#------------------------------------------------------------------------------ #$Date: 2012-02-03 17:16:24 +0000 (Fri, 03 Feb 2012) $ #$Revision: 32112 $ #$URL: svn://www.crystallography.net/cod/cif/2/01/19/2011968.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_2011968 loop_ _publ_author_name 'Zaman, Md. Badruz' 'Tomura, Masaaki' 'Yamashita, Yoshiro' _publ_section_title ; Linear hydrogen-bonded molecular tapes in the cocrystals of squaric acid with 4,4'-dipyridylacetylene and 1,2-bis(4-pyridyl)ethylene ; _journal_issue 5 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 621 _journal_page_last 624 _journal_volume 57 _journal_year 2001 _chemical_formula_moiety 'C12 H10 N2 2+ , 2C4 H O4 -' _chemical_formula_sum 'C20 H12 N2 O8' _chemical_formula_weight 408.32 _chemical_name_systematic ; bis(4-pyridinium)acetylene bis(hydrogen squarate) ; _space_group_IT_number 2 _symmetry_cell_setting triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _cell_angle_alpha 97.24(2) _cell_angle_beta 98.49(2) _cell_angle_gamma 67.649(18) _cell_formula_units_Z 1 _cell_length_a 10.221(2) _cell_length_b 12.325(3) _cell_length_c 3.7951(9) _cell_measurement_reflns_used 25 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 14.79 _cell_measurement_theta_min 13.08 _cell_volume 436.04(18) _computing_cell_refinement 'MSC/AFC Diffractometer Control Software' _computing_data_collection ; MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1988) ; _computing_data_reduction 'TEXSAN (Molecular Structure Corporation, 1995)' _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 296(2) _diffrn_measured_fraction_theta_full .999 _diffrn_measured_fraction_theta_max .999 _diffrn_measurement_device_type 'Rigaku AFC-7R' _diffrn_measurement_method \w/2\q _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'Rigaku rotating anode' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength .71069 _diffrn_reflns_av_R_equivalents .048 _diffrn_reflns_av_sigmaI/netI .148 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 4 _diffrn_reflns_limit_l_min -4 _diffrn_reflns_number 2101 _diffrn_reflns_theta_full 27.49 _diffrn_reflns_theta_max 27.49 _diffrn_reflns_theta_min 2.17 _diffrn_standards_decay_% .76 _diffrn_standards_interval_count 150 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu .123 _exptl_absorpt_correction_type none _exptl_crystal_colour gold _exptl_crystal_density_diffrn 1.555 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prismatic _exptl_crystal_F_000 210 _exptl_crystal_size_max .22 _exptl_crystal_size_mid .15 _exptl_crystal_size_min .05 _refine_diff_density_max .24 _refine_diff_density_min -.26 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref .915 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 160 _refine_ls_number_reflns 1992 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all .915 _refine_ls_R_factor_all .197 _refine_ls_R_factor_gt .045 _refine_ls_shift/su_max .001 _refine_ls_shift/su_mean .000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0564P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref .141 _reflns_number_gt 788 _reflns_number_total 1992 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file gd1134.cif _[local]_cod_data_source_block I _cod_original_cell_volume 436.06(18) _cod_database_code 2011968 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_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol O1 .9256(2) .38326(19) 1.0550(6) .0452(7) Uani d . 1 . . O O2 .6546(3) .3847(2) .5077(7) .0551(8) Uani d . 1 . . O O3 .8044(3) .10255(19) .3353(7) .0478(7) Uani d . 1 . . O O4 1.0818(3) .1085(2) .8942(7) .0496(7) Uani d . 1 . . O N1 .7316(3) .5944(2) 1.1723(8) .0372(7) Uani d . 1 . . N C1 .8936(3) .3058(3) .8556(9) .0329(8) Uani d . 1 . . C C2 .7664(4) .3084(3) .6062(9) .0351(8) Uani d . 1 . . C C3 .8394(4) .1777(3) .5309(9) .0327(8) Uani d . 1 . . C C4 .9582(3) .1831(3) .7728(9) .0336(8) Uani d . 