#------------------------------------------------------------------------------ #$Date: 2013-12-28 13:58:47 +0000 (Sat, 28 Dec 2013) $ #$Revision: 91933 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/21/2202137.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_2202137 loop_ _publ_author_name 'Lee, Ting Wai' 'Lau, Jasmine Po Kwan' 'Szeto, Lap' _publ_section_title ; 4,4'-Trimethylenedipyridinium dinitrate ; _journal_issue 6 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o792 _journal_page_last o793 _journal_volume 59 _journal_year 2003 _chemical_formula_iupac 'C13 H16 N2 2+, 2N O3 1-' _chemical_formula_moiety 'C13 H16 N2 2+, 2N O3 1-' _chemical_formula_sum 'C13 H16 N4 O6' _chemical_formula_weight 324.29 _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' _audit_creation_method 'from TEXRAY.INF file' _cell_angle_alpha 90 _cell_angle_beta 112.39(4) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 7.894(6) _cell_length_b 21.037(4) _cell_length_c 9.879(6) _cell_measurement_reflns_used 25 _cell_measurement_temperature 298(2) _cell_measurement_theta_max 16.6 _cell_measurement_theta_min 13.5 _cell_volume 1516.9(16) _computing_cell_refinement 'MSC/AFC Diffractometer Control Software' _computing_data_collection ; MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1992) ; _computing_data_reduction 'TEXSAN (Molecular Structure Corporation, 1992)' _computing_publication_material TEXSAN _computing_structure_refinement TEXSAN _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _diffrn_ambient_temperature 298(2) _diffrn_measured_fraction_theta_full 1.03 _diffrn_measured_fraction_theta_max 1.03 _diffrn_measurement_device AFC-7R _diffrn_measurement_method \w/2-\q _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'X-ray tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.7107 _diffrn_reflns_av_R_equivalents 0.019 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_number 2966 _diffrn_reflns_reduction_process none _diffrn_reflns_theta_full 25.0 _diffrn_reflns_theta_max 25.0 _diffrn_reflns_theta_min 2.16 _diffrn_standards_decay_% 2.99 _diffrn_standards_interval_count 250 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.114 _exptl_absorpt_correction_type none _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.420 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 680.00 _exptl_crystal_size_max 0.280 _exptl_crystal_size_mid 0.190 _exptl_crystal_size_min 0.150 _refine_diff_density_max 0.17 _refine_diff_density_min -0.17 _refine_ls_extinction_coef 16.860(4) _refine_ls_extinction_method 'Zachariasen_type_2_Gaussian_isotropic (Zachariasen, 1967)' _refine_ls_goodness_of_fit_ref 1.461 _refine_ls_hydrogen_treatment noref _refine_ls_matrix_type full _refine_ls_number_parameters 209 _refine_ls_number_reflns 1718 _refine_ls_number_restraints 0 _refine_ls_R_factor_gt 0.0438 _refine_ls_shift/su_max 0.001 _refine_ls_structure_factor_coef F _refine_ls_weighting_details 'calc w = 1/[(\s)^2^(Fo)+0.00025(Fo)^2^]' _refine_ls_weighting_scheme sigma _refine_ls_wR_factor_ref 0.0484 _reflns_number_gt 1718 _reflns_number_total 2761 _reflns_threshold_expression I>1.5\s(I) _[local]_cod_data_source_file ob6242.