####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_sergui _database_code_depnum_ccdc_archive 'CCDC 886323' #TrackingRef 'sergiu1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 4-Aminopyridinium 4-nitrophenolate 4-nitrophenol ; _chemical_name_common ; 4-Aminopyridinium 4-nitrophenolate 4-nitrophenol ; _chemical_melting_point ? _chemical_formula_moiety 'C12 H9 N2 O6, C5 H7 N2' _chemical_formula_sum 'C17 H16 N4 O6' _chemical_formula_weight 372.34 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 5.4942(4) _cell_length_b 15.1735(10) _cell_length_c 10.4980(7) _cell_angle_alpha 90.00 _cell_angle_beta 101.7070(10) _cell_angle_gamma 90.00 _cell_volume 856.97(10) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.09 _exptl_crystal_density_diffrn 1.443 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 388 _exptl_absorpt_coefficient_mu 0.112 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.337 _exptl_absorpt_correction_T_max 0.654 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 8252 _diffrn_reflns_av_R_equivalents 0.0157 _diffrn_reflns_av_sigmaI/netI 0.0186 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 1.98 _diffrn_reflns_theta_max 25.98 _reflns_number_total 3363 _reflns_number_gt 3283 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2005)' _computing_cell_refinement 'SAINTPlus, v. 6.2 (Bruker, 2001)' _computing_data_reduction 'SAINTPlus, v. 6.2 (Bruker, 2001)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0468P)^2^+0.0725P] 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 0.7(6) _refine_ls_number_reflns 3363 _refine_ls_number_parameters 260 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0249 _refine_ls_R_factor_gt 0.0241 _refine_ls_wR_factor_ref 0.0688 _refine_ls_wR_factor_gt 0.0681 _refine_ls_goodness_of_fit_ref 1.058 _refine_ls_restrained_S_all 1.058 _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 O1 O -0.19792(17) 0.89780(6) 0.94248(9) 0.0282(2) Uani 1 1 d . . . O2 O -0.37047(17) 0.85958(7) 0.74674(9) 0.0318(2) Uani 1 1 d . . . O3 O 0.55618(16) 0.61352(6) 0.83596(8) 0.02330(19) Uani 1 1 d . . . H1O3 H 0.532(4) 0.5775(15) 0.744(2) 0.065(6) Uiso 1 1 d . . . O4 O 1.18475(18) 0.20205(6) 0.57936(9) 0.0277(2) Uani 1 1 d . . . O5 O 1.38945(18) 0.25790(7) 0.75926(9) 0.0300(2) Uani 1 1 d . . . O6 O 0.52114(17) 0.52850(6) 0.63339(8) 0.0238(2) Uani 1 1 d . . . N1 N -0.20237(19) 0.85279(7) 0.84401(10) 0.0219(2) Uani 1 1 d . . . N2 N 1.2105(2) 0.25811(7) 0.66672(10) 0.0224(2) Uani 1 1 d . . . N3 N 0.23389(19) 0.55716(7) 0.39165(10) 0.0212(2) Uani 1 1 d . . . H1N3 H 0.357(3) 0.5623(11) 0.4602(16) 0.027(4) Uiso 1 1 d . . . N4 N -0.3452(2) 0.51998(8) 0.08127(11) 0.0229(2) Uani 1 1 d . . . H1N4 H -0.354(3) 0.5473(12) 0.0066(17) 0.030(4) Uiso 1 1 d . . . H2N4 H -0.455(3) 0.4838(13) 0.0912(16) 0.034(5) Uiso 1 1 d . . . C1 C -0.0055(2) 0.79016(8) 0.84236(12) 0.0204(2) Uani 1 1 d . . . C2 C -0.0177(2) 0.73735(8) 0.73274(12) 0.0214(3) Uani 1 1 d . . . H2 H -0.1507 0.7424 0.6625 0.026 Uiso 1 1 calc R . . C3 C 0.1693(2) 0.67766(8) 0.72963(12) 0.0207(3) Uani 1 1 d . . . H3 H 0.1619 0.6418 0.6571 0.025 Uiso 1 1 calc R . . C4 C 0.3718(2) 0.67047(8) 0.83541(11) 0.0190(2) Uani 1 1 d . . . C5 C 0.3790(2) 0.72456(8) 0.94475(12) 0.0214(2) Uani 1 1 d . . . H5 H 0.5115 0.7199 1.0153 0.026 Uiso 1 1 calc R . . C6 C 0.1919(2) 0.78450(8) 0.94873(12) 0.0206(2) Uani 1 1 d . . . H6 H 0.1975 0.8204 1.0210 0.025 Uiso 1 1 calc R . . C7 C 1.0269(2) 0.32685(8) 0.66046(11) 0.0194(2) Uani 1 1 d . . . C8 C 0.8088(2) 0.32330(8) 0.56520(12) 0.0206(2) Uani 1 1 d . . . H8 H 0.7796 0.2765 0.5070 0.025 Uiso 1 1 calc R . . C9 C 0.6380(2) 0.39036(8) 0.55903(11) 0.0204(2) Uani 1 1 d . . . H9 H 0.4912 0.3879 0.4968 0.024 Uiso 1 1 calc R . . C10 C 0.6809(2) 0.46269(8) 0.64515(11) 0.0194(2) Uani 1 1 d . . . C11 C 0.9012(2) 0.46275(8) 0.74244(12) 0.0221(3) Uani 1 1 d . . . H11 H 0.9307 0.5087 0.8022 0.026 Uiso 1 1 calc R . . C12 C 1.0723(2) 0.39557(9) 0.74976(11) 0.0218(3) Uani 1 1 d . . . H12 H 1.2168 0.3962 0.8138 0.026 Uiso 1 1 calc R . . C13 C 0.2315(2) 0.60141(8) 0.28022(12) 0.0231(3) Uani 1 1 d . . . H13 H 0.3615 0.6395 0.2747 0.028 Uiso 1 1 calc R . . C14 C 0.0414(2) 0.59119(8) 0.17539(12) 0.0222(3) Uani 1 1 d . . . H14 H 0.0422 0.6224 0.0993 0.027 Uiso 1 1 calc R . . C15 C -0.1578(2) 0.53298(8) 0.18221(12) 0.0191(2) Uani 1 1 d . . . C16 C -0.1478(2) 0.48820(8) 0.30134(12) 0.0207(3) Uani 1 1 d . . . H16 H -0.2743 0.4495 0.3105 0.025 Uiso 1 1 calc R . . C17 C 0.0464(2) 0.50168(8) 0.40237(12) 0.0211(2) Uani 1 1 d . . . H17 H 0.0505 0.4722 0.4804 0.025 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0331(5) 0.0261(5) 0.0267(5) -0.0020(4) 0.0094(4) 0.0069(4) O2 0.0283(5) 0.0405(5) 0.0252(5) 0.0061(4) 0.0024(4) 0.0158(4) O3 0.0266(4) 0.0251(4) 0.0175(4) 0.0006(4) 0.0027(3) 0.0092(4) O4 0.0381(5) 0.0210(4) 0.0248(5) -0.0017(4) 0.0078(4) 0.0071(4) O5 0.0324(5) 0.0354(5) 0.0198(4) 0.0029(4) -0.0003(4) 0.0156(4) O6 0.0255(4) 0.0247(5) 0.0197(4) -0.0024(3) 0.0011(3) 0.0081(4) N1 0.0244(5) 0.0221(5) 0.0204(5) 0.0051(4) 0.0070(4) 0.0033(4) N2 0.0288(6) 0.0209(5) 0.0185(5) 0.0050(4) 0.0074(4) 0.0057(4) N3 0.0171(5) 0.0226(5) 0.0224(5) -0.0033(4) 0.0004(4) 0.0005(4) N4 0.0230(5) 0.0250(6) 0.0195(5) 0.0045(4) 0.0016(4) -0.0030(4) C1 0.0234(6) 0.0180(6) 0.0207(6) 0.0040(5) 0.0069(5) 0.0027(5) C2 0.0218(6) 0.0245(6) 0.0165(5) 0.0011(5) 0.0005(5) 0.0011(5) C3 0.0243(6) 0.0203(6) 0.0173(6) -0.0010(4) 0.0039(5) 0.0004(5) C4 0.0212(6) 0.0181(6) 0.0181(6) 0.0035(5) 0.0052(5) 0.0019(4) C5 0.0232(6) 0.0224(6) 0.0173(5) 0.0022(4) 0.0010(5) 0.0032(5) C6 0.0266(6) 0.0190(6) 0.0162(6) -0.0017(5) 0.0046(5) -0.0004(5) C7 0.0237(6) 0.0188(6) 0.0167(5) 0.0035(5) 0.0065(5) 0.0038(5) C8 0.0262(6) 0.0178(6) 0.0181(6) -0.0001(5) 0.0054(5) -0.0017(5) C9 0.0189(5) 0.0239(6) 0.0177(5) 0.0013(5) 0.0022(4) -0.0013(5) C10 0.0202(6) 0.0211(6) 0.0176(5) 0.0031(5) 0.0053(4) 0.0024(5) C11 0.0266(6) 0.0219(6) 0.0170(5) -0.0034(5) 0.0027(5) 0.0024(5) C12 0.0218(6) 0.0259(6) 0.0165(6) 0.0025(5) 0.0008(4) 0.0032(5) C13 0.0214(6) 0.0200(6) 0.0290(6) -0.0014(5) 0.0074(5) -0.0031(5) C14 0.0265(6) 0.0190(6) 0.0224(6) 0.0033(5) 0.0079(5) -0.0003(5) C15 0.0203(5) 0.0169(5) 0.0202(6) -0.0015(4) 0.0045(4) 0.0021(5) C16 0.0193(6) 0.0195(6) 0.0231(6) 0.0015(5) 0.0038(5) -0.0012(4) C17 0.0222(6) 0.0209(6) 0.0201(6) 0.0029(5) 0.0043(5) 0.0010(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 N1 1.2351(14) . ? O2 N1 1.2343(14) . ? O3 C4 1.3309(15) . ? O3 H1O3 1.09(2) . ? O4 N2 1.2377(14) . ? O5 N2 1.2342(14) . ? O6 C10 1.3187(15) . ? O6 H1O3 1.37(2) . ? N1 C1 1.4426(16) . ? N2 C7 1.4433(16) . ? N3 C13 1.3466(16) . ? N3 C17 1.3525(16) . ? N3 H1N3 0.886(17) . ? N4 C15 1.3340(16) . ? N4 H1N4 0.879(18) . ? N4 H2N4 0.84(2) . ? C1 C6 1.3925(17) . ? C1 C2 1.3927(18) . ? C2 C3 1.3748(18) . ? C2 H2 0.9300 . ? C3 C4 1.4076(16) . ? C3 H3 0.9300 . ? C4 C5 1.4051(17) . ? C5 C6 1.3795(18) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 C12 1.3905(18) . ? C7 C8 1.3970(17) . ? C8 C9 1.3769(17) . ? C8 H8 0.9300 . ? C9 C10 1.4110(17) . ? C9 H9 0.9300 . ? C10 C11 1.4163(16) . ? C11 C12 1.3785(18) . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? C13 C14 1.3637(18) . ? C13 H13 0.9300 . ? C14 C15 1.4192(17) . ? C14 H14 0.9300 . ? C15 C16 1.4145(17) . ? C16 C17 1.3586(17) . ? C16 H16 0.9300 . ? C17 H17 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C4 O3 H1O3 111.3(12) . . ? C10 O6 H1O3 114.8(10) . . ? O2 N1 O1 122.05(10) . . ? O2 N1 C1 118.82(10) . . ? O1 N1 C1 119.13(10) . . ? O5 N2 O4 122.31(10) . . ? O5 N2 C7 118.40(10) . . ? O4 N2 C7 119.29(10) . . ? C13 N3 C17 120.61(10) . . ? C13 N3 H1N3 122.2(11) . . ? C17 N3 H1N3 117.2(11) . . ? C15 N4 H1N4 122.2(11) . . ? C15 N4 H2N4 117.2(12) . . ? H1N4 N4 H2N4 120.6(16) . . ? C6 C1 C2 121.75(11) . . ? C6 C1 N1 119.66(11) . . ? C2 C1 N1 118.58(11) . . ? C3 C2 C1 119.19(11) . . ? C3 C2 H2 120.4 . . ? C1 C2 H2 120.4 . . ? C2 C3 C4 120.47(11) . . ? C2 C3 H3 119.8 . . ? C4 C3 H3 119.8 . . ? O3 C4 C5 118.71(10) . . ? O3 C4 C3 122.21(10) . . ? C5 C4 C3 119.08(11) . . ? C6 C5 C4 120.80(11) . . ? C6 C5 H5 119.6 . . ? C4 C5 H5 119.6 . . ? C5 C6 C1 118.70(11) . . ? C5 C6 H6 120.6 . . ? C1 C6 H6 120.6 . . ? C12 C7 C8 121.48(11) . . ? C12 C7 N2 118.87(11) . . ? C8 C7 N2 119.65(11) . . ? C9 C8 C7 118.85(11) . . ? C9 C8 H8 120.6 . . ? C7 C8 H8 120.6 . . ? C8 C9 C10 121.39(11) . . ? C8 C9 H9 119.3 . . ? C10 C9 H9 119.3 . . ? O6 C10 C9 120.49(11) . . ? O6 C10 C11 121.48(11) . . ? C9 C10 C11 118.03(11) . . ? C12 C11 C10 120.87(11) . . ? C12 C11 H11 119.6 . . ? C10 C11 H11 119.6 . . ? C11 C12 C7 119.32(11) . . ? C11 C12 H12 120.3 . . ? C7 C12 H12 120.3 . . ? N3 C13 C14 121.02(11) . . ? N3 C13 H13 119.5 . . ? C14 C13 H13 119.5 . . ? C13 C14 C15 120.14(11) . . ? C13 C14 H14 119.9 . . ? C15 C14 H14 119.9 . . ? N4 C15 C16 121.09(11) . . ? N4 C15 C14 122.06(11) . . ? C16 C15 C14 116.85(11) . . ? C17 C16 C15 120.09(11) . . ? C17 C16 H16 120.0 . . ? C15 C16 H16 120.0 . . ? N3 C17 C16 121.29(11) . . ? N3 C17 H17 119.4 . . ? C16 C17 H17 119.4 . . ? 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 O3 H1O3 O6 1.09(2) 1.37(2) 2.4612(12) 175(2) . N3 H1N3 O6 0.886(17) 1.927(16) 2.7376(14) 151.2(15) . N4 H1N4 O3 0.879(18) 2.025(18) 2.8938(14) 169.1(15) 1_454 N4 H2N4 O1 0.84(2) 2.28(2) 3.0897(15) 163.2(16) 2_446 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.98 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.151 _refine_diff_density_min -0.197 _refine_diff_density_rms 0.034 data_sergiu7 _database_code_depnum_ccdc_archive 'CCDC 886324' #TrackingRef 'sergiu2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2-Amino,6-methylpyridinium 4-nitrophenolate 4-nitrophenol ; _chemical_name_common ; 2-Amino,6-methylpyridinium 4-nitrophenolate 4-nitrophenol ; _chemical_melting_point ? _chemical_formula_moiety 'C6 H5 N O3, C6 H4 N O3, C6 H9 N2' _chemical_formula_sum 'C18 H18 N4 O6' _chemical_formula_weight 386.36 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pna2(1) 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 14.0366(10) _cell_length_b 10.7686(7) _cell_length_c 11.8026(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1784.0(2) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.438 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 808 _exptl_absorpt_coefficient_mu 0.110 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.337 _exptl_absorpt_correction_T_max 0.654 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 16311 _diffrn_reflns_av_R_equivalents 0.0427 _diffrn_reflns_av_sigmaI/netI 0.0313 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.38 _diffrn_reflns_theta_max 25.99 _reflns_number_total 3500 _reflns_number_gt 3122 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2005)' _computing_cell_refinement 'SAINTPlus, v. 6.2 (Bruker, 2001)' _computing_data_reduction 'SAINTPlus, v. 6.2 (Bruker, 2001)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0365P)^2^+1.0132P] 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 -0.5(12) _refine_ls_number_reflns 3500 _refine_ls_number_parameters 270 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0514 _refine_ls_R_factor_gt 0.0434 _refine_ls_wR_factor_ref 0.0989 _refine_ls_wR_factor_gt 0.0951 _refine_ls_goodness_of_fit_ref 1.091 _refine_ls_restrained_S_all 1.091 _refine_ls_shift/su_max 0.005 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O -0.07513(13) 0.76423(17) 0.89267(18) 0.0350(5) Uani 1 1 d . . . O2 O -0.05182(13) 0.56866(17) 0.8631(2) 0.0382(5) Uani 1 1 d . . . O3 O 0.32099(13) 0.78531(17) 0.65345(17) 0.0277(4) Uani 1 1 d . . . H1O3 H 0.355(3) 0.716(4) 0.632(4) 0.094(16) Uiso 1 1 d . . . O4 O 0.79086(15) 0.66718(18) 0.30731(18) 0.0371(5) Uani 1 1 d . . . O5 O 0.76740(12) 0.85727(15) 0.35941(17) 0.0288(4) Uani 1 1 d . . . O6 O 0.41673(13) 0.59754(15) 0.58481(18) 0.0305(4) Uani 1 1 d . . . N1 N -0.02573(15) 0.67855(19) 0.85664(19) 0.0259(5) Uani 1 1 d . . . N2 N 0.74353(15) 0.74637(19) 0.35792(18) 0.0226(5) Uani 1 1 d . . . N3 N 0.38461(15) 0.3537(2) 0.6016(2) 0.0232(5) Uani 1 1 d . . . H1N3 H 0.403(2) 0.432(3) 0.598(3) 0.036(8) Uiso 1 1 d . . . N4 N 0.24418(17) 0.4083(2) 0.5064(2) 0.0335(6) Uani 1 1 d . . . H1N4 H 0.185(2) 0.375(3) 0.464(3) 0.041(9) Uiso 1 1 d . . . H2N4 H 0.272(2) 0.489(3) 0.496(3) 0.045(9) Uiso 1 1 d . . . C1 C 0.06577(18) 0.7052(2) 0.8052(2) 0.0228(6) Uani 1 1 d . . . C2 C 0.12495(19) 0.6074(2) 0.7763(2) 0.0225(5) Uani 1 1 d . . . H2 H 0.1067 0.5257 0.7900 0.027 Uiso 1 1 calc R . . C3 C 0.21150(18) 0.6335(2) 0.7267(2) 0.0212(5) Uani 1 1 d . . . H3 H 0.2527 0.5690 0.7080 0.025 Uiso 1 1 calc R . . C4 C 0.23808(17) 0.7569(2) 0.7043(2) 0.0215(5) Uani 1 1 d . . . C5 C 0.17749(19) 0.8528(2) 0.7370(2) 0.0252(6) Uani 1 1 d . . . H5 H 0.1957 0.9348 0.7249 0.030 Uiso 1 1 calc R . . C6 C 0.09072(18) 0.8278(2) 0.7872(2) 0.0224(5) Uani 1 1 d . . . H6 H 0.0500 0.8919 0.8084 0.027 Uiso 1 1 calc R . . C7 C 0.65783(17) 0.7077(2) 0.4151(2) 0.0196(5) Uani 1 1 d . . . C8 C 0.63630(18) 0.5825(2) 0.4225(2) 0.0213(5) Uani 1 1 d . . . H8 H 0.6765 0.5236 0.3902 0.026 Uiso 1 1 calc R . . C9 C 0.55505(18) 0.5462(2) 0.4779(2) 0.0239(6) Uani 1 1 d . . . H9 H 0.5405 0.4621 0.4825 0.029 Uiso 1 1 calc R . . C10 C 0.49285(18) 0.6335(2) 0.5282(2) 0.0222(5) Uani 1 1 d . . . C11 C 0.51623(18) 0.7615(2) 0.5155(2) 0.0230(5) Uani 1 1 d . . . H11 H 0.4755 0.8217 0.5446 0.028 Uiso 1 1 calc R . . C12 C 0.59762(17) 0.7971(2) 0.4613(2) 0.0198(5) Uani 1 1 d . . . H12 H 0.6128 0.8809 0.4552 0.024 Uiso 1 1 calc R . . C13 C 0.3022(2) 0.3176(3) 0.5512(2) 0.0310(6) Uani 1 1 d . . . C14 C 0.2775(2) 0.1927(3) 0.5473(3) 0.0390(8) Uani 1 1 d . . . H14 H 0.2212 0.1665 0.5134 0.047 Uiso 1 1 calc R . . C15 C 0.3386(3) 0.1109(3) 0.5947(3) 0.0482(9) Uani 1 1 d . . . H15 H 0.3233 0.0269 0.5933 0.058 Uiso 1 1 calc R . . C16 C 0.4238(3) 