#------------------------------------------------------------------------------ #$Date: 2011-09-28 15:24:46 +0100 (Wed, 28 Sep 2011) $ #$Revision: 26848 $ #$URL: svn://www.crystallography.net/cod/cif/2/01/19/2011928.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_2011928 _journal_name_full 'Acta Crystallographica, Section C' _journal_year 2001 _journal_volume 57 _journal_page_first 593 _journal_page_last 596 _publ_section_title ; Novel heterocyclic inhibitors of matrix metalloproteinases: three 6H-1,3,4-thiadiazines ; _space_group_IT_number 4 _symmetry_space_group_name_Hall 'P 2yb' _symmetry_space_group_name_H-M 'P 1 21 1' _[local]_cod_cif_authors_sg_H-M 'P 21' loop_ _publ_author_name 'Schr\"oder, J\"org' 'Wenzel, Herbert' 'Stammler, Hans-Georg' 'Stammler, Anja' 'Neumann, Beate' 'Tschesche, Harald' _chemical_formula_moiety 'C16 H15 Cl N4 O3 S3' _chemical_formula_sum 'C16 H15 Cl N4 O3 S3' _chemical_formula_weight 442.95 _symmetry_cell_setting 'monoclinic' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 10.613(4) _cell_length_b 11.193(4) _cell_length_c 16.399(5) _cell_angle_alpha 90 _cell_angle_beta 102.48(3) _cell_angle_gamma 90 _cell_volume 1902.0(11) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _exptl_crystal_density_diffrn 1.547 _diffrn_ambient_temperature 173(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 .40775(15) .81849(19) .58846(10) .0259(4) Uani d . 1 . . S S2 .16364(15) .81560(19) .26446(10) .0235(4) Uani d . 1 . . S S3 .28040(18) .57269(18) -.00242(12) .0290(5) Uani d . 1 . . S Cl1 .3719(2) .8724(3) .75937(14) .0604(8) Uani d . 1 . . Cl O1 .1612(4) .8569(5) .1016(3) .0304(14) Uani d . 1 . . O O2 .3633(5) .4811(5) -.0219(4) .0458(17) Uani d . 1 . . O O3 .1639(5) .6035(5) -.0615(3) .0395(15) Uani d . 1 . . O N1 .4014(5) .7993(5) .4035(3) .0197(13) Uani d . 1 . . N N2 .4201(5) .7802(5) .3221(3) .0174(13) Uani d . 1 . . N N3 .3557(5) .8041(5) .1809(3) .0192(13) Uani d . 1 . . N H3N .4371 .7925 .1793 .023 Uiso calc R 1 . . H N4 .3711(5) .6881(5) .0177(3) .0229(14) Uani d . 1 . . N H4N .4543 .6759 .0227 .028 Uiso calc R 1 . . H C1 .3059(7) .8449(7) .6556(4) .0274(18) Uani d . 1 . . C C2 .1796(7) .8390(7) .6185(5) .0289(19) Uani d . 1 . . C H2A .1112 .8523 .6464 .035 Uiso calc R 1 . . H C3 .1619(6) .8107(7) .5332(4) .0218(16) Uani d . 1 . . C H3A .0796 .8004 .4972 .026 Uiso calc R 1 . . H C4 .2763(6) .7994(6) .5075(4) .0174(15) Uani d . 1 . . C C5 .2920(6) .7771(6) .4220(4) .0168(16) Uani d . 1 . . C C6 .1815(6) .7287(7) .3590(4) .0227(16) Uani d . 