data_2012019 _journal_name_full 'Acta Crystallographica, Section C' _journal_year 2001 _journal_volume 57 _journal_page_first 751 _journal_page_last 753 _publ_section_title ; 4,7-Bis(4-pyridylethynyl)-2,1,3-benzothiadiazole and its dipyridinium diperchlorate ; loop_ _publ_author_name 'Akhtaruzzaman, Md.' 'Tomura, Masaaki' 'Yamashita, Yoshiro' _chemical_formula_moiety 'C20 H12 N4 S 2+, 2Cl O4 -' _chemical_formula_sum 'C20 H12 Cl2 N4 O8 S' _chemical_formula_weight 539.30 _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 5.1097(3) _cell_length_b 24.4522(16) _cell_length_c 17.8489(13) _cell_angle_alpha 90.00 _cell_angle_beta 92.281(5) _cell_angle_gamma 90.00 _cell_volume 2228.3(3) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _exptl_crystal_density_diffrn 1.608 _diffrn_ambient_temperature 296(2) 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 Cl1 .0095(2) .27338(5) .26293(6) .0502(3) Uani d . 1 . . Cl Cl2 .1575(2) .38122(4) .53621(6) .0480(3) Uani d . 1 . . Cl O1 .2857(7) .2713(2) .2756(2) .0826(12) Uani d . 1 . . O O2 -.1122(8) .27617(18) .3331(2) .0737(11) Uani d . 1 . . O O3 -.0782(8) .22629(15) .2218(2) .0738(11) Uani d . 1 . . O O4 -.0575(9) .32089(16) .2197(2) .0773(11) Uani d . 1 . . O O5 .4337(7) .38644(16) .5441(2) .0723(11) Uani d . 1 . . O O6 .0869(7) .36157(17) .4616(2) .0712(11) Uani d . 1 . . O O7 .0369(8) .43301(17) .5439(3) .0860(13) Uani d . 1 . . O O8 .0685(9) .3431(2) .5882(3) .1015(17) Uani d . 1 . . O S1 .2860(3) .46762(5) .06362(8) .0669(4) Uani d . 1 . . S N1 .5192(8) .47523(16) .1267(2) .0572(10) Uani d . 1 . . N N2 .1687(8) .52864(16) .0604(2) .0536(10) Uani d . 1 . . N N3 1.6612(8) .41586(19) .3859(2) .0563(11) Uani d . 1 . . N H3 1.783(13) .399(2) .413(4) .079(19) Uiso d . 1 . . H N4 -.6422(8) .76057(18) -.0713(2) .0545(10) Uani d . 1 . . N H4 -.750(12) .785(3) -.097(4) .09(2) Uiso d . 1 . . H C1 .6761(8) .55280(19) .2046(2) .0458(10) Uani d . 1 . . C C2 .5133(8) .52731(18) .1481(2) .0435(9) Uani d . 1 . . C C3 .3094(8) .55849(18) .1100(2) .0429(10) Uani d . 1 . . C C4 .2712(8) .61377(18) .1280(2) .0444(10) Uani d . 1 . . C C5 .4246(10) .6368(2) .1841(3) .0546(12) Uani d . 1 . . C H5 .425(10) .672(2) .193(3) .050(14) Uiso d . 1 . . H C6 .6303(10) .6068(2) .2213(3) .0529(11) Uani d . 1 . . C H6 .743(9) .6239(18) .254(2) .045(12) Uiso d . 1 . . H C7 .8839(8) .5230(2) .2425(3) .0479(10) Uani d . 1 . . C C8 1.0566(9) .4987(2) .2742(3) .0485(10) Uani d . 1 . . C C9 1.2644(8) .47005(17) .3130(2) .0414(9) Uani d . 1 . . C C10 1.3244(10) .4170(2) .2939(3) .0525(11) Uani d . 1 . . C H10 1.233(10) .4023(19) .260(3) .050(14) Uiso d . 1 . . H C11 1.5289(11) .3904(2) .3318(3) .0579(13) Uani d . 1 . . C H11 1.573(10) .360(2) .322(3) .056(15) Uiso d . 1 . . H C12 1.6093(10) .4661(2) .4067(3) .0556(12) Uani d . 1 . . C H12 1.710(9) .4800(19) .447(3) .048(13) Uiso d . 1 . . H C13 1.4108(9) .4946(2) .3715(3) .0497(11) Uani d . 1 . . C H13 1.384(7) .5304(16) .385(2) .025(9) Uiso d . 1 . . H C14 .0728(9) .64459(19) .0872(3) .0483(10) Uani d . 1 . . C C15 -.0881(9) .67010(19) .0523(3) .0510(11) Uani d . 1 . . C C16 -.2799(8) .70171(18) .0103(2) .0440(10) Uani d . 1 . . C C17 -.3046(11) .6964(2) -.0669(3) .0595(13) Uani d . 1 . . C H17 -.210(12) .669(2) -.090(3) .082(19) Uiso d . 1 . . H C18 -.4878(11) .7266(3) -.1068(3) .0641(15) Uani d . 