data_2012095 _journal_name_full 'Acta Crystallographica, Section C' _journal_year 2001 _journal_volume 57 _journal_page_first 859 _journal_page_last 860 _publ_section_title ; 5-(2-Pyridyl)-1,3-dithiane-2-thione ; loop_ _publ_author_name 'Alan Hazell, Alan' 'McKenzie, Christine J.' 'Nielsen, Jimmi' _chemical_formula_moiety 'C9 H9 N1 S3' _chemical_formula_sum 'C9 H9 N1 S3' _chemical_formula_iupac 'C9 H9 N1 S3' _chemical_formula_weight 227.380 _chemical_melting_point .393E-305 _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' 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 17.444(2) _cell_length_b 9.6329(9) _cell_length_c 12.6800(10) _cell_angle_alpha 90.0 _cell_angle_beta 110.245(2) _cell_angle_gamma 90.0 _cell_volume 1999.1(3) _cell_formula_units_Z 8 _cell_measurement_temperature 120 _exptl_crystal_density_diffrn 1.511 _diffrn_ambient_temperature 120 loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type S1 .81410(2) -.25035(3) .39418(3) .0266(2) Uij S2 .73950(2) -.36895(3) .54275(3) .0243(2) Uij S3 .67796(2) -.09741(3) .41607(3) .0215(2) Uij N1 .50040(7) -.25240(11) .60051(9) .0240(6) Uij C1 .74142(8) -.23950(12) .45032(10) .0201(6) Uij C2 .65608(8) -.33603(13) .59400(11) .0231(7) Uij C3 .63387(7) -.18392(13) .59996(10) .0192(6) Uij C4 .60245(8) -.11704(12) .48356(11) .0213(7) Uij C5 .56700(7) -.17484(12) .65053(10) .0194(6) Uij C6 .57467(8) -.08970(13) .74182(11) .0238(7) Uij C7 .51165(9) -.08622(14) .78511(12) .0279(8) Uij C8 .44298(8) -.16706(14) .73474(12) .0274(8) Uij C9 .44015(8) -.24654(14) .64331(12) .0271(7) Uij S1A .70389(2) .26815(4) .12007(3) .0247(2) Uij S2A .77025(2) .35898(3) .35036(3) .0210(2) Uij S3A .83719(2) .10558(3) .26554(3) .0232(2) Uij N1A .99364(6) .19444(11) .64777(8) .0206(6) Uij C1A .77255(7) .24448(12) .24767(10) .0186(6) Uij C2A .85181(7) .31130(12) .47850(9) .0189(6) Uij C3A .86637(7) .15540(12) .49398(9) .0168(6) Uij C4A .90488(8) .10043(12) .41110(10) .0199(6) Uij C5A .92188(7) .12700(12) .61309(10) .0167(6) Uij C6A .89795(8) .03788(12) .68229(10) .0202(6) Uij C7A .94923(8) .02037(13) .79311(10) .0234(7) Uij C8A 1.02229(8) .09199(13) .83027(10) .0237(7) Uij C9A 1.04193(8) .17599(13) .75501(10) .0227(7) Uij H2a .67077 -.37386 .66753 .0277 Uiso H2b .60901 -.38245 .54555 .0277 Uiso H3 .68061 -.13476 .64627 .0230 Uiso H4a .55927 -.17292 .43645 .0256 Uiso H4b .58202 -.02749 .49087 .0256 Uiso H6 .62224 -.03467 .77420 .0285 Uiso H7 .51555 -.02950 .84805 .0335 Uiso H8 .39897 -.16760 .76262 .0329 Uiso H9 .39255 -.30061 .60834 .0325 Uiso H2Aa .83865 .34562 .54038 .0226 Uiso H2Ab .90084 .35363 .47785 .0226 Uiso H3A .81557 .11001 .48094 .0201 Uiso H4Aa .95176 .15493 .41801 .0239 Uiso H4Ab .92088 .00683 .43015 .0239 Uiso H6A .84738 -.01026 .65429 .0242 Uiso H7A .93431 -.03963 .84225 .0280 Uiso H8A 1.05824 .08369 .90587 .0284 Uiso H9A 1.09276 .22357 .78082 .0272 Uiso 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 .0256(2) .0283(2) .0310(2) .00360(10) .01640(10) .00380(10) S2 .0246(2) .0248(2) .0263(2) .00910(10) .01240(10) .00950(10) S3 .0225(2) .01940(10) .0249(2) .00310(10) .01130(10) .00570(10) N1 .0175(5) .0289(6) .0235(5) -.0032(4) .0044(4) .0031(4) C1 .0198(6) .0206(6) .0188(6) -.0009(5) .0052(5) -.0001(4) C2 .0226(6) .0242(6) .0245(6) .0025(5) .0108(5) .0051(5) C3 .0152(6) .0220(6) .0194(6) -.0011(5) .0047(5) .0004(4) C4 .0187(6) .0225(6) .0227(6) .0005(5) .0071(5) .0023(5) C5 .0155(6) .0214(6) .0201(6) .0009(4) .0046(5) .0042(5) C6 .0208(6) .0243(6) .0264(6) -.0020(5) .0085(5) -.0002(5) C7 .0307(7) .0288(7) .0281(7) .0049(6) .0151(6) .0023(5) C8 .0210(6) .0316(7) .0332(7) .0059(5) .0141(6) .0131(6) C9 .0161(6) .0331(7) .0293(7) -.0025(5) .0044(5) .0096(5) S1A .0187(2) .0367(2) .01640(10) .00140(10) .00310(10) .00230(10) S2A .0180(2) .0242(2) .01910(10) .00710(10) .00420(10) -.00130(10) S3A .0311(2) .0220(2) .01480(10) .00700(10) .00580(10) -.00190(10) N1A .0178(5) .0225(5) .0200(5) -.0011(4) .0046(4) -.0006(4) C1A .0168(6) .0220(6) .0179(5) -.0025(4) .0073(5) .0006(4) C2A .0198(6) .0200(5) .0158(5) .0022(5) .0048(5) -.0018(4) C3A .0152(5) .0187(5) .0163(5) -.0008(4) .0054(4) -.0005(4) C4A .0210(6) .0205(6) .0173(5) .0031(5) .0053(5) -.0015(4) C5A .0174(6) .0166(5) .0166(5) .0017(4) .0063(5) -.0016(4) C6A .0201(6) .0187(5) .0226(6) .0006(5) .0085(5) .0012(5) C7A .0288(7) .0210(6) .0220(6) .0058(5) .0108(5) .0045(5) C8A .0263(7) .0225(6) .0186(6) .0064(5) .0031(5) .0002(5) C9A .0192(6) .0220(6) .0230(6) .0008(5) .0023(5) -.0017(5) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag S1 C1 1.6580(10) yes S2 C1 1.7190(10) yes S2 C2 1.8150(10) yes S3 C1 1.7190(10) yes S3 C4 1.8120(10) yes N1 C9 1.340(2) no N1 C5 1.342(2) no C2 C3 1.524(2) no C3 C5 1.516(2) no C3 C4 1.528(2) no C5 C6 1.387(2) no C6 C7 1.389(2) no C7 C8 1.386(2) no C8 C9 1.376(2) no S1A C1A 1.6620(10) yes S2A C1A 1.7170(10) yes S2A C2A 1.8100(10) yes S3A C1A 1.7140(10) yes S3A C4A 1.8150(10) yes N1A C9A 1.341(2) no N1A C5A 1.342(2) no C2A C3A 1.524(2) no C3A C5A 1.510(2) no C3A C4A 1.525(2) no C5A C6A 1.391(2) no C6A C7A 1.390(2) no C7A C8A 1.381(2) no C8A C9A 1.382(2) no C2 H2a .950 no C2 H2b .950 no C3 H3 .950 no C4 H4a .950 no C4 H4b .950 no C6 H6 .950 no C7 H7 .950 no C8 H8 .950 no C9 H9 .950 no C2A H2Aa .950 no C2A H2Ab .950 no C3A H3A .950 no C4A H4Aa .950 no C4A H4Ab .950 no C6A H6A .950 no C7A H7A .950 no C8A H8A .950 no C9A H9A .950 no