data_2009131 _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 'P21 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 11.2968(4) _cell_length_b 11.8091(7) _cell_length_c 12.8835(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1718.72(18) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _exptl_crystal_density_diffrn 1.321 _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 .15232(8) .26335(6) .75496(7) .0444(3) Uani d . 1 . . S O1 .1568(3) .1445(2) .7808(2) .0612(8) Uani d . 1 . . O O2 .2502(3) .3034(3) .6946(2) .0608(8) Uani d . 1 . . O N2 .0301(3) .2860(3) .6998(3) .0501(8) Uani d . 1 . . N C3 -.0207(3) .3868(3) .7060(3) .0433(8) Uani d . 1 . . C N4 .0044(3) .4626(3) .7831(2) .0460(8) Uani d . 1 . . N H4 -.034(4) .522(4) .780(3) .055 Uiso d . 1 . . H C5 .0769(3) .4389(3) .8675(3) .0436(8) Uani d . 1 . . C C6 .0816(4) .5140(4) .9521(3) .0570(10) Uani d . 1 . . C H6 .0348 .5788 .9523 .068 Uiso calc R 1 . . H C7 .1553(5) .4919(4) 1.0346(3) .0642(11) Uani d . 1 . . C H7 .1600 .5424 1.0898 .077 Uiso calc R 1 . . H C8 .2227(4) .3937(4) 1.0348(3) .0605(11) Uani d . 1 . . C C9 .2205(4) .3200(4) .9532(3) .0562(10) Uani d . 1 . . C H9 .2667 .2548 .9539 .067 Uiso calc R 1 . . H C10 .1477(3) .3443(3) .8687(3) .0446(8) Uani d . 1 . . C N11 -.1022(3) .4189(3) .6380(3) .0559(9) Uani d . 1 . . N H11 -.138(5) .473(4) .649(4) .067 Uiso d . 1 . . H C12 -.1379(4) .3534(4) .5466(3) .0620(11) Uani d . 1 . . C H12 -.0905 .2839 .5462 .074 Uiso calc R 1 . . H C13 -.2666(6) .3187(6) .5595(4) .104(2) Uani d . 1 . . C H13A -.3151 .3852 .5651 .156 Uiso calc R 1 . . H H13B -.2750 .2738 .6212 .156 Uiso calc R 1 . . H H13C -.2911 .2751 .5004 .156 Uiso calc R 1 . . H C14 -.1126(4) .4158(4) .4455(3) .0591(11) Uani d . 1 . . C H14 -.1420 .3678 .3890 .071 Uiso calc R 1 . . H C15 .0170(5) .4306(6) .4286(5) .0903(18) Uani d . 1 . . C H15A .0554 .3572 .4310 .108 Uiso calc R 1 . . H H15B .0495 .4766 .4840 .108 Uiso calc R 1 . . H C16 .0433(7) .4870(9) .3241(6) .131(3) Uani d . 1 . . C H16A .1281 .4978 .3169 .157 Uiso calc R 1 . . H H16B .0170 .4380 .2682 .157 Uiso calc R 1 . . H C17 -.0170(7) .5975(8) .3158(6) .117(3) Uani d . 1 . . C H17A -.0022 .6300 .2478 .140 Uiso calc R 1 . . H H17B .0144 .6489 .3676 .140 Uiso calc R 1 . . H C18 -.1466(7) .5839(7) .3313(5) .111(2) Uani d . 1 . . C H18A -.1789 .5377 .2758 .133 Uiso calc R 1 . . H H18B -.1844 .6576 .3282 .133 Uiso calc R 1 . . H C19 -.1744(5) .5283(5) .4360(4) .0807(15) Uani d . 1 . . C H19A -.1489 .5778 .4918 .097 Uiso calc R 1 . . H H19B -.2592 .5174 .4424 .097 Uiso calc R 1 . . H Cl1 .31620(13) .36654(13) 1.13925(10) .0939(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 .0518(5) .0373(4) .0440(4) -.0013(4) -.0002(4) -.0030(4) O1 .083(2) .0343(12) .0659(16) -.0011(14) -.0165(16) .0018(11) O2 .0592(18) .0627(17) .0604(17) -.0081(14) .0168(14) -.0073(14) N2 .0534(19) .0474(17) .0495(17) .0053(14) -.0121(15) -.0137(14) C3 .048(2) .0435(19) .0387(16) -.0065(16) -.0001(16) -.0029(15) N4 .0564(19) .0411(16) .0404(15) .0051(15) -.0061(15) -.0081(12) C5 .049(2) .0458(19) .0355(17) -.0058(17) -.0012(15) -.0022(15) C6 .070(3) .055(2) .046(2) -.006(2) -.004(2) -.015(2) C7 .081(3) .067(2) .045(2) -.019(3) -.006(2) -.0081(19) C8 .065(3) .074(3) .0427(19) -.017(2) -.009(2) .002(2) C9 .058(2) .058(2) .052(2) -.0098(19) -.0025(19) .0040(19) C10 .050(2) .0450(17) .0392(17) -.0113(18) -.0007(17) -.0017(14) N11 .063(2) .0549(19) .0495(17) .0128(17) -.0175(18) -.0138(16) C12 .078(3) .059(2) .049(2) -.002(2) -.017(2) -.0110(18) C13 .111(5) .140(6) .060(3) -.066(4) -.002(3) -.010(3) C14 .064(3) .064(2) .050(2) .000(2) -.009(2) -.012(2) C15 .066(3) .119(5) .086(4) .014(3) -.001(3) -.006(4) C16 .084(4) .199(9) .108(5) -.017(6) .033(4) .031(6) C17 .108(5) .132(6) .111(5) -.049(5) .000(4) .031(5) C18 .150(7) .113(5) .070(3) .020(5) -.003(4) .018(3) C19 .088(4) .088(3) .066(3) .020(3) -.005(3) .011(3) Cl1 .1073(11) .1108(10) .0637(7) -.0263(9) -.0406(7) .0083(7) 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 . 1.432(3) no S1 O1 . 1.443(2) no S1 N2 . 1.575(3) yes S1 C10 . 1.751(3) yes N2 C3 . 1.325(5) yes C3 N11 . 1.325(5) yes C3 N4 . 1.368(4) yes N4 C5 . 1.389(5) yes N4 H4 . .83(4) yes C5 C10 . 1.374(5) no C5 C6 . 1.407(5) no C6 C7 . 1.375(6) no C6 H6 . .9300 no C7 C8 . 1.386(7) no C7 H7 . .9300 no C8 C9 . 1.365(6) no C8 Cl1 . 1.740(4) no C9 C10 . 1.394(5) no C9 H9 . .9300 no N11 C12 . 1.466(5) yes N11 H11 . .77(5) yes C12 C13 . 1.520(7) yes C12 C14 . 1.524(6) yes C12 H12 . .9800 no C13 H13A . .9600 no C13 H13B . .9600 no C13 H13C . .9600 no C14 C15 . 1.490(7) no C14 C19 . 1.506(7) no C14 H14 . .9800 no C15 C16 . 1.531(9) no C15 H15A . .9700 no C15 H15B . .9700 no C16 C17 . 1.476(11) no C16 H16A . .9700 no C16 H16B . .9700 no C17 C18 . 1.487(10) no C17 H17A . .9700 no C17 H17B . .9700 no C18 C19 . 1.532(8) no C18 H18A . .9700 no C18 H18B . .9700 no C19 H19A . .9700 no C19 H19B . .9700 no