1 . . C C5 .5947(4) .8266(3) 1.3525(8) .0332(8) Uani d . 1 . . C C6 .7366(4) .7706(3) 1.4741(9) .0380(9) Uani d . 1 . . C C7 .8026(4) .6535(3) 1.3795(10) .0394(9) Uani d . 1 . . C C8 .5953(4) .6450(3) 1.0499(10) .0375(9) Uani d . 1 . . C C9 .5222(4) .7626(3) 1.1356(9) .0365(9) Uani d . 1 . . C C10 .5250(4) .9495(3) 1.4534(10) .0426(9) Uani d . 1 . . C H1 .793(4) .516(3) 1.091(10) .060(12) Uiso d . 1 . . H H4 1.106(5) .025(4) .763(12) .095(16) Uiso d . 1 . . H H6 .786(4) .813(3) 1.626(10) .052(11) Uiso d . 1 . . H H7 .895(4) .613(3) 1.459(9) .046(10) Uiso d . 1 . . H H8 .556(4) .598(3) .903(10) .058(12) Uiso d . 1 . . H H9 .429(4) .796(3) 1.042(8) .033(9) Uiso 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 .0378(14) .0289(12) .0567(16) -.0074(11) -.0074(12) -.0100(11) O2 .0385(15) .0344(14) .0732(19) -.0013(12) -.0146(13) -.0014(13) O3 .0415(15) .0302(13) .0610(16) -.0109(11) -.0091(13) -.0104(12) O4 .0408(15) .0273(13) .0613(17) -.0032(11) -.0178(12) -.0086(11) N1 .0377(17) .0283(16) .0403(17) -.0100(13) .0000(14) -.0041(13) C1 .0291(18) .0252(17) .039(2) -.0063(14) .0002(16) -.0007(14) C2 .0331(19) .0326(18) .0366(19) -.0112(15) .0030(16) -.0048(15) C3 .0365(18) .0274(17) .0327(18) -.0124(14) .0003(15) -.0010(14) C4 .0328(19) .0265(17) .0365(19) -.0096(14) -.0019(15) -.0048(14) C5 .040(2) .0249(17) .0331(19) -.0101(15) .0097(16) -.0029(14) C6 .037(2) .039(2) .039(2) -.0183(18) -.0007(17) -.0038(16) C7 .024(2) .038(2) .045(2) -.0036(15) -.0056(16) -.0010(16) C8 .036(2) .0330(18) .041(2) -.0151(16) -.0041(17) -.0052(16) C9 .032(2) .0357(19) .038(2) -.0111(16) -.0024(16) .0014(16) C10 .052(2) .0318(18) .041(2) -.0119(17) .0043(18) .0035(16) 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 C1 . 1.255(4) yes O2 C2 . 1.215(4) yes O3 C3 . 1.240(4) yes O4 C4 . 1.306(4) yes O4 H4 . 1.04(5) no N1 C7 . 1.328(4) yes N1 C8 . 1.329(4) yes N1 H1 . .98(4) no C1 C4 . 1.415(4) yes C1 C2 . 1.483(5) yes C2 C3 . 1.505(5) yes C3 C4 . 1.427(5) yes C5 C6 . 1.383(4) yes C5 C9 . 1.397(4) yes C5 C10 . 1.436(5) yes C6 C7 . 1.367(5) yes C6 H6 . .95(4) no C7 H7 . .91(3) no C8 C9 . 1.377(5) yes C8 H8 . .92(4) no C9 H9 . .92(3) no C10 C10 2_678 1.181(6) yes loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O .0106 .0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 3 2 0 4 2 0 2 1 0 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 C4 O4 H4 . 113(3) no C7 N1 C8 . 122.3(3) yes C7 N1 H1 . 113(2) no C8 N1 H1 . 124(2) no O1 C1 C4 . 136.6(3) yes O1 C1 C2 . 133.3(3) yes C4 C1 C2 . 90.0(2) yes O2 C2 C1 . 135.0(3) yes O2 C2 C3 . 137.3(3) yes C1 C2 C3 . 87.7(3) yes O3 C3 C4 . 138.2(3) yes O3 C3 C2 . 133.1(3) yes C4 C3 C2 . 88.7(2) yes O4 C4 C1 . 130.0(3) yes O4 C4 C3 . 136.5(3) yes C1 C4 C3 . 93.5(3) yes C6 C5 C9 . 119.4(3) yes C6 C5 C10 . 119.2(3) yes C9 C5 C10 . 121.4(3) yes C7 C6 C5 . 119.1(3) yes C7 C6 H6 . 121(2) no C5 C6 H6 . 120(2) no N1 C7 C6 . 120.4(3) yes N1 C7 H7 . 118(2) no C6 C7 H7 . 122(2) no N1 C8 C9 . 120.3(3) yes N1 C8 H8 . 116(2) no C9 C8 H8 . 123(2) no C8 C9 C5 . 118.4(3) yes C8 C9 H9 . 118.7(19) no C5 C9 H9 . 122.9(19) no C10 C10 C5 2_678 176.2(6) yes 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 . .98(4) 1.68(4) 2.636(4) 165(3) O4 H4 O3 2_756 1.04(5) 1.52(5) 2.511(3) 157(4) 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 O1 C1 C2 O2 . 1.9(7) no C4 C1 C2 O2 . -178.5(4) no O1 C1 C2 C3 . -179.1(4) no C4 C1 C2 C3 . .5(3) no O2 C2 C3 O3 . -1.2(8) no C1 C2 C3 O3 . 179.7(4) no O2 C2 C3 C4 . 178.5(5) no C1 C2 C3 C4 . -.5(3) no O1 C1 C4 O4 . .2(7) no C2 C1 C4 O4 . -179.4(3) no O1 C1 C4 C3 . 179.0(4) no C2 C1 C4 C3 . -.6(3) no O3 C3 C4 O4 . -1.0(8) no C2 C3 C4 O4 . 179.3(4) no O3 C3 C4 C1 . -179.7(4) no C2 C3 C4 C1 . .6(3) no C9 C5 C6 C7 . -.1(5) no C10 C5 C6 C7 . 179.6(4) no C8 N1 C7 C6 . -.3(5) no C5 C6 C7 N1 . .3(5) no C7 N1 C8 C9 . .1(5) no N1 C8 C9 C5 . .0(5) no C6 C5 C9 C8 . .0(5) no C10 C5 C9 C8 . -179.8(4) no C6 C5 C10 C10 2_678 2(9) no C9 C5 C10 C10 2_678 -178(8) no