#------------------------------------------------------------------------------ #$Date: 2008-01-14 00:15:36 +0200 (Mon, 14 Jan 2008) $ #$Revision: 14 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/2013904.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_2013904 _journal_name_full 'Acta Crystallographica, Section C' _journal_year 2004 _journal_volume 60 _journal_page_first o377 _journal_page_last o380 _publ_section_title ; Vindoline and 16-demethoxyvindoline: two Catharanthus-derived alkaloids ; loop_ _publ_author_name 'Ruszkowska, Joanna' 'Chrobak, Robert' 'Maurin, Jan K.' 'Czarnocki, Zbigniew' _chemical_name_common 'vindoline' _chemical_formula_moiety 'C25 H32 N2 O6' _chemical_formula_sum 'C25 H32 N2 O6' _chemical_formula_iupac 'C25 H32 N2 O6' _chemical_formula_weight 456.53 _chemical_melting_point .448E-305 _symmetry_cell_setting 'orthorhombic' _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_space_group_name_Hall 'P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 9.5440(19) _cell_length_b 15.711(3) _cell_length_c 15.888(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2382.3(8) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _exptl_crystal_density_diffrn 1.273 _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 O1 0.0794(2) 0.21427(14) 0.42171(12) 0.0491(5) Uani d . 1 . . O H1 -0.006(4) 0.228(2) 0.408(2) 0.069(11) Uiso d . 1 . . H O2 0.4149(2) 0.24567(15) 0.36521(16) 0.0656(6) Uani d . 1 . . O O3 0.3124(2) 0.12381(14) 0.40490(14) 0.0578(6) Uani d . 1 . . O O4 0.2027(2) 0.37161(12) 0.39215(12) 0.0503(5) Uani d . 1 . . O O5 0.3341(3) 0.45921(16) 0.31304(17) 0.0784(8) Uani d . 1 . . O O6 0.0806(3) 0.14916(18) -0.09562(13) 0.0769(8) Uani d . 1 . . O N1 0.1975(2) 0.17774(14) 0.19830(14) 0.0435(5) Uani d . 1 . . N C2 0.1117(3) 0.17132(16) 0.27590(17) 0.0396(6) Uani d . 1 . . C H2 0.1143 0.1121 0.2953 0.047 Uiso calc R 1 . . H C3 0.1627(3) 0.22872(18) 0.34848(17) 0.0408(6) Uani d . 1 . . C C4 0.1631(3) 0.32178(16) 0.31864(16) 0.0406(6) Uani d . 1 . . C H4 0.2378 0.3278 0.2768 0.049 Uiso calc R 1 . . H C5 0.0235(3) 0.35368(16) 0.27730(16) 0.0413(6) Uani d . 1 . . C C6 -0.0381(4) 0.42815(18) 0.32646(18) 0.0509(7) Uani d . 1 . . C H6 0.0108 0.4794 0.3260 0.061 Uiso calc R 1 . . H C7 -0.1555(4) 0.4249(2) 0.3695(2) 0.0577(8) Uani d . 1 . . C H7 -0.1854 0.4744 0.3962 0.069 Uiso calc R 1 . . H C8 -0.2434(4) 0.3479(2) 0.3783(2) 0.0581(8) Uani d . 1 . . C H8A -0.2746 0.3422 0.4362 0.070 Uiso calc R 1 . . H H8B -0.3255 0.3526 0.3426 0.070 Uiso calc R 1 . . H N9 -0.1609(2) 0.27236(15) 0.35394(15) 0.0474(5) Uani d . 1 . . N C10 -0.2463(3) 0.1958(2) 0.3422(2) 0.0613(9) Uani d . 1 . . C H10A -0.3303 0.2086 0.3103 0.074 Uiso calc R 1 . . H H10B -0.2730 0.1716 0.3960 0.074 Uiso calc R 1 . . H C11 -0.1515(3) 0.13525(19) 0.2938(2) 0.0534(7) Uani d . 