#------------------------------------------------------------------------------ #$Date: 2013-12-28 13:58:47 +0000 (Sat, 28 Dec 2013) $ #$Revision: 91933 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/21/2202116.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2202116 loop_ _publ_author_name 'Takeo Fukunaga' 'Setsuo Kashino' 'Hiroyuki Ishida' _publ_section_title ; 3-Hydroxypyridinium 2,5-dihydroxybenzoate ; _journal_issue 4 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o420 _journal_page_last o422 _journal_volume 59 _journal_year 2003 _chemical_formula_iupac 'C5 H6 N O 1+, C7 H5 O4 1-' _chemical_formula_moiety 'C5 H6 N O 1+, C7 H5 O4 1-' _chemical_formula_sum 'C12 H11 N O5' _chemical_formula_weight 249.22 _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _atom_type_scat_source IntTabC _cell_angle_alpha 90 _cell_angle_beta 95.454(18) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 7.659(2) _cell_length_b 7.1731(17) _cell_length_c 20.468(4) _cell_measurement_reflns_used 25 _cell_measurement_temperature 298 _cell_measurement_theta_max 11.5 _cell_measurement_theta_min 11.3 _cell_volume 1119.4(5) _computing_cell_refinement 'MSC/AFC Diffractometer Control Software' _computing_data_collection ; MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1990) ; _computing_data_reduction 'TEXSAN for Windows (Molecular Structure Corporation, 1997-1999)' _computing_publication_material 'TEXSAN for Windows' _computing_structure_refinement 'TEXSAN for Windows' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _diffrn_ambient_temperature 298 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device 'Rigaku AFC-5R' _diffrn_measurement_method \w-2\q _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'Rigaku rotating anode' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.031 _diffrn_reflns_av_sigmaI/netI 0.051 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -1 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -1 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_number 4496 _diffrn_reflns_reduction_process 'Lp corrections applied' _diffrn_reflns_theta_full 29.99 _diffrn_reflns_theta_max 29.99 _diffrn_reflns_theta_min 2.67 _diffrn_standards_decay_% 2.29 _diffrn_standards_interval_count 97 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.117 _exptl_absorpt_correction_type none _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.479 _exptl_crystal_density_meas 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 520 _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.21 _refine_diff_density_max 0.37 _refine_diff_density_min -0.36 _refine_ls_extinction_coef 1.7(3)E-6 _refine_ls_extinction_expression 'equ(3) Acta Cryst.(1968) 24, p213.' _refine_ls_extinction_method 'Zachariasen (1967)' _refine_ls_goodness_of_fit_all 1.10 _refine_ls_goodness_of_fit_ref 1.10 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_constraints 0 _refine_ls_number_parameters 208 _refine_ls_number_reflns 3252 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.066 _refine_ls_R_factor_gt 0.056 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.001 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo) + 0.00203|Fo|^2^]' _refine_ls_weighting_scheme sigma _refine_ls_wR_factor_all 0.179 _refine_ls_wR_factor_ref 0.179 _reflns_number_gt 1878 _reflns_number_total 3252 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file ob6218.