1 . . C H6A .1015 .7333 .3807 .027 Uiso calc R 1 . . H H6B .1975 .6439 .3474 .027 Uiso calc R 1 . . H C7 .3258(6) .7990(6) .2596(4) .0160(15) Uani d . 1 . . C C8 .2727(6) .8251(7) .1059(4) .0210(15) Uani d . 1 . . C C9 .3318(6) .8119(7) .0290(4) .0236(16) Uani d . 1 . . C H9A .4126 .8608 .0401 .028 Uiso calc R 1 . . H C10 .2422(7) .8672(7) -.0479(4) .0341(19) Uani d . 1 . . C H10A .2789 .8546 -.0972 .051 Uiso calc R 1 . . H H10B .2335 .9531 -.0389 .051 Uiso calc R 1 . . H H10C .1571 .8292 -.0567 .051 Uiso calc R 1 . . H C11 .2328(7) .5306(7) .0920(5) .0242(17) Uani d . 1 . . C C12 .3282(7) .5117(8) .1620(5) .038(2) Uani d . 1 . . C H12A .4165 .5235 .1611 .045 Uiso calc R 1 . . H C13 .2908(9) .4745(8) .2350(5) .046(2) Uani d . 1 . . C H13A .3545 .4614 .2846 .055 Uiso calc R 1 . . H C14 .1626(8) .4568(8) .2353(5) .037(2) Uani d . 1 . . C H14A .1382 .4306 .2848 .044 Uiso calc R 1 . . H C15 .0705(7) .4767(7) .1644(5) .035(2) Uani d . 1 . . C H15A -.0179 .4659 .1656 .042 Uiso calc R 1 . . H C16 .1036(7) .5128(7) .0904(5) .0288(19) Uani d . 1 . . C H16A .0397 .5246 .0407 .035 Uiso calc R 1 . . H S4 .62260(17) .65968(19) -.08416(12) .0313(5) Uani d . 1 . . S S5 .87898(15) .69831(18) .23384(11) .0262(4) Uani d . 1 . . S S6 .74209(17) .95360(17) .49967(11) .0226(4) Uani d . 1 . . S Cl2 .6468(2) .6173(2) -.25930(12) .0426(6) Uani d . 1 . . Cl O4 .8880(4) .6490(5) .3946(3) .0303(13) Uani d . 1 . . O O5 .8576(5) .9368(5) .5643(3) .0351(14) Uani d . 1 . . O O6 .6437(5) 1.0353(5) .5131(4) .0344(14) Uani d . 1 . . O N5 .6363(5) .7027(6) .0977(3) .0211(14) Uani d . 1 . . N N6 .6218(5) .7269(5) .1804(3) .0209(14) Uani d . 1 . . N N7 .6929(5) .7152(5) .3229(3) .0200(13) Uani d . 1 . . N H7N .6139 .7322 .3279 .024 Uiso calc R 1 . . H N8 .6715(5) .8263(5) .4790(3) .0204(12) Uani d . 1 . . N H8N .5867 .8233 .4685 .025 Uiso calc R 1 . . H C17 .7171(7) .6540(7) -.1580(5) .0284(19) Uani d . 1 . . C C18 .8396(7) .6827(7) -.1274(5) .031(2) Uani d . 1 . . C H18A .9042 .6840 -.1595 .037 Uiso calc R 1 . . H C19 .8625(6) .7114(7) -.0409(5) .0274(18) Uani d . 1 . . C H19A .9450 .7334 -.0090 .033 Uiso calc R 1 . . H C20 .7558(6) .7044(7) -.0085(4) .0221(16) Uani d . 1 . . C C21 .7438(6) .7284(7) .0769(4) .0206(17) Uani d . 1 . . C C22 .8535(6) .7838(8) .1375(4) .031(2) Uani d . 1 . . C H22A .8331 .8679 .1482 .037 Uiso calc R 1 . . H H22B .9325 .7825 .1145 .037 Uiso calc R 1 . . H C23 .7179(6) .7134(7) .2428(4) .0195(16) Uani d . 1 . . C C24 .7823(6) .6924(7) .3934(5) .0220(17) Uani d . 1 . . C C25 .7438(6) .7162(6) .4773(4) .0188(15) Uani d . 