#------------------------------------------------------------------------------ #$Date: 2008-01-13 22:15:36 +0000 (Sun, 13 Jan 2008) $ #$Revision: 14 $ #$URL: svn://www.crystallography.net/cod/cif/2/2200571.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_2200571 _journal_name_full 'Acta Crystallographica, Section E' _journal_year 2001 _journal_volume 57 _journal_page_first o652 _journal_page_last o654 _publ_section_title ; 7-Chloro-2-methyl-3-methylamino-2H-1,2,4-benzothiadiazine 1,1-dioxide ; loop_ _publ_author_name "Dupont, L\'eon" 'Somers, Fabian' "Boverie, St\'ephane" 'Pirotte, Bernard' 'Tinant, Bernard' 'de Tullio, Pascal' _chemical_formula_moiety 'C9 H10 Cl N3 O2 S' _chemical_formula_sum 'C9 H10 Cl N3 O2 S' _chemical_formula_iupac 'C9 H10 Cl N3 O2 S' _chemical_formula_weight 259.71 _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 10.0960(10) _cell_length_b 26.316(2) _cell_length_c 16.927(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.070(2) _cell_angle_gamma 90.00 _cell_volume 4497.3(8) _cell_formula_units_Z 16 _cell_measurement_temperature 293(2) _exptl_crystal_density_diffrn 1.534 _diffrn_ambient_temperature 293(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 S1A .73080(5) .313750(19) .06113(3) .03802(17) Uani d . 1 . . S O1A .65228(15) .31544(6) -.00935(10) .0526(4) Uani d . 1 . . O O2A .73479(16) .26694(5) .10321(10) .0531(4) Uani d . 1 . . O N2A .88417(16) .33030(6) .04059(11) .0387(4) Uani d . 1 . . N C3A .9039(2) .38088(7) .01607(13) .0347(5) Uani d . 1 . . C N4A .83590(17) .41918(6) .04278(11) .0385(4) Uani d . 1 . . N C5A .7424(2) .41131(7) .10169(13) .0355(5) Uani d . 1 . . C C6A .6964(2) .45310(8) .14525(14) .0431(6) Uani d . 1 . . C H6A .7285 .4854 .1337 .052 Uiso calc R 1 . . H C7A .6051(2) .44725(8) .20447(14) .0458(6) Uani d . 1 . . C H7A .5758 .4755 .2323 .055 Uiso calc R 1 . . H C8A .5559(2) .39952(9) .22323(13) .0431(6) Uani d . 1 . . C C9A .5951(2) .35730(8) .18139(13) .0428(5) Uani d . 1 . . C H9A .5610 .3253 .1928 .051 Uiso calc R 1 . . H C10A .6877(2) .36406(7) .12133(13) .0358(5) Uani d . 1 . . C N11A 1.00236(18) .38852(7) -.03531(12) .0422(5) Uani d . 1 . . N H11A 1.034(2) .3641(9) -.0535(14) .051 Uiso d . 1 . . H C12A 1.0459(2) .43882(9) -.05774(14) .0501(6) Uani d . 1 . . C H121 .9754 .4561 -.0847 .075 Uiso calc R 1 . . H H122 1.1211 .4361 -.0922 .075 Uiso calc R 1 . . H H123 1.0702 .4576 -.0113 .075 Uiso calc R 1 . . H C13A .9800(2) .28951(9) .02487(17) .0631(7) Uani d . 1 . . C H131 .9690 .2776 -.0283 .095 Uiso calc R 1 . . H H132 .9654 .2620 .0610 .095 Uiso calc R 1 . . H H133 1.0684 .3023 .0316 .095 Uiso calc R 1 . . H Cl1A .44215(6) .39293(3) .29959(4) .0644(2) Uani d . 1 . . Cl S1B -.23939(5) .689769(19) .20463(4) .03986(18) Uani d . 