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M 'P 21/c' _cod_depositor_comments ; The following automatic conversions were performed: '_atom_site_thermal_displace_type' tag value 'Uij' was replaced with 'Uani' value 39 times. Automatic conversion script Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana ; _cod_database_code 2202137 loop_ _symmetry_equiv_pos_as_xyz ' +x, +y, +z' ' -x,1/2+y,1/2-z' ' -x, -y, -z' ' +x,1/2-y,1/2+z' 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 0.098(2) 0.0560(10) 0.073(2) -0.0060(10) 0.0110(10) 0.0090(10) O2 0.0640(10) 0.0600(10) 0.0590(10) -0.0040(10) 0.0110(10) 0.0090(10) O3 0.119(2) 0.100(2) 0.0450(10) 0.025(2) 0.0000(10) 0.0210(10) O4 0.0790(10) 0.0680(10) 0.0470(10) 0.0050(10) 0.0320(10) -0.0054(10) O5 0.091(2) 0.0550(10) 0.0460(10) 0.0070(10) 0.0280(10) 0.0161(10) O6 0.109(2) 0.0390(10) 0.0760(10) 0.0130(10) 0.0470(10) 0.0026(10) N1 0.0490(10) 0.0490(10) 0.0430(10) -0.0090(10) 0.0130(10) -0.0110(10) N2 0.0510(10) 0.056(2) 0.0410(10) -0.0050(10) 0.0190(10) -0.0100(10) N3 0.058(2) 0.059(2) 0.0440(10) 0.0130(10) 0.0190(10) 0.0070(10) N4 0.0430(10) 0.0430(10) 0.0380(10) -0.0040(10) 0.0120(10) 0.0000(10) C1 0.064(2) 0.0380(10) 0.055(2) -0.0030(10) 0.025(2) 0.0000(10) C2 0.057(2) 0.043(2) 0.0400(10) 0.0030(10) 0.0180(10) 0.0060(10) C3 0.0420(10) 0.0420(10) 0.0350(10) 0.0020(10) 0.0180(10) -0.0070(10) C4 0.054(2) 0.0370(10) 0.0400(10) -0.0020(10) 0.0170(10) 0.0000(10) C5 0.055(2) 0.048(2) 0.0360(10) -0.0010(10) 0.0140(10) 0.0000(10) C6 0.045(2) 0.053(2) 0.0400(10) 0.0000(10) 0.0150(10) -0.0080(10) C7 0.043(2) 0.057(2) 0.0370(10) -0.0060(10) 0.0150(10) -0.0100(10) C8 0.050(2) 0.052(2) 0.0410(10) -0.0080(10) 0.0190(10) -0.0090(10) C9 0.0380(10) 0.0450(10) 0.0340(10) -0.0080(10) 0.0100(10) -0.0070(10) C10 0.054(2) 0.0430(10) 0.0430(10) -0.0020(10) 0.0160(10) -0.0020(10) C11 0.054(2) 0.053(2) 0.0360(10) -0.0090(10) 0.0140(10) 0.0030(10) C12 0.061(2) 0.044(2) 0.052(2) 0.0020(10) 0.0220(10) 0.0000(10) C13 0.060(2) 0.051(2) 0.0390(10) 0.0000(10) 0.0200(10) 0.0040(10) 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_calc_attached_atom O1 0.0584(3) 0.23670(10) 0.2522(2) 0.0820(8) Uani ? ? O2 0.1876(3) 0.32731(10) 0.3132(2) 0.0650(7) Uani ? ? O3 -0.0203(4) 0.31390(10) 0.0994(2) 0.0972(9) Uani ? ? O4 0.3617(3) 0.44510(9) 0.6683(2) 0.0624(6) Uani ? ? O5 0.3474(3) 0.42756(9) 0.8784(2) 0.0640(6) Uani ? ? O6 0.2798(3) 0.51917(9) 0.7807(2) 0.0713(7) Uani ? ? N1 0.3728(3) 0.23840(10) 0.0646(2) 0.0482(7) Uani ? ? N2 0.7550(3) 0.50160(10) 0.9219(2) 0.0488(7) Uani ? ? N3 0.0738(3) 0.29200(10) 0.2194(2) 0.0535(7) Uani ? ? N4 0.3295(3) 0.46420(10) 0.7737(2) 0.0427(6) Uani ? ? C1 0.4697(4) 0.20830(10) 0.1885(3) 0.0515(9) Uani ? ? C2 0.6089(4) 0.23950(10) 0.2959(3) 0.0465(8) Uani ? ? C3 0.6504(3) 0.30200(10) 0.2756(3) 0.0386(7) Uani ? ? C4 0.5421(4) 0.33130(10) 0.1455(3) 0.0438(7) Uani ? ? C5 0.4043(4) 0.29890(10) 0.0415(3) 0.0470(8) Uani ? ? C6 0.8050(3) 0.33700(10) 0.3886(3) 0.0460(8) Uani ? ? C7 0.7436(3) 0.37430(10) 0.4947(3) 0.0459(8) Uani ? ? C8 0.9007(4) 0.41450(10) 0.5961(3) 0.0471(8) Uani ? ? C9 0.8523(3) 0.44650(10) 0.7120(2) 0.0401(7) Uani ? ? C10 0.8631(4) 0.41300(10) 0.8365(3) 0.0473(8) Uani ? ? C11 0.8126(4) 0.44170(10) 0.9397(3) 0.0487(8) Uani ? ? C12 0.7459(4) 0.53590(10) 0.8056(3) 0.0523(8) Uani ? ? C13 0.7927(4) 0.50880(10) 0.6991(3) 0.0495(8) Uani ? ? H1 0.4425 0.1654 0.2023 0.0618 Uani ? ? H1n 0.2860 0.2179 -0.0035 0.0578 Uani ? ? H2 0.6773 0.2182 0.3849 0.0557 Uani ? ? H2n 0.7223 0.5191 0.9881 0.0586 Uani ? ? H4 0.5643 0.3744 0.1289 0.0526 Uani ? ? H5 0.3309 0.3193 -0.0473 0.0564 Uani ? ? H6a 0.8958 0.3072 0.4428 0.0552 Uani ? ? H6b 0.8558 0.3659 0.3404 0.0552 Uani ? ? H7a 0.6442 0.4012 0.4407 0.0551 Uani ? ? H7b 0.7055 0.3453 0.5514 0.0551 Uani ? ? H8a 1.0041 0.3880 0.6418 0.0565 Uani ? ? H8b 0.9300 0.4461 0.5398 0.0565 Uani ? ? H10 0.9053 0.3703 0.8497 0.0568 Uani ? ? H11 0.8187 0.4187 1.0243 0.0585 Uani ? ? H12 0.7070 0.5789 0.7970 0.0627 Uani ? ? H13 0.7843 0.5330 0.6155 0.0594 Uani ? ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 N3 ? ? 1.226(3) no O2 N3 ? ? 1.258(3) no O3 N3 ? ? 1.223(3) no O4 N4 ? ? 1.229(2) no O5 N4 ? ? 1.254(2) no O6 N4 ? ? 1.232(3) no N1 C1 ? ? 1.330(3) no N1 C5 ? ? 1.333(3) no N1 H1n ? ? 0.870 no N2 C11 ? ? 1.329(3) no N2 C12 ? ? 1.334(3) no N2 H2n ? ? 0.870 no C1 C2 ? ? 1.370(4) no C1 H1 ? ? 0.950 no C2 C3 ? ? 1.388(3) no C2 H2 ? ? 0.950 no C3 C4 ? ? 1.388(3) no C3 C6 ? ? 1.497(3) no C4 C5 ? ? 1.361(4) no C4 H4 ? ? 0.950 no C5 H5 ? ? 0.950 no C6 C7 ? ? 1.527(3) no C6 H6a ? ? 0.950 no C6 H6b ? ? 0.950 no C7 C8 ? ? 1.520(3) no C7 H7a ? ? 0.950 no C7 H7b ? ? 0.950 no C8 C9 ? ? 1.498(3) no C8 H8a ? ? 0.950 no C8 H8b ? ? 0.950 no C9 C10 ? ? 1.392(3) no C9 C13 ? ? 1.382(3) no C10 C11 ? ? 1.369(3) no C10 H10 ? ? 0.950 no C11 H11 ? ? 0.950 no C12 C13 ? ? 1.365(4) no C12 H12 ? ? 0.950 no C13 H13 ? ? 0.950 no loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C 0.003 0.002 'International Tables' N 0.006 0.003 'International Tables' O 0.011 0.006 'International Tables' H 0.000 0.000 'International Tables' loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 2 -3 1 2 -5 0 2 5 0 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 N1 C5 122.2(2) no C1 N1 H1n 118.9 no C5 N1 H1n 118.9 no C11 N2 C12 122.0(2) no C11 N2 H2n 119.0 no C12 N2 H2n 119.0 no O1 N3 O2 118.7(2) no O1 N3 O3 121.8(3) no O2 N3 O3 119.5(3) no O4 N4 O5 120.2(2) no O4 N4 O6 121.8(2) no O5 N4 O6 118.0(2) no N1 C1 C2 119.7(2) no N1 C1 H1 120.1 no C2 C1 H1 120.1 no C1 C2 C3 120.4(2) no C1 C2 H2 119.8 no C3 C2 H2 119.8 no C2 C3 C4 117.3(2) no C2 C3 C6 121.9(2) no C4 C3 C6 120.8(2) no C3 C4 C5 120.7(2) no C3 C4 H4 119.6 no C5 C4 H4 119.7 no N1 C5 C4 119.7(2) no N1 C5 H5 120.1 no C4 C5 H5 120.1 no C3 C6 C7 112.5(2) no C3 C6 H6a 108.7 no C3 C6 H6b 108.7 no C7 C6 H6a 108.7 no C7 C6 H6b 108.7 no H6a C6 H6b 109.5 no C6 C7 C8 110.2(2) no C6 C7 H7a 109.3 no C6 C7 H7b 109.3 no C8 C7 H7a 109.3 no C8 C7 H7b 109.3 no H7a C7 H7b 109.5 no C7 C8 C9 111.9(2) no C7 C8 H8a 108.9 no C7 C8 H8b 108.9 no C9 C8 H8a 108.9 no C9 C8 H8b 108.9 no H8a C8 H8b 109.5 no C8 C9 C10 120.0(2) no C8 C9 C13 122.2(2) no C10 C9 C13 117.8(2) no C9 C10 C11 119.9(2) no C9 C10 H10 120.1 no C11 C10 H10 120.1 no N2 C11 C10 120.1(2) no N2 C11 H11 119.9 no C10 C11 H11 119.9 no N2 C12 C13 119.8(2) no N2 C12 H12 120.1 no C13 C12 H12 120.1 no C9 C13 C12 120.4(2) no C9 C13 H13 119.8 no C12 C13 H13 119.8 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 N1 H1N O1 4_554 0.87 2.58 3.182(4) 127 N1 H1N O2 4_554 0.87 1.93 2.730(3) 153 N2 H2N O5 3_667 0.87 1.96 2.825(4) 170 N2 H2N O6 3_667 0.87 2.43 3.084(4) 133 C1 H1 O4 4_554 0.95 2.40 3.324(4) 164 C4 H4 O6 3_666 0.95 2.55 3.409(4) 151 C5 H5 O5 1_554 0.95 2.41 3.094(4) 129 C5 H5 O1 4_554 0.95 2.59 3.200(4) 123 C10 H10 O3 1_656 0.95 2.59 3.181(4) 120 C11 H11 O3 1_656 0.95 2.51 3.142(4) 124 C12 H12 O2 3_666 0.95 2.54 3.225(4) 129 _cod_database_fobs_code 2202137 _journal_paper_doi 10.1107/S1600536803009589