#------------------------------------------------------------------------------ #$Date: 2025-08-18 23:52:38 +0100 (Mon, 18 Aug 2025) $ #$Revision: 301791 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/65/2006588.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_2006588 loop_ _publ_author_name 'Dobson, Allison J.' 'Gerkin, Roger E.' _publ_section_title ; 2-Aminonicotinic Acid ; _journal_issue 10 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 1427 _journal_page_last 1429 _journal_paper_doi 10.1107/S0108270197008226 _journal_volume 53 _journal_year 1997 _chemical_formula_iupac 'C6 H6 N2 O2' _chemical_formula_moiety 'C6 H6 N2 O2 ' _chemical_formula_sum 'C6 H6 N2 O2' _chemical_formula_weight 138.13 _chemical_name_common '2-aminonicotinic acid' _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' _cell_angle_alpha 90 _cell_angle_beta 108.930(10) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 7.4460(10) _cell_length_b 12.1722(6) _cell_length_c 6.9261(7) _cell_measurement_reflns_used 25 _cell_measurement_temperature 296 _cell_measurement_theta_max 17.4 _cell_measurement_theta_min 15.0 _cell_volume 593.79(11) _computing_cell_refinement 'MSC/AFC Diffractometer Control Software' _computing_data_collection ;MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1991) ; _computing_data_reduction 'TEXSAN (Molecular Structure Corporation, 1989)' _computing_molecular_graphics ORTEPII _computing_publication_material TEXSAN _computing_structure_refinement TEXSAN _computing_structure_solution 'MITHRIL (Gilmore, 1984)' _diffrn_ambient_temperature 296 _diffrn_measurement_device_type 'Rigaku AFC5S' _diffrn_measurement_method \w _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'X-ray tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.025 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 1545 _diffrn_reflns_theta_max 27.5 _diffrn_reflns_theta_min 2.0 _diffrn_standards_decay_% 5.0 _diffrn_standards_interval_count 150 _diffrn_standards_number 6 _exptl_absorpt_coefficient_mu 0.119 _exptl_absorpt_correction_type none _exptl_crystal_colour 'pale yellow' _exptl_crystal_density_diffrn 1.545 _exptl_crystal_density_method 'not measured' _exptl_crystal_description 'cut rod' _exptl_crystal_F_000 288 _exptl_crystal_size_max 0.39 _exptl_crystal_size_mid 0.31 _exptl_crystal_size_min 0.27 _refine_diff_density_max 0.24 _refine_diff_density_min -0.26 _refine_ls_extinction_coef 3.9E-6(6) _refine_ls_extinction_method 'Zachariasen (1963, 1968)' _refine_ls_goodness_of_fit_ref 1.74 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 116 _refine_ls_number_reflns 1165 _refine_ls_R_factor_gt 0.062 _refine_ls_shift/su_max '< 0.01' _refine_ls_structure_factor_coef F _refine_ls_weighting_details 'w = 1/\s^2^(F)' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref 0.057 _reflns_number_gt 1165 _reflns_number_total 1434 _reflns_threshold_expression 'I > 0.1\s(I)' _cod_data_source_file fr1064.cif _cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius The following automatic conversions were performed: '_atom_site_adp_type' tag value 'Uij' was replaced with 'Uani' value 10 times. Automatic conversion script Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana The following automatic conversions were performed: '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana The following automatic conversions were performed: '_refine_ls_weighting_scheme' value 