0.1473(3) 0.6456(3) 0.0471(9) Uani 1 1 d . . . H16 H 0.4645 0.0883 0.6766 0.057 Uiso 1 1 calc R . . C17 C 0.4473(2) 0.2726(3) 0.6495(2) 0.0334(7) Uani 1 1 d . . . C18 C 0.53276(19) 0.3278(3) 0.7020(2) 0.0310(6) Uani 1 1 d . . . H18A H 0.5368 0.4140 0.6816 0.047 Uiso 1 1 calc R . . H18B H 0.5885 0.2851 0.6755 0.047 Uiso 1 1 calc R . . H18C H 0.5285 0.3203 0.7829 0.047 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0281(10) 0.0257(10) 0.0511(13) -0.0113(9) 0.0177(9) -0.0025(8) O2 0.0350(11) 0.0228(10) 0.0567(13) 0.0010(10) 0.0198(10) -0.0065(8) O3 0.0215(9) 0.0205(9) 0.0410(11) 0.0008(8) 0.0100(8) -0.0014(8) O4 0.0359(11) 0.0258(10) 0.0496(13) -0.0035(9) 0.0233(10) 0.0035(8) O5 0.0269(10) 0.0205(9) 0.0389(11) -0.0001(8) 0.0085(9) -0.0037(7) O6 0.0253(9) 0.0191(9) 0.0472(11) 0.0008(8) 0.0123(9) -0.0020(7) N1 0.0277(11) 0.0217(11) 0.0283(12) -0.0029(10) 0.0063(11) -0.0013(9) N2 0.0215(11) 0.0205(11) 0.0257(12) 0.0005(10) 0.0029(10) 0.0000(8) N3 0.0211(11) 0.0172(11) 0.0313(12) 0.0020(9) 0.0093(9) 0.0016(9) N4 0.0234(12) 0.0328(14) 0.0445(16) -0.0060(12) -0.0044(11) 0.0038(10) C1 0.0227(13) 0.0236(13) 0.0222(13) -0.0003(10) 0.0061(11) -0.0014(10) C2 0.0263(13) 0.0162(12) 0.0250(14) 0.0006(10) 0.0001(11) -0.0027(10) C3 0.0211(12) 0.0168(12) 0.0255(14) 0.0010(10) 0.0028(11) 0.0037(10) C4 0.0205(12) 0.0218(13) 0.0223(13) 0.0004(10) 0.0030(11) 0.0002(10) C5 0.0285(14) 0.0176(13) 0.0295(14) -0.0006(11) 0.0031(12) -0.0011(10) C6 0.0245(13) 0.0180(12) 0.0248(14) -0.0029(11) 0.0051(11) 0.0051(10) C7 0.0194(12) 0.0221(12) 0.0171(12) 0.0011(10) -0.0009(10) 0.0001(10) C8 0.0226(13) 0.0197(12) 0.0216(13) -0.0033(10) 0.0019(10) 0.0048(10) C9 0.0265(13) 0.0153(12) 0.0298(14) -0.0006(10) -0.0017(11) -0.0011(10) C10 0.0205(12) 0.0188(12) 0.0272(14) 0.0000(10) 0.0011(11) -0.0026(10) C11 0.0232(12) 0.0161(12) 0.0297(15) -0.0007(10) 0.0035(11) 0.0033(10) C12 0.0191(13) 0.0160(12) 0.0243(13) 0.0001(10) -0.0011(10) 0.0006(9) C13 0.0284(14) 0.0292(14) 0.0354(15) -0.0094(12) 0.0134(13) -0.0096(12) C14 0.0426(18) 0.0278(15) 0.0465(18) -0.0060(14) 0.0180(16) -0.0110(14) C15 0.072(2) 0.0269(16) 0.046(2) -0.0046(15) 0.0275(19) -0.0177(16) C16 0.071(2) 0.0316(17) 0.0388(18) 0.0150(15) 0.0227(18) 0.0217(17) C17 0.0399(17) 0.0297(15) 0.0308(14) 0.0130(13) 0.0146(14) 0.0104(13) C18 0.0264(15) 0.0384(15) 0.0284(14) 0.0069(12) 0.0035(12) 0.0101(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 N1 1.230(3) . ? O2 N1 1.241(3) . ? O3 C4 1.345(3) . ? O3 H1O3 0.92(5) . ? O4 N2 1.235(3) . ? O5 N2 1.240(3) . ? O6 C10 1.318(3) . ? N1 C1 1.449(3) . ? N2 C7 1.441(3) . ? N3 C13 1.357(4) . ? N3 C17 1.363(3) . ? N3 H1N3 0.88(3) . ? N4 C13 1.378(4) . ? N4 H1N4 1.03(3) . ? N4 H2N4 0.97(3) . ? C1 C6 1.382(4) . ? C1 C2 1.385(4) . ? C2 C3 1.377(4) . ? C2 H2 0.9300 . ? C3 C4 1.405(3) . ? C3 H3 0.9300 . ? C4 C5 1.393(4) . ? C5 C6 1.381(4) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 C8 1.385(3) . ? C7 C12 1.392(3) . ? C8 C9 1.371(4) . ? C8 H8 0.9300 . ? C9 C10 1.414(3) . ? C9 H9 0.9300 . ? C10 C11 1.425(3) . ? C11 C12 1.364(3) . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? C13 C14 1.389(4) . ? C14 C15 1.351(5) . ? C14 H14 0.9300 . ? C15 C16 1.394(5) . ? C15 H15 0.9300 . ? C16 C17 1.389(4) . ? C16 H16 0.9300 . ? C17 C18 1.475(4) . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? 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 C4 O3 H1O3 113(3) . . ? O1 N1 O2 121.9(2) . . ? O1 N1 C1 119.7(2) . . ? O2 N1 C1 118.4(2) . . ? O4 N2 O5 121.8(2) . . ? O4 N2 C7 118.4(2) . . ? O5 N2 C7 119.8(2) . . ? C13 N3 C17 123.2(2) . . ? C13 N3 H1N3 120(2) . . ? C17 N3 H1N3 117(2) . . ? C13 N4 H1N4 114.7(16) . . ? C13 N4 H2N4 116.6(19) . . ? H1N4 N4 H2N4 125(3) . . ? C6 C1 C2 122.5(2) . . ? C6 C1 N1 118.6(2) . . ? C2 C1 N1 118.9(2) . . ? C3 C2 C1 118.6(2) . . ? C3 C2 H2 120.7 . . ? C1 C2 H2 120.7 . . ? C2 C3 C4 120.5(2) . . ? C2 C3 H3 119.7 . . ? C4 C3 H3 119.7 . . ? O3 C4 C5 118.9(2) . . ? O3 C4 C3 121.9(2) . . ? C5 C4 C3 119.1(2) . . ? C6 C5 C4 120.9(2) . . ? C6 C5 H5 119.6 . . ? C4 C5 H5 119.6 . . ? C5 C6 C1 118.4(2) . . ? C5 C6 H6 120.8 . . ? C1 C6 H6 120.8 . . ? C8 C7 C12 121.1(2) . . ? C8 C7 N2 119.5(2) . . ? C12 C7 N2 119.4(2) . . ? C9 C8 C7 119.2(2) . . ? C9 C8 H8 120.4 . . ? C7 C8 H8 120.4 . . ? C8 C9 C10 121.6(2) . . ? C8 C9 H9 119.2 . . ? C10 C9 H9 119.2 . . ? O6 C10 C9 121.2(2) . . ? O6 C10 C11 121.6(2) . . ? C9 C10 C11 117.2(2) . . ? C12 C11 C10 120.9(2) . . ? C12 C11 H11 119.5 . . ? C10 C11 H11 119.5 . . ? C11 C12 C7 119.9(2) . . ? C11 C12 H12 120.1 . . ? C7 C12 H12 120.1 . . ? N3 C13 N4 117.9(2) . . ? N3 C13 C14 120.3(3) . . ? N4 C13 C14 121.8(3) . . ? C15 C14 C13 117.3(3) . . ? C15 C14 H14 121.3 . . ? C13 C14 H14 121.3 . . ? C14 C15 C16 122.6(3) . . ? C14 C15 H15 118.7 . . ? C16 C15 H15 118.7 . . ? C17 C16 C15 119.5(3) . . ? C17 C16 H16 120.3 . . ? C15 C16 H16 120.3 . . ? N3 C17 C16 117.0(3) . . ? N3 C17 C18 116.1(2) . . ? C16 C17 C18 126.8(3) . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 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 O3 H1O3 O6 0.92(5) 1.64(5) 2.559(2) 176(5) . N3 H1N3 O6 0.88(3) 1.80(3) 2.671(3) 169(3) . N4 H1N4 O2 1.03(3) 2.30(3) 3.196(3) 145(2) 2_564 N4 H1N4 O1 1.03(3) 2.32(3) 3.299(3) 159(2) 2_564 N4 H2N4 O5 0.97(3) 2.31(3) 3.080(3) 136(3) 3_465 N4 H2N4 O6 0.97(3) 2.56(3) 3.298(3) 133(2) . _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.99 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.251 _refine_diff_density_min -0.227 _refine_diff_density_rms 0.048 data_sergiu2 _database_code_depnum_ccdc_archive 'CCDC 886325' #TrackingRef 'sergiu3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 3,4-Diaminopyridinium 4-nitrophenolate 4-nitrophenol ; _chemical_name_common ; 3,4-Diaminopyridinium 4-nitrophenolate 4-nitrophenol ; _chemical_melting_point ? _chemical_formula_moiety 'C12 H9 N2 O6, C5 H8 N3' _chemical_formula_sum 'C17 H17 N5 O6' _chemical_formula_weight 387.36 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 5.5319(5) _cell_length_b 15.2012(15) _cell_length_c 10.6928(10) _cell_angle_alpha 90.00 _cell_angle_beta 104.581(2) _cell_angle_gamma 90.00 _cell_volume 870.21(14) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.478 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 404 _exptl_absorpt_coefficient_mu 0.115 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.337 _exptl_absorpt_correction_T_max 0.654 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 8370 _diffrn_reflns_av_R_equivalents 0.0237 _diffrn_reflns_av_sigmaI/netI 0.0307 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.97 _diffrn_reflns_theta_max 26.00 _reflns_number_total 3406 _reflns_number_gt 3260 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2005)' _computing_cell_refinement 'SAINTPlus, v. 6.2 (Bruker, 2001)' _computing_data_reduction 'SAINTPlus, v. 6.2 (Bruker, 2001)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0536P)^2^+0.2867P] 