#------------------------------------------------------------------------------ #$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $ #$Revision: 25271 $ #$URL: svn://www.crystallography.net/cod/cif/2/2007166.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, R.' 'De Almeida Santos, R. H.' 'Francisco, R. H. P.' _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_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 0.0382 _refine_ls_shift/esd_max 0.000 _refine_ls_shift/esd_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_scheme '1/[\s^2^(Fo^2^)+(0.0596P)^2^+0.3324P], P = (Fo^2^+2Fc^2^)/3' _refine_ls_wR_factor_all 0.1289 _refine_ls_wR_factor_obs 0.0995 _reflns_number_observed 1521 _reflns_number_total 2203 _reflns_observed_criterion >2sigma(I) _[local]_cod_data_source_file fg1373.cif _[local]_cod_data_source_block complex _[local]_cod_cif_authors_sg_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 0.0595(8) 0.0411(7) 0.0474(7) 0.0020(6) -0.0117(6) -0.0004(6) O2 0.0968(12) 0.0858(12) 0.0503(9) 0.0173(10) -0.0184(8) -0.0111(8) O3 0.1029(13) 0.0590(10) 0.0750(10) 0.0155(9) -0.0267(9) 0.0143(8) N1 0.0595(10) 0.0567(11) 0.0480(9) 0.0024(8) -0.0055(7) 0.0071(8) C1 0.0392(8) 0.0362(9) 0.0417(9) -0.0036(7) -0.0008(7) 0.0022(7) C2 0.0497(10) 0.0328(9) 0.0501(10) 0.0026(8) -0.0023(8) -0.0012(7) C3 0.0572(11) 0.0422(10) 0.0435(9) 0.0012(8) -0.0009(8) -0.0057(8) C4 0.0438(9) 0.0408(10) 0.0421(9) -0.0006(8) -0.0009(7) 0.0046(7) C5 0.0497(10) 0.0356(9) 0.0583(11) 0.0033(8) -0.0043(8) -0.0012(8) C6 0.0530(11) 0.0370(9) 0.0519(10) 0.0026(8) -0.0052(8) -0.0087(8) O4 0.0742(9) 0.0450(7) 0.0389(7) 0.0110(6) -0.0127(6) -0.0035(5) N2 0.0471(8) 0.0346(7) 0.0378(7) 0.0062(6) -0.0034(6) -0.0034(6) C7 0.0521(10) 0.0355(9) 0.0464(10) 0.0003(8) -0.0011(8) -0.0014(7) C8 0.0510(10) 0.0468(10) 0.0451(10) -0.0014(8) -0.0039(8) -0.0059(8) C9 0.0602(12) 0.0547(12) 0.0398(9) 0.0056(9) -0.0026(8) 0.0035(8) C10 0.0686(13) 0.0427(10) 0.0516(11) 0.0005(9) 0.0023(9) 0.0061(8) C11 0.0566(11) 0.0355(9) 0.0503(10) -0.0013(8) -0.0025(8) -0.0044(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_type_symbol O1 0.2173(2) 0.6626(2) 0.23858(5) 0.0505(4) Uani d . 1 O H1 0.261(3) 0.517(4) 0.2400(10) 0.076 Uiso d . 1 H O2 -0.2022(2) 0.7428(3) -0.00881(7) 0.0794(5) Uani d . 1 O O3 -0.2277(2) 1.0709(3) 0.02611(7) 0.0814(5) Uani d . 1 O N1 -0.1732(2) 0.8807(3) 0.03060(7) 0.0555(4) Uani d . 1 N C1 0.1211(2) 0.7060(3) 0.18809(7) 0.0394(4) Uani d . 1 C C2 0.0938(2) 0.5531(3) 0.14181(8) 0.0447(4) Uani d . 1 C H2 0.1411 0.4129 0.14593 0.054 Uiso calc R 1 H C3 -0.0027(2) 0.6090(3) 0.09029(8) 0.0480(5) Uani d . 1 C H3 -0.0211 0.5075 0.05942 0.058 Uiso calc R 1 H C4 -0.0724(2) 0.8188(3) 0.08482(7) 0.0426(4) Uani d . 1 C C5 -0.0478(2) 0.9713(3) 0.13042(9) 0.0485(5) Uani d . 1 C H5 -0.0961 1.1109 0.12624 0.059 Uiso calc R 1 H C6 0.0483(2) 0.9150(3) 0.18172(8) 0.0480(5) Uani d . 1 C H6 0.0652 1.0168 0.21255 0.058 Uiso calc R 1 H O4 0.3490(2) 0.2783(2) 0.24838(5) 0.0540(4) Uani d . 1 O N2 0.4073(2) 0.2460(2) 0.30470(6) 0.0403(4) Uani d . 1 N C7 0.4957(2) 0.4060(3) 0.33525(8) 0.0451(4) Uani d . 1 C H7 0.5157 0.5392 0.31670 0.054 Uiso calc R 1 H C8 0.5563(2) 0.3736(3) 0.39350(8) 0.0482(5) Uani d . 1 C H8 0.6160 0.4852 0.41454 0.058 Uiso calc R 1 H C9 0.5286(2) 0.1755(3) 0.42084(8) 0.0521(5) Uani d . 1 C H9 0.5699 0.1513 0.46026 0.064 Uiso calc R 1 H C10 0.4387(3) 0.0140(3) 0.38870(9) 0.0545(5) Uani d . 1 C H10 0.4187 -0.1207 0.40647 0.065 Uiso calc R 1 H C11 0.3785(2) 0.0511(3) 0.33047(8) 0.0480(5) Uani d . 1 C H11 0.3179 -0.0584 0.30887 0.058 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_distance _geom_bond_publ_flag O1 C1 1.336(2) yes O1 H1 0.95(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 0.93 ? C3 C4 1.387(3) ? C3 H3 0.93 ? C4 C5 1.383(3) ? C5 C6 1.367(3) ? C5 H5 0.93 ? C6 H6 0.93 ? 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 0.93 ? C8 C9 1.377(3) ? C8 H8 0.93 ? C9 C10 1.376(3) ? C9 H9 0.93 ? C10 C11 1.373(3) ? C10 H10 0.93 ? C11 H11 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 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)