data_2012135 _journal_name_full 'Acta Crystallographica, Section C' _journal_year 2001 _journal_volume 57 _journal_page_first 970 _journal_page_last 972 _publ_section_title ; 1-2-bis(N-fluoro-p-toluenesulfonamido)ethane ; loop_ _publ_author_name 'Ardeshir, Khazaei' 'Banks, R. Eric' 'Besheesh, Mohammed K.' 'Brisdon, Alan K.' 'Pritchard, Robin G.' _chemical_formula_moiety 'C16 H18 F2 N2 O4 S2 , C H Cl3' _chemical_formula_sum 'C17 H19 Cl3 F2 N2 O4 S2' _chemical_formula_structural 'C17 H19 Cl3 F2 N2 O4 S2' _chemical_formula_weight 523.81 _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 2/n' _symmetry_space_group_name_Hall '-P 2yac' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y, -z+1/2' '-x, -y, -z' 'x-1/2, -y, z-1/2' _cell_length_a 10.9948(10) _cell_length_b 9.6922(10) _cell_length_c 21.381(5) _cell_angle_alpha 90 _cell_angle_beta 94.815(10) _cell_angle_gamma 90 _cell_volume 2270.4(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _exptl_crystal_density_diffrn 1.532 _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 .44043(8) .73110(9) .09126(4) .0288(2) Uani d . 1 . . S S2 .55434(8) .66118(9) .39870(4) .0296(2) Uani d . 1 . . S O1 .3355(2) .7897(2) .05851(11) .0371(6) Uani d . 1 . . O O2 .5580(2) .7885(3) .08700(11) .0374(6) Uani d . 1 . . O O3 .4355(2) .6062(3) .40219(11) .0376(6) Uani d . 1 . . O O4 .6586(2) .5992(3) .43060(11) .0394(7) Uani d . 1 . . O N1 .4215(2) .7556(3) .16913(13) .0318(7) Uani d . 1 . . N N2 .5732(2) .6425(3) .32075(13) .0334(7) Uani d . 1 . . N F1 .30386(18) .7000(3) .17801(10) .0469(6) Uani d . 1 . . F F2 .69174(18) .6982(3) .31291(10) .0507(6) Uani d . 1 . . F C1 .5056(3) .6782(4) .21174(15) .0335(8) Uani d . 1 . . C H1A .5888 .6957 .2021 .04 Uiso calc R 1 . . H H1B .4897 .5802 .2069 .04 Uiso calc R 1 . . H C2 .4895(3) .7215(4) .27823(15) .0339(8) Uani d . 1 . . C H2A .5063 .8193 .2833 .041 Uiso calc R 1 . . H H2B .4061 .7047 .2878 .041 Uiso calc R 1 . . H C3 .4433(3) .5535(3) .07972(14) .0261(8) Uani d . 1 . . C C4 .3341(3) .4847(4) .06630(16) .0333(9) Uani d . 1 . . C H4 .2611 .5331 .0602 .04 Uiso calc R 1 . . H C5 .3358(3) .3441(4) .06220(16) .0374(9) Uani d . 1 . . C H5 .2629 .2968 .0529 .045 Uiso calc R 1 . . H C6 .4435(4) .2705(4) .07166(16) .0361(9) Uani d . 1 . . C C7 .5514(3) .3431(4) .08387(16) .0367(9) Uani d . 1 . . C H7 .6246 .2948 .0895 .044 Uiso calc R 1 . . H C8 .5532(3) .4838(4) .08793(16) .0325(8) Uani d . 1 . . C H8 .6263 .5314 .096 .039 Uiso calc R 1 . . H C9 .4425(4) .1149(4) .0684(2) .0541(12) Uani d . 1 . . C H9A .4153 .0781 .1065 .081 Uiso calc R 1 . . H H9B .5234 .082 .0632 .081 Uiso calc R 1 . . H H9C .3882 .0855 .0334 .081 Uiso calc R 1 . . H C10 .5556(3) .8378(3) .41312(15) .0275(8) Uani d . 1 . . C C11 .4480(3) .9117(4) .40652(16) .0320(8) Uani d . 1 . . C H11 .374 .867 .3967 .038 Uiso calc R 1 . . H C12 .4519(3) 1.0521(4) .41466(16) .0367(9) Uani d . 1 . . C H12 .3797 1.1025 .4101 .044 Uiso calc R 1 . . H C13 .5612(4) 1.1203(4) .42947(16) .0358(9) Uani d . 1 . . C C14 .6681(3) 1.0424(4) .43703(16) .0379(9) Uani d . 1 . . C H14 .7419 1.0865 .4482 .045 Uiso calc R 1 . . H C15 .6667(3) .9027(4) .42838(16) .0325(8) Uani d . 1 . . C H15 .7388 .8521 .4326 .039 Uiso calc R 1 . . H C16 .5664(4) 1.2734(4) .4374(2) .0538(12) Uani d . 