1 . . S O1B -.16326(15) .68925(6) .13292(10) .0525(4) Uani d . 1 . . O O2B -.25017(15) .73676(5) .24575(10) .0550(4) Uani d . 1 . . O N2B -.39074(16) .66897(6) .18613(11) .0392(4) Uani d . 1 . . N C3B -.4006(2) .61801(7) .16201(13) .0344(5) Uani d . 1 . . C N4B -.32518(17) .58175(6) .18860(11) .0377(4) Uani d . 1 . . N C5B -.2314(2) .59229(7) .24640(13) .0360(5) Uani d . 1 . . C C6B -.1741(2) .55231(8) .28929(13) .0431(6) Uani d . 1 . . C H6B -.1982 .5191 .2775 .052 Uiso calc R 1 . . H C7B -.0836(2) .56106(9) .34807(14) .0481(6) Uani d . 1 . . C H7B -.0475 .5338 .3756 .058 Uiso calc R 1 . . H C8B -.0454(2) .61018(9) .36680(14) .0469(6) Uani d . 1 . . C C9B -.0943(2) .65075(9) .32491(13) .0445(6) Uani d . 1 . . C H9B -.0672 .6837 .3363 .053 Uiso calc R 1 . . H C10B -.1854(2) .64117(8) .26504(13) .0373(5) Uani d . 1 . . C N11B -.49807(19) .60782(7) .11092(12) .0432(5) Uani d . 1 . . N H11B -.534(2) .6322(9) .0900(15) .052 Uiso d . 1 . . H C12B -.5316(2) .55651(9) .08651(15) .0525(6) Uani d . 1 . . C H124 -.4598 .5424 .0565 .079 Uiso calc R 1 . . H H125 -.6102 .5573 .0545 .079 Uiso calc R 1 . . H H126 -.5471 .5359 .1324 .079 Uiso calc R 1 . . H C13B -.4944(2) .70673(8) .17262(16) .0553(7) Uani d . 1 . . C H134 -.4888 .7190 .1193 .083 Uiso calc R 1 . . H H135 -.4830 .7345 .2087 .083 Uiso calc R 1 . . H H136 -.5796 .6914 .1809 .083 Uiso calc R 1 . . H Cl1B .06561(6) .62083(3) .44353(4) .0696(2) Uani d . 1 . . Cl S1C .47269(5) .683672(19) .43689(3) .03947(18) Uani d . 1 . . S O1C .39406(16) .68284(6) .50731(10) .0529(4) Uani d . 1 . . O O2C .47578(16) .72969(6) .39342(10) .0565(5) Uani d . 1 . . O N2C .62665(17) .66763(6) .45840(11) .0402(4) Uani d . 1 . . N C3C .6481(2) .61749(7) .48337(13) .0361(5) Uani d . 1 . . C N4C .58043(17) .57849(6) .45763(11) .0402(4) Uani d . 1 . . N C5C .4858(2) .58533(8) .39925(13) .0376(5) Uani d . 1 . . C C6C .4384(2) .54298(8) .35812(14) .0457(6) Uani d . 1 . . C H6C .4698 .5108 .3712 .055 Uiso calc R 1 . . H C7C .3459(2) .54785(9) .29853(14) .0508(6) Uani d . 1 . . C H7C .3158 .5191 .2720 .061 Uiso calc R 1 . . H C8C .2977(2) .59518(9) .27803(14) .0469(6) Uani d . 1 . . C C9C .3371(2) .63789(9) .31803(14) .0461(6) Uani d . 1 . . C H9C .3028 .6697 .3054 .055 Uiso calc R 1 . . H C10C .4303(2) .63221(8) .37840(13) .0382(5) Uani d . 1 . . C N11C .74755(18) .61037(7) .53443(12) .0442(5) Uani d . 1 . . N H11C .779(2) .6373(9) .5527(14) .053 Uiso d . 1 . . H C12C .7926(2) .56032(9) .55669(15) .0524(6) Uani d . 1 . . C H127 .7253 .5437 .5872 .079 Uiso calc R 1 . . H H128 .8720 .5632 .5877 .079 Uiso calc R 1 . . H H129 .8106 .5408 .5100 .079 Uiso calc R 1 . . H C13C .7195(2) .70916(9) .47544(17) .0600(7) Uani d . 