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M 'P 21/c' _[local]_cod_chemical_formula_sum_orig 'C12 H11 N O5 ' _cod_database_code 2202116 loop_ _symmetry_equiv_pos_as_xyz ' +x, +y, +z' ' -x,1/2+y,1/2-z' ' -x, -y, -z' ' +x,1/2-y,1/2+z' loop_ _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_calc_attached_atom _atom_site_refinement_flags _atom_site_occupancy O1 0.4951(3) 1.1583(2) 0.61801(10) 0.0619(5) Uani d ? . 1.000 O2 0.2621(2) 0.1928(2) 0.52261(8) 0.0585(5) Uani d ? . 1.000 O3 0.2599(2) 0.4962(2) 0.50114(7) 0.0513(5) Uani d ? . 1.000 O4 0.0893(2) 0.6228(2) 0.39858(9) 0.0546(5) Uani d ? . 1.000 O5 -0.1000(2) -0.0975(2) 0.33037(8) 0.0549(5) Uani d ? . 1.000 N1 0.4441(2) 0.6629(3) 0.60081(9) 0.0387(5) Uani d ? . 1.000 C2 0.4276(3) 0.8440(3) 0.58707(10) 0.0388(5) Uani d ? . 1.000 C3 0.5064(3) 0.9755(3) 0.62988(10) 0.0404(5) Uani d ? . 1.000 C4 0.6014(3) 0.9113(3) 0.68671(11) 0.0435(6) Uani d ? . 1.000 C5 0.6149(3) 0.7233(3) 0.69940(11) 0.0443(6) Uani d ? . 1.000 C6 0.5358(3) 0.5985(3) 0.65547(11) 0.0431(6) Uani d ? . 1.000 C7 0.0973(2) 0.2951(3) 0.42658(9) 0.0322(5) Uani d ? . 1.000 C8 0.0433(3) 0.4427(3) 0.38454(10) 0.0358(5) Uani d ? . 1.000 C9 -0.0555(3) 0.4051(3) 0.32527(10) 0.0404(5) Uani d ? . 1.000 C10 -0.1008(3) 0.2249(3) 0.30804(10) 0.0398(5) Uani d ? . 1.000 C11 -0.0497(3) 0.0777(3) 0.35006(10) 0.0371(5) Uani d ? . 1.000 C12 0.0484(3) 0.1147(3) 0.40892(10) 0.0354(5) Uani d ? . 1.000 C13 0.2143(3) 0.3294(3) 0.48844(9) 0.0371(5) Uani d ? . 1.000 H1 0.381(3) 0.577(4) 0.5691(13) 0.053(7) Uiso d ? . 1.000 H2 0.358(3) 0.881(3) 0.5457(11) 0.039(6) Uiso d ? . 1.000 H3 0.412(4) 1.184(4) 0.5847(15) 0.072(8) Uiso d ? . 1.000 H4 0.660(3) 0.999(4) 0.7144(13) 0.054(7) Uiso d ? . 1.000 H5 0.685(3) 0.676(4) 0.7393(13) 0.057(7) Uiso d ? . 1.000 H6 0.543(3) 0.472(4) 0.6596(12) 0.055(7) Uiso d ? . 1.000 H7 0.152(4) 0.619(4) 0.4392(15) 0.072(8) Uiso d ? . 1.000 H8 -0.094(4) 0.505(5) 0.2961(14) 0.070(8) Uiso d ? . 1.000 H9 -0.173(3) 0.198(3) 0.2656(11) 0.040(6) Uiso d ? . 1.000 H10 -0.044(4) -0.171(4) 0.3587(15) 0.067(8) Uiso d ? . 1.000 H11 0.085(3) 0.017(3) 0.4374(11) 0.038(5) Uiso d ? . 1.000 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 O1 0.0763(12) 0.0317(9) 0.0698(12) -0.0054(8) -0.0349(10) 0.0013(8) O2 0.0811(12) 0.0392(9) 0.0483(9) -0.0009(8) -0.0300(8) 0.0067(7) O3 0.0667(11) 0.0344(9) 0.0480(9) -0.0033(7) -0.0198(8) -0.0060(7) O4 0.0710(11) 0.0253(8) 0.0608(11) -0.0023(7) -0.0286(9) 0.0020(7) O5 0.0788(12) 0.0304(8) 0.0492(10) -0.0051(8) -0.0267(8) -0.0025(7) N1 0.0436(10) 0.0324(9) 0.0381(9) -0.0006(7) -0.0064(7) -0.0054(7) C2 0.0443(11) 0.0341(11) 0.0353(10) -0.0007(9) -0.0106(9) -0.0010(8) C3 0.0417(11) 0.0324(10) 0.0444(11) -0.0018(8) -0.0091(9) -0.0025(9) C4 0.0447(12) 0.0414(12) 0.0407(11) 0.0002(9) -0.0153(9) -0.0084(9) C5 0.0475(12) 0.0458(12) 0.0368(11) 0.0057(10) -0.0099(9) -0.0007(9) C6 0.0484(12) 0.0338(11) 0.0453(12) 0.0042(9) -0.0050(9) -0.0003(9) C7 0.0376(10) 0.0273(9) 0.0305(9) 0.0022(7) -0.0035(8) 0.0000(7) C8 0.0396(10) 0.0249(10) 0.0407(11) 0.0015(8) -0.0078(8) 0.0004(8) C9 0.0455(11) 0.0329(10) 0.0398(11) 0.0025(9) -0.0117(9) 0.0066(9) C10 0.0423(11) 0.0377(11) 0.0365(10) -0.0004(9) -0.0116(8) 0.0020(9) C11 0.0432(11) 0.0282(9) 0.0379(10) 0.0011(8) -0.0061(8) -0.0028(8) C12 0.0424(11) 0.0279(10) 0.0341(10) 0.0010(8) -0.0053(8) 0.0028(8) C13 0.0437(11) 0.0328(10) 0.0326(10) 0.0024(8) -0.0073(8) -0.0032(8) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 C3 . . 