#------------------------------------------------------------------------------ #$Date: 2011-09-10 06:16:28 +0300 (Sat, 10 Sep 2011) $ #$Revision: 25271 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/2013151.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_2013151 loop_ _publ_author_name 'B\"uy\"ukg\"ung\"or, Orhan' 'Odabasundefinedogundefinedlu, Mustafa' _publ_section_title ; Bis(2-aminopyridinium) maleate ; _journal_issue 3 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first o105 _journal_page_last o106 _journal_volume 59 _journal_year 2003 _chemical_formula_moiety '2C5 H7 N2 + , C4 H2 O4 2-' _chemical_formula_sum 'C14 H16 N4 O4' _chemical_formula_weight 304.30 _chemical_melting_point .415E-305 _chemical_name_systematic ; Bis(2-aminopyridinium) maleate ; _space_group_IT_number 43 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall 'F 2 -2d' _symmetry_space_group_name_H-M 'F d d 2' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 21.756(5) _cell_length_b 23.531(5) _cell_length_c 5.6280(11) _cell_measurement_reflns_used 161 _cell_measurement_temperature 153(2) _cell_measurement_theta_max 12.67 _cell_measurement_theta_min 2.56 _cell_volume 2881.2(11) _computing_cell_refinement XSCANS _computing_data_collection 'XSCANS (Siemens 1991)' _computing_data_reduction 'SHELXTL (Sheldrick, 1990)' _computing_molecular_graphics 'ORTEP-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX (Farrugia, 1998)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 153(2) _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device_type 'Siemens P4' _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 0.016 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_h_min -27 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_k_min -30 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_number 1564 _diffrn_reflns_theta_full 27.01 _diffrn_reflns_theta_max 27.0 _diffrn_reflns_theta_min 2.5 _diffrn_standards_decay_% <2 _diffrn_standards_interval_time 120 _diffrn_standards_number 1 _exptl_absorpt_coefficient_mu 0.105 _exptl_absorpt_correction_type none _exptl_crystal_colour 'light yellow' _exptl_crystal_density_diffrn 1.403 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_method 'not measured' _exptl_crystal_description rectangular _exptl_crystal_F_000 1280 _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _refine_diff_density_max 0.11 _refine_diff_density_min -0.11 _refine_ls_extinction_coef 0.0048(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL97 (Sheldrick, 1997)' _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 101 _refine_ls_number_reflns 873 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.046 _refine_ls_R_factor_all 0.029 _refine_ls_R_factor_gt 0.026 _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^)+(0.0451P)^2^+0.5722P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.069 _refine_ls_wR_factor_ref 0.072 _reflns_number_gt 814 _reflns_number_total 873 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file fr1408.cif _[local]_cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. '_geom_bond_publ_flag' value 'Y' changed to 'y' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29 (9 times). '_geom_angle_publ_flag' value 'Y' changed to 'y' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29 (2 times). Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_database_code 2013151 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' '-x+1/4, y+1/4, z+1/4' 'x+3/4, -y+3/4, z+1/4' 'x, y+1/2, z+1/2' '-x, -y+1/2, z+1/2' '-x+1/4, y+3/4, z+3/4' 'x+3/4, -y+5/4, z+3/4' 'x+1/2, y, z+1/2' '-x+1/2, -y, z+1/2' '-x+3/4, y+1/4, z+3/4' 'x+5/4, -y+3/4, z+3/4' 'x+1/2, y+1/2, z' '-x+1/2, -y+1/2, z' '-x+3/4, y+3/4, z+1/4' 'x+5/4, -y+5/4, z+1/4' 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_type_symbol N1 0.20760(6) 0.10405(5) 0.4447(3) 0.0369(3) Uani d . 1 N H1 0.2184 0.1279 0.5576 0.044 Uiso calc R 1 H N2 0.10908(7) 0.10719(7) 0.5886(3) 0.0537(4) Uani d . 1 N H2A 0.1212 0.1316 0.6973 0.064 Uiso calc R 1 H H2B 0.0704 0.0963 0.5835 0.064 Uiso calc R 1 H C1 0.14878(7) 0.08687(6) 0.4336(3) 0.0378(4) Uani d . 1 C C2 0.13296(8) 0.04786(8) 0.2529(4) 0.0462(4) Uani d . 1 C H2 0.0921 0.0340 0.2423 0.055 Uiso calc R 1 H C3 0.17568(9) 0.03024(8) 0.0951(4) 0.0501(5) Uani d . 1 C H3 0.1644 0.0047 -0.0281 0.060 Uiso calc R 1 H C4 0.23675(9) 0.04951(7) 0.1121(4) 0.0495(4) Uani d . 1 C H4 0.2671 0.0372 0.0024 0.059 Uiso calc R 1 H C5 0.25099(8) 0.08613(7) 0.2892(4) 0.0421(4) Uani d . 1 C H5 0.2920 0.0995 0.3047 0.051 Uiso calc R 1 H O1 0.23854(5) 0.18379(5) 0.7565(2) 0.0413(3) Uani d . 1 O O2 0.14697(6) 0.18946(6) 0.9268(3) 0.0608(4) Uani d . 1 O C11 0.20258(7) 0.19907(6) 0.9210(3) 0.0354(3) Uani d . 1 C C12 0.22988(7) 0.22893(6) 1.1315(3) 0.0355(3) Uani d . 1 C H12 0.2167 0.2160 1.2830 0.043 Uiso calc R 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 N1 0.0367(7) 0.0372(6) 0.0367(7) -0.0039(5) 0.0012(6) -0.0028(6) N2 0.0367(7) 0.0697(10) 0.0547(10) -0.0103(7) 0.0071(7) -0.0200(8) C1 0.0359(7) 0.0393(7) 0.0381(9) -0.0021(6) -0.0011(7) 0.0018(7) C2 0.0414(9) 0.0490(9) 0.0483(10) -0.0053(7) -0.0065(8) -0.0074(8) C3 0.0594(11) 0.0470(9) 0.0438(10) 0.0010(8) -0.0061(9) -0.0102(8) C4 0.0523(10) 0.0504(9) 0.0458(10) 0.0050(8) 0.0103(9) -0.0047(9) C5 0.0376(8) 0.0420(8) 0.0467(9) -0.0013(6) 0.0056(7) 0.0027(7) O1 0.0346(5) 0.0495(6) 0.0398(6) -0.0036(5) 0.0037(5) -0.0124(6) O2 0.0356(6) 0.0793(9) 0.0675(9) -0.0087(6) 0.0103(6) -0.0273(8) C11 0.0335(7) 0.0336(7) 0.0392(8) 0.0001(6) 0.0041(7) -0.0021(6) C12 0.0426(8) 0.0348(6) 0.0291(7) 0.0038(6) 0.0032(7) 0.0015(7) 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_1 _geom_angle _geom_angle_publ_flag C1 N1 C5 . 122.69(15) y C1 N1 H1 . 118.7 ? C5 N1 H1 . 118.7 ? C1 N2 H2A . 120.0 ? C1 N2 H2B . 120.0 ? H2A N2 H2B . 120.0 ? N2 C1 N1 . 118.97(16) ? N2 C1 C2 . 123.56(15) ? N1 C1 C2 . 117.47(16) y C3 C2 C1 . 120.34(16) ? C3 C2 H2 . 119.8 ? C1 C2 H2 . 119.8 ? C2 C3 C4 . 120.40(17) ? C2 C3 H3 . 119.8 ? C4 C3 H3 . 119.8 ? C5 C4 C3 . 118.12(17) ? C5 C4 H4 . 120.9 ? C3 C4 H4 . 120.9 ? C4 C5 N1 . 120.96(16) ? C4 C5 H5 . 119.5 ? N1 C5 H5 . 119.5 ? O2 C11 O1 . 125.12(16) ? O2 C11 C12 . 117.01(15) ? O1 C11 C12 . 117.81(13) ? C12 C12 C11 14 127.83(8) ? C12 C12 H12 14 116.1 ? C11 C12 H12 . 116.1 ? 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 N1 C1 . 1.3434(19) y N1 C5 . 1.354(2) y N1 H1 . 0.8800 y N2 C1 . 1.318(2) y N2 H2A . 0.8800 ? N2 H2B . 0.8800 ? C1 C2 . 1.412(3) y C2 C3 . 1.351(3) ? C2 H2 . 0.9500 ? C3 C4 . 1.407(3) ? C3 H3 . 0.9500 ? C4 C5 . 1.354(3) ? C4 H4 . 0.9500 ? C5 H5 . 0.9500 ? O1 C11 . 1.264(2) y O2 C11 . 1.2310(19) y C11 C12 . 1.500(2) y C12 C12 14 1.323(3) y C12 H12 . 0.9500 ? 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 N1 H1 O1 . 0.88 1.78 2.6557(18) 172 N2 H2A O2 . 0.88 1.96 2.837(2) 177 N2 H2B O1 8_444 0.88 1.97 2.832(2) 168 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_site_symmetry_4 _geom_torsion C5 N1 C1 N2 . -178.63(16) C5 N1 C1 C2 . 1.0(3) N2 C1 C2 C3 . 177.82(18) N1 C1 C2 C3 . -1.8(3) C1 C2 C3 C4 . 1.5(3) C2 C3 C4 C5 . -0.4(3) C3 C4 C5 N1 . -0.5(3) C1 N1 C5 C4 . 0.1(3) O2 C11 C12 C12 14 -136.4(2) O1 C11 C12 C12 14 46.3(3)