#------------------------------------------------------------------------------ #$Date: 2016-02-19 22:18:51 +0000 (Fri, 19 Feb 2016) $ #$Revision: 176760 $ #$URL: svn://www.crystallography.net/cod/cif/2/01/19/2011969.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_2011969 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_paper_doi 10.1107/S0108270101003833 _journal_volume 57 _journal_year 2001 _chemical_formula_moiety 'C12 H12 N2 2+ , 2C4 H O4 -' _chemical_formula_sum 'C20 H14 N2 O8' _chemical_formula_weight 410.33 _chemical_name_systematic ; 1,2-bis(4-pyridinium)ethylene 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 97.845(17) _cell_angle_beta 98.444(13) _cell_angle_gamma 67.259(8) _cell_formula_units_Z 1 _cell_length_a 10.2606(9) _cell_length_b 12.2942(17) _cell_length_c 3.7749(13) _cell_measurement_reflns_used 22 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 42.56 _cell_measurement_theta_min 13.88 _cell_volume 432.75(17) _computing_cell_refinement 'CAD-4 EXPRESS' _computing_data_collection 'CAD-4 EXPRESS (Enraf-Nonius, 1992)' _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 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device_type 'Enraf-Nonius CAD-4' _diffrn_measurement_method \w/2\q _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54178 _diffrn_reflns_av_R_equivalents .009 _diffrn_reflns_av_sigmaI/netI .018 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_l_max 4 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 2052 _diffrn_reflns_theta_full 74.21 _diffrn_reflns_theta_max 74.21 _diffrn_reflns_theta_min 3.91 _diffrn_standards_decay_% 2.90 _diffrn_standards_interval_time 120 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 1.060 _exptl_absorpt_correction_T_max .920 _exptl_absorpt_correction_T_min .778 _exptl_absorpt_correction_type \y-scan _exptl_absorpt_process_details '(North et al., 1968)' _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.575 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prismatic _exptl_crystal_F_000 212 _exptl_crystal_size_max .25 _exptl_crystal_size_mid .10 _exptl_crystal_size_min .08 _refine_diff_density_max .24 _refine_diff_density_min -.30 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.018 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 164 _refine_ls_number_reflns 1771 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.018 _refine_ls_R_factor_all .055 _refine_ls_R_factor_gt .044 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean .000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0919P)^2^+0.0683P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref .133 _reflns_number_gt 1468 _reflns_number_total 1771 _reflns_threshold_expression I>2\s(I) _cod_data_source_file gd1134.cif _cod_data_source_block II _cod_database_code 2011969 _cod_database_fobs_code 2011969 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 -.08498(13) .39152(10) -.4025(4) .0499(4) Uani d . 1 . . O O2 .07016(12) .11353(10) -.5637(4) .0470(3) Uani d . 1 . . O O3 .34122(13) .11285(11) -.0093(4) .0544(4) Uani d . 1 . . O O4 .19294(12) .39772(10) .1499(4) .0468(3) Uani d . 1 . . O N1 .26855(14) -.10035(11) -.6755(4) .0387(3) Uani d . 1 . . N C1 .03897(16) .31522(13) -.2828(4) .0351(4) Uani d . 1 . . C C2 .10311(16) .19053(13) -.3653(4) .0357(4) Uani d . 1 . . C C3 .23000(16) .18908(14) -.1131(4) .0365(4) Uani d . 1 . . C C4 .15808(16) .32048(13) -.0406(4) .0352(4) Uani d . 1 . . C C5 .43114(15) -.33416(13) -.8337(4) .0327(3) Uani d . 1 . . C C6 .28763(17) -.28698(14) -.9677(4) .0376(4) Uani d . 1 . . C C7 .20931(16) -.16988(14) -.8837(4) .0395(4) Uani d . 1 . . C C8 .40590(17) -.14148(14) -.5435(4) .0385(4) Uani d . 1 . . C C9 .48911(16) -.25872(14) -.6205(4) .0362(4) Uani d . 1 . . C C10 .52189(16) -.45890(13) -.9123(4) .0368(4) Uani d . 1 . . C H1A -.102(3) .472(2) -.278(6) .063(6) Uiso d . 