1 . . C H137 .7075 .7204 .5289 .090 Uiso calc R 1 . . H H138 .7029 .7369 .4400 .090 Uiso calc R 1 . . H H139 .8086 .6973 .4685 .090 Uiso calc R 1 . . H Cl1C .18374(7) .60094(3) .20151(4) .0697(2) Uani d . 1 . . Cl S1D .02320(5) .313087(19) .29261(3) .04001(18) Uani d . 1 . . S O1D .10049(15) .31330(6) .36374(10) .0527(4) Uani d . 1 . . O O2D .01531(16) .26663(5) .25003(10) .0554(5) Uani d . 1 . . O N2D -.12931(16) .33185(6) .31213(10) .0388(4) Uani d . 1 . . N C3D -.1436(2) .38230(7) .33810(13) .0342(5) Uani d . 1 . . C N4D -.07141(16) .41999(6) .31175(11) .0381(4) Uani d . 1 . . N C5D .0215(2) .41125(7) .25310(13) .0365(5) Uani d . 1 . . C C6D .0729(2) .45212(8) .20993(14) .0463(6) Uani d . 1 . . C H6D .0442 .4849 .2215 .056 Uiso calc R 1 . . H C7D .1645(2) .44526(9) .15092(14) .0510(6) Uani d . 1 . . C H7D .1968 .4732 .1233 .061 Uiso calc R 1 . . H C8D .2089(2) .39695(10) .13245(14) .0492(6) Uani d . 1 . . C C9D .1646(2) .35526(9) .17372(14) .0468(6) Uani d . 1 . . C H9D .1955 .3228 .1622 .056 Uiso calc R 1 . . H C10D .0723(2) .36322(8) .23319(13) .0397(5) Uani d . 1 . . C N11D -.23932(18) .39073(7) .39063(12) .0419(5) Uani d . 1 . . N H11D -.278(2) .3649(9) .4113(14) .050 Uiso d . 1 . . H C12D -.2739(2) .44116(9) .41822(15) .0536(6) Uani d . 1 . . C H12A -.1998 .4557 .4457 .080 Uiso calc R 1 . . H H12B -.3483 .4390 .4534 .080 Uiso calc R 1 . . H H12C -.2966 .4622 .3739 .080 Uiso calc R 1 . . H C13D -.2284(2) .29255(8) .32816(16) .0569(7) Uani d . 1 . . C H13A -.2197 .2812 .3818 .085 Uiso calc R 1 . . H H13B -.2149 .2644 .2931 .085 Uiso calc R 1 . . H H13C -.3154 .3063 .3201 .085 Uiso calc R 1 . . H Cl1D .32229(7) .38835(3) .05652(4) .0739(2) 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 S1A .0420(3) .0297(3) .0424(4) -.0012(2) -.0026(3) -.0017(2) O1A .0566(10) .0529(10) .0483(11) -.0019(7) -.0146(8) -.0101(7) O2A .0619(10) .0308(9) .0667(12) -.0022(7) .0035(8) .0065(7) N2A .0387(10) .0297(9) .0478(12) .0058(7) .0032(8) -.0001(8) C3A .0390(12) .0321(12) .0331(14) .0012(9) -.0041(9) -.0011(9) N4A .0417(10) .0339(10) .0399(12) .0022(8) .0046(8) -.0001(8) C5A .0377(12) .0337(12) .0351(14) .0031(9) -.0026(10) .0004(9) C6A .0480(13) .0340(12) .0474(16) .0043(9) .0022(11) -.0033(10) C7A .0489(14) .0467(14) .0419(16) .0080(10) .0002(11) -.0097(11) C8A .0382(13) .0562(15) .0350(15) .0036(10) .0018(10) -.0036(11) C9A .0408(13) .0471(14) .0405(15) -.0049(10) -.0026(10) .0043(11) C10A .0367(12) .0360(12) .0347(14) .0026(9) -.0017(9) .0008(9) N11A .0462(11) .0372(11) .0432(13) .0017(8) .0095(9) -.0033(9) C12A .0561(15) .0465(14) .0477(17) -.0045(11) .0086(12) .0032(11) C13A .0641(16) .0413(14) .084(2) .0182(12) .0193(14) .0006(13) Cl1A .0530(4) .0894(5) .0510(5) -.0038(3) .0163(3) -.0065(3) S1B .0430(3) .0296(3) .0471(4) -.0022(2) .0059(3) -.0009(2) O1B .0577(10) .0488(10) .0510(11) -.0034(7) .0157(8) .0076(7) O2B .0624(10) .0323(9) .0705(13) -.0019(7) .0017(9) -.0101(8) N2B .0382(10) .0312(10) .0482(12) .0043(7) .0008(8) -.0015(8) C3B .0363(12) .0322(12) .0347(14) -.0017(9) .0047(10) .0010(9) N4B .0419(10) .0311(10) .0399(12) .0008(8) -.0006(8) -.0009(8) C5B .0382(12) .0342(12) .0358(14) .0003(9) .0051(10) -.0026(9) C6B .0499(14) .0371(13) .0424(16) .0022(10) .0018(11) .0045(10) C7B .0473(14) .0547(15) .0424(16) .0052(11) -.0006(11) .0087(11) C8B .0408(13) .0618(16) .0380(16) .0001(11) -.0002(10) -.0021(11) C9B .0441(13) .0474(14) .0421(15) -.0062(10) .0033(10) -.0087(11) C10B .0367(12) .0364(12) .0388(14) .0007(9) .0048(10) -.0036(9) N11B .0461(11) .0390(12) .0445(14) .0013(8) -.0051(9) .0035(9) C12B .0590(15) .0454(14) .0529(17) -.0097(11) -.0096(12) -.0033(11) C13B .0596(15) .0428(14) .0635(18) .0174(11) -.0120(12) -.0001(12) Cl1B .0540(4) .1031(6) .0516(5) -.0078(3) -.0142(3) -.0016(4) S1C .0420(3) .0340(3) .0424(4) .0011(2) .0040(3) -.0003(2) O1C .0566(10) .0547(10) .0475(11) .0024(7) .0154(8) -.0085(8) O2C .0656(11) .0366(9) .0673(13) .0019(7) -.0024(9) .0107(8) N2C .0401(10) .0337(10) .0467(12) -.0066(8) .0003(8) -.0008(8) C3C .0389(12) .0343(12) .0353(14) -.0004(9) .0032(10) -.0010(9) N4C .0419(10) .0372(10) .0415(12) -.0030(8) -.0019(8) -.0017(8) C5C .0378(12) .0387(13) .0363(14) -.0031(9) .0033(10) -.0009(10) C6C .0485(14) .0397(13) .0489(16) -.0050(10) -.0008(11) -.0075(11) C7C .0478(14) .0570(16) .0476(17) -.0099(11) .0016(11) -.0127(12) C8C .0381(13) .0659(17) .0365(16) -.0060(11) -.0012(10) -.0050(11) C9C .0418(13) .0550(15) .0414(16) .0027(10) .0032(11) .0059(11) C10C .0374(12) .0420(13) .0351(14) -.0035(9) .0046(9) .0001(10) N11C .0479(12) .0416(12) .0433(13) -.0038(8) -.0072(9) -.0034(9) C12C .0536(15) .0522(15) .0514(17) .0070(11) -.0077(12) .0033(12) C13C .0605(16) .0434(14) .076(2) -.0160(11) -.0121(13) -.0044(13) Cl1C .0532(4) .1048(6) .0509(5) -.0024(3) -.0146(3) -.0059(4) S1D .0425(3) .0327(3) .0448(4) .0039(2) -.0041(3) -.0021(2) O1D .0567(10) .0512(10) .0502(11) .0064(7) -.0162(8) .0047(8) O2D .0653(11) .0342(9) .0666(12) .0046(7) .0006(9) -.0134(8) N2D .0398(10) .0316(10) .0451(12) -.0035(7) .0006(8) -.0007(8) C3D .0369(12) .0323(12) .0335(14) .0019(9) -.0030(9) .0024(9) N4D .0420(10) .0338(10) .0385(12) .0001(8) .0027(8) .0008(8) C5D .0371(12) .0367(12) .0358(14) -.0022(9) -.0022(10) -.0024(9) C6D .0481(14) .0419(13) .0489(16) -.0032(10) .0026(11) .0049(11) C7D .0458(14) .0604(16) .0468(17) -.0080(11) .0010(11) .0081(12) C8D .0386(13) .0694(17) .0396(16) -.0003(11) .0008(11) .0004(12) C9D .0402(13) .0558(15) .0444(16) .0078(10) -.0023(11) -.0085(12) C10D .0364(12) .0434(13) .0392(15) -.0003(9) -.0050(10) -.0048(10) N11D .0461(11) .0382(11) .0415(13) -.0001(8) .0066(9) .0034(9) C12D .0611(15) .0469(15) .0528(17) .0111(11) .0125(12) .0008(11) C13D .0609(15) .0406(14) .0694(19) -.0151(11) .0104(13) .0031(12) Cl1D .0531(4) .1160(6) .0526(5) .0097(4) .0169(3) .0048(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 S1A O1A . 