#------------------------------------------------------------------------------ #$Date: 2010-01-30 14:59:17 +0100 (Sat, 30 Jan 2010) $ #$Revision: 966 $ #$URL: svn://www.crystallography.net/cod/cif/2/2011559.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_2011559 _journal_name_full 'Acta Crystallographica, Section C' _journal_year 2000 _journal_volume 56 _journal_page_first e536 _journal_page_last e536 _publ_section_title ; 4,6-Dichloro-2-methylthiopyrimidine ; loop_ _publ_author_name 'Lynch, Daniel E.' 'McClenaghan, Ian' _chemical_formula_sum 'C5 H4 Cl2 N2 S' _chemical_formula_weight 195.07 _chemical_melting_point '305 - 311 K' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 13.6482(2) _cell_length_b 14.1294(2) _cell_length_c 14.1343(2) _cell_angle_alpha 119.9578(7) _cell_angle_beta 95.9391(6) _cell_angle_gamma 92.8349(7) _cell_volume 2332.60(6) _cell_formula_units_Z 12 _cell_measurement_temperature 150(2) _exptl_crystal_density_diffrn 1.666 _diffrn_ambient_temperature 150(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 N1A .38534(10) .20309(12) .45142(12) .0238(3) Uani d . 1 . . N C2A .39314(12) .23552(15) .37786(15) .0232(4) Uani d . 1 . . C S21A .39650(4) .37482(4) .41972(4) .02945(12) Uani d . 1 . . S C22A .38244(14) .43636(16) .56270(16) .0337(5) Uani d . 1 . . C H21A .3199 .4044 .5692 .042 Uiso calc R 1 . . H H22A .3818 .5159 .5948 .042 Uiso calc R 1 . . H H23A .4379 .4224 .6022 .042 Uiso calc R 1 . . H N3A .39832(11) .17091(13) .26982(13) .0263(4) Uani d . 1 . . N C4A .39408(13) .06466(16) .23484(15) .0256(4) Uani d . 1 . . C Cl4A .39692(4) -.02227(4) .09511(4) .03840(13) Uani d . 1 . . Cl C5A .38798(13) .01918(16) .30139(15) .0261(4) Uani d . 1 . . C H5A .3869 -.0574 .2745 .033 Uiso calc R 1 . . H C6A .38369(12) .09512(16) .40987(15) .0241(4) Uani d . 1 . . C Cl6A .37358(4) .04948(4) .50201(4) .03126(12) Uani d . 1 . . Cl N1B .37395(10) -.64194(13) -.05875(12) .0240(3) Uani d . 1 . . N C2B .36984(12) -.56773(16) .04714(15) .0247(4) Uani d . 1 . . C S21B .36834(4) -.60995(5) .14405(4) .03389(13) Uani d . 1 . . S C22B .37360(15) -.75550(17) .06153(17) .0358(5) Uani d . 1 . . C H21B .3144 -.7894 .0054 .045 Uiso calc R 1 . . H H22B .3762 -.7878 .1089 .045 Uiso calc R 1 . . H H23B .4330 -.7686 .0253 .045 Uiso calc R 1 . . H N3B .36811(11) -.45863(13) .09106(12) .0265(4) Uani d . 1 . . N C4B .37426(13) -.42366(16) .02107(15) .0252(4) Uani d . 1 . . C Cl4B .37424(4) -.28314(4) .07432(4) .03737(13) Uani d . 1 . . Cl C5B .38106(12) -.48975(16) -.08984(15) .0259(4) Uani d . 1 . . C H5B .3862 -.4618 -.1381 .032 Uiso calc R 1 . . H C6B .37965(12) -.59970(16) -.12390(14) .0240(4) Uani d . 1 . . C Cl6B .38529(4) -.69211(4) -.26081(4) .03322(12) Uani d . 1 . . Cl N1C .36536(10) -.13544(13) .60558(12) .0244(3) Uani d . 1 . . N C2C .36130(12) -.24285(16) .57346(15) .0244(4) Uani d . 1 . . C S21C .35783(4) -.34074(4) .43411(4) .03170(13) Uani d . 