#------------------------------------------------------------------------------ #$Date: 2010-01-30 13:59:17 +0000 (Sat, 30 Jan 2010) $ #$Revision: 966 $ #$URL: svn://www.crystallography.net/cod/cif/2/2011180.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_2011180 _journal_name_full 'Acta Crystallographica, Section C' _journal_year 2000 _journal_volume 56 _journal_page_first 865 _journal_page_last 867 _publ_section_title ; Hydrogen-bonded molecular ladders in trans-1,2-bis(2-nitroanilino)cyclohexane ; _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 'Ward, Mark F.' 'Wardell, Solange M. S. V.' 'Wardell, James L.' 'Low, John N.' 'Glidewell, Christopher' _chemical_formula_moiety 'C18 H20 N4 O4' _chemical_formula_sum 'C18 H20 N4 O4' _chemical_formula_weight 356.38 _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 13.1140(10) _cell_length_b 12.7121(19) _cell_length_c 20.959(3) _cell_angle_alpha 90.00 _cell_angle_beta 105.594(7) _cell_angle_gamma 90.00 _cell_volume 3365.3(8) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _exptl_crystal_density_diffrn 1.407 _diffrn_ambient_temperature 150(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 O1 -.0423(2) .0934(3) .18727(18) .0341(10) Uani d . 1 . . O O2 -.0812(2) .0784(3) .07987(18) .0428(11) Uani d . 1 . . O O3 .4292(2) .2568(3) .18483(17) .0367(11) Uani d . 1 . . O O4 .3822(2) .2938(3) .0798(2) .0637(14) Uani d . 1 . . O N1 .1558(2) .0794(3) .2596(2) .0224(11) Uani d . 1 . . N N2 .2899(2) .2593(3) .2538(2) .0213(11) Uani d . 1 . . N N3 -.0155(3) .0787(3) .1349(2) .0293(12) Uani d . 1 . . N N4 .3605(3) .2822(3) .1335(2) .0349(13) Uani d . 1 . . N C1 .2376(3) .1133(4) .3184(2) .0227(14) Uani d . 1 . . C C2 .2623(3) .2320(4) .3147(2) .0234(14) Uani d . 1 . . C C3 .3509(3) .2620(4) .3748(2) .0212(13) Uani d . 1 . . C C4 .3212(3) .2395(4) .4389(2) .0263(14) Uani d . 1 . . C C5 .2907(3) .1241(4) .4418(2) .0283(14) Uani d . 1 . . C C6 .2043(3) .0915(4) .3808(2) .0219(14) Uani d . 1 . . C C7 .1741(3) .0554(4) .2005(3) .0195(14) Uani d . 1 . . C C8 .0941(3) .0568(4) .1390(3) .0244(14) Uani d . 1 . . C C9 .1182(3) .0397(3) .0787(3) .0248(14) Uani d . 1 . . C C10 .2195(4) .0147(4) .0777(3) .0325(15) Uani d . 1 . . C C11 .2972(4) .0066(4) .1367(3) .0305(15) Uani d . 1 . . C C12 .2767(3) .0263(4) .1961(3) .0253(15) Uani d . 1 . . C C13 .2224(3) .2896(4) .1960(3) .0203(13) Uani d . 1 . . C C14 .2540(3) .3003(4) .1367(3) .0219(14) Uani d . 1 . . C C15 .1811(3) .3276(4) .0765(3) .0294(14) Uani d . 1 . . C C16 .0777(3) .3478(4) .0739(3) .0307(15) Uani d . 1 . . C C17 .0464(3) .3407(4) .1318(3) .0266(14) Uani d . 1 . . C C18 .1153(3) .3127(4) .1906(3) .0254(14) Uani d . 1 . . C O5 .5095(2) .0850(3) .30688(17) .0296(10) Uani d . 