1 . . C H25A .8252 .7229 .5211 .023 Uiso calc R 1 . . H C26 .6667(7) .6109(6) .5012(4) .0328(19) Uani d . 1 . . C H26A .6527 .6232 .5578 .049 Uiso calc R 1 . . H H26B .7149 .5366 .4995 .049 Uiso calc R 1 . . H H26C .5832 .6057 .4618 .049 Uiso calc R 1 . . H C27 .7938(7) 1.0000(6) .4091(4) .0196(16) Uani d . 1 . . C C28 .9248(7) 1.0217(6) .4133(5) .0272(18) Uani d . 1 . . C H28A .9856 1.0142 .4649 .033 Uiso calc R 1 . . H C29 .9648(8) 1.0542(7) .3419(5) .037(2) Uani d . 1 . . C H29A 1.0537 1.0684 .3441 .045 Uiso calc R 1 . . H C30 .8765(8) 1.0664(7) .2669(5) .038(2) Uani d . 1 . . C H30A .9047 1.0901 .2182 .046 Uiso calc R 1 . . H C31 .7466(8) 1.0441(8) .2628(5) .037(2) Uani d . 1 . . C H31A .6862 1.0516 .2110 .044 Uiso calc R 1 . . H C32 .7048(7) 1.0108(6) .3342(5) .0274(19) Uani d . 1 . . C H32A .6159 .9956 .3316 .033 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 .0224(9) .0408(12) .0148(9) -.0048(9) .0044(7) -.0030(9) S2 .0132(8) .0401(12) .0167(9) .0008(9) .0023(7) .0040(9) S3 .0295(10) .0368(12) .0221(10) -.0056(9) .0091(8) -.0076(9) Cl1 .0623(14) .101(2) .0210(12) -.0311(15) .0158(10) -.0204(13) O1 .020(3) .048(4) .022(3) .011(3) .001(2) .010(3) O2 .051(4) .042(4) .053(4) -.003(3) .031(3) -.013(3) O3 .033(3) .060(4) .020(3) -.017(3) -.007(2) .002(3) N1 .021(3) .026(4) .012(3) -.001(3) .005(2) .001(3) N2 .015(3) .023(3) .013(3) .000(2) .001(2) -.001(2) N3 .018(3) .031(4) .010(3) .003(3) .006(2) .001(3) N4 .017(3) .034(4) .017(3) -.001(3) .003(2) -.009(3) C1 .046(5) .025(5) .015(4) -.006(4) .014(3) -.001(3) C2 .026(4) .033(5) .033(5) -.003(4) .019(3) -.001(4) C3 .017(3) .024(4) .026(4) -.001(3) .009(3) .000(4) C4 .021(3) .016(4) .014(3) .000(3) .001(3) .004(3) C5 .016(3) .019(4) .015(4) .002(3) .002(3) .004(3) C6 .021(3) .028(4) .018(4) -.010(3) .003(3) .004(3) C7 .019(3) .014(4) .015(4) .001(3) .004(3) -.003(3) C8 .024(4) .022(4) .016(4) -.003(3) .003(3) .005(3) C9 .018(3) .041(5) .011(3) .004(4) .003(3) -.003(4) C10 .044(5) .039(5) .019(4) .010(4) .007(3) .003(3) C11 .030(4) .021(4) .022(4) -.001(3) .007(3) -.008(3) C12 .024(4) .054(6) .034(5) -.002(4) .002(4) -.002(4) C13 .058(6) .051(7) .023(5) .000(5) -.003(4) .003(4) C14 .062(6) .028(5) .026(5) -.011(5) .023(4) .000(4) C15 .033(4) .033(5) .043(5) -.004(4) .019(4) -.010(4) C16 .025(4) .032(5) .032(5) -.002(4) .011(3) -.002(4) S4 .0222(9) .0529(14) .0189(10) -.0040(9) .0044(8) -.0066(9) S5 .0135(8) .0452(13) .0206(10) .0016(9) .0053(7) .0007(9) S6 .0259(10) .0238(10) .0198(10) -.0071(8) .0088(8) -.0071(8) Cl2 .0547(13) .0571(15) .0157(10) -.0008(11) .0069(9) -.0062(10) O4 .025(3) .041(3) .027(3) .012(3) .010(2) .001(3) O5 .040(3) .045(4) .020(3) -.019(3) .005(2) -.002(3) O6 .048(3) .019(3) .047(4) .002(3) .032(3) -.009(3) N5 .013(3) .034(4) .017(3) .002(3) .004(2) -.006(3) N6 .019(3) .034(4) .011(3) .000(3) .007(2) -.006(3) N7 .013(3) .029(4) .019(3) .003(3) .005(2) -.001(3) N8 .013(3) .020(3) .028(3) -.002(3) .006(2) -.007(3) C17 .032(4) .035(5) .021(4) .001(4) .014(3) -.002(4) C18 .034(4) .040(5) .026(4) .001(4) .021(3) .004(4) C19 .023(4) .036(5) .025(4) .002(4) .009(3) .006(4) C20 .018(3) .030(4) .020(4) .002(3) .005(3) .002(4) C21 .015(3) .024(4) .023(4) .005(3) .005(3) -.002(3) C22 .019(4) .057(6) .016(4) -.007(4) .003(3) -.007(4) C23 .009(3) .031(4) .019(4) .001(3) .003(3) .004(3) C24 .018(4) .020(4) .029(4) .003(3) .006(3) .000(3) C25 .020(4) .018(4) .017(3) .002(3) .000(3) -.002(3) C26 .045(5) .023(4) .038(5) -.002(4) .026(4) .006(4) C27 .027(4) .020(4) .011(4) -.002(3) .003(3) -.002(3) C28 .025(4) .021(4) .034(5) .000(3) .005(3) -.007(4) C29 .042(5) .037(5) .041(5) -.004(4) .023(4) .002(4) C30 .060(6) .029(5) .028(5) .000(4) .016(4) -.004(4) C31 .054(5) .027(5) .023(5) -.010(4) -.005(4) .004(4) C32 .033(4) .019(4) .029(5) -.002(3) .004(4) .005(4) 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 C4 . 1.718(7) ? S1 C1 . 1.727(7) ? S2 C7 . 1.750(6) y S2 C6 . 1.805(7) y S3 O2 . 1.431(6) ? S3 O3 . 1.439(5) ? S3 N4 . 1.602(6) ? S3 C11 . 1.792(8) ? Cl1 C1 . 1.722(8) ? O1 C8 . 1.223(7) ? N1 C5 . 1.286(8) y N1 N2 . 1.407(7) y N2 C7 . 1.286(8) y N3 C8 . 1.369(8) ? N3 C7 . 1.395(8) y N4 C9 . 1.470(9) ? C1 C2 . 1.349(10) ? C2 C3 . 1.406(10) ? C3 C4 . 1.375(8) ? C4 C5 . 1.469(9) ? C5 C6 . 1.487(9) ? C8 C9 . 1.533(8) ? C9 C10 . 1.536(9) ? C11 C12 . 1.373(10) ? C11 C16 . 1.380(9) ? C12 C13 . 1.404(11) ? C13 C14 . 1.376(11) ? C14 C15 . 1.366(11) ? C15 C16 . 1.395(10) ? S4 C17 . 1.732(7) ? S4 C20 . 1.741(7) ? S5 C23 . 1.755(6) y S5 C22 . 1.817(7) y S6 O6 . 1.440(5) ? S6 O5 . 1.449(5) ? S6 N8 . 1.611(6) ? S6 C27 . 1.769(7) ? Cl2 C17 . 1.718(8) ? O4 C24 . 1.218(8) ? N5 C21 . 1.292(8) y N5 N6 . 1.423(7) y N6 C23 . 1.288(8) y N7 C24 . 1.351(9) ? N7 C23 . 1.396(8) y N8 C25 . 1.456(8) ? C17 C18 . 1.328(11) ? C18 C19 . 1.423(10) ? C19 C20 . 1.354(9) ? C20 C21 . 1.458(9) ? C21 C22 . 1.492(9) ? C24 C25 . 1.540(9) ? C25 C26 . 1.533(9) ? C27 C32 . 1.384(10) ? C27 C28 . 1.399(9) ? C28 C29 . 1.379(10) ? C29 C30 . 1.382(11) ? C30 C31 . 1.388(11) ? C31 C32 . 1.390(11) ? _cod_database_code 2011928