#------------------------------------------------------------------------------ #$Date: 2011-09-28 16:24:46 +0200 (Wed, 28 Sep 2011) $ #$Revision: 26848 $ #$URL: svn://www.crystallography.net/cod/cif/2/01/22/2012214.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_2012214 _journal_name_full 'Acta Crystallographica, Section C' _journal_year 2001 _journal_volume 57 _journal_page_first 1112 _journal_page_last 1115 _publ_section_title ; X-ray investigations of sulfur-containing fungicides. IV. 4'-{[Benzoyl(4-chlorophenylhydrazono)methyl]sulfonyl}acetanilide and 4'-{[benzoyl(4-methoxyphenylhydrazono)methyl]sulfonyl}acetanilide ; _space_group_IT_number 14 _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _[local]_cod_cif_authors_sg_H-M 'P 21/n' loop_ _publ_author_name 'Wolf, Wojciech M.' _chemical_formula_moiety 'C22 H18 Cl N3 O4 S' _chemical_formula_sum 'C22 H18 Cl N3 O4 S' _chemical_formula_weight 455.90 _symmetry_cell_setting monoclinic loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 11.603(4) _cell_length_b 7.5960(10) _cell_length_c 24.110(4) _cell_angle_alpha 90 _cell_angle_beta 96.44(2) _cell_angle_gamma 90 _cell_volume 2111.6(9) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _exptl_crystal_density_diffrn 1.434 _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 S .61868(9) .60363(15) .18650(4) .0585(3) Uani d . 1 . . S Cl .47058(12) .2171(2) .52316(4) .0921(4) Uani d . 1 . . Cl O1 .6105(3) .7858(4) .17140(11) .0743(9) Uani d . 1 . . O O2 .7079(2) .5511(5) .23044(10) .0755(9) Uani d . 1 . . O O3 .3862(2) .5934(4) .12263(10) .0666(8) Uani d . 1 . . O O4 .6324(3) -.0928(4) .00754(13) .0799(9) Uani d . 1 . . O N1 .4748(2) .4714(4) .26002(11) .0463(7) Uani d . 1 . . N N2 .5589(3) .4417(5) .29851(12) .0518(8) Uani d . 1 . . N H2 .628(4) .459(6) .2941(18) .088(16) Uiso d . 1 . . H N3 .6403(3) .1915(5) -.01967(14) .0569(9) Uani d . 1 . . N H3 .633(4) .256(6) -.0490(17) .074(14) Uiso d . 1 . . H C1 .4851(3) .5346(5) .21046(14) .0484(9) Uani d . 1 . . C C2 .3792(3) .5511(5) .17141(13) .0479(9) Uani d . 1 . . C C3 .2618(3) .5137(5) .18941(13) .0454(8) Uani d . 1 . . C C4 .2289(3) .5739(5) .23997(14) .0515(9) Uani d . 1 . . C H4 .283(2) .635(3) .2659(11) .072(6) Uiso calc R 1 . . H C5 .1172(3) .5443(6) .25196(16) .0611(11) Uani d . 1 . . C H5 .0922(10) .5897(18) .2893(14) .072(6) Uiso calc R 1 . . H C6 .0395(4) .4571(6) .21595(17) .0690(13) Uani d . 1 . . C H6 -.033(3) .4396(10) .2246(4) .072(6) Uiso calc R 1 . . H C7 .0708(4) .3951(6) .16619(17) .0689(12) Uani d . 1 . . C H7 .020(2) .335(3) .1427(11) .072(6) Uiso calc R 1 . . H C8 .1817(3) .4263(5) .15270(15) .0560(10) Uani d . 1 . . C H8 .2039(9) .3855(17) .1164(14) .072(6) Uiso calc R 1 . . H C9 .6342(3) .4788(5) .12698(14) .0497(9) Uani d . 1 . . C C10 .6524(4) .2996(6) .13097(17) .0669(12) Uani d . 1 . . C H10 .6628(6) .244(2) .1664(14) .059(6) Uiso calc R 1 . . H C11 .6554(4) .2008(6) .08308(16) .0698(13) Uani d . 1 . . C H11 .6641(6) .094(5) .08530(19) .059(6) Uiso calc R 1 . . H C12 .6436(3) .2822(5) .03106(14) .0496(9) Uani d . 1 . . C C13 .6327(3) .4635(5) .02829(15) .0484(9) Uani d . 1 . . C H13 .6302(3) .521(2) -.0066(14) .059(6) Uiso calc R 1 . . H C14 .6256(3) .5606(5) .07553(14) .0496(9) Uani d . 1 . . C H14 .6156(5) .676(5) .07315(17) .059(6) Uiso calc R 1 . . H C15 .6326(3) .0163(6) -.02914(18) .0608(11) Uani d . 1 . . C C16 .6238(4) -.0357(6) -.08984(19) .0840(16) Uani d . 