#------------------------------------------------------------------------------ #$Date: 2025-08-18 23:52:38 +0100 (Mon, 18 Aug 2025) $ #$Revision: 301791 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/71/2007166.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_2007166 loop_ _publ_author_name 'Moreno-Fuquen, Rodolfo' 'De Almeida Santos, Regina Helena' 'Francisco, Regina Helena Porto' _publ_section_title ; Pyridine N-Oxide and 4-Nitrophenol (1:1 Complex) ; _journal_issue 4 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 513 _journal_page_last 515 _journal_paper_doi 10.1107/S0108270197013474 _journal_volume 54 _journal_year 1998 _chemical_formula_moiety 'C5 H5 N O . C6 H5 N O3' _chemical_formula_sum 'C11 H10 N2 O4' _chemical_formula_weight 234.21 _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 90.00 _cell_angle_beta 95.740(10) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 7.983(4) _cell_length_b 6.054(3) _cell_length_c 22.5950(10) _cell_measurement_reflns_used 25 _cell_measurement_temperature 253 _cell_measurement_theta_max 18.2 _cell_measurement_theta_min 10.6 _cell_volume 1086.5(8) _computing_cell_refinement 'CAD-4 Software' _computing_data_collection 'CAD-4 Software (Enraf-Nonius, 1989)' _computing_data_reduction 'VAXSDP (Frenz, 1978)' _computing_molecular_graphics 'ZORTEP (Zsolnai, 1995)' _computing_publication_material VAXSDP _computing_structure_refinement 'SHELXL93 (Sheldrick, 1993)' _computing_structure_solution 'SHELXS86 (Sheldrick, 1985)' _diffrn_ambient_temperature 253 _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 0.0362 _diffrn_reflns_av_sigmaI/netI 0.0396 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_number 4400 _diffrn_reflns_theta_max 26.31 _diffrn_reflns_theta_min 2.56 _diffrn_standards_decay_% 0.53 _diffrn_standards_interval_time 120 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.111 _exptl_absorpt_correction_type none _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.432 _exptl_crystal_density_method not_measured _exptl_crystal_description transparent_prisms _exptl_crystal_F_000 488 _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.05 _refine_diff_density_max 0.193 _refine_diff_density_min -0.242 _refine_ls_extinction_coef 0.012(2) _refine_ls_extinction_method SHELXL _refine_ls_goodness_of_fit_all 1.003 _refine_ls_goodness_of_fit_obs 0.947 _refine_ls_matrix_type full _refine_ls_number_parameters 158 _refine_ls_number_reflns 2202 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.005 _refine_ls_restrained_S_obs 0.947 _refine_ls_R_factor_all 0.0653 _refine_ls_R_factor_obs .0382 _refine_ls_shift/esd_max 0.000 _refine_ls_shift/esd_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0596P)^2^+0.3324P], P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all 