#------------------------------------------------------------------------------ #$Date: 2010-01-30 13:59:17 +0000 (Sat, 30 Jan 2010) $ #$Revision: 966 $ #$URL: svn://www.crystallography.net/cod/cif/2/2103838.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_2103838 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 'C12 H12 N2, C4 H4 O4' _chemical_formula_sum 'C16 H16 N2 O4' _chemical_formula_weight 300.31 _chemical_name_systematic ; 1,2-Bis(4-pyridyl)ethane--fumaric acid (1/1) ; _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 _cell_angle_alpha 90.00 _cell_angle_beta 118.394(3) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 21.0296(14) _cell_length_b 4.7456(3) _cell_length_c 16.6875(11) _cell_measurement_reflns_used 1653 _cell_measurement_temperature 150.0(10) _cell_measurement_theta_max 27.45 _cell_measurement_theta_min 2.78 _cell_volume 1465.03(17) _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 0.99 _diffrn_measured_fraction_theta_max 0.99 _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 0.035 _diffrn_reflns_av_sigmaI/netI 0.0664 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_k_min -4 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_number 4699 _diffrn_reflns_theta_full 27.4 _diffrn_reflns_theta_max 27.4 _diffrn_reflns_theta_min 2.78 _diffrn_standards_decay_% 0 _exptl_absorpt_coefficient_mu 0.099 _exptl_absorpt_correction_T_max 0.987 _exptl_absorpt_correction_T_min 0.963 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_process_details 'DENZO-SMN (Otwinowski & Minor, 1997)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.362 _exptl_crystal_density_method 'not measured' _exptl_crystal_description needle _exptl_crystal_F_000 632 _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.12 _refine_diff_density_max 0.267 _refine_diff_density_min -0.234 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.057 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 101 _refine_ls_number_reflns 1653 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.057 _refine_ls_R_factor_all 0.0611 _refine_ls_R_factor_gt 0.0444 _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^)+(0.0482P)^2^+0.3635P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1140 _refine_ls_wR_factor_ref 0.1230 _reflns_number_gt 1247 _reflns_number_total 1653 _reflns_threshold_expression >2\s(I) _[local]_cod_data_source_file na0143.cif _[local]_cod_data_source_block VII _[local]_cod_cif_authors_sg_H-M 'C 2/c' 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_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_ _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 0.35423(6) -0.0264(3) 0.24699(8) 0.0255(3) Uani d . 1 N C12 0.41433(8) 0.0954(3) 0.25494(10) 0.0290(4) Uani d . 1 C C13 0.45224(8) 0.2946(3) 0.32133(10) 0.0302(4) Uani d . 1 C C14 0.42827(7) 0.3712(3) 0.38275(9) 0.0253(3) Uani d . 1 C C15 0.36608(8) 0.2428(3) 0.37441(10) 0.0284(3) Uani d . 1 C C16 0.33076(8) 0.0469(3) 0.30593(10) 0.0282(4) Uani d . 1 C C17 0.47056(8) 0.5768(3) 0.45852(9) 0.0289(4) Uani d . 1 C O1 0.28603(5) -0.3937(2) 0.12220(7) 0.0300(3) Uani d . 1 O O2 0.37848(5) -0.3841(2) 0.09086(7) 0.0341(3) Uani d . 