#------------------------------------------------------------------------------ #$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $ #$Revision: 25271 $ #$URL: svn://www.crystallography.net/cod/cif/2/2204615.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_2204615 loop_ _publ_author_name 'Gao, Shan' 'Lu, Zhen-Zhong' 'Huo, Li-Hua' 'Zain, Shariffudin M.' 'Ng, Seik Weng' _publ_section_title ; Rerefinement of the co-crystal of 4-hydroxypyridine with 4-hydroxypyridinium nitrate ; _journal_issue 12 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o2195 _journal_page_last o2196 _journal_volume 60 _journal_year 2004 _chemical_formula_iupac 'C5 H6 N O +, N O3 -, C5 H5 N O' _chemical_formula_moiety 'C5 H6 N O +, N O3 -, C5 H5 N O' _chemical_formula_sum 'C10 H11 N3 O5' _chemical_formula_weight 253.22 _chemical_name_systematic ; 4-Hydroxypyridinium nitrate 4-hydroxypyridine ; _space_group_IT_number 15 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-C 2yc' _symmetry_space_group_name_H-M 'C 1 2/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 127.74(3) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 17.993(4) _cell_length_b 6.5280(10) _cell_length_c 12.501(3) _cell_measurement_reflns_used 5340 _cell_measurement_temperature 295(2) _cell_measurement_theta_max 27.5 _cell_measurement_theta_min 3.3 _cell_volume 1161.2(6) _computing_cell_refinement RAPID-AUTO _computing_data_collection 'RAPID-AUTO (Rigaku, 1998)' _computing_data_reduction 'CrystalStructure (Rigaku/MSC, 2002)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 295(2) _diffrn_measured_fraction_theta_full 1.00 _diffrn_measured_fraction_theta_max 1.00 _diffrn_measurement_device_type 'Rigaku R-AXIS RAPID' _diffrn_measurement_method \w _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 0.016 _diffrn_reflns_av_sigmaI/netI 0.014 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 5541 _diffrn_reflns_theta_full 27.5 _diffrn_reflns_theta_max 27.5 _diffrn_reflns_theta_min 3.3 _diffrn_standards_decay_% 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.118 _exptl_absorpt_correction_T_max 0.979 _exptl_absorpt_correction_T_min 0.858 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(ABSCOR; Higashi, 1995)' _exptl_crystal_colour Colorless _exptl_crystal_density_diffrn 1.448 _exptl_crystal_density_method 'not measured' _exptl_crystal_description Prism _exptl_crystal_F_000 528 _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.18 _refine_diff_density_max 0.21 _refine_diff_density_min -0.17 _refine_ls_extinction_coef 0.005(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL97 _refine_ls_goodness_of_fit_ref 1.08 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 108 _refine_ls_number_reflns 1338 _refine_ls_number_restraints 6 _refine_ls_restrained_S_all 1.08 _refine_ls_R_factor_all 0.050 _refine_ls_R_factor_gt 0.037 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0639P)^2^+0.2278P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.110 _refine_ls_wR_factor_ref 0.117 _reflns_number_gt 1010 _reflns_number_total 1338 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file bt6556.