data_2200777 _journal_name_full 'Acta Crystallographica, Section E' _journal_year 2001 _journal_volume 57 _journal_page_first o1012 _journal_page_last o1013 _publ_section_title ; FJ6, N-methyl-N-(4-nitro-2-phenoxyphenyl)methanesulfonamide ; loop_ _publ_author_name 'Michaux, Catherine' 'Charlier, Caroline' "Jul\'emont, Fabien" 'Norberg, Bernadette' "Dogn\'e Jean-Michel" 'Durant, Fran\,cois' _chemical_formula_moiety 'C14 H14 N2 O5 S' _chemical_formula_sum 'C14 H14 N2 O5 S' _chemical_formula_iupac 'C14 H14 N2 O5 S' _chemical_formula_weight 322.33 _symmetry_cell_setting 'monoclinic' _symmetry_space_group_name_H-M 'P 21/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 14.5220(10) _cell_length_b 10.4390(10) _cell_length_c 10.5230(10) _cell_angle_alpha 90.00 _cell_angle_beta 109.460(4) _cell_angle_gamma 90.00 _cell_volume 1504.1(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _exptl_crystal_density_diffrn 1.423 _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 S19 .09820(3) .39270(5) .16659(4) .05765(19) Uani d . 1 . . S O21 .04416(12) .27815(16) .12467(17) .0850(5) Uani d . 1 . . O O7 .22028(10) .50640(18) .50900(13) .0797(5) Uani d . 1 . . O O16 .51319(13) .77639(18) .56081(16) .0869(5) Uani d . 1 . . O O15 .55160(14) .7375(2) .38477(18) .0973(6) Uani d . 1 . . O O20 .12730(11) .4642(2) .07183(15) .0857(5) Uani d . 1 . . O N17 .19856(10) .35423(14) .28886(15) .0552(4) Uani d . 1 . . N N14 .50130(11) .71966(16) .45550(16) .0618(4) Uani d . 1 . . N C10 .42369(11) .62339(16) .41260(16) .0491(4) Uani d . 1 . . C C12$ .33644(13) .46585(18) .25715(17) .0542(4) Uani d . 1 . . C C8 .28922(11) .52039(17) .44807(16) .0504(4) Uani d . 1 . . C C13 .27459(11) .44752(16) .33146(15) .0469(3) Uani d . 1 . . C C9 .36518(12) .60666(17) .49095(16) .0521(4) Uani d . 1 . . C H9 .3766 .6523 .5706 .063 Uiso calc R 1 . . H C11 .41069(13) .55540(19) .29531(17) .0563(4) Uani d . 1 . . C H11 .4507 .5695 .2436 .068 Uiso calc R 1 . . H C3 .31187(16) .4931(2) .7455(2) .0681(5) Uani d . 1 . . C H3 .3537 .4333 .7283 .082 Uiso calc R 1 . . H C4 .23891(13) .54821(19) .64109(17) .0567(4) Uani d . 1 . . C C22 .03142(16) .4925(3) .2367(3) .0801(6) Uani d . 1 . . C H22A .0673 .5701 .2678 .120 Uiso calc R 1 . . H H22B .0205 .4496 .3112 .120 Uiso calc R 1 . . H H22C -.0302 .5125 .1697 .120 Uiso calc R 1 . . H C1 .26067(18) .6124(2) .9017(2) .0724(6) Uani d . 1 . . C H1 .2673 .6329 .9903 .087 Uiso calc R 1 . . H C2 .32242(18) .5271(2) .8760(2) .0719(5) Uani d . 1 . . C H2 .3724 .4913 .9471 .086 Uiso calc R 1 . . H C5 .17718(15) .6381(2) .6648(2) .0714(5) Uani d . 