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 -0.1(10) _refine_ls_number_reflns 3406 _refine_ls_number_parameters 277 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0391 _refine_ls_R_factor_gt 0.0372 _refine_ls_wR_factor_ref 0.1010 _refine_ls_wR_factor_gt 0.0993 _refine_ls_goodness_of_fit_ref 1.069 _refine_ls_restrained_S_all 1.069 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O -0.5796(3) -0.06184(10) 0.08376(15) 0.0262(3) Uani 1 1 d . . . O2 O -0.5794(3) -0.01385(12) 0.27441(15) 0.0308(4) Uani 1 1 d . . . O3 O 0.2373(3) 0.22942(10) 0.15007(14) 0.0253(3) Uani 1 1 d . . . H1O3 H 0.308(8) 0.273(3) 0.251(4) 0.098(14) Uiso 1 1 d . . . O4 O 1.1155(3) 0.63890(10) 0.41763(15) 0.0288(4) Uani 1 1 d . . . O5 O 1.1523(3) 0.59081(11) 0.23283(15) 0.0334(4) Uani 1 1 d . . . O6 O 0.3669(3) 0.32502(11) 0.33868(14) 0.0316(4) Uani 1 1 d . . . N1 N -0.4995(3) -0.01270(12) 0.17697(16) 0.0207(4) Uani 1 1 d . . . N2 N 1.0556(3) 0.58819(11) 0.32525(17) 0.0243(4) Uani 1 1 d . . . N3 N 0.3105(4) 0.29196(12) 0.58290(19) 0.0287(4) Uani 1 1 d . . . H1N3 H 0.375(5) 0.2863(17) 0.503(3) 0.027(6) Uiso 1 1 d . . . N4 N 0.4450(4) 0.21082(17) 0.9129(2) 0.0433(6) Uani 1 1 d . . . H1N4 H 0.589(6) 0.179(2) 0.912(3) 0.045(8) Uiso 1 1 d . . . H2N4 H 0.372(6) 0.226(2) 0.979(3) 0.058(10) Uiso 1 1 d . . . N5 N 0.0243(4) 0.31847(14) 0.8978(2) 0.0278(4) Uani 1 1 d . . . H1N5 H 0.083(6) 0.301(2) 0.969(3) 0.045(9) Uiso 1 1 d . . . H2N5 H -0.105(7) 0.353(2) 0.891(4) 0.065(11) Uiso 1 1 d . . . C1 C -0.3030(4) 0.04919(13) 0.17176(19) 0.0188(4) Uani 1 1 d . . . C2 C -0.2321(4) 0.11117(15) 0.2701(2) 0.0227(4) Uani 1 1 d . . . H2 H -0.3070 0.1118 0.3388 0.027 Uiso 1 1 calc R . . C3 C -0.0497(4) 0.17144(14) 0.2641(2) 0.0228(4) Uani 1 1 d . . . H3 H -0.0017 0.2132 0.3292 0.027 Uiso 1 1 calc R . . C4 C 0.0652(4) 0.17072(13) 0.16060(19) 0.0203(4) Uani 1 1 d . . . C5 C -0.0083(4) 0.10627(13) 0.06400(19) 0.0203(4) Uani 1 1 d . . . H5 H 0.0688 0.1042 -0.0038 0.024 Uiso 1 1 calc R . . C6 C -0.1928(4) 0.04612(13) 0.06825(19) 0.0204(4) Uani 1 1 d . . . H6 H -0.2425 0.0044 0.0033 0.024 Uiso 1 1 calc R . . C7 C 0.8661(4) 0.52185(14) 0.3254(2) 0.0218(4) Uani 1 1 d . . . C8 C 0.7402(4) 0.52244(14) 0.42200(19) 0.0216(4) Uani 1 1 d . . . H8 H 0.7717 0.5660 0.4850 0.026 Uiso 1 1 calc R . . C9 C 0.5673(4) 0.45736(15) 0.4233(2) 0.0241(4) Uani 1 1 d . . . H9 H 0.4795 0.4580 0.4869 0.029 Uiso 1 1 calc R . . C10 C 0.5214(4) 0.39001(14) 0.33000(19) 0.0228(4) Uani 1 1 d . . . C11 C 0.6481(4) 0.39294(15) 0.2310(2) 0.0266(5) Uani 1 1 d . . . H11 H 0.6161 0.3502 0.1666 0.032 Uiso 1 1 calc R . . C12 C 0.8184(4) 0.45828(15) 0.2287(2) 0.0259(4) Uani 1 1 d . . . H12 H 0.9012 0.4600 0.1631 0.031 Uiso 1 1 calc R . . C13 C 0.4205(4) 0.24904(14) 0.6936(2) 0.0271(5) Uani 1 1 d . . . H13 H 0.5594 0.2142 0.6953 0.032 Uiso 1 1 calc R . . C14 C 0.3361(4) 0.25479(13) 0.8033(2) 0.0251(4) Uani 1 1 d . . . C15 C 0.1200(4) 0.30949(13) 0.7964(2) 0.0229(4) Uani 1 1 d . . . C16 C 0.0149(4) 0.35233(14) 0.6804(2) 0.0262(5) Uani 1 1 d . . . H16 H -0.1234 0.3883 0.6746 0.031 Uiso 1 1 calc R . . C17 C 0.1103(4) 0.34294(14) 0.5736(2) 0.0249(4) Uani 1 1 d . . . H17 H 0.0365 0.3716 0.4966 0.030 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0220(7) 0.0237(8) 0.0304(8) 0.0002(6) 0.0019(6) -0.0062(6) O2 0.0293(8) 0.0394(9) 0.0252(8) 0.0061(7) 0.0095(6) -0.0104(7) O3 0.0272(7) 0.0282(8) 0.0207(7) -0.0011(6) 0.0061(6) -0.0129(6) O4 0.0333(8) 0.0223(8) 0.0264(8) -0.0019(6) -0.0007(6) -0.0073(6) O5 0.0363(9) 0.0396(10) 0.0230(8) 0.0047(7) 0.0048(7) -0.0169(8) O6 0.0367(9) 0.0386(9) 0.0210(7) -0.0045(7) 0.0102(6) -0.0188(7) N1 0.0192(8) 0.0212(8) 0.0204(8) 0.0049(7) 0.0028(7) -0.0025(7) N2 0.0250(9) 0.0237(9) 0.0212(9) 0.0059(8) 0.0003(7) -0.0022(7) N3 0.0316(10) 0.0283(10) 0.0286(10) -0.0014(8) 0.0121(8) -0.0048(8) N4 0.0338(11) 0.0517(14) 0.0471(13) 0.0204(11) 0.0150(10) 0.0182(10) N5 0.0271(9) 0.0303(10) 0.0251(10) 0.0065(8) 0.0048(8) 0.0043(8) C1 0.0165(9) 0.0173(9) 0.0219(10) 0.0052(8) 0.0035(7) -0.0021(8) C2 0.0238(10) 0.0275(11) 0.0182(9) 0.0007(8) 0.0081(8) -0.0036(8) C3 0.0268(10) 0.0232(10) 0.0183(9) -0.0030(8) 0.0056(8) -0.0053(8) C4 0.0204(9) 0.0202(10) 0.0188(9) 0.0042(8) 0.0020(8) -0.0019(8) C5 0.0220(9) 0.0227(10) 0.0171(9) 0.0017(8) 0.0063(8) -0.0007(8) C6 0.0204(9) 0.0179(10) 0.0214(10) -0.0019(8) 0.0026(8) -0.0002(8) C7 0.0218(10) 0.0196(9) 0.0205(9) 0.0052(8) -0.0012(8) -0.0031(8) C8 0.0256(10) 0.0185(9) 0.0191(9) -0.0008(8) 0.0025(8) 0.0012(8) C9 0.0228(10) 0.0299(11) 0.0201(10) 0.0014(8) 0.0062(8) 0.0003(8) C10 0.0227(10) 0.0248(11) 0.0195(10) 0.0016(8) 0.0026(8) -0.0080(8) C11 0.0319(11) 0.0290(11) 0.0187(10) -0.0037(9) 0.0060(8) -0.0093(10) C12 0.0284(11) 0.0315(11) 0.0179(10) 0.0021(9) 0.0058(8) -0.0075(9) C13 0.0237(10) 0.0217(11) 0.0364(12) -0.0013(9) 0.0086(9) -0.0046(8) C14 0.0262(11) 0.0194(10) 0.0311(11) 0.0017(9) 0.0100(9) -0.0044(8) C15 0.0208(10) 0.0189(10) 0.0298(11) -0.0026(9) 0.0075(8) -0.0053(8) C16 0.0237(10) 0.0230(11) 0.0301(11) 0.0017(9) 0.0034(9) 0.0011(8) C17 0.0263(10) 0.0212(10) 0.0295(11) -0.0039(9) 0.0112(9) -0.0055(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 N1 1.235(2) . ? O2 N1 1.230(2) . ? O3 C4 1.330(2) . ? O3 H1O3 1.24(5) . ? O4 N2 1.231(2) . ? O5 N2 1.237(2) . ? O6 C10 1.325(3) . ? O6 H1O3 1.21(5) . ? N1 C1 1.449(2) . ? N2 C7 1.455(3) . ? N3 C17 1.335(3) . ? N3 C13 1.355(3) . ? N3 H1N3 1.01(3) . ? N4 C14 1.352(3) . ? N4 H1N4 0.93(3) . ? N4 H2N4 0.92(4) . ? N5 C15 1.328(3) . ? N5 H1N5 0.79(3) . ? N5 H2N5 0.87(4) . ? C1 C2 1.392(3) . ? C1 C6 1.393(3) . ? C2 C3 1.376(3) . ? C2 H2 0.9300 . ? C3 C4 1.408(3) . ? C3 H3 0.9300 . ? C4 C5 1.407(3) . ? C5 C6 1.379(3) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 C8 1.383(3) . ? C7 C12 1.391(3) . ? C8 C9 1.378(3) . ? C8 H8 0.9300 . ? C9 C10 1.407(3) . ? C9 H9 0.9300 . ? C10 C11 1.410(3) . ? C11 C12 1.374(3) . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? C13 C14 1.370(3) . ? C13 H13 0.9300 . ? C14 C15 1.443(3) . ? C15 C16 1.393(3) . ? C16 C17 1.380(3) . ? C16 H16 0.9300 . ? C17 H17 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C4 O3 H1O3 111(2) . . ? C10 O6 H1O3 119(2) . . ? O2 N1 O1 122.84(17) . . ? O2 N1 C1 118.34(17) . . ? O1 N1 C1 118.82(16) . . ? O4 N2 O5 122.52(18) . . ? O4 N2 C7 118.79(17) . . ? O5 N2 C7 118.68(17) . . ? C17 N3 C13 121.8(2) . . ? C17 N3 H1N3 116.9(14) . . ? C13 N3 H1N3 121.4(14) . . ? C14 N4 H1N4 116.4(18) . . ? C14 N4 H2N4 111(2) . . ? H1N4 N4 H2N4 132(3) . . ? C15 N5 H1N5 127(2) . . ? C15 N5 H2N5 119(2) . . ? H1N5 N5 H2N5 114(3) . . ? C2 C1 C6 121.75(18) . . ? C2 C1 N1 118.80(17) . . ? C6 C1 N1 119.45(17) . . ? C3 C2 C1 119.06(19) . . ? C3 C2 H2 120.5 . . ? C1 C2 H2 120.5 . . ? C2 C3 C4 120.85(19) . . ? C2 C3 H3 119.6 . . ? C4 C3 H3 119.6 . . ? O3 C4 C5 119.04(18) . . ? O3 C4 C3 122.39(18) . . ? C5 C4 C3 118.56(18) . . ? C6 C5 C4 121.11(18) . . ? C6 C5 H5 119.4 . . ? C4 C5 H5 119.4 . . ? C5 C6 C1 118.66(18) . . ? C5 C6 H6 120.7 . . ? C1 C6 H6 120.7 . . ? C8 C7 C12 121.50(19) . . ? C8 C7 N2 119.66(18) . . ? C12 C7 N2 118.83(19) . . ? C9 C8 C7 118.93(19) . . ? C9 C8 H8 120.5 . . ? C7 C8 H8 120.5 . . ? C8 C9 C10 121.15(19) . . ? C8 C9 H9 119.4 . . ? C10 C9 H9 119.4 . . ? O6 C10 C9 119.85(18) . . ? O6 C10 C11 121.84(19) . . ? C9 C10 C11 118.29(18) . . ? C12 C11 C10 120.6(2) . . ? C12 C11 H11 119.7 . . ? C10 C11 H11 119.7 . . ? C11 C12 C7 119.4(2) . . ? C11 C12 H12 120.3 . . ? C7 C12 H12 120.3 . . ? N3 C13 C14 122.8(2) . . ? N3 C13 H13 118.6 . . ? C14 C13 H13 118.6 . . ? N4 C14 C13 122.5(2) . . ? N4 C14 C15 120.8(2) . . ? C13 C14 C15 116.75(19) . . ? N5 C15 C16 121.1(2) . . ? N5 C15 C14 120.89(19) . . ? C16 C15 C14 117.99(19) . . ? C17 C16 C15 121.9(2) . . ? C17 C16 H16 119.1 . . ? C15 C16 H16 119.1 . . ? N3 C17 C16 118.8(2) . . ? N3 C17 H17 120.6 . . ? C16 C17 H17 120.6 . . ? 