1 . . H H1 .201(3) -.015(2) -.617(7) .075(8) Uiso d . 1 . . H H6 .244(2) -.3352(17) -1.120(5) .040(5) Uiso d . 1 . . H H7 .109(2) -.1318(19) -.975(6) .054(6) Uiso d . 1 . . H H8 .4400(19) -.0845(16) -.385(5) .036(4) Uiso d . 1 . . H H9 .588(2) -.2933(19) -.519(6) .055(6) Uiso d . 1 . . H H10 .622(2) -.4786(19) -.818(6) .057(6) 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 .0370(6) .0303(6) .0636(8) -.0034(5) -.0163(5) -.0066(5) O2 .0374(6) .0313(6) .0606(8) -.0092(5) -.0075(5) -.0108(5) O3 .0392(7) .0363(6) .0690(9) -.0026(5) -.0135(6) -.0020(6) O4 .0371(6) .0309(6) .0605(8) -.0093(5) -.0105(5) -.0083(5) N1 .0377(7) .0279(6) .0429(7) -.0072(5) -.0001(5) -.0024(5) C1 .0316(7) .0290(7) .0394(8) -.0088(6) -.0021(6) -.0009(6) C2 .0327(7) .0300(7) .0402(8) -.0103(6) .0004(6) -.0036(6) C3 .0325(7) .0302(7) .0413(8) -.0093(6) -.0022(6) -.0015(6) C4 .0322(7) .0286(7) .0399(8) -.0092(6) .0000(6) -.0024(6) C5 .0321(7) .0301(8) .0332(7) -.0105(6) .0014(6) -.0010(6) C6 .0339(8) .0335(8) .0414(8) -.0131(6) -.0030(6) -.0042(6) C7 .0312(8) .0356(8) .0446(8) -.0084(6) -.0029(6) -.0005(6) C8 .0391(8) .0327(8) .0405(8) -.0149(7) -.0024(6) -.0044(6) C9 .0315(7) .0328(8) .0402(8) -.0114(6) -.0031(6) -.0017(6) C10 .0337(8) .0310(8) .0403(8) -.0088(6) .0008(6) -.0017(6) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C .0181 .0091 '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 .0311 .0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O .0492 .0322 '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 1 -3 1 0 -1 -4 -1 -2 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 C1 O1 H1A . 110.9(14) no C7 N1 C8 . 121.94(13) yes C7 N1 H1 . 115.2(15) no C8 N1 H1 . 122.9(15) no O1 C1 C2 . 130.32(14) yes O1 C1 C4 . 136.15(14) yes C2 C1 C4 . 93.53(12) yes O2 C2 C1 . 136.23(14) yes O2 C2 C3 . 134.37(14) yes C1 C2 C3 . 89.40(12) yes O3 C3 C2 . 135.13(15) yes O3 C3 C4 . 136.64(15) yes C2 C3 C4 . 88.22(11) yes O4 C4 C1 . 137.42(14) yes O4 C4 C3 . 133.73(14) yes C1 C4 C3 . 88.84(12) yes C9 C5 C6 . 118.14(14) yes C9 C5 C10 . 119.34(14) yes C6 C5 C10 . 122.51(14) yes C7 C6 C5 . 119.41(15) yes C7 C6 H6 . 119.8(12) no C5 C6 H6 . 120.8(12) no N1 C7 C6 . 120.71(14) yes N1 C7 H7 . 116.4(13) no C6 C7 H7 . 122.9(13) no N1 C8 C9 . 119.52(14) yes N1 C8 H8 . 116.5(11) no C9 C8 H8 . 123.9(11) no C8 C9 C5 . 120.27(14) yes C8 C9 H9 . 122.2(13) no C5 C9 H9 . 117.5(13) no C10 C10 C5 2_643 125.34(19) yes C10 C10 H10 2_643 120.6(12) no C5 C10 H10 . 114.0(12) 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 O1 C1 . 1.3138(19) yes O1 H1A . .99(2) no O2 C2 . 1.2453(19) yes O3 C3 . 1.215(2) yes O4 C4 . 1.2440(19) yes N1 C7 . 1.340(2) yes N1 C8 . 1.342(2) yes N1 H1 . 1.02(3) no C1 C2 . 1.425(2) yes C1 C4 . 1.432(2) yes C2 C3 . 1.491(2) yes C3 C4 . 1.499(2) yes C5 C9 . 1.394(2) yes C5 C6 . 1.400(2) yes C5 C10 . 1.470(2) yes C6 C7 . 1.369(2) yes C6 H6 . .96(2) no C7 H7 . .98(2) no C8 C9 . 1.378(2) yes C8 H8 . .993(18) no C9 H9 . .98(2) no C10 C10 2_643 1.320(3) yes C10 H10 . .98(2) 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 O1 H1A O4 2_565 .99(2) 1.56(2) 2.5033(17) 156(2) N1 H1 O2 . 1.02(3) 1.64(3) 2.6546(17) 170(2) 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 . .4(3) no C4 C1 C2 O2 . -178.9(2) no O1 C1 C2 C3 . 179.96(19) no C4 C1 C2 C3 . .75(13) no O2 C2 C3 O3 . -2.5(4) no C1 C2 C3 O3 . 177.9(2) no O2 C2 C3 C4 . 178.9(2) no C1 C2 C3 C4 . -.71(12) no O1 C1 C4 O4 . -.6(4) no C2 C1 C4 O4 . 178.5(2) no O1 C1 C4 C3 . -179.9(2) no C2 C1 C4 C3 . -.74(13) no O3 C3 C4 O4 . 2.8(4) no C2 C3 C4 O4 . -178.6(2) no O3 C3 C4 C1 . -177.9(2) no C2 C3 C4 C1 . .71(12) no C9 C5 C6 C7 . -.5(2) no C10 C5 C6 C7 . -179.98(15) no C8 N1 C7 C6 . .5(3) no C5 C6 C7 N1 . .0(3) no C7 N1 C8 C9 . -.5(3) no N1 C8 C9 C5 . .0(3) no C6 C5 C9 C8 . .5(2) no C10 C5 C9 C8 . 180.00(14) no C9 C5 C10 C10 2_643 174.8(2) no C6 C5 C10 C10 2_643 -5.8(3) no