . C15 C 0.6514(8) 0.6196(2) 0.08677(12) 0.0189(6) Uani 1 1 d . . . C16 C 0.7970(8) 0.5365(2) 0.11540(12) 0.0187(6) Uani 1 1 d . . . H16 H 0.7949 0.5381 0.1533 0.022 Uiso 1 1 calc R . . C17 C 1.1197(9) 0.3630(2) 0.11985(12) 0.0196(6) Uani 1 1 d . . . O11 O 1.1342(7) 0.36718(16) 0.16905(8) 0.0284(5) Uani 1 1 d . . . O12 O 1.2485(6) 0.28737(15) 0.09190(8) 0.0246(5) Uani 1 1 d . . . O13 O 1.0718(7) 0.36792(16) 0.00494(8) 0.0256(5) Uani 1 1 d . . . H13A H 1.1684 0.3247 0.0259 0.038 Uiso 1 1 d R . . O14 O 0.3613(7) 0.78108(16) 0.08836(9) 0.0356(6) Uani 1 1 d . . . O15 O 0.4694(7) 0.70417(17) 0.16391(9) 0.0332(6) Uani 1 1 d . . . N11 N 0.4852(7) 0.70696(18) 0.11466(10) 0.0229(6) Uani 1 1 d . . . C21 C 0.5942(9) 0.1368(2) 0.20648(13) 0.0242(7) Uani 1 1 d . . . H21A H 0.4893 0.1910 0.2275 0.029 Uiso 1 1 calc R . . C22 C 0.7295(9) 0.0493(2) 0.23070(12) 0.0198(7) Uani 1 1 d . . . H22 H 0.7196 0.0426 0.2684 0.024 Uiso 1 1 calc R . . C23 C 0.8856(8) -0.0323(2) 0.19951(12) 0.0194(6) Uani 1 1 d . . . C24 C 0.8944(9) -0.0174(2) 0.14360(12) 0.0220(7) Uani 1 1 d . . . H24 H 0.9963 -0.0698 0.1211 0.026 Uiso 1 1 calc R . . C25 C 0.7551(9) 0.0730(2) 0.12228(12) 0.0236(7) Uani 1 1 d . . . H25 H 0.7633 0.0831 0.0848 0.028 Uiso 1 1 calc R . . N21 N 0.6064(8) 0.14805(18) 0.15312(10) 0.0249(6) Uani 1 1 d . . . H21 H 0.5160 0.2052 0.1383 0.030 Uiso 1 1 d R . . N22 N 1.0201(8) -0.11979(18) 0.22215(10) 0.0243(6) Uani 1 1 d . . . H22A H 1.1165 -0.1694 0.2022 0.029 Uiso 1 1 d R . . H22B H 1.0122 -0.1276 0.2570 0.029 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 C11 0.0169(16) 0.0142(12) 0.0181(14) 0.0002(10) 0.0015(13) -0.0028(12) C12 0.0186(17) 0.0164(13) 0.0224(15) -0.0004(11) 0.0006(13) 0.0002(12) C13 0.0273(18) 0.0246(14) 0.0140(14) 0.0018(11) -0.0010(13) 0.0014(13) C14 0.0240(19) 0.0163(13) 0.0264(16) 0.0033(11) -0.0031(14) 0.0000(13) C15 0.0198(17) 0.0129(12) 0.0239(15) -0.0016(11) 0.0017(14) -0.0005(12) C16 0.0196(17) 0.0168(12) 0.0198(14) -0.0013(11) 0.0006(13) -0.0012(12) C17 0.0209(16) 0.0162(12) 0.0217(15) 0.0022(11) 0.0006(13) 0.0006(13) O11 0.0394(15) 0.0258(10) 0.0200(11) 0.0024(9) -0.0015(11) 0.0069(11) O12 0.0308(13) 0.0171(9) 0.0259(11) -0.0004(8) 0.0007(10) 0.0062(10) O13 0.0367(14) 0.0206(9) 0.0195(11) -0.0010(8) 0.0008(10) 0.0056(11) O14 0.0459(16) 0.0199(10) 0.0410(14) 