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 O6 H1O3 O3 1.21(5) 1.24(5) 2.442(2) 171(4) . N3 H1N3 O6 1.01(3) 1.84(3) 2.753(2) 148(2) . N4 H2N4 O3 0.92(4) 2.14(4) 3.049(3) 166(3) 1_556 N5 H1N5 O3 0.79(3) 2.20(3) 2.983(3) 170(3) 1_556 N5 H2N5 O1 0.87(4) 2.24(4) 3.105(3) 169(3) 2_456 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.429 _refine_diff_density_min -0.210 _refine_diff_density_rms 0.042 data_sergiu3n _database_code_depnum_ccdc_archive 'CCDC 886326' #TrackingRef 'sergiu4.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2,3-Diaminopyridinium 4-nitrophenolate 4-nitrophenol ; _chemical_name_common ; 2,3-Diaminopyridinium 4-nitrophenolate 4-nitrophenol ; _chemical_melting_point ? _chemical_formula_moiety 'C6 H5 N O3, C6 H4 N O3, C5 H8 N3' _chemical_formula_sum 'C17 H17 N5 O6' _chemical_formula_weight 387.36 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 5.4588(4) _cell_length_b 15.0882(12) _cell_length_c 10.8815(9) _cell_angle_alpha 90.00 _cell_angle_beta 104.2100(10) _cell_angle_gamma 90.00 _cell_volume 868.82(12) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour brown _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.481 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 404 _exptl_absorpt_coefficient_mu 0.115 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.337 _exptl_absorpt_correction_T_max 0.654 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 8396 _diffrn_reflns_av_R_equivalents 0.0178 _diffrn_reflns_av_sigmaI/netI 0.0226 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.93 _diffrn_reflns_theta_max 25.98 _reflns_number_total 3418 _reflns_number_gt 3234 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2005)' _computing_cell_refinement 'SAINTPlus, v. 6.2 (Bruker, 2001)' _computing_data_reduction 'SAINTPlus, v. 6.2 (Bruker, 2001)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0386P)^2^+0.1411P] 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 0.1(7) _refine_ls_number_reflns 3418 _refine_ls_number_parameters 277 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0300 _refine_ls_R_factor_gt 0.0277 _refine_ls_wR_factor_ref 0.0729 _refine_ls_wR_factor_gt 0.0714 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_restrained_S_all 1.031 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 1.6716(2) 0.31917(9) 0.72569(11) 0.0364(3) Uani 1 1 d . . . H1O H 0.799(5) 0.6118(18) 0.757(3) 0.063(7) Uiso 1 1 d . . . O2 O 1.6584(2) 0.27697(8) 0.91361(11) 0.0328(3) Uani 1 1 d . . . O3 O 0.8435(2) 0.57402(9) 0.82585(12) 0.0364(3) Uani 1 1 d . . . O4 O -0.0929(2) 0.92484(9) 0.78199(12) 0.0350(3) Uani 1 1 d . . . O5 O -0.0756(2) 0.97969(8) 0.60022(11) 0.0319(3) Uani 1 1 d . . . O6 O 0.7247(2) 0.68084(8) 0.64537(10) 0.0270(3) Uani 1 1 d . . . N1 N 1.5837(2) 0.32475(9) 0.82013(13) 0.0276(3) Uani 1 1 d . . . N2 N -0.0027(2) 0.92643(9) 0.68858(13) 0.0261(3) Uani 1 1 d . . . N3 N 0.9364(3) 0.67759(10) 0.22018(14) 0.0295(3) Uani 1 1 d . . . H1N3 H 1.090(4) 0.7138(15) 0.230(2) 0.050(6) Uiso 1 1 d . . . N4 N 0.9385(3) 0.70527(10) 0.43028(14) 0.0289(3) Uani 1 1 d . . . H1N4 H 0.875(4) 0.7026(14) 0.496(2) 0.044(6) Uiso 1 1 d . . . H2N4 H 1.066(4) 0.7313(14) 0.4358(19) 0.037(6) Uiso 1 1 d . . . N5 N 0.5026(3) 0.60005(10) 0.40044(15) 0.0314(3) Uani 1 1 d . . . H1N5 H 0.573(4) 0.6215(13) 0.4831(19) 0.033(5) Uiso 1 1 d . . . H2N5 H 0.383(4) 0.5599(14) 0.3938(18) 0.032(5) Uiso 1 1 d . . . C1 C 1.3877(3) 0.38912(11) 0.81942(15) 0.0259(3) Uani 1 1 d . . . C2 C 1.3179(3) 0.44746(11) 0.71841(15) 0.0289(4) Uani 1 1 d . . . H2 H 1.3945 0.4442 0.6511 0.035 Uiso 1 1 calc R . . C3 C 1.1353(3) 0.51012(11) 0.71820(15) 0.0291(4) Uani 1 1 d . . . H3 H 1.0887 0.5497 0.6509 0.035 Uiso 1 1 calc R . . C4 C 1.0191(3) 0.51432(11) 0.81983(15) 0.0272(4) Uani 1 1 d . . . C5 C 1.0899(3) 0.45362(12) 0.92006(15) 0.0293(4) Uani 1 1 d . . . H5 H 1.0114 0.4554 0.9868 0.035 Uiso 1 1 calc R . . C6 C 1.2749(3) 0.39150(11) 0.92021(15) 0.0273(3) Uani 1 1 d . . . H6 H 1.3234 0.3517 0.9871 0.033 Uiso 1 1 calc R . . C7 C 0.1917(3) 0.86400(10) 0.68026(15) 0.0244(3) Uani 1 1 d . . . C8 C 0.3073(3) 0.87060(11) 0.58012(15) 0.0243(3) Uani 1 1 d . . . H8 H 0.2625 0.9156 0.5204 0.029 Uiso 1 1 calc R . . C9 C 0.4892(3) 0.80946(10) 0.57074(14) 0.0238(3) Uani 1 1 d . . . H9 H 0.5682 0.8139 0.5044 0.029 Uiso 1 1 calc R . . C10 C 0.5584(3) 0.74017(11) 0.65970(14) 0.0231(3) Uani 1 1 d . . . C11 C 0.4394(3) 0.73709(12) 0.76155(15) 0.0275(3) Uani 1 1 d . . . H11 H 0.4844 0.6929 0.8225 0.033 Uiso 1 1 calc R . . C12 C 0.2592(3) 0.79797(11) 0.77195(15) 0.0275(4) Uani 1 1 d . . . H12 H 0.1829 0.7953 0.8394 0.033 Uiso 1 1 calc R . . C13 C 0.8347(3) 0.66530(10) 0.31970(15) 0.0232(3) Uani 1 1 d . . . C14 C 0.6171(3) 0.61004(10) 0.30373(15) 0.0242(3) Uani 1 1 d . . . C15 C 0.6462(4) 0.58502(13) 0.08764(16) 0.0371(4) Uani 1 1 d . . . H15 H 0.5834 0.5579 0.0095 0.045 Uiso 1 1 calc R . . C16 C 0.8482(3) 0.63887(13) 0.10524(17) 0.0354(4) Uani 1 1 d . . . H16 H 0.9261 0.6494 0.0397 0.042 Uiso 1 1 calc R . . C17 C 0.5298(3) 0.56966(11) 0.18808(17) 0.0297(4) Uani 1 1 d . . . H17 H 0.3918 0.5316 0.1758 0.036 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0409(7) 0.0433(8) 0.0265(6) -0.0023(5) 0.0110(5) 0.0135(6) O2 0.0371(7) 0.0297(6) 0.0301(6) 0.0051(5) 0.0056(5) 0.0079(5) O3 0.0416(7) 0.0433(8) 0.0272(6) 0.0068(6) 0.0136(5) 0.0195(6) O4 0.0326(7) 0.0459(8) 0.0276(6) -0.0099(5) 0.0096(5) 0.0064(5) O5 0.0277(6) 0.0287(6) 0.0384(7) 0.0018(5) 0.0066(5) 0.0062(5) O6 0.0268(6) 0.0293(6) 0.0246(6) -0.0001(5) 0.0058(4) 0.0060(5) N1 0.0295(7) 0.0264(7) 0.0264(7) -0.0055(6) 0.0061(6) 0.0027(6) N2 0.0226(7) 0.0286(7) 0.0258(7) -0.0066(6) 0.0032(6) -0.0007(5) N3 0.0278(7) 0.0292(8) 0.0342(8) 0.0026(6) 0.0125(6) 0.0014(6) N4 0.0228(7) 0.0343(8) 0.0319(8) -0.0096(6) 0.0108(6) -0.0103(6) N5 0.0275(7) 0.0351(8) 0.0354(8) -0.0081(7) 0.0154(6) -0.0125(6) C1 0.0278(8) 0.0233(8) 0.0256(8) -0.0024(7) 0.0045(6) 0.0023(6) C2 0.0328(9) 0.0333(9) 