1 . . O O6 .5671(2) .0848(3) .41390(18) .0415(11) Uani d . 1 . . O O7 .9749(2) .2546(3) .29533(18) .0350(11) Uani d . 1 . . O O8 1.0252(2) .2997(3) .39799(17) .0442(12) Uani d . 1 . . O N5 .6430(3) .0703(3) .2333(2) .0230(11) Uani d . 1 . . N N6 .7745(2) .2553(3) .2315(2) .0237(12) Uani d . 1 . . N N7 .5837(3) .0761(3) .3592(2) .0269(12) Uani d . 1 . . N N8 .9540(3) .2818(3) .3474(2) .0299(13) Uani d . 1 . . N C19 .6707(3) .1031(4) .1734(2) .0191(13) Uani d . 1 . . C C20 .6915(3) .2228(4) .1734(2) .0230(14) Uani d . 1 . . C C21 .7222(3) .2526(4) .1105(2) .0230(14) Uani d . 1 . . C C22 .6342(3) .2244(4) .0494(2) .0278(14) Uani d . 1 . . C C23 .6088(3) .1071(4) .0496(2) .0281(14) Uani d . 1 . . C C24 .5809(3) .0754(4) .1126(2) .0239(14) Uani d . 1 . . C C25 .7146(3) .0511(4) .2936(3) .0205(14) Uani d . 1 . . C C26 .6895(3) .0560(4) .3547(3) .0207(14) Uani d . 1 . . C C27 .7663(3) .0433(3) .4147(3) .0296(15) Uani d . 1 . . C C28 .8681(4) .0229(4) .4156(3) .0323(15) Uani d . 1 . . C C29 .8946(3) .0138(4) .3561(3) .0311(16) Uani d . 1 . . C C30 .8210(3) .0270(3) .2973(3) .0230(14) Uani d . 1 . . C C31 .7611(3) .2838(4) .2900(3) .0226(14) Uani d . 1 . . C C32 .8450(3) .2950(4) .3485(3) .0211(14) Uani d . 1 . . C C33 .8279(4) .3155(4) .4103(3) .0270(14) Uani d . 1 . . C C34 .7284(3) .3330(4) .4165(3) .0302(14) Uani d . 1 . . C C35 .6436(3) .3301(4) .3583(3) .0302(15) Uani d . 1 . . C C36 .6593(3) .3073(4) .2987(2) .0240(14) Uani d . 1 . . C H1N1 .0904 .0742 .2627 .027 Uiso calc R 1 . . H H1N2 .3574 .2555 .2549 .026 Uiso calc R 1 . . H H1 .3037 .0727 .3205 .014(5) Uiso calc R 1 . . H H2 .1977 .2728 .3160 .014(5) Uiso calc R 1 . . H H3A .3669 .3378 .3726 .022(3) Uiso calc R 1 . . H H3B .4155 .2219 .3745 .022(3) Uiso calc R 1 . . H H4A .2610 .2848 .4415 .022(3) Uiso calc R 1 . . H H4B .3819 .2561 .4773 .022(3) Uiso calc R 1 . . H H5A .3540 .0796 .4454 .022(3) Uiso calc R 1 . . H H5B .2658 .1122 .4818 .022(3) Uiso calc R 1 . . H H6A .1893 .0155 .3834 .022(3) Uiso calc R 1 . . H H6B .1385 .1308 .3794 .022(3) Uiso calc R 1 . . H H9 .0641 .0455 .0383 .028(3) Uiso calc R 1 . . H H10 .2359 .0032 .0368 .028(3) Uiso calc R 1 . . H H11 .3667 -.0133 .1360 .028(3) Uiso calc R 1 . . H H12 .3327 .0205 .2356 .028(3) Uiso calc R 1 . . H H15 .2039 .3319 .0372 .028(3) Uiso calc R 1 . . H H16 .0284 .3664 .0333 .028(3) Uiso calc R 1 . . H H17 -.0250 .3557 .1306 .028(3) Uiso calc R 1 . . H H18 .0904 .3087 .2291 .028(3) Uiso calc R 1 . . H H1N5 .5754 .0622 .2307 .028 Uiso calc R 1 . . H H1N6 .8396 .2561 .2277 .028 Uiso calc R 1 . . H H19 .7361 .0649 .1708 .014(5) Uiso calc R 1 . . H H20 .6247 .2606 .1736 .014(5) Uiso calc R 1 . . H H21A .7363 .3291 .1107 .022(3) Uiso calc R 1 . . H H21B .7878 .2151 .1094 .022(3) Uiso calc R 1 . . H H22A .6564 .2419 .0090 .022(3) Uiso calc R 1 . . H H22B .5700 .2660 .0487 .022(3) Uiso calc R 1 . . H H23A .5487 .0905 .0109 .022(3) Uiso calc R 1 . . H H23B .6709 .0659 .0455 .022(3) Uiso calc R 1 . . H H24A .5674 -.0012 .1120 .022(3) Uiso calc R 1 . . H H24B .5155 .1122 .1150 .022(3) Uiso calc R 1 . . H H27 .7472 .0488 .4552 .028(3) Uiso calc R 1 . . H H28 .9206 .0149 .4565 .028(3) Uiso calc R 1 . . H H29 .9656 -.0019 .3565 .028(3) Uiso calc R 1 . . H H30 .8418 .0199 .2575 .028(3) Uiso calc R 1 . . H H33 .8864 .3174 .4486 .028(3) Uiso calc R 1 . . H H34 .7165 .3467 .4584 .028(3) Uiso calc R 1 . . H H35 .5739 .3445 .3611 .028(3) Uiso calc R 1 . . H H36 .5999 .3069 .2608 .028(3) 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 O1 .0243(19) .052(3) .026(3) -.0009(16) .0065(17) -.007(2) O2 .0281(19) .067(3) .026(3) .0057(18) -.0057(18) -.006(2) O3 .0206(18) .060(3) .028(3) .0010(18) .0050(17) .005(2) O4 .045(2) .124(4) .031(3) .020(2) .026(2) .022(3) N1 .014(2) .033(3) .021(3) -.0040(18) .007(2) -.003(2) N2 .013(2) .034(3) .020(3) -.0014(19) .009(2) -.005(3) N3 .028(3) .027(3) .031(4) .000(2) .005(2) -.005(3) N4 .029(3) .048(4) .029(4) .001(2) .010(3) .004(3) C1 .019(3) .029(4) .020(4) .007(2) .003(3) .000(3) C2 .019(3) .030(4) .022(4) .008(2) .006(2) .000(3) C3 .021(3) .023(4) .018(4) .000(2) .003(2) -.005(3) C4 .022(3) .037(4) .014(4) .003(2) -.004(2) -.002(3) C5 .037(3) .024(4) .025(4) -.001(3) .010(3) .003(3) C6 .021(3) .021(3) .023(4) -.001(2) .004(2) .003(3) C7 .021(3) .016(3) .024(4) -.003(2) .009(3) -.004(3) C8 .024(3) .027(4) .023(4) -.001(2) .008(3) -.003(3) C9 .030(3) .020(4) .022(4) -.003(2) .001(3) .003(3) C10 .047(3) .024(4) .033(5) .000(3) .024(3) -.004(3) C11 .025(3) .028(4) .039(5) -.003(2) .009(3) -.013(3) C12 .022(3) .026(4) .025(4) -.001(2) .002(3) -.009(3) C13 .019(3) .021(4) .019(4) .000(2) .000(2) .002(3) C14 .022(3) .021(4) .025(4) -.004(2) .009(3) -.003(3) C15 .033(3) .038(4) .018(4) -.002(3) .008(3) -.001(3) C16 .033(3) .031(4) .025(4) .001(2) .002(3) -.002(3) C17 .025(3) .025(4) .032(4) .005(2) .011(3) .003(3) C18 .020(3) .026(4) .030(4) -.006(2) .006(3) .003(3) O5 .0246(17) .044(3) .019(3) .0006(17) .0038(16) -.001(2) O6 .042(2) .061(3) .027(3) .0044(18) .020(2) .003(2) O7 .0224(19) .058(3) .027(3) -.0009(16) .0102(17) -.010(2) O8 .0260(19) .071(3) .029(3) .0035(18) -.0040(18) -.019(2) N5 .017(2) .035(3) .018(3) -.0073(19) .007(2) .001(3) N6 .015(2) .037(3) .019(3) -.0035(18) .005(2) -.002(2) N7 .033(3) .026(3) .027(4) -.003(2) .017(2) .003(3) N8 .025(3) .031(3) .032(4) -.003(2) .005(2) -.004(3) C19 .016(2) .019(4) .022(4) .000(2) .004(2) .003(3) C20 .015(3) .037(4) .017(4) .002(2) .005(2) -.004(3) C21 .022(3) .026(4) .021(4) .001(2) .006(2) .003(3) C22 .026(3) .039(4) .019(4) .004(3) .007(2) .008(3) C23 .027(3) .037(4) .017(4) .001(3) -.001(2) .001(3) C24 .026(3) .023(4) .023(4) -.002(2) .007(3) -.003(3) C25 .022(3) .015(4) .024(4) -.003(2) .003(3) -.001(3) C26 .018(3) .025(4) .021(4) -.002(2) .009(3) -.003(3) C27 .030(3) .033(4) .024(4) .003(3) .004(3) .004(3) C28 .032(3) .042(4) .017(4) .002(3) -.003(3) .002(3) C29 .020(3) .034(4) .036(5) .005(2) .002(3) .004(3) C30 .017(3) .023(4) .030(4) -.001(2) .008(3) .001(3) C31 .021(3) .025(4) .024(4) -.005(2) .009(3) .004(3) C32 .020(3) .025(4) .021(4) -.002(2) .010(3) -.001(3) C33 .035(3) .024(4) .020(4) -.006(2) .003(3) -.004(3) C34 .040(3) .033(4) .023(4) -.003(3) .020(3) -.012(3) C35 .026(3) .034(4) .034(4) -.006(2) .016(3) -.004(3) C36 .022(3) .029(4) .021(4) .001(2) .006(2) -.002(3) 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 O1 N3 . 1.253(5) y O2 N3 . 1.240(5) y O3 N4 . 1.247(5) y O4 N4 . 1.242(5) y N1 C1 . 1.465(5) y N1 C7 . 1.357(5) y N1 H1N1 . .8800 no N2 C2 . 1.459(5) y N2 C13 . 1.351(5) y N2 H1N2 . .8800 no N3 C8 . 1.444(5) y N4 C14 . 1.435(5) y C1 C6 . 1.513(6) no C1 C2 . 1.549(6) no C1 H1 . 1.0000 no C2 C3 . 1.515(5) no C2 H2 . 1.0000 no C3 C4 . 1.523(6) no C3 H3A . .9900 no C3 H3B . .9900 no C4 C5 . 1.526(5) no C4 H4A . .9900 no C4 H4B . .9900 no C5 C6 . 1.520(5) no C5 H5A . .9900 no C5 H5B . .9900 no C6 H6A . .9900 no C6 H6B . .9900 no C7 C8 . 1.427(6) ? C8 C9 . 1.400(6) ? C9 C10 . 1.371(5) ? C9 H9 . .9500 no C10 C11 . 1.378(6) ? C10 H10 . .9500 no C11 C12 . 1.365(6) ? C11 H11 . .9500 no C12 C7 . 1.423(5) ? C12 H12 . .9500 no C13 C14 . 1.419(6) ? C14 C15 . 1.407(6) ? C15 C16 . 1.368(5) ? C15 H15 . .9500 no C16 C17 . 1.385(6) ? C16 H16 . .9500 no C17 C18 . 1.365(6) ? C17 H17 . .9500 no C18 C13 . 1.409(5) ? C18 H18 . .9500 no O5 N7 . 1.261(4) y O6 N7 . 1.227(5) y O7 N8 . 1.244(5) y O8 N8 . 1.231(4) y N5 C19 . 1.459(5) y N5 C25 . 1.379(5) y N5 H1N5 . .8800 no N6 C20 . 1.458(5) y N6 C31 . 1.334(5) y N6 H1N6 . .8800 no N7 C26 . 1.437(5) y N8 C32 . 1.445(5) y C19 C24 . 1.525(5) no C19 C20 . 1.545(6) no C19 H19 . 1.0000 no C20 C21 . 1.525(6) no C20 H20 . 1.0000 no C21 C22 . 1.519(5) no C21 H21A . .9900 no C21 H21B . .9900 no C22 C23 . 1.529(6) no C22 H22A . .9900 no C22 H22B . .9900 no C23 C24 . 1.517(6) no C23 H23A . .9900 no C23 H23B . .9900 no C24 H24A . .9900 no C24 H24B . .9900 no C25 C26 . 1.407(6) ? C26 C27 . 1.394(6) ? C27 C28 . 1.355(5) ? C27 H27 . .9500 no C28 C29 . 1.388(6) ? C28 H28 . .9500 no C29 C30 . 1.355(6) ? C29 H29 . .9500 no C30 C25 . 1.410(5) ? C30 H30 . .9500 no C31 C32 . 1.417(6) ? C32 C33 . 1.398(6) ? C33 C34 . 1.364(5) ? C33 H33 . .9500 no C34 C35 . 1.413(6) ? C34 H34 . .9500 no C35 C36 . 1.351(6) ? C35 H35 . .9500 no C36 C31 . 1.427(5) ? C36 H36 . .9500 no _cod_database_code 2011180