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M 'C 2/c' _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_values 1715 2011-07-08 13:25:40Z adriana ; _cod_original_cell_volume 1161.2(4) _cod_database_code 2204615 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' 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_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol O1 0.27860(10) 0.4265(2) 0.52090(10) 0.0661(4) Uani d D 1 . . O O2 0.5000 0.7139(2) 0.2500 0.0605(4) Uani d S 1 . . O O3 0.46370(10) 0.9979(2) 0.2932(2) 0.0872(5) Uani d . 1 . . O N1 0.40230(10) 0.5926(2) 0.35150(10) 0.0531(3) Uani d D 1 . . N N2 0.5000 0.9060(3) 0.2500 0.0524(4) Uani d S 1 . . N C1 0.39610(10) 0.7254(2) 0.4275(2) 0.0570(4) Uani d D 1 . . C C2 0.35500(10) 0.6731(2) 0.4850(2) 0.0584(4) Uani d D 1 . . C C3 0.31810(10) 0.4757(2) 0.46630(10) 0.0491(4) Uani d . 1 . . C C4 0.32680(10) 0.3394(2) 0.38690(10) 0.0526(4) Uani d D 1 . . C C5 0.36830(10) 0.4023(2) 0.3314(2) 0.0553(4) Uani d D 1 . . C H1o 0.255(3) 0.306(3) 0.502(4) 0.053(9) Uiso d PD 0.50 A -1 H H1n 0.4270(10) 0.632(3) 0.312(2) 0.076(5) Uiso d D 1 . . H H1 0.4230(10) 0.856(2) 0.437(2) 0.071(5) Uiso d D 1 . . H H2 0.3510(10) 0.767(2) 0.539(2) 0.075(5) Uiso d D 1 . . H H4 0.3060(10) 0.202(2) 0.375(2) 0.065(5) Uiso d D 1 . . H H5 0.3760(10) 0.315(2) 0.2770(10) 0.065(5) Uiso d D 1 . . H 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 0.0830(10) 0.0720(10) 0.0810(10) -0.0100(10) 0.0690(10) -0.0060(10) O2 0.0810(10) 0.0470(10) 0.0880(10) 0.000 0.0690(10) 0.000 O3 0.1380(10) 0.0610(10) 0.1290(10) 0.0030(10) 0.1150(10) -0.0090(10) N1 0.0580(10) 0.0630(10) 0.0570(10) -0.0010(10) 0.0450(10) 0.0040(10) N2 0.0680(10) 0.0500(10) 0.0580(10) 0.000 0.0480(10) 0.000 C1 0.0660(10) 0.0540(10) 0.0640(10) -0.0070(10) 0.0470(10) -0.0010(10) C2 0.0730(10) 0.0570(10) 0.0650(10) -0.0060(10) 0.0530(10) -0.0090(10) C3 0.0510(10) 0.0590(10) 0.0500(10) 0.0000(10) 0.0370(10) 0.0020(10) C4 0.0600(10) 0.0530(10) 0.0580(10) -0.0050(10) 0.0430(10) -0.0040(10) C5 0.0640(10) 0.0620(10) 0.0580(10) 0.0030(10) 0.0460(10) -0.0030(10) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C1 N1 C5 . 120.60(10) yes O2 N2 O3 . 119.30(10) no O2 N2 O3 2_655 119.30(10) no O3 N2 O3 2_655 121.5(2) no N1 C1 C2 . 121.5(2) yes C1 C2 C3 . 120.00(10) yes O1 C3 C2 . 119.90(10) yes O1 C3 C4 . 123.30(10) yes C2 C3 C4 . 116.80(10) yes C3 C4 C5 . 120.10(10) yes N1 C5 C4 . 121.00(10) yes C3 O1 H1o . 115(3) no C1 N1 H1n . 120.0(10) no C5 N1 H1n . 120.0(10) no N1 C1 H1 . 115.0(10) no C2 C1 H1 . 124.0(10) no C1 C2 H2 . 122.0(10) no C3 C2 H2 . 118.0(10) no C5 C4 H4 . 120.0(10) no C3 C4 H4 . 120.0(10) no N1 C5 H5 . 116.0(10) no C4 C5 H5 . 123.0(10) no 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 C3 . 1.291(2) yes O2 N2 . 1.254(2) no O3 N2 . 1.2280(10) no N1 C1 . 1.339(2) yes N1 C5 . 1.339(2) yes N2 O3 2_655 1.2280(10) no C1 C2 . 1.354(2) yes C2 C3 . 1.403(2) yes C3 C4 . 1.411(2) yes C4 C5 . 1.358(2) yes O1 H1o . 0.860(10) no N1 H1n . 0.870(10) no C1 H1 . 0.950(10) no C2 H2 . 0.950(10) no C4 H4 . 0.950(10) no C5 H5 . 0.960(10) 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 H1n O2 . 0.870(10) 1.970(10) 2.8400(10) 172(2) no O1 H1o O1 7_556 0.860(10) 1.590(10) 2.446(3) 174(4) no 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 C5 N1 C1 C2 -0.7(2) no N1 C1 C2 C3 0.4(3) no C1 C2 C3 O1 -179.8(2) no C1 C2 C3 C4 0.3(2) no O1 C3 C4 C5 179.3(2) no C2 C3 C4 C5 -0.8(2) no C1 N1 C5 C4 0.2(2) no C3 C4 C5 N1 0.6(2) no