1 . . C H5 .1291 .6777 .5942 .086 Uiso calc R 1 . . H C6 .18948(18) .6677(2) .7993(3) .0796(6) Uani d . 1 . . C H6 .1478 .7266 .8184 .095 Uiso calc R 1 . . H C18 .18954(18) .2569(2) .3867(3) .0826(7) Uani d . 1 . . C H18A .2531 .2380 .4498 .124 Uiso calc R 1 . . H H18B .1613 .1801 .3395 .124 Uiso calc R 1 . . H H18C .1485 .2894 .4343 .124 Uiso calc R 1 . . H H12 .3296 .4224 .1782 .071(6) Uiso d R 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 S19 .0491(3) .0693(3) .0530(3) -.00738(17) .01497(18) -.00689(18) O21 .0707(9) .0824(10) .0943(11) -.0200(7) .0170(8) -.0286(8) O7 .0535(7) .1426(14) .0514(7) -.0261(8) .0286(6) -.0203(8) O16 .0821(10) .1003(12) .0759(9) -.0309(9) .0229(8) -.0212(8) O15 .0878(11) .1210(14) .0976(11) -.0441(10) .0503(9) -.0093(10) O20 .0648(8) .1299(14) .0572(8) -.0108(9) .0132(6) .0203(8) N17 .0506(7) .0555(8) .0597(8) -.0035(6) .0187(6) .0047(6) N14 .0523(8) .0684(9) .0625(9) -.0063(7) .0164(7) .0074(7) C10 .0408(7) .0566(9) .0484(8) .0006(6) .0131(6) .0084(6) C12$ .0517(9) .0661(10) .0493(8) .0004(7) .0227(7) -.0039(7) C8 .0428(8) .0678(10) .0434(8) .0027(7) .0183(6) .0053(7) C13 .0421(7) .0529(8) .0461(8) .0039(6) .0150(6) .0061(6) C9 .0467(8) .0653(10) .0445(8) .0025(7) .0155(6) -.0002(7) C11 .0491(8) .0751(11) .0511(8) -.0015(8) .0253(7) .0046(8) C3 .0701(12) .0756(12) .0620(11) .0078(9) .0268(9) -.0037(9) C4 .0529(9) .0754(11) .0493(8) -.0099(8) .0271(7) -.0036(8) C22 .0548(11) .0934(15) .0839(14) .0104(10) .0122(10) -.0186(12) C1 .0928(15) .0701(12) .0627(11) -.0159(11) .0371(11) -.0128(9) C2 .0870(14) .0734(12) .0548(10) -.0037(10) .0229(10) .0033(9) C5 .0615(11) .0752(12) .0790(13) .0038(9) .0254(10) .0055(10) C6 .0859(15) .0712(13) .0953(16) .0028(11) .0484(13) -.0201(12) C18 .0760(13) .0714(13) .0967(16) -.0074(10) .0239(12) .0275(11) 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 S19 O21 . 1.4177(15) ? S19 O20 . 1.4183(16) ? S19 N17 . 1.6405(15) ? S19 C22 . 1.745(2) ? O7 C8 . 1.3647(19) ? O7 C4 . 1.395(2) ? O16 N14 . 1.217(2) ? O15 N14 . 1.218(2) ? N17 C13 . 1.428(2) ? N17 C18 . 1.484(2) ? N14 C10 . 1.465(2) ? C10 C9 . 1.378(2) ? C10 C11 . 1.381(3) ? C12$ C11 . 1.382(3) ? C12$ C13 . 1.387(2) ? C12$ H12 . .9229 ? C8 C9 . 1.378(2) ? C8 C13 . 1.399(2) ? C9 H9 . .9300 ? C11 H11 . .9300 ? C3 C4 . 1.373(3) ? C3 C2 . 1.376(3) ? C3 H3 . .9300 ? C4 C5 . 1.377(3) ? C22 H22A . .9600 ? C22 H22B . .9600 ? C22 H22C . .9600 ? C1 C6 . 1.349(3) ? C1 C2 . 1.353(3) ? C1 H1 . .9300 ? C2 H2 . .9300 ? C5 C6 . 1.400(3) ? C5 H5 . .9300 ? C6 H6 . .9300 ? C18 H18A . .9600 ? C18 H18B . .9600 ? C18 H18C . .9600 ?