1 . . S C22C .36817(15) -.25618(18) .37330(16) .0357(5) Uani d . 1 . . C H21C .3135 -.2105 .3891 .045 Uiso calc R 1 . . H H22C .3651 -.3031 .2932 .045 Uiso calc R 1 . . H H23C .4316 -.2088 .4043 .045 Uiso calc R 1 . . H N3C .35872(10) -.28674(13) .63869(13) .0258(3) Uani d . 1 . . N C4C .35788(12) -.21496(16) .74394(15) .0248(4) Uani d . 1 . . C Cl4C .35552(4) -.26781(4) .83095(4) .03655(13) Uani d . 1 . . Cl C5C .35842(13) -.10257(16) .78816(15) .0267(4) Uani d . 1 . . C H5C .3560 -.0530 .8641 .033 Uiso calc R 1 . . H C6C .36282(13) -.06935(15) .71234(15) .0245(4) Uani d . 1 . . C Cl6C .36721(4) .06942(4) .75702(4) .03605(13) Uani d . 1 . . Cl N1D -.13026(10) .57481(13) .10062(12) .0238(3) Uani d . 1 . . N C2D -.12170(12) .60705(16) .02722(15) .0245(4) Uani d . 1 . . C S21D -.11406(4) .74656(4) .06969(4) .03232(13) Uani d . 1 . . S C22D -.12531(15) .80767(17) .21327(17) .0377(5) Uani d . 1 . . C H21D -.1892 .7793 .2209 .047 Uiso calc R 1 . . H H22D -.1216 .8877 .2469 .047 Uiso calc R 1 . . H H23D -.0713 .7894 .2505 .047 Uiso calc R 1 . . H N3D -.11544(11) .54151(14) -.08108(13) .0265(4) Uani d . 1 . . N C4D -.11707(12) .43629(16) -.11474(14) .0249(4) Uani d . 1 . . C Cl4D -.10867(4) .34975(4) -.25278(4) .03609(13) Uani d . 1 . . Cl C5D -.12364(12) .39137(16) -.04771(15) .0250(4) Uani d . 1 . . C H5D -.1238 .3150 -.0740 .031 Uiso calc R 1 . . H C6D -.12989(12) .46759(16) .06058(15) .0240(4) Uani d . 1 . . C Cl6D -.13668(4) .42284(4) .15354(4) .03442(13) Uani d . 1 . . Cl N1E -.13631(10) -.26910(13) -.40530(12) .0245(3) Uani d . 1 . . N C2E -.14368(12) -.19540(16) -.30031(14) .0230(4) Uani d . 1 . . C S21E -.14966(4) -.23771(4) -.20408(4) .03033(12) Uani d . 1 . . S C22E -.13719(15) -.38207(17) -.28445(17) .0351(5) Uani d . 1 . . C H21E -.1920 -.4185 -.3459 .044 Uiso calc R 1 . . H H22E -.1387 -.4148 -.2376 .044 Uiso calc R 1 . . H H23E -.0740 -.3915 -.3136 .044 Uiso calc R 1 . . H N3E -.14731(11) -.08639(13) -.25718(12) .0261(4) Uani d . 1 . . N C4E -.14168(13) -.05132(16) -.32751(16) .0262(4) Uani d . 1 . . C Cl4E -.14325(4) .08865(4) -.27476(4) .03697(13) Uani d . 1 . . Cl C5E -.13493(13) -.11798(16) -.43852(15) .0266(4) Uani d . 1 . . C H5E -.1320 -.0907 -.4876 .033 Uiso calc R 1 . . H C6E -.13288(13) -.22724(16) -.47106(14) .0237(4) Uani d . 1 . . C Cl6E -.12455(4) -.31956(4) -.60781(4) .03154(12) Uani d . 1 . . Cl N1F -.11133(10) 1.24180(13) .26273(12) .0245(3) Uani d . 1 . . N C2F -.10841(13) 1.13584(16) .23193(15) .0248(4) Uani d . 1 . . C S21F -.10814(4) 1.03782(4) .09317(4) .03462(13) Uani d . 1 . . S C22F -.11303(15) 1.12010(18) .02900(16) .0365(5) Uani d . 1 . . C H21F -.1713 1.1603 .0461 .046 Uiso calc R 1 . . H H22F -.1177 1.0723 -.0512 .046 Uiso calc R 1 . . H H23F -.0528 1.1725 .0571 .046 Uiso calc R 1 . . H N3F -.10731(11) 1.09240(13) .29836(13) .0267(4) Uani d . 1 . . N C4F -.11196(13) 1.16331(16) .40246(16) .0258(4) Uani d . 