0.0222(8) -0.0021(7) 0.0100(7) 0.0037(7) C3 0.0358(9) 0.0299(9) 0.0218(8) 0.0034(7) 0.0075(7) 0.0057(7) C4 0.0302(8) 0.0282(9) 0.0224(8) -0.0011(7) 0.0046(7) 0.0062(7) C5 0.0321(9) 0.0360(9) 0.0219(8) -0.0007(7) 0.0103(7) 0.0030(7) C6 0.0325(9) 0.0251(8) 0.0232(8) 0.0014(7) 0.0050(6) 0.0008(7) C7 0.0211(7) 0.0247(8) 0.0256(8) -0.0081(6) 0.0025(6) -0.0006(6) C8 0.0255(8) 0.0215(8) 0.0247(8) -0.0013(6) 0.0038(6) -0.0029(6) C9 0.0250(7) 0.0259(8) 0.0210(7) -0.0024(6) 0.0063(6) -0.0024(6) C10 0.0201(7) 0.0243(8) 0.0229(7) -0.0038(6) 0.0015(6) -0.0022(6) C11 0.0272(8) 0.0294(8) 0.0246(8) 0.0038(7) 0.0041(7) 0.0028(7) C12 0.0257(8) 0.0356(9) 0.0212(8) -0.0026(7) 0.0061(6) -0.0009(7) C13 0.0201(7) 0.0228(8) 0.0276(8) 0.0003(6) 0.0078(6) 0.0019(6) C14 0.0210(7) 0.0211(8) 0.0313(9) -0.0013(6) 0.0076(6) 0.0029(6) C15 0.0437(10) 0.0376(10) 0.0257(8) -0.0082(8) 0.0003(7) 0.0164(8) C16 0.0400(10) 0.0398(10) 0.0285(9) 0.0022(8) 0.0127(8) 0.0126(8) C17 0.0199(7) 0.0236(8) 0.0407(9) -0.0085(7) -0.0018(7) -0.0009(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 N1 1.2392(17) . ? O2 N1 1.2317(18) . ? O3 C4 1.329(2) . ? O3 H1O 0.93(3) . ? O4 N2 1.2337(19) . ? O5 N2 1.2413(18) . ? O6 C10 1.3111(19) . ? N1 C1 1.444(2) . ? N2 C7 1.438(2) . ? N3 C13 1.346(2) . ? N3 C16 1.357(2) . ? N3 H1N3 0.98(2) . ? N4 C13 1.341(2) . ? N4 H1N4 0.87(2) . ? N4 H2N4 0.79(2) . ? N5 C14 1.358(2) . ? N5 H1N5 0.94(2) . ? N5 H2N5 0.88(2) . ? C1 C6 1.384(2) . ? C1 C2 1.387(2) . ? C2 C3 1.374(2) . ? C2 H2 0.9300 . ? C3 C4 1.405(2) . ? C3 H3 0.9300 . ? C4 C5 1.404(2) . ? C5 C6 1.378(2) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 C8 1.390(2) . ? C7 C12 1.394(2) . ? C8 C9 1.377(2) . ? C8 H8 0.9300 . ? C9 C10 1.412(2) . ? C9 H9 0.9300 . ? C10 C11 1.416(2) . ? C11 C12 1.371(2) . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? C13 C14 1.427(2) . ? C14 C17 1.374(2) . ? C15 C16 1.345(3) . ? C15 C17 1.412(3) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? C17 H17 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C4 O3 H1O 115.1(16) . . ? O2 N1 O1 121.87(14) . . ? O2 N1 C1 119.53(13) . . ? O1 N1 C1 118.60(14) . . ? O4 N2 O5 122.25(14) . . ? O4 N2 C7 119.27(14) . . ? O5 N2 C7 118.47(13) . . ? C13 N3 C16 123.99(16) . . ? C13 N3 H1N3 120.1(13) . . ? C16 N3 H1N3 115.8(13) . . ? C13 N4 H1N4 123.5(14) . . ? C13 N4 H2N4 117.6(15) . . ? H1N4 N4 H2N4 119(2) . . ? C14 N5 H1N5 123.0(12) . . ? C14 N5 H2N5 119.1(13) . . ? H1N5 N5 H2N5 115.6(17) . . ? C6 C1 C2 121.52(15) . . ? C6 C1 N1 119.12(14) . . ? C2 C1 N1 119.36(14) . . ? C3 C2 C1 119.76(15) . . ? C3 C2 H2 120.1 . . ? C1 C2 H2 120.1 . . ? C2 C3 C4 119.84(15) . . ? C2 C3 H3 120.1 . . ? C4 C3 H3 120.1 . . ? O3 C4 C5 117.93(15) . . ? O3 C4 C3 122.68(15) . . ? C5 C4 C3 119.39(14) . . ? C6 C5 C4 120.44(15) . . ? C6 C5 H5 119.8 . . ? C4 C5 H5 119.8 . . ? C5 C6 C1 119.04(15) . . ? C5 C6 H6 120.5 . . ? C1 C6 H6 120.5 . . ? C8 C7 C12 121.40(14) . . ? C8 C7 N2 119.09(15) . . ? C12 C7 N2 119.51(14) . . ? C9 C8 C7 118.96(15) . . ? C9 C8 H8 120.5 . . ? C7 C8 H8 120.5 . . ? C8 C9 C10 121.43(14) . . ? C8 C9 H9 119.3 . . ? C10 C9 H9 119.3 . . ? O6 C10 C9 120.04(14) . . ? O6 C10 C11 122.30(15) . . ? C9 C10 C11 117.65(14) . . ? C12 C11 C10 121.26(15) . . ? C12 C11 H11 119.4 . . ? C10 C11 H11 119.4 . . ? C11 C12 C7 119.26(15) . . ? C11 C12 H12 120.4 . . ? C7 C12 H12 120.4 . . ? N4 C13 N3 119.56(15) . . ? N4 C13 C14 121.86(15) . . ? N3 C13 C14 118.57(14) . . ? N5 C14 C17 122.58(15) . . ? N5 C14 C13 119.90(14) . . ? C17 C14 C13 117.51(15) . . ? C16 C15 C17 119.87(16) . . ? C16 C15 H15 120.1 . . ? C17 C15 H15 120.1 . . ? C15 C16 N3 118.98(17) . . ? C15 C16 H16 120.5 . . ? N3 C16 H16 120.5 . . ? C14 C17 C15 121.03(16) . . ? C14 C17 H17 119.5 . . ? C15 C17 H17 119.5 . . ? 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 O3 H1O O6 0.93(3) 1.57(3) 2.5000(16) 176(3) . N4 H1N4 O6 0.87(2) 2.02(2) 2.884(2) 173(2) . N5 H1N5 O6 0.94(2) 1.97(2) 2.911(2) 172.7(18) . N5 H2N5 O5 0.88(2) 2.08(2) 2.9532(19) 169.8(19) 2_546 N3 H1N3 O1 0.98(2) 2.04(2) 2.9781(19) 159.4(19) 2_856 N3 H1N3 O2 0.98(2) 2.51(2) 3.2924(19) 136.8(17) 2_856 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.98 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.171 _refine_diff_density_min -0.157 _refine_diff_density_rms 0.030 data_sad5 _database_code_depnum_ccdc_archive 'CCDC 886327' #TrackingRef 'sad5.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 3-Aminopyridine 4-nitrophenol ; _chemical_name_common '3-Aminopyridine 4-nitrophenol' _chemical_melting_point ? _chemical_formula_moiety 'C6 H4 N O3, C5 H7 N2' _chemical_formula_sum 'C11 H11 N3 O3' _chemical_formula_weight 233.23 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 11.367(2) _cell_length_b 3.8092(7) _cell_length_c 13.278(3) _cell_angle_alpha 90.00 _cell_angle_beta 112.892(3) _cell_angle_gamma 90.00 _cell_volume 529.64(17) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.462 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 244 _exptl_absorpt_coefficient_mu 0.109 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.337 _exptl_absorpt_correction_T_max 0.654 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3682 _diffrn_reflns_av_R_equivalents 0.0462 _diffrn_reflns_av_sigmaI/netI 0.0607 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -4 _diffrn_reflns_limit_k_max 4 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.01 _diffrn_reflns_theta_max 24.98 _reflns_number_total 1828 _reflns_number_gt 1654 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2005)' _computing_cell_refinement 'SAINTPlus, v. 6.2 (Bruker, 2001)' _computing_data_reduction 'SAINTPlus, v. 6.2 (Bruker, 2001)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0983P)^2^+0.0039P] 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 0.1(17) _refine_ls_number_reflns 1828 _refine_ls_number_parameters 166 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0579 _refine_ls_R_factor_gt 0.0527 _refine_ls_wR_factor_ref 0.1393 _refine_ls_wR_factor_gt 0.1347 _refine_ls_goodness_of_fit_ref 1.071 _refine_ls_restrained_S_all 1.071 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.27521(17) 0.1938(6) -0.16154(14) 0.0328(5) Uani 1 1 d . . . O2 O 0.07950(17) 0.3020(7) -0.18402(15) 0.0399(6) Uani 1 1 d . . . O3 O 0.36112(16) 0.9535(5) 0.27809(12) 0.0281(5) Uani 1 1 d . . . H1O3 H 0.466(2) 0.970(9) 0.322(2) 0.023(6) Uiso 1 1 d . . . N1 N 0.19538(19) 0.3227(6) -0.13034(16) 0.0263(5) Uani 1 1 d . . . N2 N 0.60355(19) 1.0265(6) 0.38699(15) 0.0259(5) Uani 1 1 d . . . N3 N 0.8370(2) 0.8601(7) 0.66266(17) 0.0318(6) Uani 1 1 d . . . H2N3 H 0.786(3) 0.764(11) 0.684(3) 0.042(10) Uiso 1 1 d . . . H1N3 H 0.916(3) 0.917(9) 0.703(3) 0.028(7) Uiso 1 1 d . . . C1 C 0.2400(2) 0.4956(7) -0.02495(18) 0.0234(5) Uani 1 1 d . . . C2 C 0.1512(2) 0.6065(7) 0.01712(19) 0.0245(6) Uani 1 1 d . . . H2 H 0.0642 0.5795 -0.0235 0.029 Uiso 1 1 calc R . . C3 C 0.1938(2) 