#------------------------------------------------------------------------------ #$Date: 2009-11-16 01:43:51 +0000 (Mon, 16 Nov 2009) $ #$Revision: 853 $ #$URL: svn://www.crystallography.net/cod/cif/2/2006550.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_2006550 _journal_name_full 'Acta Crystallographica Section C' _journal_year 1997 _journal_volume 53 _journal_page_first 1472 _journal_page_last 1475 _publ_section_title ; A Putrescine Triamide from Lilium regale ; _space_group_IT_number 14 _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _[local]_cod_cif_authors_sg_H-M 'P 21/c' loop_ _publ_author_name 'Linden, Anthony' 'Kuehne, Paul' 'Hesse, Manfred' _chemical_formula_moiety 'C18 H22 N2 O4' _chemical_formula_sum 'C18 H22 N2 O4' _chemical_formula_weight 330.38 _chemical_melting_point 466 _symmetry_cell_setting 'monoclinic' 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 16.488(7) _cell_length_b 18.221(3) _cell_length_c 11.670(8) _cell_angle_alpha 90.00 _cell_angle_beta 103.76(4) _cell_angle_gamma 90.00 _cell_volume 3405(3) _cell_formula_units_Z 8 _cell_measurement_temperature 173.0(10) _exptl_crystal_density_diffrn 1.289 _diffrn_ambient_temperature 173.0(10) 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_group _atom_site_type_symbol O1 .5262(2) .29684(14) .4091(2) .0414(7) Uani d . 1 . O O7 .5451(2) -.16658(15) .3145(3) .0452(8) Uani d . 1 . O O14 .7615(2) .6363(2) .7986(3) .0569(9) Uani d . 1 . O O17 .6293(2) .6424(2) .4103(3) .0668(10) Uani d . 1 . O N1 .6108(2) .2857(2) .5899(3) .0308(7) Uani d . 1 . N N2 .6982(2) .6227(2) .6020(3) .0353(8) Uani d . 1 . N C1 .5686(2) .2572(2) .4869(3) .0277(8) Uani d . 1 . C C2 .5766(2) .1768(2) .4754(3) .0298(8) Uani d . 1 . C H2 .6165 .1514 .5341 .036 Uiso calc R 1 . H C3 .5304(2) .1387(2) .3864(3) .0286(8) Uani d . 1 . C H3 .4917 .1656 .3281 .034 Uiso calc R 1 . H C4 .5336(2) .0587(2) .3696(3) .0259(8) Uani d . 1 . C C5 .5939(2) .0139(2) .4412(3) .0350(9) Uani d . 1 . C H5 .6337 .0353 .5048 .042 Uiso calc R 1 . H C6 .5967(2) -.0600(2) .4216(3) .0373(10) Uani d . 1 . C H6 .6386 -.0892 .4711 .045 Uiso calc R 1 . H C7 .5388(2) -.0926(2) .3299(3) .0308(9) Uani d . 1 . C C8 .4781(2) -.0498(2) .2584(3) .0346(9) Uani d . 1 . C H8 .4378 -.0717 .1959 .042 Uiso calc R 1 . H C9 .4760(2) .0246(2) .2780(3) .0326(9) Uani d . 1 . C H9 .4343 .0535 .2278 .039 Uiso calc R 1 . H C10 .6029(2) .3621(2) .6223(3) .0357(9) Uani d . 1 . C H10A .6089 .3649 .7087 .043 Uiso calc R 1 . H H10B .5461 .3794 .5837 .043 Uiso calc R 1 . H C11 .6661(2) .4135(2) .5891(3) .0321(9) Uani d . 1 . C H11A .6633 .4086 .5038 .038 Uiso calc R 1 . H H11B .7230 .3993 .6330 .038 Uiso calc R 1 . H C12 .6499(2) .4936(2) .6168(4) .0348(9) Uani d . 