#------------------------------------------------------------------------------ #$Date: 2010-01-30 13:59:17 +0000 (Sat, 30 Jan 2010) $ #$Revision: 966 $ #$URL: svn://www.crystallography.net/cod/cif/2/2011542.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_2011542 _journal_name_full 'Acta Crystallographica, Section C' _journal_year 2000 _journal_volume 56 _journal_page_first e509 _journal_page_last e510 _publ_section_title ; 4,5-Dichlorophthalic acid--trans-cinnamamide (1/2) and 3,4,5,6-tetrachlorophthalic acid--trans-cinnamamide (1/2) ; loop_ _publ_author_name 'Hosomi, Hiroyuki' 'Ohba, Shigeru' 'Ito, Yoshikatsu' _chemical_formula_moiety 'C8 H2 Cl4 O4, 2C9 H9 N1 O1' _chemical_formula_sum 'C26 H20 Cl4 N2 O6' _chemical_formula_iupac 'C8 H2 Cl4 O4, 2C9 H9 N1 O1' _chemical_formula_weight 598.27 _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z _cell_length_a 9.937(2) _cell_length_b 15.895(4) _cell_length_c 9.015(2) _cell_angle_alpha 93.48(2) _cell_angle_beta 110.570(10) _cell_angle_gamma 91.58(2) _cell_volume 1328.8(5) _cell_formula_units_Z 2 _cell_measurement_temperature 298.0(10) _exptl_crystal_density_diffrn 1.495 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 Cl1 .49893(6) .23519(4) -.17381(6) .0550(2) Uani d . 1.00 . . Cl Cl2 .64513(7) .41052(4) -.03325(7) .0635(2) Uani d . 1.00 . . Cl Cl3 .65204(7) .48141(4) .29897(8) .0643(2) Uani d . 1.00 . . Cl Cl4 .50722(7) .37683(4) .48784(7) .0607(2) Uani d . 1.00 . . Cl O5 .4875(2) .17930(10) .4817(2) .0567(4) Uani d . 1.00 . . O O6 .2718(2) .16860(10) .2854(2) .0551(4) Uani d . 1.00 . . O O7 .4347(2) .07527(9) .1171(2) .0536(4) Uani d . 1.00 . . O O8 .2709(2) .13090(10) -.0871(2) .0609(4) Uani d . 1.00 . . O O9 .1870(2) .04000(10) .3962(2) .0590(4) Uani d . 1.00 . . O O10 .2815(2) -.05220(10) .0875(2) .0695(5) Uani d . 1.00 . . O N11 .3913(3) .0297(2) .6034(3) .0685(6) Uani d . 1.00 . . N N12 .0986(2) -.02010(10) -.1292(3) .0569(5) Uani d . 1.00 . . N C13 .4064(2) .19670(10) .3535(2) .0430(4) Uani d . 1.00 . . C C14 .4556(2) .25340(10) .2517(2) .0383(4) Uani d . 1.00 . . C C15 .5132(2) .33440(10) .3097(2) .0406(4) Uani d . 1.00 . . C C16 .5719(2) .38350(10) .2217(3) .0432(4) Uani d . 1.00 . . C C17 .5685(2) .35180(10) .0734(2) .0427(4) Uani d . 1.00 . . C C18 .5043(2) .27210(10) .0119(2) .0401(4) Uani d . 1.00 . . C C19 .4483(2) .22260(10) .1004(2) .0383(4) Uani d . 1.00 . . C C20 .3764(2) .13670(10) .0330(2) .0424(4) Uani d . 1.00 . . C C21 .2616(3) .00150(10) .5111(3) .0497(5) Uani d . 1.00 . . C C22 .2127(3) -.0784(2) .5549(3) .0558(6) Uani d . 1.00 . . C C23 .0864(3) -.1170(2) .4802(3) .0540(5) Uani d . 1.00 . . C C24 .0322(2) -.19660(10) .5209(3) .0497(5) Uani d . 1.00 . . C C25 -.1025(3) -.2299(2) .4246(3) .0565(6) Uani d . 1.00 . . C C26 -.1583(3) -.3039(2) .4577(4) .0659(7) Uani d . 1.00 . . C C27 -.0817(3) -.3456(2) .5868(4) .0678(7) Uani d . 