1 O C1 0.32025(7) -0.4766(3) 0.07838(9) 0.0251(3) Uani d . 1 C C2 0.28176(7) -0.7003(3) 0.00932(10) 0.0267(3) Uani d . 1 C H12 0.4315 0.0436 0.2137 0.035 Uiso calc R 1 H H13 0.4945 0.3786 0.3249 0.036 Uiso calc R 1 H H15 0.3480 0.2889 0.4152 0.034 Uiso calc R 1 H H16 0.2881 -0.0392 0.3005 0.034 Uiso calc R 1 H H17A 0.4375 0.6746 0.4761 0.035 Uiso calc R 1 H H17B 0.4931 0.7204 0.4370 0.035 Uiso calc R 1 H H1 0.3114 -0.2751 0.1620 0.045 Uiso calc R 1 H H2 0.3048 -0.7751 -0.0231 0.032 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 0.0244(6) 0.0274(7) 0.0241(6) -0.0024(5) 0.0110(5) -0.0044(5) C12 0.0299(8) 0.0329(9) 0.0270(7) -0.0041(6) 0.0160(7) -0.0040(6) C13 0.0280(7) 0.0318(9) 0.0321(8) -0.0052(6) 0.0153(7) -0.0026(6) C14 0.0247(7) 0.0230(8) 0.0232(7) 0.0012(6) 0.0074(6) 0.0006(5) C15 0.0278(7) 0.0311(8) 0.0272(7) 0.0010(6) 0.0137(6) -0.0019(6) C16 0.0248(7) 0.0311(9) 0.0293(7) -0.0025(6) 0.0133(6) -0.0026(6) C17 0.0293(8) 0.0246(8) 0.0278(7) -0.0004(6) 0.0096(7) -0.0022(6) O1 0.0281(6) 0.0342(7) 0.0313(6) -0.0082(5) 0.0171(5) -0.0143(4) O2 0.0271(6) 0.0410(7) 0.0376(6) -0.0082(5) 0.0181(5) -0.0105(5) C1 0.0244(7) 0.0274(8) 0.0239(7) -0.0005(6) 0.0118(6) -0.0010(6) C2 0.0284(7) 0.0274(8) 0.0272(7) -0.0011(6) 0.0156(6) -0.0046(6) 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 C12 . 1.3379(19) no N11 C16 . 1.3393(18) no C12 C13 . 1.384(2) no C12 H12 . 0.95 no C13 C14 . 1.388(2) no C13 H13 . 0.95 no C14 C15 . 1.388(2) no C14 C17 . 1.508(2) no C15 C16 . 1.384(2) no C15 H15 . 0.95 no C16 H16 . 0.95 no C17 C17 5_666 1.533(3) no C17 H17A . 0.99 no C17 H17B . 0.99 no O1 C1 . 1.3068(16) no O1 H1 . 0.84 no O2 C1 . 1.2218(17) no C1 C2 . 1.491(2) no C2 C2 7_535 1.307(3) no C2 H2 . 0.95 no 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 C12 N11 C16 . . 118.40(12) no N11 C12 C13 . . 122.13(13) no N11 C12 H12 . . 118.9 no C13 C12 H12 . . 118.9 no C12 C13 C14 . . 119.75(13) no C12 C13 H13 . . 120.1 no C14 C13 H13 . . 120.1 no C15 C14 C13 . . 117.81(13) no C15 C14 C17 . . 121.33(13) no C13 C14 C17 . . 120.80(13) no C16 C15 C14 . . 119.19(13) no C16 C15 H15 . . 120.4 no C14 C15 H15 . . 120.4 no N11 C16 C15 . . 122.70(13) no N11 C16 H16 . . 118.6 no C15 C16 H16 . . 118.6 no C14 C17 C17 . 5_666 110.51(16) no C14 C17 H17A . . 109.5 no C17 C17 H17A 5_666 . 109.5 no C14 C17 H17B . . 109.5 no C17 C17 H17B 5_666 . 109.5 no H17A C17 H17B . . 108.1 no C1 O1 H1 . . 109.5 no O2 C1 O1 . . 124.78(13) no O2 C1 C2 . . 121.28(13) no O1 C1 C2 . . 113.94(12) no C2 C2 C1 7_535 . 123.97(17) no C2 C2 H2 7_535 . 118.0 no C1 C2 H2 . . 118.0 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_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag C16 N11 C12 C13 . -0.5(2) no N11 C12 C13 C14 . 0.6(2) no C12 C13 C14 C15 . -0.2(2) no C12 C13 C14 C17 . 176.97(14) no C13 C14 C15 C16 . -0.2(2) no C17 C14 C15 C16 . -177.39(14) no C12 N11 C16 C15 . 0.0(2) no C14 C15 C16 N11 . 0.3(2) no C15 C14 C17 C17 5_666 91.2(2) no C13 C14 C17 C17 5_666 -85.9(2) no O2 C1 C2 C2 7_535 -177.37(18) no O1 C1 C2 C2 7_535 2.6(3) 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 1.73 2.567(2) 172 y C16 H16 O1 4 0.95 2.55 3.217(2) 128 y _cod_database_code 2103838