1 . C H12A .5943 .5086 .5694 .042 Uiso calc R 1 . H H12B .6495 .4980 .7012 .042 Uiso calc R 1 . H C13 .7159(2) .5444(2) .5900(4) .0399(10) Uani d . 1 . C H13A .7703 .5326 .6439 .048 Uiso calc R 1 . H H13B .7209 .5351 .5084 .048 Uiso calc R 1 . H C14 .7234(3) .6620(2) .7060(4) .0444(11) Uani d . 1 . C C15 .6910(3) .7403(2) .6839(4) .0603(13) Uani d . 1 . C H15 .6396 .7426 .7152 .072 Uiso calc R 1 . H C16 .6607(3) .7443(2) .5496(3) .0437(10) Uani d . 1 . C H16A .6045 .7669 .5267 .052 Uiso calc R 1 . H H16B .6996 .7738 .5155 .052 Uiso calc R 1 . H C17 .6581(3) .6659(2) .5075(4) .0451(11) Uani d . 1 . C C18 .7446(4) .7970(3) .7432(5) .078(2) Uani d . 1 . C H18A .7164 .8445 .7265 .117 Uiso calc R 1 . H H18B .7962 .7976 .7155 .117 Uiso calc R 1 . H H18C .7580 .7879 .8284 .117 Uiso calc R 1 . H H1 .634(3) .255(2) .635(4) .045(13) Uiso d . 1 . H H7 .511(2) -.181(2) .248(3) .032(11) Uiso d . 1 . H O21 .0529(2) .50299(13) -.1078(2) .0405(7) Uani d . 1 . O O27 .0528(2) .03665(14) -.1876(3) .0425(7) Uani d . 1 . O O34 .2699(2) .8344(2) .2825(3) .0597(9) Uani d . 1 . O O37 .1166(2) .8515(2) -.0957(2) .0508(8) Uani d . 1 . O N21 .1446(2) .4880(2) .0671(3) .0364(8) Uani d . 1 . N N22 .1990(2) .8278(2) .0889(3) .0341(8) Uani d . 1 . N C21 .0978(2) .4618(2) -.0348(3) .0313(9) Uani d . 1 . C C22 .1020(2) .3812(2) -.0498(3) .0309(9) Uani d . 1 . C H22 .1403 .3542 .0086 .037 Uiso calc R 1 . H C23 .0553(2) .3448(2) -.1399(3) .0298(9) Uani d . 1 . C H23 .0208 .3727 -.2014 .036 Uiso calc R 1 . H C24 .0529(2) .2647(2) -.1520(3) .0256(8) Uani d . 1 . C C25 .0864(2) .2180(2) -.0577(3) .0365(9) Uani d . 1 . C H25 .1099 .2385 .0177 .044 Uiso calc R 1 . H C26 .0861(3) .1431(2) -.0717(3) .0410(10) Uani d . 1 . C H26 .1096 .1127 -.0059 .049 Uiso calc R 1 . H C27 .0521(2) .1111(2) -.1801(3) .0286(8) Uani d . 1 . C C28 .0169(2) .1560(2) -.2754(3) .0302(8) Uani d . 1 . C H28 -.0075 .1352 -.3503 .036 Uiso calc R 1 . H C29 .0180(2) .2314(2) -.2598(3) .0304(8) Uani d . 1 . C H29 -.0060 .2617 -.3253 .036 Uiso calc R 1 . H C30 .1369(2) .5627(2) .1058(3) .0333(9) Uani d . 1 . C H30A .1477 .5629 .1929 .040 Uiso calc R 1 . H H30B .0786 .5791 .0744 .040 Uiso calc R 1 . H C31 .1949(2) .6179(2) .0690(3) .0349(9) Uani d . 1 . C H31A .1903 .6141 -.0169 .042 Uiso calc R 1 . H H31B .2534 .6073 .1105 .042 Uiso calc R 1 . H C32 .1712(2) .6952(2) .0995(3) .0335(9) Uani d . 1 . C H32A .1758 .6983 .1855 .040 Uiso calc R 1 . H H32B .1123 .7048 .0588 .040 Uiso calc R 1 . H C33 .2265(2) .7541(2) .0642(4) .0379(9) Uani d . 