0.1289 _refine_ls_wR_factor_obs .0995 _reflns_number_observed 1521 _reflns_number_total 2203 _reflns_observed_criterion >2sigma(I) _cod_data_source_file fg1373.cif _cod_data_source_block complex _cod_depositor_comments ; The following automatic conversions were performed: '_refine_ls_weighting_scheme' value '1/[\s^2^(Fo^2^)+(0.0596P)^2^+0.3324P], 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^)+(0.0596P)^2^+0.3324P], 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/c' _cod_database_code 2007166 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' 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 .0595(8) .0411(7) .0474(7) .0020(6) -.0117(6) -.0004(6) O2 .0968(12) .0858(12) .0503(9) .0173(10) -.0184(8) -.0111(8) O3 .1029(13) .0590(10) .0750(10) .0155(9) -.0267(9) .0143(8) N1 .0595(10) .0567(11) .0480(9) .0024(8) -.0055(7) .0071(8) C1 .0392(8) .0362(9) .0417(9) -.0036(7) -.0008(7) .0022(7) C2 .0497(10) .0328(9) .0501(10) .0026(8) -.0023(8) -.0012(7) C3 .0572(11) .0422(10) .0435(9) .0012(8) -.0009(8) -.0057(8) C4 .0438(9) .0408(10) .0421(9) -.0006(8) -.0009(7) .0046(7) C5 .0497(10) .0356(9) .0583(11) .0033(8) -.0043(8) -.0012(8) C6 .0530(11) .0370(9) .0519(10) .0026(8) -.0052(8) -.0087(8) O4 .0742(9) .0450(7) .0389(7) .0110(6) -.0127(6) -.0035(5) N2 .0471(8) .0346(7) .0378(7) .0062(6) -.0034(6) -.0034(6) C7 .0521(10) .0355(9) .0464(10) .0003(8) -.0011(8) -.0014(7) C8 .0510(10) .0468(10) .0451(10) -.0014(8) -.0039(8) -.0059(8) C9 .0602(12) .0547(12) .0398(9) .0056(9) -.0026(8) .0035(8) C10 .0686(13) .0427(10) .0516(11) .0005(9) .0023(9) .0061(8) C11 .0566(11) .0355(9) .0503(10) -.0013(8) -.0025(8) -.0044(8) 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 .2173(2) .6626(2) .23858(5) .0505(4) Uani d . 1 . O H1 .261(3) .517(4) .2400(10) .076 Uiso d . 1 . H O2 -.2022(2) .7428(3) -.00881(7) .0794(5) Uani d . 1 . O O3 -.2277(2) 1.0709(3) .02611(7) .0814(5) Uani d . 1 . O N1 -.1732(2) .8807(3) .03060(7) .0555(4) Uani d . 1 . N C1 .1211(2) .7060(3) .18809(7) .0394(4) Uani d . 1 . C C2 .0938(2) .5531(3) .14181(8) .0447(4) Uani d . 1 . C H2 .1411 .4129 .14593 .054 Uiso calc R 1 . H C3 -.0027(2) .6090(3) .09029(8) .0480(5) Uani d . 1 . C H3 -.0211 .5075 .05942 .058 Uiso calc R 1 . H C4 -.0724(2) .8188(3) .08482(7) .0426(4) Uani d . 1 . C C5 -.0478(2) .9713(3) .13042(9) .0485(5) Uani d . 1 . C H5 -.0961 1.1109 .12624 .059 Uiso calc R 1 . H C6 .0483(2) .9150(3) .18172(8) .0480(5) Uani d . 1 . C H6 .0652 1.0168 .21255 .058 Uiso calc R 1 . H O4 .3490(2) .2783(2) .24838(5) .0540(4) Uani d . 1 . O N2 .4073(2) .2460(2) .30470(6) .0403(4) Uani d . 1 . N C7 .4957(2) .4060(3) .33525(8) .0451(4) Uani d . 1 . C H7 .5157 .5392 .31670 .054 Uiso calc R 1 . H C8 .5563(2) .3736(3) .39350(8) .0482(5) Uani d . 