############################################################################## ### ### ### Electronic paper (Acta Crystallographica Section E) ### ### ### ############################################################################## # # # This CIF contains the data in a paper accepted for publication in Acta # # Crystallographica Section E. It conforms to the requirements of Notes # # for Authors for Section E, and has been peer reviewed under the auspices # # of the IUCr Commission on Journals. # # # # Full details of the Crystallographic Information File format # # are given in the paper "The Crystallographic Information File (CIF): # # a New Standard Archive File for Crystallography" by S. R. Hall, F. H. # # Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685]. # # # # The current version of the core CIF dictionary is obtainable from # # ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.4. # # # # Software is freely available for graphical display of the structure(s) in # # this CIF. For information consult the CIF home page http://www.iucr.org/ # # cif/home.html # # # # This file may be used for bona fide research purposes within the # # scientific community so long as proper attribution is given to the journal # # article from which it was obtained. # # # ############################################################################## data_global _audit_creation_method 'form.cif (version 2.0)' _journal_data_validation_number ? _journal_date_recd_electronic 2010-04-12 _journal_date_accepted 2010-04-20 _journal_name_full 'Acta Crystallographica, Section E' _journal_year 2010 _journal_volume 66 _journal_issue 5 _journal_page_first o1194 _journal_page_last o1195 _journal_paper_category QO _journal_coeditor_code HB5405 _publ_contact_author_name 'Prof. Fun, Hoong-Kun' _publ_contact_author_address ; X-ray Crystallography Unit School of Physics Universiti Sains Malaysia 11800 USM, Penang MALAYSIA ; _publ_contact_author_email 'hkfun@usm.my' _publ_contact_author_fax '604 6579150' _publ_contact_author_phone '604 6533652' _publ_section_title ; 2-Amino-5-methylpyridinium 2-hydroxy-3,5-dinitrobenzoate ; loop_ _publ_author_name _publ_author_footnote _publ_author_address 'Madhukar Hemamalini' ; Additional correspondence author, e-mail: mhemamalini2k3@yahoo.co.in. ; ; X-ray Crystallography Unit School of Physics Universiti Sains Malaysia 11800 USM, Penang Malaysia ; 'Hoong-Kun Fun' ; Thomson Reuters ResearcherID: A-3561-2009. ; ; X-ray Crystallography Unit School of Physics Universiti Sains Malaysia 11800 USM, Penang Malaysia ; data_I _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2-Amino-5-methylpyridinium 2-hydroxy-3,5-dinitrobenzoate ; _chemical_name_common ; 2-amino-5-methylpyridinium 3,5-dinitrosalicylate ; _chemical_formula_moiety 'C6 H9 N2 +, C7 H3 N2 O7 -' _chemical_formula_sum 'C13 H12 N4 O7' _chemical_formula_iupac 'C6 H9 N2 +, C7 H3 N2 O7 -' _chemical_formula_weight 336.27 _chemical_melting_point ? _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.8673(7) _cell_length_b 8.0991(9) _cell_length_c 15.2437(17) _cell_angle_alpha 86.844(3) _cell_angle_beta 84.252(3) _cell_angle_gamma 81.209(3) _cell_volume 711.69(14) _cell_formula_units_Z 2 _cell_measurement_reflns_used 5139 _cell_measurement_theta_min 2.69 _cell_measurement_theta_max 32.42 _cell_measurement_temperature 100.00(10) _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.29 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.08 _exptl_crystal_density_diffrn 1.569 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 348 _exptl_absorpt_coefficient_mu 0.130 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Bruker, 2009)' _exptl_absorpt_correction_T_min 0.9631 _exptl_absorpt_correction_T_max 0.9903 _exptl_special_details ; The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0(1) K. ; _diffrn_ambient_temperature 100.00(10) _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ; Bruker APEX DUO CCD area-detector diffractometer ; _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean . _diffrn_reflns_number 12709 _diffrn_reflns_av_R_equivalents 0.0229 _diffrn_reflns_av_sigmaI/netI 0.0304 _diffrn_reflns_theta_min 1.34 _diffrn_reflns_theta_max 32.50 _diffrn_reflns_theta_full 32.50 _diffrn_measured_fraction_theta_max 0.962 _diffrn_measured_fraction_theta_full 0.962 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 23 _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _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. ; _reflns_number_total 4947 _reflns_number_gt 3922 _reflns_threshold_expression I>2\s(I) _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_R_factor_all 0.0614 _refine_ls_R_factor_gt 0.0454 _refine_ls_wR_factor_gt 0.1263 _refine_ls_wR_factor_ref 0.1498 _refine_ls_goodness_of_fit_ref 1.076 _refine_ls_restrained_S_all 1.076 _refine_ls_number_reflns 4947 _refine_ls_number_parameters 219 _refine_ls_number_restraints 0 _refine_ls_hydrogen_treatment constr _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0741P)^2^+0.3055P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max ? _refine_ls_shift/su_max_lt 0.001 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.507 _refine_diff_density_min -0.459 _refine_ls_extinction_method none _refine_ls_extinction_coef ? 