1.00 . . C C28 .0522(3) -.3132(2) .6834(4) .0688(7) Uani d . 1.00 . . C C29 .1096(3) -.2390(2) .6514(3) .0610(6) Uani d . 1.00 . . C C30 .1571(2) -.06900(10) -.0148(3) .0488(5) Uani d . 1.00 . . C C31 .0757(3) -.14590(10) -.0068(3) .0520(5) Uani d . 1.00 . . C C32 .1273(3) -.19610(10) .1102(3) .0497(5) Uani d . 1.00 . . C C33 .0623(2) -.27700(10) .1278(3) .0493(5) Uani d . 1.00 . . C C34 -.0698(3) -.3102(2) .0222(4) .0637(7) Uani d . 1.00 . . C C35 -.1225(3) -.3881(2) .0424(4) .0822(9) Uani d . 1.00 . . C C36 -.0447(4) -.4341(2) .1665(5) .0823(9) Uani d . 1.00 . . C C37 .0843(4) -.4016(2) .2715(4) .0767(8) Uani d . 1.00 . . C C38 .1376(3) -.3229(2) .2528(3) .0601(6) Uani d . 1.00 . . C H6 .251(4) .128(2) .345(4) .09620(10) Uiso d . 1.00 . . H H7 .367(4) .022(2) .089(4) .1159(2) Uiso d . 1.00 . . H H11A .422(3) .073(2) .582(3) .06250(10) Uiso d . 1.00 . . H H11B .439(4) -.002(2) .681(5) .1079(2) Uiso d . 1.00 . . H H12A .144(3) .028(2) -.133(3) .06037(9) Uiso d . 1.00 . . H H12B .014(4) -.034(2) -.203(4) .08500(10) Uiso d . 1.00 . . H H22 .278(4) -.104(2) .640(4) .10720(10) Uiso d . 1.00 . . H H23 .023(3) -.089(2) .389(4) .08090(10) Uiso d . 1.00 . . H H25 -.156(3) -.201(2) .335(4) .07560(10) Uiso d . 1.00 . . H H26 -.248(4) -.326(2) .392(4) .09050(10) Uiso d . 1.00 . . H H27 -.119(3) -.396(2) .609(4) .08290(10) Uiso d . 1.00 . . H H28 .101(3) -.336(2) .769(3) .07150(10) Uiso d . 1.00 . . H H29 .204(3) -.217(2) .723(3) .07180(10) Uiso d . 1.00 . . H H31 -.017(3) -.160(2) -.092(3) .07510(10) Uiso d . 1.00 . . H H32 .223(3) -.180(2) .196(3) .06392(9) Uiso d . 1.00 . . H H34 -.123(3) -.280(2) -.064(3) .07240(10) Uiso d . 1.00 . . H H35 -.215(4) -.411(2) -.035(4) .1119(2) Uiso d . 1.00 . . H H36 -.081(4) -.493(2) .170(4) .10160(10) Uiso d . 1.00 . . H H37 .138(3) -.431(2) .355(4) .08620(10) Uiso d . 1.00 . . H H38 .224(3) -.301(2) .326(3) .06197(9) Uiso d . 1.00 . . 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 Cl1 .0602(3) .0640(4) .0420(3) -.0087(3) .0213(2) -.0018(2) Cl2 .0689(4) .0640(4) .0612(4) -.0174(3) .0268(3) .0174(3) Cl3 .0750(4) .0415(3) .0736(4) -.0175(3) .0256(3) -.0052(3) Cl4 .0696(4) .0611(4) .0547(3) -.0114(3) .0301(3) -.0137(3) O5 .0578(9) .0660(10) .0400(8) -.0163(8) .0093(7) .0122(7) O6 .0426(8) .0640(10) .0564(9) -.0130(7) .0133(7) .0182(8) O7 .0507(9) .0377(8) .0585(9) -.0060(6) .0021(7) .0066(7) O8 .0650(10) .0507(9) .0465(8) -.0200(8) -.0044(8) .0096(7) O9 .0509(9) .0600(10) .0622(10) -.0125(7) .0143(8) .0168(8) O10 .0580(10) .0460(9) .0820(10) -.0142(8) -.0034(9) .0181(8) N11 .0660(10) .0640(10) .0650(10) -.0120(10) .0090(10) .0210(10) N12 .0570(10) .0470(10) .0560(10) -.0147(9) .0080(10) .0092(9) C13 .0450(10) .0420(10) .0410(10) -.0063(8) .0152(9) .0024(8) C14 .0345(9) .0386(10) .0394(9) -.0040(7) .0100(8) .0048(8) C15 .0401(10) .0385(10) .0418(10) -.0031(8) .0135(8) -.0001(8) C16 .0410(10) .0334(9) .0520(10) -.0053(8) .0122(9) .0032(8) C17 .0381(10) .0440(10) .0450(10) -.0043(8) .0140(8) .0113(8) C18 .0362(10) .0450(10) .0369(9) -.0011(8) .0099(8) .0044(8) C19 .0346(9) .0394(10) .0374(9) -.0033(7) .0084(8) .0049(8) C20 .0460(10) .0377(10) .0410(10) -.0080(8) .0127(9) .0028(8) C21 .0550(10) .0490(10) .0510(10) .0004(10) .0250(10) .0088(10) C22 .0570(10) .0560(10) .0590(10) .0010(10) .0230(10) .0150(10) C23 .0550(10) .0570(10) .0530(10) .0010(10) .0220(10) .0140(10) C24 .0520(10) .0480(10) .0560(10) .0019(9) .0260(10) .0106(10) C25 .0560(10) .0530(10) .0600(10) .0020(10) .0190(10) .0180(10) C26 .0570(10) .060(2) .077(2) -.0090(10) .0180(10) .0150(10) C27 .068(2) .0500(10) .088(2) -.0040(10) .0290(10) .0240(10) C28 .067(2) .070(2) .069(2) .0070(10) .0190(10) .0320(10) C29 .0510(10) .067(2) .0630(10) -.0030(10) .0170(10) .0140(10) C30 .0480(10) .0400(10) .0550(10) -.0048(9) .0143(10) .0024(9) C31 .0490(10) .0430(10) .0600(10) -.0078(9) .0150(10) .0035(10) C32 .0470(10) .0410(10) .0600(10) -.0039(9) .0180(10) .0034(10) C33 .0480(10) .0440(10) .0610(10) -.0004(9) .0250(10) .0052(10) C34 .0550(10) .0520(10) .079(2) -.0070(10) .0170(10) .0160(10) C35 .065(2) .067(2) .106(2) -.0220(10) .019(2) .018(2) C36 .082(2) .057(2) .112(3) -.0120(10) .038(2) .026(2) C37 .076(2) .068(2) .089(2) .0030(10) .030(2) .033(2) C38 .0560(10) .0560(10) .068(2) -.0010(10) .0210(10) .0130(10) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag Cl1 C18 . . 1.722(2) yes Cl2 C17 . . 1.720(3) yes Cl3 C16 . . 1.718(2) yes Cl4 C15 . . 1.725(2) yes O5 C13 . . 1.208(2) yes O6 C13 . . 1.312(2) yes O6 H6 . . .93(4) no O7 C20 . . 1.294(2) yes O7 H7 . . 1.03(4) no O8 C20 . . 1.210(2) yes O9 C21 . . 1.249(3) yes O10 C30 . . 1.265(3) yes N11 C21 . . 1.313(3) yes N11 H11A . . .81(3) no N11 H11B . . .89(4) no N12 C30 . . 1.306(3) yes N12 H12A . . .88(3) no N12 H12B . . .88(3) no C13 C14 . . 1.511(3) no C14 C15 . . 1.389(3) no C14 C19 . . 1.397(3) no C15 C16 . . 1.397(3) no C16 C17 . . 1.389(3) no C17 C18 . . 1.393(3) no C18 C19 . . 1.389(3) no C19 C20 . . 1.511(3) no C21 C22 . . 1.472(4) yes C22 C23 . . 1.311(3) yes C22 H22 . . .94(3) no C23 C24 . . 1.477(4) no C23 H23 . . .99(3) no C24 C25 . . 1.383(3) no C24 C29 . . 1.385(3) no C25 C26 . . 1.379(4) no C25 H25 . . .95(3) no C26 C27 . . 1.369(4) no C26 H26 . . .93(3) no C27 C28 . . 1.375(4) no C27 H27 . . .94(3) no C28 C29 . . 1.385(4) no C28 H28 . . .87(3) no C29 H29 . . .97(3) no C30 C31 . . 1.467(3) yes C31 C32 . . 1.326(3) yes C31 H31 . . .98(3) no C32 C33 . . 1.465(3) no C32 H32 . . 1.01(2) no C33 C34 . . 1.390(3) no C33 C38 . . 1.378(3) no C34 C35 . . 1.379(4) no C34 H34 . . .94(3) no C35 C36 . . 1.381(5) no C35 H35 . . .98(3) no C36 C37 . . 1.363(4) no C36 H36 . . 1.01(4) no C37 C38 . . 1.388(4) no C37 H37 . . .92(3) no C38 H38 . . .92(2) no _cod_database_code 2011542