#------------------------------------------------------------------------------ #$Date: 2008-01-13 22:15:36 +0000 (Sun, 13 Jan 2008) $ #$Revision: 14 $ #$URL: svn://www.crystallography.net/cod/cif/2/2009132.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_2009132 _journal_name_full 'Acta Crystallographica' _journal_year 1999 _journal_volume C55 _journal_page_first 1945 _journal_page_last 1947 _publ_section_title ; 7-Chloro-(R)-3-[1-(cyclohexyl)ethylamino]-4H-1,2,4-benzothiadiazine 1,1-dioxide and 7-chloro-(S)-3-[1-(cyclohexyl)ethylamino]-4H-1,2,4- benzothiadiazine 1,1-dioxide ; loop_ _publ_author_name "Dupont, L\'eon" 'de Tullio, Pascal' 'Khelili, Smail' 'Somers, Fabian' 'Delarge, Jacques' 'Pirotte, Bernard' _chemical_formula_sum 'C15 H20 Cl N3 O2 S' _chemical_formula_weight 341.85 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 11.2963(8) _cell_length_b 11.8026(11) _cell_length_c 12.8831(11) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1717.6(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _exptl_crystal_density_diffrn 1.322 _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 S1 .84771(7) .73657(6) .24489(6) .0501(2) Uani d . 1 . . S O1 .8431(2) .85582(17) .21852(17) .0681(7) Uani d . 1 . . O O2 .7496(2) .6964(2) .30584(18) .0674(7) Uani d . 1 . . O N2 .9706(2) .7139(2) .3007(2) .0545(7) Uani d . 1 . . N C3 1.0205(3) .6126(3) .2938(2) .0482(8) Uani d . 1 . . C N4 .9958(3) .5378(2) .2172(2) .0522(7) Uani d . 1 . . N H4 1.029(3) .477(3) .222(3) .063 Uiso d . 1 . . H C5 .9230(3) .5598(3) .1324(2) .0478(8) Uani d . 1 . . C C6 .9181(3) .4862(3) .0476(3) .0623(10) Uani d . 1 . . C H6 .9648 .4213 .0473 .075 Uiso calc R 1 . . H C7 .8455(4) .5085(3) -.0350(3) .0700(10) Uani d . 1 . . C H7 .8420 .4588 -.0909 .084 Uiso calc R 1 . . H C8 .7769(3) .6066(4) -.0345(3) .0656(10) Uani d . 1 . . C C9 .7799(3) .6802(3) .0469(3) .0592(9) Uani d . 1 . . C H9 .7345 .7459 .0458 .071 Uiso calc R 1 . . H C10 .8518(3) .6559(3) .1315(2) .0492(7) Uani d . 1 . . C N11 1.1015(3) .5814(3) .3621(2) .0619(8) Uani d . 1 . . N H11 1.135(4) .528(3) .352(3) .074 Uiso d . 1 . . H C12 1.1381(4) .6461(3) .4531(3) .0659(10) Uani d . 1 . . C H12 1.0907 .7156 .4539 .079 Uiso calc R 1 . . H C13 1.2665(4) .6816(5) .4404(4) .1083(18) Uani d . 1 . . C H13A 1.3149 .6156 .4308 .162 Uiso calc R 1 . . H H13B 1.2920 .7216 .5013 .162 Uiso calc R 1 . . H H13C 1.2738 .7302 .3809 .162 Uiso calc R 1 . . H C14 1.1126(3) .5840(3) .5541(3) .0628(10) Uani d . 1 . . C H14 1.1417 .6325 .6103 .075 Uiso calc R 1 . . H C15 .9818(4) .5694(5) .5710(4) .0960(15) Uani d . 1 . . C H15A .9492 .5228 .5160 .115 Uiso calc R 1 . . H H15B .9433 .6428 .5682 .115 Uiso calc R 1 . . H C16 .9566(5) .5135(7) .6767(5) .135(2) Uani d . 1 . . C H16A .9840 .5626 .7321 .162 Uiso calc R 1 . . H H16B .8720 .5027 .6850 .162 Uiso calc R 1 . . H C17 1.0177(6) .4021(6) .6838(5) .123(2) Uani d . 