0.0024(10) -0.0011(13) 0.0116(11) O15 0.0435(16) 0.0272(11) 0.0290(12) -0.0047(10) 0.0059(12) 0.0100(12) N11 0.0225(15) 0.0165(11) 0.0298(14) -0.0005(11) 0.0015(12) 0.0005(11) C21 0.0210(17) 0.0186(13) 0.0330(17) -0.0029(12) -0.0011(15) -0.0008(13) C22 0.0176(16) 0.0216(14) 0.0201(15) -0.0015(11) 0.0005(13) 0.0001(13) C23 0.0162(16) 0.0181(13) 0.0240(15) 0.0008(11) -0.0016(13) -0.0017(12) C24 0.0251(17) 0.0190(13) 0.0219(15) -0.0004(11) 0.0030(14) -0.0016(13) C25 0.0263(18) 0.0265(14) 0.0179(14) 0.0021(12) -0.0030(14) -0.0053(14) N21 0.0235(15) 0.0152(11) 0.0361(15) 0.0044(10) -0.0061(13) 0.0010(11) N22 0.0312(17) 0.0186(11) 0.0230(13) 0.0021(10) 0.0004(12) 0.0047(12) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 C11 C16 1.382(4) . ? C11 C12 1.413(4) . ? C11 C17 1.505(4) . ? C12 O13 1.334(3) . ? C12 C13 1.407(4) . ? C13 C14 1.369(4) . ? C14 C15 1.396(4) . ? C15 C16 1.384(4) . ? C15 N11 1.447(3) . ? C17 O11 1.236(3) . ? C17 O12 1.279(3) . ? O14 N11 1.235(3) . ? O15 N11 1.237(3) . ? C21 N21 1.347(4) . ? C21 C22 1.359(4) . ? C22 C23 1.420(4) . ? C23 N22 1.340(4) . ? C23 C24 1.415(4) . ? C24 C25 1.363(4) . ? C25 N21 1.345(4) . ? 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 C16 C11 C12 119.1(3) . . ? C16 C11 C17 120.4(3) . . ? C12 C11 C17 120.5(2) . . ? O13 C12 C13 118.5(3) . . ? O13 C12 C11 122.0(3) . . ? C13 C12 C11 119.5(3) . . ? C14 C13 C12 120.9(3) . . ? C13 C14 C15 118.9(3) . . ? C16 C15 C14 121.5(3) . . ? C16 C15 N11 119.8(3) . . ? C14 C15 N11 118.7(3) . . ? C11 C16 C15 120.1(3) . . ? O11 C17 O12 124.2(3) . . ? O11 C17 C11 120.1(3) . . ? O12 C17 C11 115.7(2) . . ? O14 N11 O15 122.4(2) . . ? O14 N11 C15 118.8(2) . . ? O15 N11 C15 118.8(2) . . ? N21 C21 C22 121.1(3) . . ? C21 C22 C23 119.8(3) . . ? N22 C23 C24 121.4(3) . . ? N22 C23 C22 121.3(3) . . ? C24 C23 C22 117.4(3) . . ? C25 C24 C23 119.4(3) . . ? N21 C25 C24 121.5(3) . . ? C25 N21 C21 120.8(3) . . ? 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 N21 H21 O12 0.88 1.86 2.696(3) 158.9 1_455 N22 H22A O15 0.88 2.29 3.152(3) 167.1 1_645 N22 H22B O11 0.88 1.94 2.795(3) 164.7 3_745 O13 H13A O12 0.84 1.75 2.497(3) 147.4 . _diffrn_measured_fraction_theta_max 0.976 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.976 _refine_diff_density_max 0.244 _refine_diff_density_min -0.264 _refine_diff_density_rms 0.061