1.334(3) yes O1 H3 . . 0.90(3) no O2 C13 . . 1.239(3) yes O3 C13 . . 1.267(3) yes O4 C8 . . 1.363(3) yes O4 H7 . . 0.92(3) no O5 C11 . . 1.364(3) yes O5 H10 . . 0.87(4) no N1 C2 . . 1.332(3) yes N1 C6 . . 1.345(3) yes N1 H1 . . 0.99(3) no C2 C3 . . 1.387(3) yes C2 H2 . . 0.99(2) no C3 C4 . . 1.391(3) yes C4 C5 . . 1.375(3) yes C4 H4 . . 0.93(3) no C5 C6 . . 1.369(3) yes C5 H5 . . 0.99(3) no C6 H6 . . 0.91(3) no C7 C8 . . 1.402(3) yes C7 C12 . . 1.386(3) yes C7 C13 . . 1.500(3) yes C8 C9 . . 1.393(3) yes C9 C10 . . 1.376(3) yes C9 H8 . . 0.96(3) no C10 C11 . . 1.394(3) yes C10 H9 . . 1.00(2) no C11 C12 . . 1.383(3) yes C12 H11 . . 0.94(2) no loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 2 -1 -1 2 0 2 1 -1 0 loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag C3 O1 H3 111(2) no C8 O4 H7 105(2) no C11 O5 H10 105(2) no C2 N1 C6 122.8(2) no C2 N1 H1 115.8(16) no C6 N1 H1 121.3(16) no N1 C2 C3 120.22(19) no N1 C2 H2 118.4(14) no C3 C2 H2 121.4(14) no O1 C3 C2 122.5(2) yes O1 C3 C4 119.8(2) yes C2 C3 C4 117.7(2) no C3 C4 C5 120.5(2) no C3 C4 H4 117.8(17) no C5 C4 H4 121.6(17) no C4 C5 C6 119.8(2) no C4 C5 H5 121.1(16) no C6 C5 H5 119.1(16) no N1 C6 C5 119.0(2) no N1 C6 H6 116.1(18) no C5 C6 H6 124.9(18) no C8 C7 C12 119.23(18) no C8 C7 C13 120.82(18) yes C12 C7 C13 119.88(18) yes O4 C8 C7 122.07(18) yes O4 C8 C9 118.37(18) yes C7 C8 C9 119.51(18) no C8 C9 C10 120.52(19) no C8 C9 H8 120.3(18) no C10 C9 H8 119.1(18) no C9 C10 C11 120.28(19) no C9 C10 H9 120.6(14) no C11 C10 H9 119.1(14) no O5 C11 C10 117.43(19) yes O5 C11 C12 123.28(19) yes C10 C11 C12 119.29(19) no C7 C12 C11 121.16(18) no C7 C12 H11 118.6(15) no C11 C12 H11 120.2(15) no O2 C13 O3 124.78(19) yes O2 C13 C7 117.88(18) yes O3 C13 C7 117.33(18) yes loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_2 _geom_contact_publ_flag O2 C3 3.158(3) 1_545 no O3 H2 2.98(2) . no O3 H3 2.99(3) 1_545 no O3 C2 3.246(3) . no N1 C13 3.331(3) 3_666 no C2 C11 3.325(3) 3_566 no C6 C8 3.414(3) 3_666 no C8 H10 2.89(3) 1_565 no C13 H3 2.59(3) 1_545 no C13 H1 2.67(3) . no 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 H3 O2 1_565 0.90(3) 1.63(4) 2.530(2) 171(3) yes O4 H7 O3 . 0.92(3) 1.70(3) 2.533(2) 150(3) yes O5 H10 O4 1_545 0.87(4) 1.93(4) 2.773(3) 163(3) yes N1 H1 O3 . 0.99(3) 1.70(3) 2.652(2) 161(2) yes C2 H2 O2 1_565 0.99(2) 2.39(2) 3.048(3) 123.3(16) yes C5 H5 O5 4_655 0.99(3) 2.43(3) 3.414(3) 169.2(19) yes C6 H6 O1 1_545 0.91(3) 2.42(3) 3.257(3) 152(2) yes loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_publ_flag O1 C3 C2 N1 179.3(2) no O1 C3 C4 C5 -179.6(2) no O2 C13 C7 C8 -177.8(2) no O2 C13 C7 C12 -0.9(3) no O3 C13 C7 C8 0.7(3) no O3 C13 C7 C12 177.6(2) no O4 C8 C7 C12 -178.9(2) no O4 C8 C7 C13 -2.0(3) no O4 C8 C9 C10 178.1(2) no O5 C11 C10 C9 179.5(2) no O5 C11 C12 C7 179.5(2) no N1 C2 C3 C4 -0.1(4) no N1 C6 C5 C4 -0.8(4) no C2 N1 C6 C5 0.5(4) no C2 C3 C4 C5 -0.2(4) no C3 C2 N1 C6 -0.1(4) no C3 C4 C5 C6 0.6(4) no C7 C8 C9 C10 0.4(4) no C7 C12 C11 C10 -0.4(4) no C8 C7 C12 C11 1.3(3) no C8 C9 C10 C11 0.6(4) no C9 C8 C7 C12 -1.3(3) no C9 C8 C7 C13 175.7(2) no C9 C10 C11 C12 -0.6(4) no C11 C12 C7 C13 -175.7(2) no _journal_paper_doi 10.1107/S1600536803004525