1.4322(16) yes S1A O2A . 1.4235(16) yes S1A N2A . 1.6461(18) yes S1A C10A . 1.727(2) yes N2A C3A . 1.408(3) yes N2A C13A . 1.470(3) yes C3A N4A . 1.301(3) yes C3A N11A . 1.337(3) yes N4A C5A . 1.390(3) yes C5A C10A . 1.401(3) no C5A C6A . 1.403(3) no C6A C7A . 1.371(3) no C6A H6A . .9300 no C7A C8A . 1.387(3) no C7A H7A . .9300 no C8A C9A . 1.376(3) no C8A Cl1A . 1.739(2) no C9A C10A . 1.393(3) no C9A H9A . .9300 no N11A C12A . 1.446(3) yes N11A H11A . .78(2) no C12A H121 . .9600 no C12A H122 . .9600 no C12A H123 . .9600 no C13A H131 . .9600 no C13A H132 . .9600 no C13A H133 . .9600 no S1B O1B . 1.4376(16) yes S1B O2B . 1.4233(15) yes S1B N2B . 1.6526(17) yes S1B C10B . 1.725(2) yes N2B C3B . 1.405(2) yes N2B C13B . 1.461(3) yes C3B N4B . 1.301(3) yes C3B N11B . 1.336(3) yes N4B C5B . 1.389(3) yes C5B C6B . 1.402(3) no C5B C10B . 1.403(3) no C6B C7B . 1.370(3) no C6B H6B . .9300 no C7B C8B . 1.386(3) no C7B H7B . .9300 no C8B C9B . 1.373(3) no C8B Cl1B . 1.737(2) no C9B C10B . 1.391(3) no C9B H9B . .9300 no N11B C12B . 1.452(3) yes N11B H11B . .82(2) no C12B H124 . .9600 no C12B H125 . .9600 no C12B H126 . .9600 no C13B H134 . .9600 no C13B H135 . .9600 no C13B H136 . .9600 no S1C O1C . 1.4332(16) yes S1C O2C . 1.4173(16) yes S1C N2C . 1.6509(18) yes S1C C10C . 1.731(2) yes N2C C3C . 1.402(3) yes N2C C13C . 1.468(3) yes C3C N4C . 1.307(3) yes C3C N11C . 1.337(3) yes N4C C5C . 1.386(3) yes C5C C6C . 1.398(3) no C5C C10C . 1.400(3) no C6C C7C . 1.379(3) no C6C H6C . .9300 no C7C C8C . 1.381(3) no C7C H7C . .9300 no C8C C9C . 1.371(3) no C8C Cl1C . 1.738(2) no C9C C10C . 1.396(3) no C9C H9C . .9300 no N11C C12C . 1.444(3) yes N11C H11C . .84(2) no C12C H127 . .9600 no C12C H128 . .9600 no C12C H129 . .9600 no C13C H137 . .9600 no C13C H138 . .9600 no C13C H139 . .9600 no S1D O1D . 1.4340(16) yes S1D O2D . 1.4214(15) yes S1D N2D . 1.6508(17) yes S1D C10D . 1.732(2) yes N2D C3D . 1.406(3) yes N2D C13D . 1.464(3) yes C3D N4D . 1.309(3) yes C3D N11D . 1.333(3) yes N4D C5D . 1.386(3) yes C5D C6D . 1.401(3) no C5D C10D . 1.405(3) no C6D C7D . 1.374(3) no C6D H6D . .9300 no C7D C8D . 1.384(3) no C7D H7D . .9300 no C8D C9D . 1.376(3) no C8D Cl1D . 1.737(2) no C9D C10D . 1.389(3) no C9D H9D . .9300 no N11D C12D . 1.450(3) yes N11D H11D . .86(2) no C12D H12A . .9600 no C12D H12B . .9600 no C12D H12C . .9600 no C13D H13A . .9600 no C13D H13B . .9600 no C13D H13C . .9600 no