1 . . C H161 .5635(18) .0218(18) -.1090(6) .138(13) Uiso calc R 1 . . H H162 .6122(6) -.154(4) -.0930(2) .138(13) Uiso calc R 1 . . H H163 .691(2) -.0068(11) -.1040(5) .138(13) Uiso calc R 1 . . H C17 .5355(3) .3827(5) .35146(13) .0443(8) Uani d . 1 . . C C18 .4232(3) .3653(6) .36444(15) .0595(11) Uani d . 1 . . C H18 .361(3) .3889(11) .3381(11) .067(6) Uiso calc R 1 . . H C19 .4057(3) .3120(6) .41750(15) .0638(12) Uani d . 1 . . C H19 .335(3) .3000(8) .4263(4) .067(6) Uiso calc R 1 . . H C20 .4973(3) .2780(5) .45611(14) .0539(10) Uani d . 1 . . C C21 .6070(4) .2875(6) .44284(16) .0685(12) Uani d . 1 . . C H21 .672(3) .2565(14) .4703(11) .067(6) Uiso calc R 1 . . H C22 .6264(3) .3413(6) .39015(15) .0623(11) Uani d . 1 . . C H22 .701(3) .3494(7) .3810(4) .067(6) Uiso calc 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 S .0580(6) .0750(7) .0460(5) -.0130(5) .0214(4) .0020(5) Cl .1214(10) .1121(11) .0470(6) .0171(9) .0280(6) .0208(6) O1 .099(2) .0637(19) .0662(18) -.0203(17) .0381(16) -.0003(15) O2 .0473(15) .130(3) .0505(16) -.0166(17) .0100(12) .0048(17) O3 .0652(17) .095(2) .0413(14) .0081(16) .0158(12) .0225(14) O4 .094(2) .0602(19) .088(2) .0048(17) .0228(18) .0212(17) N1 .0482(16) .0527(18) .0394(16) .0006(15) .0108(13) .0030(14) N2 .0422(17) .072(2) .0424(17) -.0043(17) .0110(14) .0050(15) N3 .069(2) .057(2) .0483(19) .0063(17) .0254(16) .0091(17) C1 .052(2) .054(2) .0415(19) -.0046(18) .0157(16) .0024(17) C2 .056(2) .052(2) .0373(19) .0049(18) .0141(15) .0048(16) C3 .050(2) .051(2) .0359(17) .0050(17) .0076(15) .0090(16) C4 .058(2) .059(2) .039(2) .0051(19) .0111(16) -.0004(17) C5 .061(2) .079(3) .046(2) .011(2) .0208(19) .009(2) C6 .050(2) .094(3) .065(3) .000(2) .014(2) .020(3) C7 .064(3) .085(3) .056(2) -.018(2) .002(2) .006(2) C8 .064(2) .066(3) .0388(19) .002(2) .0080(17) .0020(18) C9 .047(2) .061(3) .0436(19) .0008(19) .0175(15) .0081(18) C10 .085(3) .072(3) .046(2) .016(2) .022(2) .022(2) C11 .102(3) .054(3) .059(3) .024(2) .031(2) .021(2) C12 .049(2) .056(2) .048(2) .0067(18) .0206(16) .0066(18) C13 .049(2) .057(2) .0420(19) -.0015(18) .0175(15) .0138(18) C14 .053(2) .052(2) .046(2) -.0017(18) .0161(16) .0061(17) C15 .061(2) .054(3) .071(3) .005(2) .026(2) .006(2) C16 .104(4) .074(3) .079(3) -.012(3) .032(3) -.016(3) C17 .0429(18) .054(2) .0370(17) -.0006(17) .0091(14) .0028(16) C18 .0435(19) .090(3) .046(2) .001(2) .0071(16) .018(2) C19 .051(2) .088(3) .056(2) .001(2) .0212(19) .014(2) C20 .067(2) .055(2) .042(2) .007(2) .0146(18) .0033(17) C21 .058(2) .097(3) .049(2) .011(2) -.0004(19) .015(2) C22 .043(2) .092(3) .053(2) .003(2) .0094(17) .007(2) 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 S O1 . 1.431(3) y S O2 . 1.451(3) y S C1 . 1.792(3) y S C9 . 1.746(4) y O3 C2 . 1.231(4) y N1 N2 . 1.289(4) y N1 C1 . 1.306(4) y N2 C17 . 1.408(4) y C1 C2 . 1.467(5) y C2 C3 . 1.502(5) y C3 C8 . 1.380(5) n C3 C4 . 1.395(5) n C4 C5 . 1.378(5) n C5 C6 . 1.352(6) n C6 C7 . 1.375(6) n C7 C8 . 1.383(5) n C9 C10 . 1.379(6) n C9 C14 . 1.381(5) n C10 C11 . 1.381(6) n C11 C12 . 1.391(5) n C12 C13 . 1.384(5) n C13 C14 . 1.367(5) n C17 C22 . 1.364(5) n C17 C18 . 1.380(5) n C18 C19 . 1.379(5) n C19 C20 . 1.357(5) n C20 C21 . 1.349(5) n C21 C22 . 1.377(5) n N3 C12 . 1.400(5) y N3 C15 . 1.352(5) y O4 C15 . 1.212(5) y C15 C16 . 1.508(6) n Cl C20 . 1.742(3) y N2 H2 . .83(4) n N3 H3 . .86(4) n C4 H4 . .95 n C5 H5 . 1.04 n C6 H6 . .90 n C7 H7 . .90 n C8 H8 . .99 n C10 H10 . .95 n C11 H11 . .82 n C13 H13 . .94 n C14 H14 . .88 n C16 H161 . .91 n C16 H162 . .91 n C16 H163 . .91 n C18 H18 . .92 n C19 H19 . .87 n C21 H21 . .98 n C22 H22 . .92 n _cod_database_code 2012214