data_2012018 _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 H10 N4 S' _chemical_formula_sum 'C20 H10 N4 S' _chemical_formula_weight 338.38 _chemical_melting_point 524 _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/a' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x-1/2, -y-1/2, z' _cell_length_a 12.487(2) _cell_length_b 7.5477(13) _cell_length_c 17.513(3) _cell_angle_alpha 90.00 _cell_angle_beta 105.22(2) _cell_angle_gamma 90.00 _cell_volume 1592.8(5) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _exptl_crystal_density_diffrn 1.411 _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 S1 .73678(9) .07406(18) .78638(6) .0666(4) Uani d . 1 . . S N1 .6460(3) .1108(5) .83501(18) .0544(8) Uani d . 1 . . N N2 .6621(3) -.0274(5) .70975(18) .0548(8) Uani d . 1 . . N N3 .3540(3) .3989(5) 1.14848(17) .0537(8) Uani d . 1 . . N N4 .5864(3) -.4239(5) .33033(18) .0606(10) Uani d . 1 . . N C1 .4457(3) .0464(5) .81057(18) .0433(8) Uani d . 1 . . C C2 .5499(3) .0443(5) .79170(18) .0430(8) Uani d . 1 . . C C3 .5594(3) -.0351(5) .71896(19) .0437(8) Uani d . 1 . . C C4 .4642(3) -.1088(5) .66424(19) .0465(9) Uani d . 1 . . C C5 .3667(3) -.1089(6) .6856(2) .0527(10) Uani d . 1 . . C H5 .3044 -.1609 .6519 .063 Uiso calc R 1 . . H C6 .3570(3) -.0321(5) .7579(2) .0486(9) Uani d . 1 . . C H6 .2886 -.0351 .7697 .058 Uiso calc R 1 . . H C7 .4348(3) .1264(5) .8830(2) .0471(9) Uani d . 1 . . C C8 .4198(3) .1887(5) .94134(19) .0499(9) Uani d . 1 . . C C9 .3987(3) .2616(5) 1.01131(18) .0440(8) Uani d . 1 . . C C10 .4800(3) .3453(5) 1.0694(2) .0505(9) Uani d . 1 . . C H10 .5515 .3575 1.0636 .061 Uiso calc R 1 . . H C11 .4541(3) .4102(6) 1.1357(2) .0549(10) Uani d . 1 . . C H11 .5101 .4652 1.1740 .066 Uiso calc R 1 . . H C12 .2776(4) .3207(6) 1.0921(2) .0570(11) Uani d . 1 . . C H12 .2069 .3114 1.0997 .068 Uiso calc R 1 . . H C13 .2930(3) .2518(6) 1.0233(2) .0546(10) Uani d . 1 . . C H13 .2346 .2001 .9857 .065 Uiso calc R 1 . . H C14 .4766(3) -.1775(5) .5900(2) .0505(9) Uani d . 1 . . C C15 .4958(4) -.2288(6) .5320(2) .0568(10) Uani d . 1 . . C C16 .5251(4) -.2938(5) .4627(2) .0512(10) Uani d . 1 . . C C17 .6354(4) -.3077(7) .4619(2) .0691(13) Uani d . 1 . . C H17 .6912 -.2716 .5056 .083 Uiso calc R 1 . . H C18 .6621(4) -.3758(7) .3957(3) .0696(13) Uani d . 1 . . C H18 .7366 -.3884 .3970 .084 Uiso calc R 1 . . H C19 .4815(4) -.4092(6) .3322(2) .0585(11) Uani d . 1 . . C H19 .4271 -.4429 .2872 .070 Uiso calc R 1 . . H C20 .4473(4) -.3482(6) .3954(2) .0553(10) Uani d . 1 . . C H20 .3720 -.3434 .3930 .066 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 S1 .0588(6) .0885(9) .0556(6) -.0093(6) .0202(5) -.0071(6) N1 .060(2) .062(2) .0436(16) -.0068(17) .0174(15) -.0061(16) N2 .059(2) .065(2) .0465(17) .0000(17) .0244(15) -.0019(16) N3 .065(2) .062(2) .0410(16) -.0010(17) .0268(15) -.0132(15) N4 .088(3) .063(2) .0387(16) -.008(2) .0314(17) -.0103(16) C1 .059(2) .045(2) .0295(15) .0048(18) .0184(15) .0021(15) C2 .057(2) .045(2) .0288(15) .0010(17) .0154(15) -.0001(14) C3 .058(2) .045(2) .0334(16) .0006(17) .0196(15) .0009(15) C4 .064(2) .048(2) .0318(16) .0004(18) .0209(16) -.0027(15) C5 .064(2) .059(2) .0358(18) -.008(2) .0136(17) -.0076(17) C6 .054(2) .058(2) .0376(18) .0000(19) .0192(16) -.0013(17) C7 .059(2) .051(2) .0364(17) .0083(18) .0213(16) .0000(16) C8 .065(2) .056(2) .0314(16) .009(2) .0177(16) .0023(16) C9 .058(2) .048(2) .0283(15) .0090(18) .0161(15) -.0022(15) C10 .046(2) .067(3) .0414(18) .0070(19) .0171(16) -.0042(18) C11 .058(2) .074(3) .0323(16) -.003(2) .0111(16) -.0126(18) C12 .059(2) .069(3) .050(2) -.004(2) .0256(19) -.012(2) C13 .062(2) .062(3) .0407(19) -.005(2) .0153(17) -.0148(18) C14 .071(3) .048(2) .0402(18) -.0020(19) .0272(18) -.0034(16) C15 .082(3) .052(2) .0410(19) -.003(2) .0252(19) .0011(18) C16 .083(3) .043(2) .0341(17) .000(2) .0273(18) -.0008(16) C17 .082(3) .089(4) .040(2) -.024(3) .021(2) -.017(2) C18 .078(3) .085(4) .058(3) -.016(3) .040(2) -.013(2) C19 .087(3) .057(3) .0312(17) .010(2) .0151(19) -.0051(17) C20 .065(2) .065(3) .0363(18) .014(2) .0147(17) -.0041(18) 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 S1 N1 . 1.611(3) yes S1 N2 . 1.613(4) yes N1 C2 . 1.338(5) yes N2 C3 . 1.334(5) yes N3 C12 . 1.318(5) ? N3 C11 . 1.329(5) ? N4 C19 . 1.324(5) ? N4 C18 . 1.329(5) ? C1 C6 . 1.376(5) yes C1 C2 . 1.424(5) yes C1 C7 . 1.444(4) yes C2 C3 . 1.441(4) yes C3 C4 . 1.430(5) yes C4 C5 . 1.365(5) yes C4 C14 . 1.445(4) yes C5 C6 . 1.426(5) yes C5 H5 . .9300 no C6 H6 . .9300 no C7 C8 . 1.183(4) yes C8 C9 . 1.429(4) yes C9 C10 . 1.386(5) ? C9 C13 . 1.391(5) ? C10 C11 . 1.375(5) ? C10 H10 . .9300 no C11 H11 . .9300 no C12 C13 . 1.372(5) ? C12 H12 . .9300 no C13 H13 . .9300 no C14 C15 . 1.170(5) yes C15 C16 . 1.442(5) yes C16 C20 . 1.378(5) ? C16 C17 . 1.385(6) ? C17 C18 . 1.387(5) ? C17 H17 . .9300 no C18 H18 . .9300 no C19 C20 . 1.367(5) ? C19 H19 . .9300 no C20 H20 . .9300 no