#------------------------------------------------------------------------------ #$Date: 2011-09-17 21:27:16 +0100 (Sat, 17 Sep 2011) $ #$Revision: 26029 $ #$URL: svn://www.crystallography.net/cod/cif/2/2012519.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_2012519 _journal_name_full 'Acta Crystallographica, Section C' _journal_year 2002 _journal_volume 58 _journal_page_first o88 _journal_page_last o89 _publ_section_title ; N-(3-Phenoxy-4-pyridyl)methanesulfonamide, a strict pyridine analogue of nimesulide, a selective inhibitor of cyclooxygenase-2 ; loop_ _publ_author_name 'Michaux, Catherine' 'Charlier, Caroline' "Jul\'emont, Fabien" "Dogn\'e, Jean-Michel" 'de Leval, Xavier' 'Norberg, Bernadette' 'Pirotte, Bernard' 'Durant, Fran\,cois' _chemical_formula_moiety 'C12 H12 N2 O3 S' _chemical_formula_sum 'C12 H12 N2 O3 S' _chemical_formula_weight 264.30 _symmetry_cell_setting 'orthorhombic' _symmetry_space_group_name_H-M 'P b c a' _symmetry_space_group_name_Hall '-P 2ac 2ab' 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' '-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 8.0590(10) _cell_length_b 12.1160(10) _cell_length_c 24.744(2) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 2416.1(4) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _exptl_crystal_density_diffrn 1.453 _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 C1 .6341(3) .22801(16) -.02154(9) .0642(5) Uani d . 1 . . C C2 .7231(3) .15945(16) -.05550(8) .0601(5) Uani d . 1 . . C C3 .7953(2) .06568(16) -.03440(7) .0565(4) Uani d . 1 . . C C4 .7806(2) .04045(13) .01998(6) .0475(4) Uani d . 1 . . C C5 .69306(17) .11064(11) .05346(6) .0374(3) Uani d . 1 . . C C6 .6196(2) .20474(14) .03275(8) .0536(4) Uani d . 1 . . C O7 .67108(13) .09362(8) .10838(4) .0404(3) Uani d . 1 . . O C8 .74286(17) .00172(10) .13191(5) .0330(3) Uani d . 1 . . C C9 .65682(19) -.09512(12) .13105(7) .0429(3) Uani d . 1 . . C N10 .71742(18) -.18453(9) .15635(5) .0461(3) Uani d . 1 . . N C11 .8617(2) -.17949(12) .18302(6) .0465(4) Uani d . 1 . . C C12 .9512(2) -.08399(11) .18597(6) .0407(3) Uani d . 1 . . C C13 .89577(16) .01331(10) .15974(5) .0301(3) Uani d . 1 . . C N14 .97024(14) .11339(8) .15794(4) .0324(3) Uani d . 1 . . N S15 1.13367(4) .13824(3) .193283(12) .03378(15) Uani d . 1 . . S O16 1.12025(13) .09799(9) .24791(4) .0439(3) Uani d . 1 . . O O17 1.16398(16) .25480(9) .18717(4) .0504(3) Uani d . 1 . . O C18 1.3016(2) .06796(18) .16336(8) .0565(4) Uani d . 1 . . C H9 .555(3) -.1052(16) .1134(7) .051(5) Uiso d . 1 . . H H12 1.044(2) -.0837(15) .2055(7) .046(4) Uiso d . 1 . . H H6 .559(3) .2483(18) .0572(8) .068(6) Uiso d . 1 . . H H3 .862(3) .0198(19) -.0583(9) .068(6) Uiso d . 1 . . H H4 .830(3) -.0222(18) .0340(8) .060(5) Uiso d . 1 . . H H1 .584(4) .295(2) -.0362(11) .091(8) Uiso d . 1 . . H H2 .729(3) .1757(19) -.0926(9) .071(6) Uiso d . 1 . . H H18A 1.399(3) .082(2) .1859(9) .080(7) Uiso d . 1 . . H H18B 1.317(3) .095(2) .1277(10) .074(7) Uiso d . 1 . . H H11 .899(2) -.2409(18) .1997(7) .052(5) Uiso d . 1 . . H H18C 1.269(4) -.014(2) .1650(9) .086(7) Uiso d . 1 . . H H10 .651(3) -.247(2) .1541(9) .071(6) Uiso d . 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 C1 .0764(13) .0436(9) .0727(12) .0033(8) -.0258(9) .0143(8) C2 .0692(12) .0586(10) .0523(9) -.0138(9) -.0179(8) .0100(8) C3 .0609(10) .0587(10) .0500(9) .0022(8) -.0063(7) -.0035(8) C4 .0534(9) .0394(7) .0498(8) .0096(6) -.0075(7) -.0012(6) C5 .0342(6) .0296(6) .0485(7) -.0003(5) -.0111(6) -.0003(5) C6 .0588(10) .0356(8) .0664(11) .0109(7) -.0153(8) .0002(7) O7 .0426(5) .0286(5) .0501(6) .0107(4) -.0051(4) -.0029(4) C8 .0368(6) .0216(6) .0405(6) .0024(5) .0020(5) -.0014(5) C9 .0397(7) .0312(7) .0577(9) -.0052(5) .0041(6) -.0087(6) N10 .0581(8) .0220(5) .0581(7) -.0103(5) .0114(6) -.0033(5) C11 .0758(11) .0205(6) .0432(7) -.0001(6) .0033(7) .0054(5) C12 .0559(9) .0232(6) .0428(7) .0021(6) -.0087(6) .0041(5) C13 .0374(6) .0197(6) .0332(6) .0009(5) .0037(5) .0000(4) N14 .0361(6) .0196(5) .0415(6) -.0004(4) -.0013(4) .0021(4) S15 .0371(2) .0272(2) .0370(2) -.00319(11) .00110(11) -.00497(11) O16 .0584(7) .0361(5) .0372(5) -.0017(4) -.0028(4) -.0033(4) O17 .0632(7) .0316(6) .0564(6) -.0170(5) -.0009(5) -.0021(4) C18 .0377(8) .0718(12) .0600(10) .0033(8) .0017(7) -.0227(9) 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 C1 C6 . 1.377(3) ? C1 C2 . 1.382(3) ? C1 H1 . .97(3) ? C2 C3 . 1.379(3) ? C2 H2 . .94(2) ? C3 C4 . 1.385(2) ? C3 H3 . .97(2) ? C4 C5 . 1.381(2) ? C4 H4 . .92(2) ? C5 C6 . 1.383(2) ? C5 O7 . 1.3859(17) ? C6 H6 . .94(2) ? O7 C8 . 1.3833(15) ? C8 C9 . 1.363(2) yes C8 C13 . 1.418(2) yes C9 N10 . 1.343(2) yes C9 H9 . .94(2) ? N10 C11 . 1.338(2) yes N10 H10 . .92(2) ? C11 C12 . 1.366(2) yes C11 H11 . .90(2) ? C12 C13 . 1.418(2) yes C12 H12 . .893(19) ? C13 N14 . 1.354(2) yes N14 S15 . 1.6094(11) ? S15 O16 . 1.4411(10) ? S15 O17 . 1.4412(11) ? S15 C18 . 1.7623(17) ? C18 H18A . .98(3) ? C18 H18B . .95(2) ? C18 H18C . 1.03(3) ? _cod_database_code 2012519