1 . . C H18 -.483(11) .727(2) -.154(3) .072(18) Uiso d . 1 . . H C19 -.6266(10) .7669(2) .0029(3) .0514(11) Uani d . 1 . . C H19 -.751(11) .791(2) .024(3) .067(16) Uiso d . 1 . . H C20 -.4410(10) .7384(2) .0448(3) .0518(11) Uani d . 1 . . C H20 -.429(9) .7397(19) .094(3) .048(13) 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 Cl1 .0471(6) .0586(7) .0444(6) .0004(5) -.0055(4) .0005(5) Cl2 .0413(5) .0453(5) .0566(6) -.0052(4) -.0095(4) .0056(5) O1 .046(2) .129(4) .072(3) .002(2) -.0047(18) .001(2) O2 .072(2) .102(3) .048(2) .014(2) .0081(17) -.001(2) O3 .092(3) .059(2) .069(2) .004(2) -.020(2) -.0066(18) O4 .090(3) .061(2) .079(3) -.011(2) -.014(2) .011(2) O5 .0388(18) .080(3) .097(3) -.0069(17) -.0122(18) .000(2) O6 .065(2) .086(3) .061(2) .0151(19) -.0187(18) -.0068(19) O7 .069(3) .063(2) .125(4) .008(2) -.014(2) -.022(2) O8 .094(3) .124(4) .084(3) -.052(3) -.027(2) .047(3) S1 .0742(9) .0495(7) .0752(9) .0038(6) -.0179(7) -.0041(6) N1 .059(2) .047(2) .065(3) .0106(18) -.003(2) .0064(19) N2 .051(2) .053(2) .055(2) .0023(18) -.0121(18) -.0009(18) N3 .043(2) .063(3) .063(3) .0074(19) -.0073(19) .026(2) N4 .049(2) .058(2) .055(2) .0085(19) -.0082(18) .015(2) C1 .035(2) .058(3) .044(2) .0069(19) -.0057(17) .012(2) C2 .038(2) .048(2) .045(2) .0045(18) -.0019(17) .0093(19) C3 .035(2) .047(2) .046(2) .0033(18) -.0049(17) .0096(18) C4 .041(2) .046(2) .046(2) .0052(18) -.0055(18) .0093(19) C5 .059(3) .046(3) .058(3) .008(2) -.008(2) .002(2) C6 .046(2) .057(3) .054(3) .000(2) -.014(2) .002(2) C7 .034(2) .061(3) .049(2) .0032(19) -.0019(18) .010(2) C8 .042(2) .053(3) .050(2) .003(2) -.0042(19) .010(2) C9 .036(2) .044(2) .044(2) .0052(17) .0015(17) .0094(18) C10 .057(3) .048(3) .052(3) -.001(2) -.014(2) -.002(2) C11 .064(3) .040(3) .069(3) .017(2) -.001(3) .004(2) C12 .048(3) .064(3) .053(3) -.010(2) -.014(2) .012(2) C13 .051(3) .046(3) .051(3) .002(2) -.004(2) .003(2) C14 .041(2) .050(3) .053(3) .0049(19) -.0048(19) .007(2) C15 .048(2) .049(3) .056(3) .004(2) -.009(2) .004(2) C16 .039(2) .046(2) .046(2) .0015(18) -.0074(18) .0050(19) C17 .060(3) .067(3) .051(3) .021(3) -.003(2) -.003(2) C18 .057(3) .095(4) .039(3) .006(3) -.014(2) .003(3) C19 .046(2) .047(3) .061(3) .005(2) -.002(2) .002(2) C20 .061(3) .053(3) .041(2) .010(2) -.006(2) -.002(2) 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 Cl1 O1 . 1.421(4) no Cl1 O2 . 1.423(4) no Cl1 O3 . 1.428(4) no Cl1 O4 . 1.429(4) no Cl2 O8 . 1.405(4) no Cl2 O7 . 1.417(4) no Cl2 O5 . 1.418(3) no Cl2 O6 . 1.447(4) no S1 N2 . 1.608(4) yes S1 N1 . 1.617(4) yes N1 C2 . 1.330(6) yes N2 C3 . 1.335(6) yes N3 C12 . 1.314(7) ? N3 C11 . 1.314(7) ? N3 H3 . .88(7) no N4 C18 . 1.324(7) ? N4 C19 . 1.332(6) ? N4 H4 . .91(6) no C1 C6 . 1.375(7) yes C1 C2 . 1.426(6) yes C1 C7 . 1.434(6) yes C2 C3 . 1.440(5) yes C3 C4 . 1.405(6) yes C4 C5 . 1.367(7) yes C4 C14 . 1.438(6) yes C5 C6 . 1.424(7) yes C5 H5 . .87(5) no C6 H6 . .91(5) no C7 C8 . 1.188(6) yes C8 C9 . 1.428(6) yes C9 C10 . 1.378(6) ? C9 C13 . 1.395(6) ? C10 C11 . 1.385(7) ? C10 H10 . .83(5) no C11 H11 . .80(5) no C12 C13 . 1.362(7) ? C12 H12 . .94(5) no C13 H13 . .92(4) no C14 C15 . 1.188(6) yes C15 C16 . 1.435(6) yes C16 C20 . 1.379(6) ? C16 C17 . 1.385(7) ? C17 C18 . 1.370(7) ? C17 H17 . .93(6) no C18 H18 . .84(6) no C19 C20 . 1.374(7) ? C19 H19 . .95(6) no C20 H20 . .88(5) no