1 . . C H11A -0.2051 0.1029 0.2530 0.064 Uiso calc R 1 . . H H11B -0.1057 0.0958 0.3320 0.064 Uiso calc R 1 . . H C12 -0.0413(3) 0.19238(16) 0.24877(16) 0.0394(6) Uani d . 1 . . C C13 -0.0333(3) 0.18012(17) 0.15389(17) 0.0428(6) Uani d . 1 . . C C14 -0.1364(3) 0.1797(2) 0.0942(2) 0.0570(8) Uani d . 1 . . C H14 -0.2294 0.1867 0.1104 0.068 Uiso calc R 1 . . H C15 -0.1039(4) 0.1691(2) 0.0100(2) 0.0608(8) Uani d . 1 . . C H15 -0.1747 0.1682 -0.0303 0.073 Uiso calc R 1 . . H C16 0.0356(4) 0.1596(2) -0.01413(19) 0.0548(8) Uani d . 1 . . C C17 0.1422(3) 0.16043(19) 0.04523(18) 0.0494(7) Uani d . 1 . . C H17 0.2353 0.1542 0.0291 0.059 Uiso calc R 1 . . H C18 0.1064(3) 0.17085(16) 0.12957(18) 0.0426(6) Uani d . 1 . . C C19 -0.0890(3) 0.28418(17) 0.27243(16) 0.0402(6) Uani d . 1 . . C H19 -0.1592 0.3022 0.2311 0.048 Uiso calc R 1 . . H C20 0.0593(4) 0.38689(18) 0.18793(17) 0.0508(7) Uani d . 1 . . C H20A 0.1284 0.4318 0.1934 0.061 Uiso calc R 1 . . H H20B 0.1027 0.3409 0.1567 0.061 Uiso calc R 1 . . H C21 -0.0631(4) 0.4211(2) 0.1360(2) 0.0691(10) Uani d . 1 . . C H21A -0.0296 0.4393 0.0820 0.104 Uiso calc R 1 . . H H21B -0.1048 0.4685 0.1648 0.104 Uiso calc R 1 . . H H21C -0.1317 0.3770 0.1287 0.104 Uiso calc R 1 . . H C22 0.3294(3) 0.1300(2) 0.1960(2) 0.0621(9) Uani d . 1 . . C H22A 0.3812 0.1405 0.2467 0.093 Uiso calc R 1 . . H H22B 0.3837 0.1479 0.1483 0.093 Uiso calc R 1 . . H H22C 0.3096 0.0703 0.1914 0.093 Uiso calc R 1 . . H C23 0.3115(3) 0.20299(18) 0.37429(17) 0.0445(6) Uani d . 1 . . C C24 0.4492(4) 0.0904(3) 0.4273(2) 0.0698(10) Uani d . 1 . . C H24A 0.4394 0.0331 0.4474 0.105 Uiso calc R 1 . . H H24B 0.4897 0.1252 0.4707 0.105 Uiso calc R 1 . . H H24C 0.5089 0.0909 0.3787 0.105 Uiso calc R 1 . . H C25 -0.0215(5) 0.1385(3) -0.1601(2) 0.0928(14) Uani d . 1 . . C H25A 0.0247 0.1319 -0.2134 0.139 Uiso calc R 1 . . H H25B -0.0813 0.1876 -0.1619 0.139 Uiso calc R 1 . . H H25C -0.0767 0.0888 -0.1485 0.139 Uiso calc R 1 . . H C26 0.2965(4) 0.4334(2) 0.3809(2) 0.0579(8) Uani d . 1 . . C C27 0.3481(5) 0.4668(3) 0.4637(3) 0.0947(15) Uani d . 1 . . C H27A 0.3008 0.4379 0.5087 0.142 Uiso calc R 1 . . H H27B 0.3293 0.5267 0.4672 0.142 Uiso calc R 1 . . H H27C 0.4472 0.4572 0.4682 0.142 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 0.0460(12) 0.0608(12) 0.0406(10) 0.0021(11) 0.0062(9) 0.0087(9) O2 0.0428(11) 0.0632(13) 0.0910(17) -0.0059(11) -0.0080(12) 0.0008(13) O3 0.0494(12) 0.0616(12) 0.0626(13) 0.0057(11) 0.0018(11) 0.0163(11) O4 0.0578(12) 0.0495(10) 0.0435(10) -0.0055(10) -0.0034(10) -0.0072(8) O5 0.094(2) 0.0680(14) 0.0728(16) -0.0360(15) -0.0012(16) -0.0014(12) O6 0.0809(17) 0.108(2) 0.0418(11) 0.0035(17) -0.0047(12) -0.0091(12) N1 0.0364(10) 0.0514(12) 0.0427(12) -0.0033(11) 0.0012(10) -0.0093(10) C2 