#------------------------------------------------------------------------------ #$Date: 2011-09-28 15:24:46 +0100 (Wed, 28 Sep 2011) $ #$Revision: 26848 $ #$URL: svn://www.crystallography.net/cod/cif/2/10/38/2103836.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_2103836 loop_ _publ_author_name 'Bowes, Katharine F.' 'Ferguson, George' 'Lough, Alan J.' 'Glidewell, Christopher' _publ_section_title ; Salts of maleic and fumaric acids with organic polyamines: comparison of isomeric acids as building blocks in supramolecular chemistry ; _journal_issue 1 _journal_name_full 'Acta Crystallographica Section B' _journal_page_first 100 _journal_page_last 117 _journal_volume 59 _journal_year 2003 _chemical_formula_moiety 'C10 H8 N2, C4 H4 O4' _chemical_formula_sum 'C14 H12 N2 O4' _chemical_formula_weight 272.26 _chemical_name_systematic ; 4,4'-Bipyridyl--fumaric acid (1/1) ; _space_group_IT_number 2 _symmetry_cell_setting triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 109.757(2) _cell_angle_beta 97.246(3) _cell_angle_gamma 96.813(3) _cell_formula_units_Z 1 _cell_length_a 3.8040(2) _cell_length_b 8.8743(5) _cell_length_c 9.8764(6) _cell_measurement_reflns_used 1376 _cell_measurement_temperature 150.0(10) _cell_measurement_theta_max 27.50 _cell_measurement_theta_min 2.67 _cell_volume 306.59(3) _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_collection 'Kappa-CCD server software (Nonius, 1997)' _computing_data_reduction 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_molecular_graphics 'PLATON (Spek, 2002)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997a) and PRPKAPPA (Ferguson, 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997a)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997b)' _diffrn_ambient_temperature 150.0(10) _diffrn_measured_fraction_theta_full 0.990 _diffrn_measured_fraction_theta_max 0.990 _diffrn_measurement_device_type Kappa-CCD _diffrn_measurement_method '\f scans, and \w scans with \k offsets' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed X-ray tube' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.032 _diffrn_reflns_av_sigmaI/netI 0.0512 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 3277 _diffrn_reflns_theta_full 27.50 _diffrn_reflns_theta_max 27.50 _diffrn_reflns_theta_min 2.67 _diffrn_standards_decay_% negligible _exptl_absorpt_coefficient_mu 0.110 _exptl_absorpt_correction_T_max 0.978 _exptl_absorpt_correction_T_min 0.945 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'DENZO-SMN (Otwinowski & Minor, 1997)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.475 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 142 _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.25 _refine_diff_density_max 0.326 _refine_diff_density_min -0.225 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 92 _refine_ls_number_reflns 1376 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.049 _refine_ls_R_factor_all 0.0572 _refine_ls_R_factor_gt 0.0434 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0681P)^2^+0.0475P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1139 _refine_ls_wR_factor_ref 0.1250 _reflns_number_gt 1105 _reflns_number_total 1376 _reflns_threshold_expression >2\s(I) _[local]_cod_data_source_file na0143.cif _[local]_cod_data_source_block V _cod_depositor_comments ; The following automatic conversions were performed: '_exptl_absorpt_correction_type' value 'Multi-scan' changed to 'multi-scan' 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_enum 1527 2010-12-29 10:47:43Z saulius ; _cod_database_code 2103836 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' 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 N11 0.0669(3) 0.65709(14) 0.24935(12) 0.0256(3) Uani d . 