1 . C H33A .2851 .7466 .1083 .046 Uiso calc R 1 . H H33B .2244 .7497 -.0211 .046 Uiso calc R 1 . H C34 .2209(3) .8608(2) .1978(4) .0448(11) Uani d . 1 . C C35 .1714(3) .9324(2) .1958(4) .0561(12) Uani d . 1 . C H35 .1272 .9231 .2398 .067 Uiso calc R 1 . H C36 .1275(3) .9394(2) .0647(3) .0418(10) Uani d . 1 . C H36A .0668 .9467 .0551 .050 Uiso calc R 1 . H H36B .1501 .9818 .0291 .050 Uiso calc R 1 . H C37 .1435(2) .8697(2) .0064(3) .0362(9) Uani d . 1 . C C38 .2214(3) .9936(3) .2530(4) .070(2) Uani d . 1 . C H38A .1857 1.0368 .2512 .106 Uiso calc R 1 . H H38B .2650 1.0046 .2114 .106 Uiso calc R 1 . H H38C .2473 .9807 .3351 .106 Uiso calc R 1 . H H21 .175(2) .459(2) .110(3) .027(10) Uiso d . 1 . H H27 .019(3) .022(2) -.256(4) .060(14) 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 O1 .053(2) .0284(15) .036(2) .0043(13) -.0016(13) .0048(12) O7 .065(2) .026(2) .038(2) .0011(14) -.002(2) -.0051(13) O14 .067(2) .039(2) .049(2) .012(2) -.017(2) .0017(14) O17 .086(3) .060(2) .044(2) -.016(2) -.006(2) -.006(2) N1 .040(2) .018(2) .033(2) .0016(14) .007(2) .0005(14) N2 .036(2) .024(2) .041(2) -.0046(14) -.0016(15) -.0023(14) C1 .026(2) .026(2) .031(2) -.005(2) .008(2) .003(2) C2 .036(2) .024(2) .029(2) -.001(2) .007(2) .0017(15) C3 .031(2) .026(2) .030(2) .001(2) .009(2) .001(2) C4 .029(2) .022(2) .028(2) -.001(2) .010(2) -.0018(15) C5 .047(2) .027(2) .028(2) -.004(2) .002(2) -.003(2) C6 .044(2) .031(2) .032(2) -.002(2) -.001(2) .003(2) C7 .039(2) .025(2) .030(2) -.005(2) .011(2) -.002(2) C8 .034(2) .031(2) .034(2) -.004(2) -.002(2) -.006(2) C9 .033(2) .032(2) .030(2) .002(2) .002(2) .000(2) C10 .042(2) .029(2) .038(2) .000(2) .012(2) -.006(2) C11 .035(2) .025(2) .036(2) .002(2) .007(2) -.003(2) C12 .037(2) .023(2) .044(2) -.002(2) .011(2) -.003(2) C13 .040(2) .026(2) .055(3) .000(2) .013(2) -.005(2) C14 .044(3) .031(2) .048(3) .000(2) -.009(2) .001(2) C15 .072(3) .035(3) .060(3) .004(2) -.013(3) -.004(2) C16 .043(2) .030(2) .049(3) -.004(2) -.006(2) .005(2) C17 .046(3) .036(2) .046(3) -.013(2) -.004(2) .004(2) C18 .112(5) .044(3) .064(3) .010(3) -.005(3) -.013(3) O21 .050(2) .0218(14) .040(2) .0030(12) -.0084(13) .0045(12) O27 .061(2) .019(2) .038(2) .0056(13) -.0076(15) -.0037(12) O34 .076(2) .036(2) .050(2) .016(2) -.019(2) .0009(14) O37 .063(2) .046(2) .036(2) -.0111(15) -.0025(15) -.0037(14) N21 .043(2) .016(2) .042(2) .0032(14) -.007(2) .0012(14) N22 .041(2) .023(2) .035(2) -.0039(14) .003(2) .0000(14) C21 .030(2) .024(2) .036(2) .002(2) .000(2) .001(2) C22 .034(2) .020(2) .035(2) .002(2) .001(2) .002(2) C23 .032(2) .023(2) .032(2) .003(2) .002(2) .000(2) C24 .026(2) .022(2) .028(2) .0022(15) .004(2) .0004(15) C25 .047(2) .030(2) .028(2) -.003(2) .000(2) -.003(2) C26 .060(3) .023(2) .033(2) .005(2) -.004(2) .004(2) C27 .030(2) .023(2) .030(2) .003(2) .002(2) -.001(2) C28 .033(2) .024(2) .030(2) -.003(2) .000(2) -.008(2) C29 .033(2) .027(2) .027(2) .001(2) -.001(2) .003(2) C30 .039(2) .024(2) .034(2) .000(2) .003(2) -.003(2) C31 .037(2) .026(2) .041(2) .002(2) .007(2) -.006(2) C32 .035(2) .023(2) .043(2) .000(2) .009(2) -.001(2) C33 .042(2) .026(2) .049(2) -.004(2) .017(2) .000(2) C34 .057(3) .026(2) .042(2) .002(2) -.008(2) .001(2) C35 .067(3) .038(3) .053(3) .011(2) -.006(2) -.006(2) C36 .049(3) .027(2) .041(2) .002(2) -.005(2) .006(2) C37 .043(2) .024(2) .040(2) -.012(2) .005(2) .003(2) C38 .087(4) .046(3) .064(3) .016(3) -.009(3) -.018(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 O1 C1 . 1.238(4) no O7 C7 . 1.366(4) yes O7 H7 . .89(4) no O14 C14 . 1.208(5) no O17 C17 . 1.200(5) no N1 C1 . 1.343(5) yes N1 C10 . 1.458(4) yes N1 H1 . .81(4) no N2 C14 . 1.385(5) yes N2 C17 . 1.388(5) yes N2 C13 . 1.469(4) yes C1 C2 . 1.479(5) yes C2 C3 . 1.329(5) yes C2 H2 . .95 no C3 C4 . 1.474(5) yes C3 H3 . .95 no C4 C9 . 1.395(5) no C4 C5 . 1.398(5) no C5 C6 . 1.369(5) no C5 H5 . .95 no C6 C7 . 1.387(5) no C6 H6 . .95 no C7 C8 . 1.383(5) no C8 C9 . 1.377(5) no C8 H8 . .95 no C9 H9 . .95 no C10 C11 . 1.518(5) no C10 H10A . .99 no C10 H10B . .99 no C11 C12 . 1.531(5) no C11 H11A . .99 no C11 H11B . .99 no C12 C13 . 1.517(5) no C12 H12A . .99 no C12 H12B . .99 no C13 H13A . .99 no C13 H13B . .99 no C14 C15 . 1.523(6) yes C15 C16 . 1.530(6) yes C15 C18 . 1.428(6) yes C15 H15 . 1.00 no C16 C17 . 1.508(6) no C16 H16A . .99 no C16 H16B . .99 no C18 H18A . .98 no C18 H18B . .98 no C18 H18C . .98 no O21 C21 . 1.241(4) no O27 C27 . 1.360(4) yes O27 H27 . .90(5) no O34 C34 . 1.218(5) no O37 C37 . 1.214(4) no N21 C21 . 1.341(5) yes N21 C30 . 1.450(5) yes N21 H21 . .81(4) no N22 C34 . 1.373(5) yes N22 C37 . 1.389(5) yes N22 C33 . 1.469(5) yes C21 C22 . 1.481(5) yes C22 C23 . 1.324(5) yes C22 H22 . .95 no C23 C24 . 1.465(5) yes C23 H23 . .95 no C24 C29 . 1.392(5) no C24 C25 . 1.396(5) no C25 C26 . 1.376(5) no C25 H25 . .95 no C26 C27 . 1.385(5) no C26 H26 . .95 no C27 C28 . 1.391(5) no C28 C29 . 1.386(5) no C28 H28 . .95 no C29 H29 . .95 no C30 C31 . 1.518(5) no C30 H30A . .99 no C30 H30B . .99 no C31 C32 . 1.526(5) no C31 H31A . .99 no C31 H31B . .99 no C32 C33 . 1.527(5) no C32 H32A . .99 no C32 H32B . .99 no C33 H33A . .99 no C33 H33B . .99 no C34 C35 . 1.537(6) yes C35 C36 . 1.535(6) yes C35 C38 . 1.452(6) yes C35 H35 . 1.00 no C36 C37 . 1.493(5) no C36 H36A . .99 no C36 H36B . .99 no C38 H38A . .98 no C38 H38B . .98 no C38 H38C . .98 no