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' _computing_data_collection 'APEX2 (Bruker, 2009)' _computing_cell_refinement 'SAINT (Bruker, 2009)' _computing_data_reduction 'SAINT (Bruker, 2009)' _computing_structure_solution 'SHELXTL (Sheldrick, 2008)' _computing_structure_refinement 'SHELXTL (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)' loop_ _atom_site_type_symbol _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group N N1 0.50349(18) 0.28625(13) 0.24313(7) 0.0151(2) Uani d . 1 . . H H1 0.4877 0.2768 0.1882 0.018 Uiso d R 1 . . N N2 0.82364(19) 0.41676(14) 0.19955(7) 0.0176(2) Uani d . 1 . . H H2A 0.8060 0.4015 0.1454 0.021 Uiso d R 1 . . H H2B 0.9352 0.4662 0.2121 0.021 Uiso d R 1 . . C C1 0.6777(2) 0.36374(15) 0.26413(8) 0.0146(2) Uani d . 1 . . C C2 0.3509(2) 0.22205(16) 0.30452(8) 0.0162(2) Uani d . 1 . . H H2 0.2353 0.1692 0.2859 0.019 Uiso d R 1 . . C C3 0.3654(2) 0.23421(16) 0.39271(8) 0.0177(2) Uani d . 1 . . C C4 0.5424(2) 0.31915(17) 0.41660(8) 0.0196(2) Uani d . 1 . . H H4 0.5553 0.3318 0.4761 0.023 Uiso d R 1 . . C C5 0.6949(2) 0.38321(16) 0.35500(8) 0.0180(2) Uani d . 1 . . H H5 0.8088 0.4391 0.3726 0.022 Uiso d R 1 . . C C6 0.2014(2) 0.1628(2) 0.46135(9) 0.0252(3) Uani d . 1 . . H H6A 0.0930 0.1115 0.4329 0.038 Uiso d R 1 . . H H6B 0.1192 0.2508 0.4971 0.038 Uiso d R 1 . . H H6C 0.2873 0.0806 0.4980 0.038 Uiso d R 1 . . O O1 0.17251(16) 0.61810(13) 0.14298(6) 0.01924(19) Uani d . 1 . . H H1A 0.1638 0.6119 0.0899 0.029 Uiso calc R 1 . . O O2 0.10528(18) 0.60967(13) 0.31694(7) 0.0243(2) Uani d . 1 . . O O3 0.28454(18) 0.76459(15) 0.38862(6) 0.0270(2) Uani d . 1 . . O O4 0.93341(17) 0.99542(13) 0.26211(7) 0.0237(2) Uani d . 1 . . O O5 1.00019(18) 1.02494(14) 0.11971(8) 0.0274(2) Uani d . 1 . . O O6 0.55546(18) 0.76372(13) -0.07527(6) 0.0222(2) Uani d . 1 . . O O7 0.26539(17) 0.63243(12) -0.01529(6) 0.01923(19) Uani d . 1 . . N N3 0.25086(18) 0.70325(14) 0.31952(7) 0.0166(2) Uani d . 1 . . N N4 0.89119(18) 0.97295(13) 0.18590(8) 0.0181(2) Uani d . 1 . . C C7 0.3389(2) 0.70035(15) 0.15497(8) 0.0136(2) Uani d . 1 . . C C8 0.3891(2) 0.74498(15) 0.23904(8) 0.0141(2) Uani d . 1 . . C C9 0.5696(2) 0.83248(15) 0.24908(8) 0.0152(2) Uani d . 1 . . H H9 0.6004 0.8588 0.3049 0.018 Uiso d R 1 . . C C10 0.7029(2) 0.87992(15) 0.17497(8) 0.0148(2) Uani d . 1 . . C C11 0.6613(2) 0.84379(15) 0.09005(8) 0.0154(2) Uani d . 1 . . H H11 0.7517 0.8788 0.0409 0.018 Uiso d R 1 . . C C12 0.4831(2) 0.75506(14) 0.08054(7) 0.0136(2) Uani d . 1 . . C C13 0.4365(2) 0.71642(15) -0.01015(8) 0.0160(2) Uani d . 1 . