#------------------------------------------------------------------------------ #$Date: 2025-08-18 23:52:38 +0100 (Mon, 18 Aug 2025) $ #$Revision: 301791 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/81/2008146.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_2008146 loop_ _publ_author_name 'Moreno-Fuquen, Rodolfo' 'Valderrama-Naranjo, Jaime' 'Monta\~no, Angela Marcela' _publ_section_title ; A 1:1 complex of 4-nitropyridine N-oxide and 3-hydroxybenzoic acid ; _journal_issue 2 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 218 _journal_page_last 220 _journal_paper_doi 10.1107/S0108270198009949 _journal_volume 55 _journal_year 1999 _chemical_formula_moiety 'C5 H4 N2 O3 . C7 H6 O3' _chemical_formula_sum 'C12 H10 N2 O6' _chemical_formula_weight 278.22 _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _audit_creation_method SHELXL _cell_angle_alpha 90.00 _cell_angle_beta 95.46(2) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 6.5453(6) _cell_length_b 7.5995(8) _cell_length_c 24.855(3) _cell_measurement_reflns_used 25 _cell_measurement_temperature 293 _cell_measurement_theta_max 18.2 _cell_measurement_theta_min 9.9 _cell_volume 1230.7(2) _computing_cell_refinement 'CAD-4 Software' _computing_data_collection 'CAD-4 Software (Enraf-Nonius, 1989)' _computing_data_reduction 'SDP (Frenz, 1978)' _computing_molecular_graphics 'ZORTEP (Zsolnai, 1995)' _computing_publication_material SDP _computing_structure_refinement SHELXL93 _computing_structure_solution 'SHELXS86 (Sheldrick, 1985)' _diffrn_measurement_device 'Enraf-Nonius CAD-4' _diffrn_measurement_method \w/2\q _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.019 _diffrn_reflns_av_sigmaI/netI 0.035 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_number 2719 _diffrn_reflns_theta_max 26.29 _diffrn_reflns_theta_min 2.80 _diffrn_standards_decay_% 0.70 _diffrn_standards_interval_time 120 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.12 _exptl_absorpt_correction_type none _exptl_crystal_colour pale_yellow _exptl_crystal_density_diffrn 1.502 _exptl_crystal_density_method not_measured _exptl_crystal_description prism _exptl_crystal_F_000 576 _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _refine_diff_density_max 0.221 _refine_diff_density_min -0.167 _refine_ls_extinction_coef 0.054(3) _refine_ls_extinction_method 'SHELXL93 (Sheldrick, 1993)' _refine_ls_goodness_of_fit_all 1.114 _refine_ls_goodness_of_fit_obs 1.028 _refine_ls_hydrogen_treatment 'H atoms: see below' _refine_ls_matrix_type full _refine_ls_number_parameters 188 _refine_ls_number_reflns 2493 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.117 _refine_ls_restrained_S_obs 1.028 _refine_ls_R_factor_all 0.083 _refine_ls_R_factor_obs 0.038 _refine_ls_shift/esd_max <0.001 _refine_ls_shift/esd_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/(\s^2^(Fo^2^)+(0.0306P)^2^+0.6014P) where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all 0.117 _refine_ls_wR_factor_obs 0.084 _reflns_number_observed 1613 _reflns_number_total 2495 _reflns_observed_criterion I>2\s(I) _cod_data_source_file fr1126.cif _cod_data_source_block global _cod_depositor_comments ; The following automatic conversions were performed: '_refine_ls_weighting_scheme' value 'w = 1/(\s^2^(Fo^2^)+(0.0306P)^2^+0.6014P) where P=(Fo^2^+2Fc^2^)/3' 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^(Fo^2^)+(0.0306P)^2^+0.6014P) where P=(Fo^2^+2Fc^2^)/3'. Automatic conversion script Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas ; _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 2008146 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, z+1/2' '-x, -y, -z' '-x-1/2, y-1/2, -z-1/2' 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 0.0662(11) 0.0531(11) 0.0696(12) -0.0046(9) -0.0213(9) 0.0065(9) O2 0.0714(12) 0.0703(13) 0.0548(11) -0.0012(10) 0.0069(9) -0.0101(9) O3 0.0514(10) 0.0746(13) 0.0848(13) -0.0139(10) 0.0160(10) -0.0001(11) N1 0.0521(11) 0.0398(11) 0.0521(11) 0.0040(9) -0.0031(9) 0.0089(9) N2 0.0471(11) 0.0427(11) 0.0586(12) 0.0021(9) 0.0082(10) 0.0045(10) C1 0.0452(12) 0.0455(14) 0.0603(15) 0.0057(11) 0.0126(11) 0.0074(12) C2 0.0489(13) 0.0427(13) 0.0493(12) 0.0043(11) 0.0143(10) 0.0012(11) C3 0.0435(12) 0.0355(12) 0.0457(12) 0.0050(10) 0.0067(9) 0.0058(10) C4 0.0525(13) 0.0495(14) 0.0465(12) 0.0019(11) 0.0167(11) 0.0075(11) C5 0.064(2) 0.0529(15) 0.0426(12) 0.0035(13) 0.0089(11) 0.0051(11) O4 0.0524(10) 0.0610(11) 0.0412(8) 0.0106(8) 0.0086(7) 0.0112(8) O5 0.0480(9) 0.0622(11) 0.0471(9) 0.0127(8) 0.0103(7) 0.0095(8) O6 0.0635(11) 0.0827(14) 0.0411(9) 0.0232(10) 0.0110(8) 0.0168(9) C6 0.0438(12) 0.0427(13) 0.0378(11) -0.0036(10) 0.0032(9) 0.0008(10) C7 0.0409(11) 0.0343(11) 0.0364(10) -0.0015(9) 0.0023(9) -0.0015(9) C8 0.0511(13) 0.0489(14) 0.0391(11) 0.0032(11) 0.0116(10) -0.0001(10) C9 0.0433(12) 0.0521(14) 0.0530(13) 0.0080(11) 0.0117(10) -0.0007(12) C10 0.0400(11) 0.0437(13) 0.0455(12) 0.0042(10) 0.0023(9) -0.0006(10) C11 0.0446(12) 0.0342(11) 0.0356(10) -0.0022(10) 0.0036(9) -0.0005(9) C12 0.0386(11) 0.0328(11) 0.0415(11) 0.0005(9) 0.0057(9) -0.0028(9) loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_group _atom_site_type_symbol O1 -0.2038(3) 0.6422(2) 0.23714(7) 0.0647(5) Uani d . 1 . O O2 -0.7565(3) 0.2264(3) 0.06711(7) 0.0654(5) Uani d . 1 . O O3 -0.9418(3) 0.2184(3) 0.13452(8) 0.0697(6) Uani d . 1 . O N1 -0.3415(3) 0.5492(2) 0.20792(8) 0.0485(5) Uani d . 1 . N N2 -0.7865(3) 0.2601(3) 0.11371(8) 0.0492(5) Uani d . 1 . N C1 -0.3056(4) 0.4979(3) 0.15750(10) 0.0499(6) Uani d . 1 . C H1 -0.1825 0.5281 0.14405 0.076 Uiso calc R 1 . H C2 -0.4483(3) 0.4024(3) 0.12616(9) 0.0463(6) Uani d . 1 . C H2 -0.4236 0.3671 0.09154 0.076 Uiso calc R 1 . H C3 -0.6291(3) 0.3596(3) 0.14686(8) 0.0414(5) Uani d . 1 . C C4 -0.6655(4) 0.4100(3) 0.19819(9) 0.0487(6) Uani d . 1 . C H4 -0.7873 0.3794 0.21223 0.076 Uiso calc R 1 . H C5 -0.5193(4) 0.5059(3) 0.22820(9) 0.0531(6) Uani d . 1 . C H5 -0.5424 0.5416 0.26290 0.076 Uiso calc R 1 . H O4 0.0792(3) 0.4581(2) 0.29551(6) 0.0513(4) Uani d . 1 . O HO4 -0.033(4) 0.521(4) 0.2779(11) 0.076 Uiso d . 1 . H O5 0.4614(2) 0.0989(2) 0.43939(6) 0.0520(4) Uani d . 1 . O O6 0.2740(3) 0.1174(3) 0.50932(6) 0.0620(5) Uani d . 1 . O HO6 0.380(4) 0.037(4) 0.5283(11) 0.076 Uiso d . 1 . H C6 0.3091(3) 0.1556(3) 0.46043(8) 0.0415(5) Uani d . 