0.7559(7) 0.11919(19) 0.0251(6) Uani 1 1 d . . . H3 H 0.1353 0.8254 0.1485 0.030 Uiso 1 1 calc R . . C4 C 0.3245(2) 0.8044(7) 0.17937(18) 0.0230(6) Uani 1 1 d . . . C5 C 0.4124(2) 0.6978(8) 0.13427(19) 0.0243(6) Uani 1 1 d . . . H5 H 0.4994 0.7324 0.1731 0.029 Uiso 1 1 calc R . . C6 C 0.3691(2) 0.5417(7) 0.03239(19) 0.0244(6) Uani 1 1 d . . . H6 H 0.4268 0.4682 0.0027 0.029 Uiso 1 1 calc R . . C7 C 0.7856(2) 0.9791(7) 0.55694(18) 0.0251(6) Uani 1 1 d . . . C8 C 0.8599(2) 1.1491(8) 0.5090(2) 0.0262(6) Uani 1 1 d . . . H8 H 0.9459 1.1940 0.5496 0.031 Uiso 1 1 calc R . . C9 C 0.8041(2) 1.2498(8) 0.4004(2) 0.0282(6) Uani 1 1 d . . . H9 H 0.8524 1.3613 0.3671 0.034 Uiso 1 1 calc R . . C10 C 0.6769(2) 1.1834(8) 0.34230(19) 0.0270(6) Uani 1 1 d . . . H10 H 0.6403 1.2498 0.2692 0.032 Uiso 1 1 calc R . . C11 C 0.6565(2) 0.9295(8) 0.49228(19) 0.0263(6) Uani 1 1 d . . . H11 H 0.6049 0.8248 0.5235 0.032 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0359(9) 0.0467(12) 0.0190(9) -0.0043(8) 0.0142(7) -0.0011(9) O2 0.0274(10) 0.0660(15) 0.0224(9) -0.0111(10) 0.0054(7) -0.0047(10) O3 0.0293(9) 0.0431(12) 0.0117(8) -0.0042(8) 0.0078(7) -0.0006(9) N1 0.0281(11) 0.0371(13) 0.0150(10) 0.0002(9) 0.0098(9) -0.0030(10) N2 0.0287(10) 0.0337(13) 0.0138(9) -0.0018(9) 0.0068(8) -0.0007(10) N3 0.0301(13) 0.0473(16) 0.0148(11) 0.0021(10) 0.0052(10) -0.0046(12) C1 0.0288(12) 0.0293(13) 0.0134(11) 0.0010(10) 0.0097(9) -0.0002(12) C2 0.0211(11) 0.0349(15) 0.0154(11) 0.0022(10) 0.0046(9) -0.0014(11) C3 0.0278(12) 0.0346(14) 0.0163(12) 0.0024(11) 0.0122(9) 0.0030(11) C4 0.0266(12) 0.0292(14) 0.0129(11) 0.0010(10) 0.0075(10) 0.0003(11) C5 0.0202(11) 0.0331(15) 0.0189(11) 0.0010(10) 0.0069(9) 0.0013(11) C6 0.0291(12) 0.0298(15) 0.0178(11) 0.0025(10) 0.0128(10) 0.0029(11) C7 0.0325(13) 0.0293(14) 0.0135(11) -0.0029(11) 0.0091(10) -0.0018(12) C8 0.0221(11) 0.0350(15) 0.0188(11) -0.0020(11) 0.0051(9) -0.0006(12) C9 0.0363(14) 0.0353(15) 0.0168(11) 0.0002(11) 0.0143(10) -0.0014(12) C10 0.0287(12) 0.0370(15) 0.0147(11) 0.0021(11) 0.0078(9) 0.0022(12) C11 0.0281(12) 0.0370(15) 0.0146(11) -0.0013(10) 0.0093(9) -0.0005(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 N1 1.236(3) . ? O2 N1 1.232(3) . ? O3 C4 1.338(3) . ? O3 H1O3 1.10(3) . ? N1 C1 1.448(3) . ? N2 C10 1.337(3) . ? N2 C11 1.341(3) . ? N2 H1O3 1.48(3) . ? N3 C7 1.371(3) . ? N3 H2N3 0.82(4) . ? N3 H1N3 0.88(3) . ? C1 C6 1.376(3) . ? C1 C2 1.396(3) . ? C2 C3 1.373(3) . ? C2 H2 0.9300 . ? C3 C4 1.399(3) . ? C3 H3 0.9300 . ? C4 C5 1.409(3) . ? C5 C6 1.381(3) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 C11 1.395(4) . ? C7 C8 1.399(3) . ? C8 C9 1.385(3) . ? C8 H8 0.9300 . ? C9 C10 1.372(4) . ? C9 H9 0.9300 . ? C10 H10 0.9300 . ? C11 H11 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C4 O3 H1O3 114.0(14) . . ? O2 N1 O1 122.6(2) . . ? O2 N1 C1 118.82(19) . . ? O1 N1 C1 118.51(19) . . ? C10 N2 C11 118.8(2) . . ? C10 N2 H1O3 120.6(10) . . ? C11 N2 H1O3 120.6(10) . . ? C7 N3 H2N3 115(2) . . ? C7 N3 H1N3 118(2) . . ? H2N3 N3 H1N3 126(3) . . ? C6 C1 C2 121.4(2) . . ? C6 C1 N1 119.34(19) . . ? C2 C1 N1 119.2(2) . . ? C3 C2 C1 119.2(2) . . ? C3 C2 H2 120.4 . . ? C1 C2 H2 120.4 . . ? C2 C3 C4 120.5(2) . . ? C2 C3 H3 119.8 . . ? C4 C3 H3 119.8 . . ? O3 C4 C3 118.16(19) . . ? O3 C4 C5 122.5(2) . . ? C3 C4 C5 119.4(2) . . ? C6 C5 C4 119.9(2) . . ? C6 C5 H5 120.0 . . ? C4 C5 H5 120.0 . . ? C1 C6 C5 119.6(2) . . ? C1 C6 H6 120.2 . . ? C5 C6 H6 120.2 . . ? N3 C7 C11 120.9(2) . . ? N3 C7 C8 121.8(2) . . ? C11 C7 C8 117.3(2) . . ? C9 C8 C7 119.3(2) . . ? C9 C8 H8 120.4 . . ? C7 C8 H8 120.3 . . ? C10 C9 C8 119.3(2) . . ? C10 C9 H9 120.3 . . ? C8 C9 H9 120.3 . . ? N2 C10 C9 122.4(2) . . ? N2 C10 H10 118.8 . . ? C9 C10 H10 118.8 . . ? N2 C11 C7 122.8(2) . . ? N2 C11 H11 118.6 . . ? C7 C11 H11 118.6 . . ? 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 O3 H1O3 N2 1.10(3) 1.48(3) 2.581(3) 174(3) . N3 H2N3 O3 0.82(4) 2.26(4) 3.077(3) 172(3) 2_646 N3 H1N3 O2 0.88(3) 2.38(3) 3.195(3) 154(3) 1_666 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 24.98 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.254 _refine_diff_density_min -0.445 _refine_diff_density_rms 0.074 data_sergiu5 _database_code_depnum_ccdc_archive 'CCDC 886329' #TrackingRef 'sergiu7.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2,3-Diaminopyrimidinium 4-nitrophenolate 4-nitrophenol ; _chemical_name_common ; 2,3-Diaminopyrimidinium 4-nitrophenolate 4-nitrophenol ; _chemical_melting_point ? _chemical_formula_moiety 'C6 H5 N O3, C6 H4 N O3, C4 H7 N4' _chemical_formula_sum 'C16 H16 N6 O6' _chemical_formula_weight 388.35 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 P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 5.0160(4) _cell_length_b 21.6277(16) _cell_length_c 15.7012(13) _cell_angle_alpha 90.00 _cell_angle_beta 90.7690(10) _cell_angle_gamma 90.00 _cell_volume 1703.2(2) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.514 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 808 _exptl_absorpt_coefficient_mu 0.119 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.337 _exptl_absorpt_correction_T_max 0.654 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 30660 _diffrn_reflns_av_R_equivalents 0.0237 _diffrn_reflns_av_sigmaI/netI 0.0125 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.88 _diffrn_reflns_theta_max 26.00 _reflns_number_total 3343 _reflns_number_gt 3084 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2005)' _computing_cell_refinement 'SAINTPlus, v. 6.2 (Bruker, 2001)' _computing_data_reduction 'SAINTPlus, v. 6.2 (Bruker, 2001)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0380P)^2^+1.0262P] 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 3343 _refine_ls_number_parameters 277 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0362 _refine_ls_R_factor_gt 0.0331 _refine_ls_wR_factor_ref 0.0891 _refine_ls_wR_factor_gt 0.0850 _refine_ls_goodness_of_fit_ref 1.075 _refine_ls_restrained_S_all 1.075 _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 O1 O 0.2248(2) 0.29009(5) 0.54603(7) 0.0307(3) Uani 1 1 d . . . O2 O 0.4742(2) 0.31861(5) 0.65267(7) 0.0283(2) Uani 1 1 d . . . O3 O -0.2840(2) 0.54679(5) 0.62006(7) 0.0227(2) Uani 1 1 d . . . H1O3 H -0.221(4) 0.5724(10) 0.6607(14) 0.045(6) Uiso 1 1 d . . . O4 O 0.3858(2) 0.87423(5) 0.65532(7) 0.0275(2) Uani 1 1 d . . . O5 O 0.6524(2) 0.81196(5) 0.58959(7) 0.0269(2) Uani 1 1 d . . . O6 O -0.12333(19) 0.61898(4) 0.74372(6) 0.0197(2) Uani 1 1 d . . . N1 N 0.2893(2) 0.32789(5) 0.60159(7) 0.0212(3) Uani 1 1 d . . . N2 N 0.4552(2) 0.82125(5) 0.63462(7) 0.0205(3) Uani 1 1 d . . . N3 N -0.4989(2) 0.62039(5) 0.85880(7) 0.0181(2) Uani 1 1 d . . . H1N3 H -0.365(4) 0.6263(9) 0.8201(13) 0.035(5) Uiso 1 1 d . . . N4 N -0.4201(2) 0.51612(6) 0.84477(8) 0.0217(3) Uani 1 1 d . . . H1N4 H -0.289(4) 0.5259(9) 0.8145(12) 0.032(5) Uiso 1 1 d . . . H2N4 H -0.442(4) 0.4773(10) 0.8614(12) 0.034(5) Uiso 1 1 d . . . N5 N -1.0887(2) 0.58071(6) 1.02138(8) 0.0195(2) Uani 1 1 d . . . H1N5 H -1.172(3) 0.6107(8) 1.0443(11) 0.025(4) Uiso 1 1 d . . . H2N5 H -1.123(3) 0.5416(8) 1.0326(10) 0.022(4) Uiso 1 1 d . . . N6 N -0.7556(2) 0.54764(5) 0.93393(7) 0.0167(2) Uani 1 1 d . . . C1 C 0.1404(3) 0.38506(6) 0.60746(8) 0.0184(3) Uani 1 1 d . . . C2 C 0.2131(3) 0.42816(6) 0.66931(9) 0.0195(3) Uani 1 1 d . . . H2 H 0.3546 0.4203 0.7066 0.023 Uiso 1 1 calc R . . C3 C 0.0717(3) 0.48275(6) 0.67437(9) 0.0192(3) Uani 1 1 d . . . H3 H 0.1177 0.5120 0.7154 0.023 Uiso 1 1 calc R . . C4 C -0.1413(3) 0.49424(6) 0.61775(8) 0.0182(3) Uani 1 1 d . . . C5 C -0.2103(3) 0.45002(6) 0.55601(9) 0.0214(3) Uani 1 1 d . . . H5 H -0.3515 0.4575 0.5184 0.026 Uiso 1 1 calc R . . C6 C -0.0698(3) 0.39557(6) 0.55096(9) 0.0211(3) Uani 1 1 d . . . H6 H -0.1151 0.3661 0.5101 0.025 Uiso 1 1 calc R . . C7 C 0.3040(3) 0.76903(6) 0.66279(8) 0.0184(3) Uani 1 1 d . . . C8 C 0.3759(3) 0.71003(6) 0.63499(8) 0.0189(3) Uani 1 1 d . . . H8 H 0.5186 0.7048 0.5985 0.023 Uiso 1 1 calc R . . C9 C 0.2320(3) 0.65969(6) 0.66252(8) 0.0181(3) Uani 1 1 d . . . H9 H 0.2789 0.6203 0.6443 0.022 Uiso 1 1 calc R . . C10 C 0.0145(3) 0.66691(6) 0.71800(8) 0.0166(3) Uani 1 1 d . . . C11 C -0.0494(3) 0.72753(6) 0.74542(9) 0.0189(3) Uani 1 1 d . . . H11 H -0.1898 0.7333 0.7827 0.023 Uiso 1 1 calc R . . C12 C 0.0927(3) 0.77797(6) 0.71791(9) 0.0193(3) Uani 1 1 d . . . H12 H 0.0481 0.8175 0.7360 0.023 Uiso 1 1 calc R . . C13 C -0.5615(3) 0.56188(6) 0.88041(8) 0.0168(3) Uani 1 1 d . . . C14 C -0.8945(3) 0.59485(6) 0.96862(8) 0.0164(3) Uani 1 1 d . . . C15 C -0.8361(3) 0.65766(6) 0.94876(9) 0.0190(3) Uani 1 1 d . . . H15 H -0.9310 0.6900 0.9728 0.023 Uiso 1 1 calc R . . C16 C -0.6371(3) 0.66820(6) 0.89352(9) 0.0190(3) Uani 1 1 d . . . H16 H -0.5939 0.7086 0.8790 0.023 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0425(7) 0.0206(5) 0.0289(6) -0.0064(4) 0.0010(5) 0.0054(5) O2 0.0271(5) 0.0216(5) 0.0360(6) 0.0028(4) -0.0036(5) 0.0045(4) O3 0.0225(5) 0.0183(5) 0.0271(5) -0.0030(4) -0.0008(4) 0.0033(4) O4 0.0357(6) 0.0160(5) 0.0308(6) 0.0026(4) 0.0000(5) -0.0043(4) O5 0.0241(5) 0.0271(5) 0.0298(6) 0.0063(4) 0.0064(4) -0.0053(4) O6 0.0205(5) 0.0168(5) 0.0219(5) -0.0003(4) 0.0057(4) -0.0033(4) N1 0.0245(6) 0.0170(6) 0.0221(6) 0.0018(5) 0.0049(5) -0.0001(5) N2 0.0230(6) 0.0198(6) 0.0186(6) 0.0038(4) -0.0032(5) -0.0044(5) N3 0.0166(5) 0.0179(6) 0.0197(6) 0.0021(4) 0.0029(4) -0.0031(4) N4 0.0211(6) 0.0186(6) 0.0255(6) 0.0006(5) 0.0098(5) -0.0003(5) N5 0.0212(6) 0.0141(6) 0.0233(6) -0.0011(5) 0.0070(5) 0.0006(5) N6 0.0167(5) 0.0149(5) 0.0186(5) 0.0004(4) 0.0026(4) -0.0012(4) C1 0.0204(6) 0.0154(6) 0.0194(6) 0.0019(5) 0.0056(5) 0.0005(5) C2 0.0191(6) 0.0198(7) 0.0196(6) 0.0014(5) 0.0004(5) -0.0018(5) C3 0.0209(7) 0.0177(6) 0.0190(6) -0.0022(5) 0.0016(5) -0.0029(5) C4 0.0182(6) 0.0164(6) 0.0200(7) 0.0016(5) 0.0054(5) -0.0004(5) C5 0.0213(7) 0.0216(7) 0.0212(7) -0.0001(5) -0.0027(5) -0.0001(5) C6 0.0263(7) 0.0191(7) 0.0180(6) -0.0021(5) 0.0013(5) -0.0022(5) C7 0.0197(6) 0.0178(6) 0.0176(6) 0.0027(5) -0.0022(5) -0.0042(5) C8 0.0177(6) 0.0222(7) 0.0168(6) 0.0007(5) 0.0019(5) -0.0011(5) C9 0.0190(6) 0.0166(6) 0.0188(6) -0.0023(5) 0.0004(5) 0.0008(5) C10 0.0164(6) 0.0175(6) 0.0158(6) 0.0010(5) -0.0018(5) -0.0021(5) C11 0.0184(6) 0.0194(7) 0.0189(6) -0.0013(5) 0.0039(5) 0.0003(5) C12 0.0223(7) 0.0157(6) 0.0199(6) -0.0019(5) -0.0012(5) 0.0005(5) C13 0.0162(6) 0.0185(6) 0.0157(6) -0.0001(5) -0.0006(5) -0.0017(5) C14 0.0165(6) 0.0178(6) 0.0150(6) -0.0007(5) -0.0010(5) 0.0001(5) C15 0.0206(7) 0.0153(6) 0.0210(7) -0.0017(5) -0.0005(5) 0.0006(5) C16 0.0209(7) 0.0150(6) 0.0211(7) 0.0016(5) -0.0024(5) -0.0031(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 N1 1.2355(16) . ? O2 N1 1.2342(16) . ? O3 C4 1.3440(16) . ? O3 H1O3 0.90(2) . ? O4 N2 1.2421(16) . ? O5 N2 1.2398(16) . ? O6 C10 1.3126(16) . ? N1 C1 1.4482(17) . ? N2 C7 1.4338(17) . ? N3 C13 1.3485(17) . ? N3 C16 1.3629(18) . ? N3 H1N3 0.92(2) . ? N4 C13 1.3439(18) . ? N4 H1N4 0.85(2) . ? N4 H2N4 0.89(2) . ? N5 C14 1.3230(18) . ? N5 H1N5 0.855(19) . ? N5 H2N5 0.880(18) . ? N6 C13 1.3306(17) . ? N6 C14 1.3545(17) . ? C1 C6 1.3872(19) . ? C1 C2 1.3913(19) . ? C2 C3 1.3799(19) . ? C2 H2 0.9300 . ? C3 C4 1.4028(19) . ? C3 H3 0.9300 . ? C4 C5 1.4020(19) . ? C5 C6 1.375(2) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 C12 1.391(2) . ? C7 C8 1.3975(19) . ? C8 C9 1.3787(19) . ? C8 H8 0.9300 . ? C9 C10 1.4141(18) . ? C9 H9 0.9300 . ? C10 C11 1.4178(19) . ? C11 C12 1.3758(19) . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? C14 C15 1.4251(18) . ? C15 C16 1.3502(19) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C4 O3 H1O3 110.9(14) . . ? O2 N1 O1 122.57(12) . . ? O2 N1 C1 118.77(11) . . ? O1 N1 C1 118.65(12) . . ? O5 N2 O4 121.83(11) . . ? O5 N2 C7 118.53(12) . . ? O4 N2 C7 119.64(12) . . ? C13 N3 C16 119.33(12) . . ? C13 N3 H1N3 118.1(12) . . ? C16 N3 H1N3 122.5(12) . . ? C13 N4 H1N4 118.0(13) . . ? C13 N4 H2N4 120.6(12) . . ? H1N4 N4 H2N4 120.1(18) . . ? C14 N5 H1N5 117.2(12) . . ? C14 N5 H2N5 119.5(11) . . ? H1N5 N5 H2N5 123.2(16) . . ? C13 N6 C14 117.65(11) . . ? C6 C1 C2 121.77(13) . . ? C6 C1 N1 119.17(12) . . ? C2 C1 N1 119.07(12) . . ? C3 C2 C1 118.90(13) . . ? C3 C2 H2 120.6 . . ? C1 C2 H2 120.6 . . ? C2 C3 C4 120.18(12) . . ? C2 C3 H3 119.9 . . ? C4 C3 H3 119.9 . . ? O3 C4 C5 117.96(12) . . ? O3 C4 C3 122.29(12) . . ? C5 C4 C3 119.75(12) . . ? C6 C5 C4 120.12(13) . . ? C6 C5 H5 119.9 . . ? C4 C5 H5 119.9 . . ? C5 C6 C1 119.28(13) . . ? C5 C6 H6 120.4 . . ? C1 C6 H6 120.4 . . ? C12 C7 C8 121.54(12) . . ? C12 C7 N2 119.55(12) . . ? C8 C7 N2 118.90(12) . . ? C9 C8 C7 119.01(12) . . ? C9 C8 H8 120.5 . . ? C7 C8 H8 120.5 . . ? C8 C9 C10 121.15(12) . . ? C8 C9 H9 119.4 . . ? C10 C9 H9 119.4 . . ? O6 C10 C9 121.08(12) . . ? O6 C10 C11 120.98(12) . . ? C9 C10 C11 117.93(12) . . ? C12 C11 C10 121.19(12) . . ? C12 C11 H11 119.4 . . ? C10 C11 H11 119.4 . . ? C11 C12 C7 119.17(12) . . ? C11 C12 H12 120.4 . . ? C7 C12 H12 120.4 . . ? N6 C13 N4 119.16(12) . . ? N6 C13 N3 123.44(12) . . ? N4 C13 N3 117.40(12) . . ? N5 C14 N6 117.68(12) . . ? N5 C14 C15 120.84(12) . . ? N6 C14 C15 121.48(12) . . ? C16 C15 C14 117.22(12) . . ? C16 C15 H15 121.4 . . ? C14 C15 H15 121.4 . . ? C15 C16 N3 120.88(12) . . ? C15 C16 H16 119.6 . . ? N3 C16 H16 119.6 . . ? 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 O3 H1O3 O6 0.90(2) 1.71(2) 2.6105(14) 175(2) . N3 H1N3 O6 0.92(2) 1.73(2) 2.6278(15) 166.5(18) . N4 H1N4 O6 0.85(2) 2.45(2) 3.1219(16) 137.1(16) . N4 H2N4 O4 0.89(2) 2.26(2) 3.0736(16) 152.1(16) 2_546 N5 H1N5 O5 0.855(19) 2.023(19) 2.8739(16) 173.6(17) 4_376 N5 H2N5 N6 0.880(18) 2.094(19) 2.9702(16) 173.3(16) 3_367 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.227 _refine_diff_density_min -0.244 _refine_diff_density_rms 0.049