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 N1 0.0161(4) 0.0167(5) 0.0128(4) -0.0032(4) -0.0022(3) -0.0010(3) N2 0.0184(5) 0.0215(5) 0.0143(4) -0.0086(4) -0.0004(3) -0.0001(4) C1 0.0161(5) 0.0138(5) 0.0138(5) -0.0018(4) -0.0014(4) -0.0003(4) C2 0.0144(5) 0.0164(5) 0.0180(5) -0.0032(4) -0.0014(4) -0.0009(4) C3 0.0183(5) 0.0184(5) 0.0156(5) -0.0022(4) 0.0005(4) 0.0009(4) C4 0.0238(6) 0.0234(6) 0.0123(5) -0.0048(5) -0.0033(4) -0.0007(4) C5 0.0200(5) 0.0205(6) 0.0149(5) -0.0058(5) -0.0039(4) -0.0005(4) C6 0.0225(6) 0.0321(7) 0.0206(6) -0.0078(5) 0.0030(5) 0.0045(5) O1 0.0192(4) 0.0257(5) 0.0154(4) -0.0105(4) -0.0028(3) -0.0014(3) O2 0.0271(5) 0.0276(5) 0.0202(5) -0.0141(4) 0.0037(4) -0.0011(4) O3 0.0285(5) 0.0422(6) 0.0122(4) -0.0098(5) -0.0019(4) -0.0062(4) O4 0.0210(4) 0.0230(5) 0.0296(5) -0.0032(4) -0.0110(4) -0.0068(4) O5 0.0235(5) 0.0269(5) 0.0337(6) -0.0121(4) -0.0010(4) 0.0021(4) O6 0.0286(5) 0.0266(5) 0.0127(4) -0.0099(4) 0.0000(3) -0.0007(3) O7 0.0215(4) 0.0242(5) 0.0142(4) -0.0094(4) -0.0031(3) -0.0008(3) N3 0.0163(4) 0.0197(5) 0.0134(4) -0.0017(4) -0.0011(3) -0.0005(4) N4 0.0144(4) 0.0149(5) 0.0261(5) -0.0027(4) -0.0048(4) -0.0025(4) C7 0.0133(5) 0.0139(5) 0.0135(5) -0.0018(4) -0.0015(4) -0.0009(4) C8 0.0137(5) 0.0158(5) 0.0128(5) -0.0021(4) -0.0006(4) -0.0009(4) C9 0.0145(5) 0.0151(5) 0.0162(5) -0.0007(4) -0.0038(4) -0.0030(4) C10 0.0125(5) 0.0132(5) 0.0195(5) -0.0031(4) -0.0028(4) -0.0017(4) C11 0.0148(5) 0.0140(5) 0.0171(5) -0.0019(4) -0.0007(4) -0.0010(4) C12 0.0147(5) 0.0144(5) 0.0119(5) -0.0029(4) -0.0014(4) -0.0008(4) C13 0.0187(5) 0.0162(5) 0.0136(5) -0.0028(4) -0.0028(4) -0.0014(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_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag N1 C1 . 1.3509(15) ? N1 C2 . 1.3668(15) ? N1 H1 . 0.8600 ? N2 C1 . 1.3355(15) ? N2 H2A . 0.8600 ? N2 H2B . 0.8600 ? C1 C5 . 1.4181(16) ? C2 C3 . 1.3652(17) ? C2 H2 . 0.9300 ? C3 C4 . 1.4164(18) ? C3 C6 . 1.5019(18) ? C4 C5 . 1.3681(18) ? C4 H4 . 0.9300 ? C5 H5 . 0.9300 ? C6 H6A . 0.9600 ? C6 H6B . 0.9600 ? C6 H6C . 0.9600 ? O1 C7 . 1.2957(14) ? O1 H1A . 0.8200 ? O2 N3 . 1.2302(14) ? O3 N3 . 1.2348(14) ? O4 N4 . 1.2404(15) ? O5 N4 . 1.2291(15) ? O6 C13 . 1.2331(15) ? O7 C13 . 1.3067(15) ? N3 C8 . 1.4546(15) ? N4 C10 . 1.4563(15) ? C7 C8 . 1.4208(16) ? C7 C12 . 1.4372(16) ? C8 C9 . 1.3861(16) ? C9 C10 . 1.3794(17) ? C9 H9 . 0.9300 ? C10 C11 . 1.3956(17) ? C11 C12 . 1.3793(16) ? C11 H11 . 0.9300 ? C12 C13 . 1.4943(16) ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C1 N1 C2 . . 123.48(10) ? C1 N1 H1 . . 118.2 ? C2 N1 H1 . . 118.3 ? C1 N2 H2A . . 120.0 ? C1 N2 H2B . . 120.0 ? H2A N2 H2B . . 120.0 ? N2 C1 N1 . . 119.16(11) ? N2 C1 C5 . . 123.65(11) ? N1 C1 C5 . . 117.18(11) ? C3 C2 N1 . . 121.14(11) ? C3 C2 H2 . . 119.4 ? N1 C2 H2 . . 119.4 ? C2 C3 C4 . . 116.59(11) ? C2 C3 C6 . . 122.06(12) ? C4 C3 C6 . . 121.34(12) ? C5 C4 C3 . . 122.13(11) ? C5 C4 H4 . . 118.9 ? C3 C4 H4 . . 