1 . C H8 .6160 .4852 .41454 .058 Uiso calc R 1 . H C9 .5286(2) .1755(3) .42084(8) .0521(5) Uani d . 1 . C H9 .5699 .1513 .46026 .064 Uiso calc R 1 . H C10 .4387(3) .0140(3) .38870(9) .0545(5) Uani d . 1 . C H10 .4187 -.1207 .40647 .065 Uiso calc R 1 . H C11 .3785(2) .0511(3) .33047(8) .0480(5) Uani d . 1 . C H11 .3179 -.0584 .30887 .058 Uiso calc R 1 . H loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C .017 .009 International_Tables_Vol_IV_Table_2.3.1 H 0 0 International_Tables_Vol_IV_Table_2.3.1 O .047 .032 International_Tables_Vol_IV_Table_2.3.1 N .029 .018 International_Tables_Vol_IV_Table_2.3.1 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 2 -3 3 -2 -1 8 2 6 8 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 C1 O1 H1 113.0(14) ? O2 N1 O3 122.5(2) yes O2 N1 C4 119.2(2) yes O3 N1 C4 118.3(2) yes O1 C1 C6 117.7(2) yes O1 C1 C2 122.8(2) yes C6 C1 C2 119.5(2) ? C3 C2 C1 120.2(2) ? C3 C2 H2 119.89(11) ? C1 C2 H2 119.89(10) ? C2 C3 C4 119.2(2) ? C2 C3 H3 120.41(11) ? C4 C3 H3 120.41(10) ? C5 C4 C3 121.3(2) ? C5 C4 N1 118.9(2) yes C3 C4 N1 119.8(2) yes C6 C5 C4 119.4(2) ? C6 C5 H5 120.29(11) ? C4 C5 H5 120.29(11) ? C5 C6 C1 120.4(2) ? C5 C6 H6 119.79(11) ? C1 C6 H6 119.79(10) ? O4 N2 C11 119.10(14) yes O4 N2 C7 120.09(15) yes C11 N2 C7 120.80(15) ? N2 C7 C8 120.4(2) ? N2 C7 H7 119.82(10) ? C8 C7 H7 119.82(11) ? C7 C8 C9 119.9(2) ? C7 C8 H8 120.04(11) ? C9 C8 H8 120.04(11) ? C10 C9 C8 118.7(2) ? C10 C9 H9 120.64(11) ? C8 C9 H9 120.64(10) ? C11 C10 C9 120.2(2) ? C11 C10 H10 119.89(11) ? C9 C10 H10 119.89(12) ? N2 C11 C10 120.0(2) ? N2 C11 H11 120.02(10) ? C10 C11 H11 120.02(11) ? 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 C1 . 1.336(2) yes O1 H1 . .95(3) yes O2 N1 . 1.226(2) yes O3 N1 . 1.232(2) yes N1 C4 . 1.446(2) yes C1 C6 . 1.394(2) ? C1 C2 . 1.397(2) ? C2 C3 . 1.372(2) ? C2 H2 . .93 ? C3 C4 . 1.387(3) ? C3 H3 . .93 ? C4 C5 . 1.383(3) ? C5 C6 . 1.367(3) ? C5 H5 . .93 ? C6 H6 . .93 ? O4 N2 . 1.325(2) yes N2 C11 . 1.346(2) yes N2 C7 . 1.348(2) yes C7 C8 . 1.370(2) ? C7 H7 . .93 ? C8 C9 . 1.377(3) ? C8 H8 . .93 ? C9 C10 . 1.376(3) ? C9 H9 . .93 ? C10 C11 . 1.373(3) ? C10 H10 . .93 ? C11 H11 . .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 C1 C2 C3 -178.3(2) C6 C1 C2 C3 0.6(3) C1 C2 C3 C4 0.0(3) C2 C3 C4 C5 -0.6(3) C2 C3 C4 N1 179.5(2) O2 N1 C4 C5 -176.5(2) O3 N1 C4 C5 3.0(3) O2 N1 C4 C3 3.5(3) O3 N1 C4 C3 -177.1(2) C3 C4 C5 C6 0.5(3) N1 C4 C5 C6 -179.5(2) C4 C5 C6 C1 0.1(3) O1 C1 C6 C5 178.3(2) C2 C1 C6 C5 -0.6(3) O4 N2 C7 C8 180.0(2) C11 N2 C7 C8 -0.7(3) N2 C7 C8 C9 0.8(3) C7 C8 C9 C10 -0.5(3) C8 C9 C10 C11 0.1(3) O4 N2 C11 C10 179.7(2) C7 N2 C11 C10 0.3(3) C9 C10 C11 N2 0.0(3) loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 21137148 2 PubChem 139055966