1 . . C H16A .6176 1.2958 .4746 .081 Uiso calc R 1 . . H H16B .4857 1.3084 .4412 .081 Uiso calc R 1 . . H H16C .5993 1.3144 .4016 .081 Uiso calc R 1 . . H C1A .7322(13) .1319(14) .2707(5) .111(5) Uani d PDU .5 A -1 C H1A1 .7019 .1311 .3125 .133 Uiso calc PR .5 A -1 H Cl1A .7819(8) .3068(5) .2331(3) .167(3) Uani d PDU .5 A -1 Cl Cl2A .6507(5) .0434(6) .2067(2) .1073(15) Uani d PDU .5 A -1 Cl Cl3A .8873(8) .0958(11) .2615(4) .224(4) Uani d PDU .5 A -1 Cl C1B .2276(14) .2717(13) .2700(5) .104(5) Uani d PDU .5 B -2 C H1B1 .191 .301 .3081 .125 Uiso calc PR .5 B -2 H Cl1B .2203(10) .1003(4) .2645(5) .157(4) Uani d PDU .5 B -2 Cl Cl2B .1552(6) .3600(7) .2045(2) .0919(14) Uani d PDU .5 B -2 Cl Cl3B .3801(9) .3230(12) .2748(5) .222(5) Uani d PDU .5 B -2 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 .0290(5) .0237(5) .0335(5) .0003(4) .0008(4) -.0001(4) S2 .0270(5) .0279(5) .0336(5) .0003(4) .0004(4) -.0029(4) O1 .0368(15) .0325(14) .0405(14) .0067(12) -.0048(11) .0037(11) O2 .0327(15) .0322(14) .0476(15) -.0067(12) .0061(12) -.0015(11) O3 .0302(14) .0372(15) .0457(15) -.0092(12) .0056(11) -.0018(12) O4 .0370(16) .0342(15) .0451(15) .0055(12) -.0078(12) -.0001(12) N1 .0231(16) .0346(17) .0377(16) .0002(14) .0024(12) -.0060(14) N2 .0203(16) .0418(18) .0378(17) .0035(14) .0014(12) -.0050(14) F1 .0231(11) .0726(16) .0455(13) -.0024(11) .0065(9) -.0049(11) F2 .0242(12) .0849(18) .0436(12) -.0050(12) .0063(9) -.0087(12) C1 .028(2) .037(2) .0356(19) .0037(17) .0018(15) -.0067(16) C2 .031(2) .037(2) .0344(19) .0028(17) .0016(15) -.0037(16) C3 .0265(19) .0268(18) .0252(17) .0009(16) .0036(14) -.0016(14) C4 .028(2) .033(2) .038(2) .0020(17) -.0016(15) -.0001(16) C5 .037(2) .033(2) .041(2) -.0085(18) -.0028(17) -.0032(17) C6 .050(3) .028(2) .0310(19) .0003(19) .0055(17) -.0014(16) C7 .035(2) .038(2) .037(2) .0134(18) .0002(16) -.0041(17) C8 .026(2) .036(2) .035(2) .0029(17) -.0002(15) -.0052(16) C9 .075(3) .029(2) .057(3) .003(2) .000(2) -.0056(19) C10 .0275(19) .0269(19) .0282(18) -.0002(17) .0041(14) -.0018(15) C11 .0243(19) .036(2) .035(2) .0014(16) .0027(15) -.0037(16) C12 .037(2) .035(2) .038(2) .0098(18) .0018(16) -.0022(17) C13 .050(2) .027(2) .0304(19) -.0052(19) .0046(17) -.0025(15) C14 .032(2) .041(2) .040(2) -.0091(18) .0012(16) -.0045(17) C15 .027(2) .036(2) .035(2) .0006(17) .0028(15) -.0024(16) C16 .073(3) .034(2) .054(3) .001(2) .002(2) -.0018(19) C1A .116(10) .160(12) .054(8) .023(10) -.021(8) -.007(6) Cl1A .213(9) .148(3) .131(6) -.045(4) -.043(5) .023(3) Cl2A .111(4) .128(3) .078(3) -.030(3) -.018(2) .005(2) Cl3A .174(7) .280(11) .211(8) .077(7) -.020(6) -.102(7) C1B .124(12) .127(10) .058(8) .017(10) -.015(8) .021(6) Cl1B .178(10) .110(3) .169(9) -.030(4) -.058(6) .035(4) Cl2B .107(3) .099(3) .0668(19) .029(2) -.0142(19) .0148(19) Cl3B .178(8) .225(10) .246(11) -.076(7) -.073(7) .115(8) 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 O1 . 1.417(2) YES S1 O2 . 1.418(2) YES S1 N1 . 1.712(3) YES S1 C3 . 1.740(3) YES S2 O4 . 1.417(2) YES S2 O3 . 1.419(2) YES S2 N2 . 1.706(3) YES S2 C10 . 1.739(3) YES N1 F1 . 1.428(3) YES N1 C1 . 1.451(4) YES N2 F2 . 1.433(3) YES N2 C2 . 1.456(4) YES C1 C2 . 1.507(5) YES C1 H1A . .97 NO C1 H1B . .97 NO C2 H2A . .97 NO C2 H2B . .97 NO C3 C4 . 1.382(5) YES C3 C8 . 1.382(5) NO C4 C5 . 1.366(5) NO C4 H4 . .93 NO C5 C6 . 1.383(5) NO C5 H5 . .93 ? C6 C7 . 1.385(5) NO C6 C9 . 1.510(5) NO C7 C8 . 1.367(5) NO C7 H7 . .93 NO C8 H8 . .93 NO C9 H9A . .96 NO C9 H9B . .96 NO C9 H9C . .96 NO C10 C11 . 1.380(5) NO C10 C15 . 1.389(5) NO C11 C12 . 1.373(5) NO C11 H11 . .93 NO C12 C13 . 1.385(5) NO C12 H12 . .93 NO C13 C14 . 1.395(5) NO C13 C16 . 1.494(5) NO C14 C15 . 1.366(5) NO C14 H14 . .93 NO C15 H15 . .93 NO C16 H16A . .96 NO C16 H16B . .96 NO C16 H16C . .96 NO C1A Cl3A . 1.767(15) NO C1A Cl2A . 1.790(13) NO C1A Cl1A . 1.973(13) NO C1A H1A1 . .98 NO Cl1A Cl3A . 2.403(11) NO C1B Cl1B . 1.666(13) NO C1B Cl3B . 1.744(15) NO C1B Cl2B . 1.773(11) NO C1B H1B1 . .98 NO