1 . C C7 0.1550(3) 0.2674(3) 0.42947(8) 0.0373(5) Uani d . 1 . C C8 -0.0243(3) 0.3165(3) 0.45133(9) 0.0459(6) Uani d . 1 . C H8 -0.0452 0.2853 0.48656 0.076 Uiso calc R 1 . H C9 -0.1711(3) 0.4123(3) 0.42013(9) 0.0490(6) Uani d . 1 . C H9 -0.2914 0.4453 0.43455 0.076 Uiso calc R 1 . H C10 -0.1412(3) 0.4594(3) 0.36786(9) 0.0432(5) Uani d . 1 . C H10 -0.2418 0.5223 0.34703 0.076 Uiso calc R 1 . H C11 0.0398(3) 0.4127(3) 0.34639(8) 0.0381(5) Uani d . 1 . C C12 0.1878(3) 0.3169(3) 0.37719(8) 0.0375(5) Uani d . 1 . C H12 0.3090 0.2857 0.36293 0.076 Uiso calc R 1 . H loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source O O 0.0106 0.0060 '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' 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' loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l -1 -3 -6 -3 1 4 -1 2 -9 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 O1 N1 C5 119.8(2) yes O1 N1 C1 119.8(2) yes C5 N1 C1 120.4(2) yes O2 N2 O3 124.1(2) ? O2 N2 C3 118.3(2) ? O3 N2 C3 117.6(2) ? N1 C1 C2 120.7(2) ? N1 C1 H1 119.6 ? C2 C1 H1 119.6 ? C1 C2 C3 118.6(2) ? C1 C2 H2 120.7 ? C3 C2 H2 120.7 ? C2 C3 C4 120.9(2) ? C2 C3 N2 119.7(2) ? C4 C3 N2 119.4(2) ? C5 C4 C3 118.8(2) ? C5 C4 H4 120.6 ? C3 C4 H4 120.6 ? N1 C5 C4 120.6(2) ? N1 C5 H5 119.7 ? C4 C5 H5 119.7 ? C11 O4 HO4 110.5(17) ? C6 O6 HO6 113.7(15) yes O5 C6 O6 122.6(2) yes O5 C6 C7 120.9(2) yes O6 C6 C7 116.5(2) yes C12 C7 C8 120.3(2) yes C12 C7 C6 119.0(2) yes C8 C7 C6 120.7(2) yes C9 C8 C7 119.3(2) ? C9 C8 H8 120.4 ? C7 C8 H8 120.4 ? C10 C9 C8 120.8(2) ? C10 C9 H9 119.6 ? C8 C9 H9 119.6 ? C9 C10 C11 119.8(2) ? C9 C10 H10 120.1 ? C11 C10 H10 120.1 ? O4 C11 C12 117.6(2) yes O4 C11 C10 122.4(2) yes C12 C11 C10 119.9(2) yes C11 C12 C7 119.9(2) ? C11 C12 H12 120.1 ? C7 C12 H12 120.1 ? 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 O1 N1 . 1.310(2) yes O2 N2 . 1.221(2) ? O3 N2 . 1.225(2) ? N1 C5 . 1.353(3) yes N1 C1 . 1.354(3) yes N2 C3 . 1.467(3) yes C1 C2 . 1.367(3) ? C1 H1 . 0.93 ? C2 C3 . 1.373(3) ? C2 H2 . 0.93 ? C3 C4 . 1.374(3) ? C4 C5 . 1.366(3) ? C4 H4 . 0.93 ? C5 H5 . 0.93 ? O4 C11 . 1.359(2) yes O4 HO4 . 0.95(3) yes O5 C6 . 1.246(3) yes O6 C6 . 1.291(2) yes O6 HO6 . 1.01(3) yes C6 C7 . 1.478(3) yes C7 C12 . 1.389(3) yes C7 C8 . 1.390(3) yes C8 C9 . 1.383(3) ? C8 H8 . 0.93 ? C9 C10 . 1.379(3) ? C9 H9 . 0.93 ? C10 C11 . 1.391(3) yes C10 H10 . 0.93 ? C11 C12 . 1.383(3) yes C12 H12 . 0.93 ? 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 O1 N1 C1 C2 -179.3(2) C5 N1 C1 C2 0.3(3) N1 C1 C2 C3 0.1(3) C1 C2 C3 C4 -0.6(3) C1 C2 C3 N2 178.8(2) O2 N2 C3 C2 -4.0(3) O3 N2 C3 C2 177.0(2) O2 N2 C3 C4 175.4(2) O3 N2 C3 C4 -3.5(3) C2 C3 C4 C5 0.9(4) N2 C3 C4 C5 -178.6(2) O1 N1 C5 C4 179.5(2) C1 N1 C5 C4 -0.1(3) C3 C4 C5 N1 -0.5(4) O5 C6 C7 C12 -3.5(3) O6 C6 C7 C12 178.2(2) O5 C6 C7 C8 173.8(2) O6 C6 C7 C8 -4.5(3) C12 C7 C8 C9 1.2(3) C6 C7 C8 C9 -176.1(2) C7 C8 C9 C10 -0.1(4) C8 C9 C10 C11 -1.0(4) C9 C10 C11 O4 -178.8(2) C9 C10 C11 C12 1.0(3) O4 C11 C12 C7 179.9(2) C10 C11 C12 C7 0.1(3) C8 C7 C12 C11 -1.2(3) C6 C7 C12 C11 176.2(2) loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 21105661 2 PubChem 139056421