1 N C12 0.0527(4) 0.49682(18) 0.21575(15) 0.0278(4) Uani d . 1 C C13 0.2181(4) 0.43131(18) 0.31066(15) 0.0270(3) Uani d . 1 C C14 0.4094(3) 0.53270(16) 0.44697(14) 0.0219(3) Uani d . 1 C C15 0.4234(4) 0.69908(18) 0.48087(16) 0.0281(3) Uani d . 1 C C16 0.2489(4) 0.75511(18) 0.38030(17) 0.0301(4) Uani d . 1 C O1 -0.2741(3) 0.78815(12) 0.08487(11) 0.0299(3) Uani d . 1 O O2 -0.0576(3) 1.02003(12) 0.27466(11) 0.0351(3) Uani d . 1 O C1 -0.2323(4) 0.94605(17) 0.15273(15) 0.0243(3) Uani d . 1 C C2 -0.4145(3) 1.03429(16) 0.06782(15) 0.0245(3) Uani d . 1 C H12 -0.0760 0.4251 0.1230 0.033 Uiso calc R 1 H H13 0.2006 0.3168 0.2825 0.032 Uiso calc R 1 H H15 0.5520 0.7738 0.5724 0.034 Uiso calc R 1 H H16 0.2594 0.8690 0.4059 0.036 Uiso calc R 1 H H1 -0.1607 0.7471 0.1382 0.045 Uiso calc R 1 H H2 -0.4063 1.1477 0.1150 0.029 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 N11 0.0279(6) 0.0246(7) 0.0265(7) 0.0058(5) 0.0014(5) 0.0128(5) C12 0.0321(8) 0.0264(8) 0.0240(8) 0.0072(6) 0.0003(6) 0.0087(6) C13 0.0329(7) 0.0213(7) 0.0255(8) 0.0064(6) 0.0000(6) 0.0081(6) C14 0.0207(6) 0.0240(7) 0.0233(7) 0.0058(5) 0.0033(5) 0.0111(6) C15 0.0334(7) 0.0234(7) 0.0246(7) 0.0035(6) -0.0045(6) 0.0091(6) C16 0.0356(8) 0.0213(7) 0.0325(8) 0.0041(6) -0.0028(6) 0.0119(6) O1 0.0395(6) 0.0209(6) 0.0271(6) 0.0064(4) -0.0057(4) 0.0096(4) O2 0.0469(7) 0.0254(6) 0.0275(6) 0.0062(5) -0.0102(5) 0.0085(5) C1 0.0274(7) 0.0229(7) 0.0226(7) 0.0044(5) 0.0008(5) 0.0095(6) C2 0.0276(7) 0.0196(7) 0.0273(7) 0.0053(5) 0.0011(5) 0.0106(6) 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_site_symmetry_3 _geom_angle _geom_angle_publ_flag C16 N11 C12 . . 117.46(12) no N11 C12 C13 . . 122.70(13) no N11 C12 H12 . . 118.6 no C13 C12 H12 . . 118.6 no C12 C13 C14 . . 120.14(13) no C12 C13 H13 . . 119.9 no C14 C13 H13 . . 119.9 no C13 C14 C15 . . 116.78(12) no C13 C14 C14 . 2_666 121.95(15) no C15 C14 C14 . 2_666 121.27(15) no C16 C15 C14 . . 119.62(13) no C16 C15 H15 . . 120.2 no C14 C15 H15 . . 120.2 no N11 C16 C15 . . 123.29(13) no N11 C16 H16 . . 118.4 no C15 C16 H16 . . 118.4 no C1 O1 H1 . . 109.5 no O2 C1 O1 . . 124.72(13) no O2 C1 C2 . . 120.49(12) no O1 C1 C2 . . 114.79(12) no C2 C2 C1 2_475 . 124.35(16) no C2 C2 H2 2_475 . 117.8 no C1 C2 H2 . . 117.8 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 N11 C16 . 1.3339(19) no N11 C12 . 1.3395(18) no C12 C13 . 1.385(2) no C12 H12 . 0.95 no C13 C14 . 1.389(2) no C13 H13 . 0.95 no C14 C15 . 1.392(2) no C14 C14 2_666 1.494(3) no C15 C16 . 1.386(2) no C15 H15 . 0.95 no C16 H16 . 0.95 no O1 C1 . 1.3127(17) no O1 H1 . 0.84 no O2 C1 . 1.2177(17) no C1 C2 . 1.4910(19) no C2 C2 2_475 1.313(3) no C2 H2 . 0.95 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 O1 H1 N11 . 0.84 1.76 2.603(2) 179 y C15 H15 O2 2_676 0.95 2.43 3.301(2) 153 y 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_1 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag C16 N11 C12 C13 . . -0.1(2) no N11 C12 C13 C14 . . -0.2(2) no C12 C13 C14 C15 . . 0.0(2) no C12 C13 C14 C14 . 2_666 179.74(14) no C13 C14 C15 C16 . . 0.4(2) no C14 C14 C15 C16 2_666 . -179.33(14) no C12 N11 C16 C15 . . 0.5(2) no C14 C15 C16 N11 . . -0.7(2) no O2 C1 C2 C2 . 2_475 174.8(2) no O1 C1 C2 C2 . 2_475 -4.4(2) no