'w = 1/\s^2^(F)' was changed to 'calc'. New tag '_refine_ls_weighting_details' was created. The value of the new tag was set to 'w = 1/\s^2^(F)'. Automatic conversion script Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas ; _cod_original_cell_volume 593.80(10) _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 2006588 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 O1 .2458(2) .00230(10) .8173(3) .0524(5) Uani ? ? O2 -.0352(2) .08140(10) .7654(2) .0442(4) Uani ? ? N1 .2171(2) .39100(10) .7765(2) .0298(4) Uani ? ? N2 -.0616(2) .29810(10) .7296(3) .0377(5) Uani ? ? C2 .1244(3) .29410(10) .7700(3) .0262(5) Uani ? ? C3 .2331(3) .19550(10) .8065(3) .0271(5) Uani ? ? C4 .4268(3) .2039(2) .8559(3) .0313(5) Uani ? ? C5 .5163(3) .3054(2) .8622(3) .0342(5) Uani ? ? C6 .4068(3) .3968(2) .8184(3) .0328(5) Uani ? ? C7 .1418(3) .0835(2) .7953(3) .0323(5) Uani ? ? H1 .143(3) .457(2) .760(3) .052(7) Uiso ? ? H2 -.125(3) .360(2) .706(3) .039(6) Uiso ? ? H3 -.118(3) .228(2) .723(4) .055(7) Uiso ? ? H4 .502(3) .137(2) .881(3) .038(6) Uiso ? ? H5 .644(3) .312(2) .889(3) .044(6) Uiso ? ? H6 .459(3) .473(2) .810(3) .042(6) Uiso ? ? 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 .0404(9) .0195(7) .0960(10) .0032(7) .0203(8) -.0032(8) O2 .0327(8) .0219(7) .0780(10) -.0033(6) .0185(7) -.0003(7) N1 .0327(9) .0182(8) .0386(9) .0001(7) .0116(7) .0007(7) N2 .0287(9) .0210(8) .0630(10) .0034(8) .0145(9) .0037(9) C2 .0283(9) .0206(9) .0308(10) -.0022(8) .0114(8) -.0012(7) C3 .0324(10) .0200(9) .0296(10) .0004(8) .0112(8) -.0012(7) C4 .0290(10) .0280(10) .0370(10) .0027(9) .0109(8) -.0006(8) C5 .0260(10) .0360(10) .0410(10) -.0046(9) .0114(8) -.0017(9) C6 .0350(10) .0260(10) .0390(10) -.0089(8) .0141(9) -.0037(8) C7 .0370(10) .0191(9) .0410(10) -.0026(8) .0132(9) -.0014(8) loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source H 0 0 'Stewart, Davidson & Simpson (1965)' C .003 .002 'Creagh & McAuley (1992)' N .006 .003 'Creagh & McAuley (1992)' O .011 .006 'Creagh & McAuley (1992)' 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 C2 N1 C6 122.5(2) yes C2 N1 H1 117.0(10) no C6 N1 H1 120.0(10) no C2 N2 H2 122.0(10) no C2 N2 H3 113.0(10) no H2 N2 H3 124(2) no N1 C2 N2 117.4(2) no N1 C2 C3 118.2(2) no N2 C2 C3 124.4(2) no C2 C3 C4 118.2(2) no C2 C3 C7 122.0(2) no C4 C3 C7 119.8(2) no C3 C4 C5 121.7(2) no C3 C4 H4 118.0(10) no C5 C4 H4 119.0(10) no C4 C5 C6 118.2(2) no C4 C5 H5 123.0(10) no C6 C5 H5 118.0(10) no N1 C6 C5 121.2(2) no N1 C6 H6 115.0(10) no C5 C6 H6 123.0(10) no O1 C7 O2 125.6(2) yes O1 C7 C3 117.4(2) yes O2 C7 C3 116.9(2) yes 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 C7 ? ? 1.234(2) yes O2 C7 ? ? 1.266(2) yes N1 C2 ? ? 1.360(2) yes N1 C6 ? ? 1.348(2) yes N1 H1 ? ? .96(2) no N2 C2 ? ? 1.322(2) yes N2 H2 ? ? .88(2) no N2 H3 ? ? .94(3) no C2 C3 ? ? 1.423(2) yes C3 C4 ? ? 1.374(3) yes C3 C7 ? ? 1.514(2) yes C4 C5 ? ? 1.398(3) yes C4 H4 ? ? .97(2) no C5 C6 ? ? 1.355(3) yes C5 H5 ? ? .91(2) no C6 H6 ? ? 1.02(2) 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 N1 H1 O2 2_556 0.96(2) 1.70(2) 2.652(2) 174(2) yes N2 H2 O1 2_556 0.88(2) 1.93(2) 2.807(2) 173(2) yes N2 H3 O2 ? 0.94(3) 1.88(3) 2.651(2) 137(2) yes C4 H4 O1 3_657 0.97(2) 2.87(2) 3.713(2) 146.0(10) yes C5 H5 O2 4_655 0.91(2) 3.18(2) 3.847(3) 131(2) yes C6 H6 O1 4_554 1.02(2) 3.28(2) 3.506(3) 94.0(10) yes loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 PubChem 72930