118.9 ? C4 C5 C1 . . 119.43(11) ? C4 C5 H5 . . 120.3 ? C1 C5 H5 . . 120.3 ? C3 C6 H6A . . 109.5 ? C3 C6 H6B . . 109.5 ? H6A C6 H6B . . 109.5 ? C3 C6 H6C . . 109.5 ? H6A C6 H6C . . 109.5 ? H6B C6 H6C . . 109.5 ? C7 O1 H1A . . 109.5 ? O2 N3 O3 . . 122.24(11) ? O2 N3 C8 . . 119.70(10) ? O3 N3 C8 . . 118.06(11) ? O5 N4 O4 . . 123.31(11) ? O5 N4 C10 . . 118.76(11) ? O4 N4 C10 . . 117.93(11) ? O1 C7 C8 . . 123.94(11) ? O1 C7 C12 . . 120.07(10) ? C8 C7 C12 . . 115.98(10) ? C9 C8 C7 . . 122.15(11) ? C9 C8 N3 . . 116.22(10) ? C7 C8 N3 . . 121.63(10) ? C10 C9 C8 . . 118.97(11) ? C10 C9 H9 . . 120.5 ? C8 C9 H9 . . 120.5 ? C9 C10 C11 . . 122.23(11) ? C9 C10 N4 . . 118.70(11) ? C11 C10 N4 . . 119.06(11) ? C12 C11 C10 . . 118.54(11) ? C12 C11 H11 . . 120.7 ? C10 C11 H11 . . 120.7 ? C11 C12 C7 . . 122.12(10) ? C11 C12 C13 . . 118.93(10) ? C7 C12 C13 . . 118.95(10) ? O6 C13 O7 . . 123.31(11) ? O6 C13 C12 . . 120.35(11) ? O7 C13 C12 . . 116.34(10) ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag C2 N1 C1 N2 . . . . 177.44(11) ? C2 N1 C1 C5 . . . . -2.27(17) ? C1 N1 C2 C3 . . . . 0.56(19) ? N1 C2 C3 C4 . . . . 1.24(18) ? N1 C2 C3 C6 . . . . -179.26(12) ? C2 C3 C4 C5 . . . . -1.29(19) ? C6 C3 C4 C5 . . . . 179.21(13) ? C3 C4 C5 C1 . . . . -0.4(2) ? N2 C1 C5 C4 . . . . -177.56(12) ? N1 C1 C5 C4 . . . . 2.14(18) ? O1 C7 C8 C9 . . . . 179.70(12) ? C12 C7 C8 C9 . . . . -1.52(17) ? O1 C7 C8 N3 . . . . -1.24(19) ? C12 C7 C8 N3 . . . . 177.54(10) ? O2 N3 C8 C9 . . . . -171.71(11) ? O3 N3 C8 C9 . . . . 8.51(17) ? O2 N3 C8 C7 . . . . 9.17(18) ? O3 N3 C8 C7 . . . . -170.60(11) ? C7 C8 C9 C10 . . . . 0.96(18) ? N3 C8 C9 C10 . . . . -178.15(10) ? C8 C9 C10 C11 . . . . 0.44(18) ? C8 C9 C10 N4 . . . . 179.53(11) ? O5 N4 C10 C9 . . . . -175.21(11) ? O4 N4 C10 C9 . . . . 4.88(17) ? O5 N4 C10 C11 . . . . 3.91(17) ? O4 N4 C10 C11 . . . . -176.00(11) ? C9 C10 C11 C12 . . . . -1.15(18) ? N4 C10 C11 C12 . . . . 179.76(11) ? C10 C11 C12 C7 . . . . 0.51(18) ? C10 C11 C12 C13 . . . . 179.74(11) ? O1 C7 C12 C11 . . . . 179.60(11) ? C8 C7 C12 C11 . . . . 0.77(17) ? O1 C7 C12 C13 . . . . 0.37(17) ? C8 C7 C12 C13 . . . . -178.46(10) ? C11 C12 C13 O6 . . . . -0.21(18) ? C7 C12 C13 O6 . . . . 179.05(11) ? C11 C12 C13 O7 . . . . -179.85(11) ? C7 C12 C13 O7 . . . . -0.59(16) ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag O1 H1A O7 . 0.82 1.66 2.4200(13) 152 yes N1 H1 O6 2_665 0.86 1.82 2.6768(14) 174 yes N2 H2A O7 2_665 0.86 2.11 2.9668(15) 176 yes N2 H2B O1 1_655 0.86 2.16 2.8468(15) 137 yes N2 H2B O2 1_655 0.86 2.40 3.1723(16) 149 yes C2 H2 O4 1_445 0.93 2.49 3.4073(16) 169 yes C4 H4 O3 2_666 0.93 2.39 3.2371(16) 151 yes C5 H5 O2 1_655 0.93 2.44 3.2328(17) 143 yes