1 . . C H17A 1.0029 .3687 .7513 .148 Uiso calc R 1 . . H H17B .9865 .3513 .6313 .148 Uiso calc R 1 . . H C18 1.1461(6) .4161(5) .6686(4) .1113(18) Uani d . 1 . . C H18A 1.1840 .3424 .6718 .134 Uiso calc R 1 . . H H18B 1.1779 .4621 .7244 .134 Uiso calc R 1 . . H C19 1.1752(4) .4718(4) .5647(3) .0844(13) Uani d . 1 . . C H19A 1.2600 .4834 .5596 .101 Uiso calc R 1 . . H H19B 1.1512 .4221 .5086 .101 Uiso calc R 1 . . H Cl1 .68404(11) .63344(11) -.13912(8) .0985(5) 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 S1 .0574(4) .0428(4) .0500(4) -.0007(4) .0002(4) -.0030(3) O1 .0909(18) .0405(11) .0728(15) .0005(13) -.0155(15) .0026(11) O2 .0656(16) .0698(15) .0668(15) -.0099(13) .0157(13) -.0053(12) N2 .0558(17) .0521(16) .0557(17) .0045(13) -.0120(14) -.0122(13) C3 .0492(19) .0532(19) .0423(16) -.0047(15) -.0004(14) -.0024(14) N4 .0645(18) .0455(16) .0465(14) .0032(13) -.0044(14) -.0055(12) C5 .055(2) .0517(19) .0367(16) -.0100(15) .0047(14) -.0053(15) C6 .075(2) .060(2) .0527(19) -.0048(18) -.0043(18) -.0099(19) C7 .090(3) .074(2) .0462(18) -.019(3) -.005(2) -.0105(18) C8 .071(2) .078(3) .0477(19) -.019(2) -.0137(18) .0017(19) C9 .060(2) .062(2) .0558(19) -.0116(17) -.0075(16) .0027(18) C10 .0532(19) .0503(17) .0440(16) -.0069(17) -.0003(15) .0008(13) N11 .072(2) .0586(19) .0553(16) .0107(15) -.0167(16) -.0118(15) C12 .080(3) .063(2) .0542(18) .003(2) -.014(2) -.0127(17) C13 .115(4) .138(5) .072(3) -.065(4) -.013(3) -.005(3) C14 .066(2) .069(2) .0533(19) .0002(18) -.0083(19) -.0106(19) C15 .066(3) .121(4) .101(3) .013(3) .001(3) -.006(3) C16 .094(4) .203(8) .108(4) -.020(5) .037(4) .020(5) C17 .121(5) .139(6) .108(4) -.052(4) .005(4) .029(4) C18 .145(5) .110(4) .079(3) .028(4) -.002(4) .021(3) C19 .089(3) .088(3) .076(3) .018(3) .004(2) .006(2) Cl1 .1098(10) .1158(9) .0701(6) -.0251(7) -.0406(6) .0073(6) 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 O2 . 1.438(2) no S1 O1 . 1.449(2) no S1 N2 . 1.586(3) yes S1 C10 . 1.745(3) yes N2 C3 . 1.325(4) yes C3 N11 . 1.322(4) yes C3 N4 . 1.353(4) yes N4 C5 . 1.392(4) yes N4 H4 . .81(4) yes C5 C10 . 1.391(4) no C5 C6 . 1.397(4) no C6 C7 . 1.369(5) no C6 H6 . .9300 no C7 C8 . 1.393(6) no C7 H7 . .9300 no C8 C9 . 1.362(5) no C8 Cl1 . 1.737(4) no C9 C10 . 1.389(4) no C9 H9 . .9300 no N11 C12 . 1.459(4) yes N11 H11 . .75(4) yes C12 C13 . 1.519(6) yes C12 C14 . 1.520(5) yes C12 H12 . .9800 no C13 H13A . .9600 no C13 H13B . .9600 no C13 H13C . .9600 no C14 C15 . 1.504(6) no C14 C19 . 1.507(5) no C14 H14 . .9800 no C15 C16 . 1.541(7) no C15 H15A . .9700 no C15 H15B . .9700 no C16 C17 . 1.487(9) no C16 H16A . .9700 no C16 H16B . .9700 no C17 C18 . 1.472(8) no C17 H17A . .9700 no C17 H17B . .9700 no C18 C19 . 1.527(6) no C18 H18A . .9700 no C18 H18B . .9700 no C19 H19A . .9700 no C19 H19B . .9700 no