1 . . C Cl4F -.11438(4) 1.11032(5) .48962(4) .03747(13) Uani d . 1 . . Cl C5F -.11586(13) 1.27476(16) .44580(15) .0254(4) Uani d . 1 . . C H5F -.1186 1.3241 .5217 .032 Uiso calc R 1 . . H C6F -.11542(12) 1.30811(15) .36917(15) .0239(4) Uani d . 1 . . C Cl6F -.12257(4) 1.44450(4) .41160(4) .03168(12) Uani d . 1 . . Cl 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 N1A .0251(8) .0201(9) .0270(8) .0024(6) .0041(6) .0126(7) C2A .0194(9) .0224(10) .0297(10) .0035(7) .0037(7) .0146(9) S21A .0365(3) .0213(3) .0351(3) .0040(2) .0074(2) .0172(2) C22A .0405(11) .0214(11) .0359(12) .0054(8) .0108(9) .0111(9) N3A .0273(8) .0264(10) .0270(9) .0024(7) .0036(6) .0150(8) C4A .0253(9) .0276(11) .0210(9) .0030(8) .0023(7) .0104(9) Cl4A .0549(3) .0325(3) .0210(3) .0026(2) .0046(2) .0090(2) C5A .0313(10) .0184(10) .0284(10) .0036(8) .0052(8) .0115(9) C6A .0234(9) .0252(11) .0272(10) .0025(7) .0035(7) .0159(9) Cl6A .0453(3) .0261(3) .0281(3) .0051(2) .0070(2) .0177(2) N1B .0259(8) .0231(9) .0247(8) .0038(6) .0050(6) .0131(7) C2B .0226(9) .0298(11) .0232(10) .0038(7) .0042(7) .0145(9) S21B .0459(3) .0367(3) .0258(3) .0084(2) .0088(2) .0199(2) C22B .0464(12) .0361(13) .0365(12) .0099(10) .0077(9) .0261(11) N3B .0287(8) .0256(9) .0239(8) .0028(7) .0034(6) .0118(7) C4B .0241(9) .0211(10) .0285(10) .0021(7) .0036(7) .0113(9) Cl4B .0513(3) .0205(3) .0366(3) .0035(2) .0083(2) .0115(2) C5B .0286(10) .0249(11) .0298(10) .0026(8) .0056(8) .0179(9) C6B .0243(9) .0255(11) .0208(9) .0034(7) .0030(7) .0107(8) Cl6B .0492(3) .0269(3) .0228(2) .0067(2) .0106(2) .0110(2) N1C .0257(8) .0230(9) .0249(8) .0045(6) .0047(6) .0122(7) C2C .0197(9) .0259(11) .0266(10) .0038(7) .0040(7) .0123(9) S21C .0383(3) .0243(3) .0245(3) .0034(2) .0042(2) .0066(2) C22C .0402(11) .0372(13) .0232(10) .0008(9) .0051(8) .0108(10) N3C .0236(8) .0247(9) .0292(9) .0026(6) .0036(6) .0140(8) C4C .0231(9) .0282(11) .0301(11) .0033(8) .0037(7) .0199(9) Cl4C .0475(3) .0368(3) .0366(3) .0055(2) .0067(2) .0268(3) C5C .0295(10) .0279(11) .0237(10) .0066(8) .0076(7) .0128(9) C6C .0275(9) .0203(10) .0265(10) .0068(7) .0056(7) .0118(9) Cl6C .0580(3) .0212(3) .0310(3) .0112(2) .0109(2) .0135(2) N1D .0251(8) .0225(9) .0248(8) .0027(6) .0046(6) .0125(7) C2D .0203(9) .0254(11) .0303(10) .0025(7) .0037(7) .0161(9) S21D .0389(3) .0245(3) .0385(3) .0032(2) .0065(2) .0195(2) C22D .0438(12) .0229(11) .0413(13) .0042(9) .0093(9) .0119(10) N3D .0251(8) .0301(10) .0280(9) .0029(7) .0034(6) .0175(8) C4D .0228(9) .0291(11) .0217(10) .0038(8) .0037(7) .0120(9) Cl4D .0454(3) .0366(3) .0208(2) .0052(2) .0049(2) .0105(2) C5D .0268(9) .0215(10) .0263(10) .0039(7) .0043(7) .0116(9) C6D .0241(9) .0263(11) .0254(10) .0023(7) .0029(7) .0160(9) Cl6D .0536(3) .0286(3) .0275(3) .0057(2) .0082(2) .0185(2) N1E .0243(8) .0267(9) .0249(8) .0026(6) .0043(6) .0147(7) C2E .0218(9) .0281(11) .0219(9) .0021(7) .0023(7) .0150(9) S21E .0379(3) .0350(3) .0241(3) .0066(2) .0078(2) .0187(2) C22E .0452(12) .0349(13) .0373(12) .0103(9) .0108(9) .0259(11) N3E .0260(8) .0268(9) .0247(8) .0026(6) .0040(6) .0125(7) C4E .0253(9) .0216(10) .0303(10) .0019(7) .0036(7) .0124(9) Cl4E .0495(3) .0198(3) .0370(3) .0008(2) .0062(2) .0113(2) C5E .0298(10) .0275(11) .0270(10) .0030(8) .0047(8) .0171(9) C6E .0244(9) .0268(11) .0218(9) .0046(7) .0049(7) .0133(9) Cl6E .0466(3) .0270(3) .0206(2) .0059(2) .00906(19) .0110(2) N1F .0264(8) .0258(9) .0212(8) .0046(6) .0037(6) .0115(7) C2F .0249(9) .0231(11) .0240(10) .0026(7) .0044(7) .0100(9) S21F .0483(3) .0251(3) .0237(3) .0072(2) .0071(2) .0068(2) C22F .0489(12) .0372(13) .0218(10) .0085(10) .0055(9) .0133(10) N3F .0306(8) .0233(9) .0262(9) .0043(7) .0057(6) .0122(8) C4F .0222(9) .0298(11) .0301(10) .0030(8) .0039(7) .0186(9) Cl4F .0512(3) .0373(3) .0361(3) .0072(2) .0118(2) .0265(3) C5F .0281(10) .0291(11) .0187(9) .0063(8) .0061(7) .0111(9) C6F .0211(9) .0221(10) .0268(10) .0030(7) .0033(7) .0111(9) Cl6F .0445(3) .0219(3) .0284(3) .0073(2) .0063(2) .0122(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 N1A C6A . 1.331(2) ? N1A C2A . 1.340(2) ? C2A N3A . 1.344(2) ? C2A S21A . 1.7460(19) ? S21A C22A . 1.794(2) ? C22A H21A . .9800 ? C22A H22A . .9800 ? C22A H23A . .9800 ? N3A C4A . 1.321(2) ? C4A C5A . 1.385(3) ? C4A Cl4A . 1.7345(18) ? C5A C6A . 1.374(3) ? C5A H5A . .9500 ? C6A Cl6A . 1.7315(18) ? N1B C6B . 1.330(2) ? N1B C2B . 1.341(2) ? C2B N3B . 1.347(2) ? C2B S21B . 1.7472(19) ? S21B C22B . 1.798(2) ? C22B H21B . .9800 ? C22B H22B . .9800 ? C22B H23B . .9800 ? N3B C4B . 1.316(2) ? C4B C5B . 1.384(3) ? C4B Cl4B . 1.7366(19) ? C5B C6B . 1.376(3) ? C5B H5B . .9500 ? C6B Cl6B . 1.7243(18) ? N1C C6C . 1.326(2) ? N1C C2C . 1.346(2) ? C2C N3C . 1.346(2) ? C2C S21C . 1.7459(19) ? S21C C22C . 1.794(2) ? C22C H21C . .9800 ? C22C H22C . .9800 ? C22C H23C . .9800 ? N3C C4C . 1.319(2) ? C4C C5C . 1.385(3) ? C4C Cl4C . 1.7304(18) ? C5C C6C . 1.373(3) ? C5C H5C . .9500 ? C6C Cl6C . 1.7294(19) ? N1D C6D . 1.327(2) ? N1D C2D . 1.338(2) ? C2D N3D . 1.352(2) ? C2D S21D . 1.744(2) ? S21D C22D . 1.793(2) ? C22D H21D . .9800 ? C22D H22D . .9800 ? C22D H23D . .9800 ? N3D C4D . 1.313(3) ? C4D C5D . 1.386(3) ? C4D Cl4D . 1.7298(18) ? C5D C6D . 1.378(3) ? C5D H5D . .9500 ? C6D Cl6D . 1.7274(18) ? N1E C6E . 1.331(2) ? N1E C2E . 1.340(2) ? C2E N3E . 1.350(2) ? C2E S21E . 1.7447(18) ? S21E C22E . 1.800(2) ? C22E H21E . .9800 ? C22E H22E . .9800 ? C22E H23E . .9800 ? N3E C4E . 1.320(2) ? C4E C5E . 1.386(3) ? C4E Cl4E . 1.733(2) ? C5E C6E . 1.376(3) ? C5E H5E . .9500 ? C6E Cl6E . 1.7299(18) ? N1F C6F . 1.326(2) ? N1F C2F . 1.338(2) ? C2F N3F . 1.354(2) ? C2F S21F . 1.7475(18) ? S21F C22F . 1.796(2) ? C22F H21F . .9800 ? C22F H22F . .9800 ? C22F H23F . .9800 ? N3F C4F . 1.314(2) ? C4F C5F . 1.382(3) ? C4F Cl4F . 1.7340(19) ? C5F C6F . 1.381(3) ? C5F H5F . .9500 ? C6F Cl6F . 1.7203(19) ? _cod_database_code 2011559