0.0397(13) 0.0347(12) 0.0443(13) -0.0014(12) 0.0029(12) 0.0021(10) C3 0.0388(13) 0.0443(13) 0.0392(13) -0.0004(12) 0.0064(12) 0.0038(11) C4 0.0457(14) 0.0405(12) 0.0356(12) -0.0087(12) 0.0030(12) -0.0034(10) C5 0.0476(14) 0.0379(12) 0.0383(12) -0.0036(12) 0.0003(12) 0.0020(10) C6 0.0635(19) 0.0407(14) 0.0485(15) 0.0041(15) -0.0066(16) -0.0026(12) C7 0.073(2) 0.0499(15) 0.0506(16) 0.0207(16) -0.0021(18) -0.0050(14) C8 0.0545(18) 0.0719(19) 0.0479(16) 0.0196(16) 0.0089(15) 0.0005(15) N9 0.0439(12) 0.0505(12) 0.0479(13) 0.0060(11) 0.0094(12) 0.0049(11) C10 0.0425(15) 0.0663(18) 0.075(2) -0.0044(15) 0.0142(16) 0.0166(17) C11 0.0456(15) 0.0467(15) 0.0680(19) -0.0088(13) 0.0106(16) 0.0020(14) C12 0.0365(12) 0.0382(12) 0.0434(13) -0.0039(12) 0.0037(12) 0.0010(11) C13 0.0418(13) 0.0390(13) 0.0477(15) 0.0001(12) -0.0021(13) -0.0065(11) C14 0.0468(17) 0.0637(19) 0.0605(19) 0.0021(15) -0.0052(15) -0.0077(16) C15 0.060(2) 0.0679(19) 0.0547(18) 0.0050(18) -0.0163(16) -0.0073(16) C16 0.0634(19) 0.0556(17) 0.0454(16) 0.0003(17) -0.0033(15) -0.0044(13) C17 0.0436(15) 0.0566(16) 0.0481(15) -0.0032(14) 0.0037(13) -0.0083(13) C18 0.0434(14) 0.0368(13) 0.0476(15) -0.0030(12) 0.0009(13) -0.0042(12) C19 0.0372(12) 0.0440(13) 0.0393(13) 0.0024(12) 0.0021(11) 0.0024(11) C20 0.0645(19) 0.0433(13) 0.0447(15) -0.0163(14) -0.0041(16) 0.0067(11) C21 0.082(3) 0.0643(19) 0.0610(18) -0.012(2) -0.013(2) 0.0245(17) C22 0.0432(16) 0.081(2) 0.0623(19) 0.0091(16) -0.0038(16) -0.0214(18) C23 0.0454(15) 0.0504(14) 0.0376(13) 0.0033(13) -0.0006(12) -0.0018(12) C24 0.055(2) 0.081(2) 0.073(2) 0.0177(19) 0.0011(19) 0.0186(19) C25 0.098(3) 0.130(4) 0.050(2) 0.004(3) -0.020(2) -0.005(2) C26 0.063(2) 0.0491(15) 0.0612(19) -0.0107(16) -0.0093(18) -0.0038(14) C27 0.122(4) 0.085(3) 0.077(3) -0.030(3) -0.031(3) -0.017(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 C3 . 1.427(3) no O1 H1 . 0.88(4) no O2 C23 . 1.201(4) no O3 C23 . 1.336(4) no O3 C24 . 1.451(4) no O4 C26 . 1.333(4) no O4 C4 . 1.456(3) no O5 C26 . 1.207(4) no O6 C16 . 1.374(4) no O6 C25 . 1.424(5) no N1 C18 . 1.400(4) no N1 C22 . 1.466(4) no N1 C2 . 1.483(3) no C2 C3 . 1.543(4) no C2 C12 . 1.558(4) no C2 H2 . 0.9800 no C3 C23 . 1.533(4) no C3 C4 . 1.537(4) no C4 C5 . 1.568(4) no C4 H4 . 0.9800 no C5 C6 . 1.525(4) no C5 C19 . 1.533(4) no C5 C20 . 1.551(4) no C6 C7 . 1.313(5) no C6 H6 . 0.9300 no C7 C8 . 1.480(5) no C7 H7 . 0.9300 no C8 N9 . 1.476(4) no C8 H8A . 0.9700 no C8 H8B . 0.9700 no N9 C10 . 1.465(4) no N9 C19 . 1.477(3) no C10 C11 . 1.521(5) no C10 H10A . 0.9700 no C10 H10B . 0.9700 no C11 C12 . 1.557(4) no C11 H11A . 0.9700 no C11 H11B . 0.9700 no C12 C13 . 1.522(4) no C12 C19 . 1.558(4) no C13 C14 . 1.367(4) no C13 C18 . 1.395(4) no C14 C15 . 1.384(5) no C14 H14 . 0.9300 no C15 C16 . 1.394(5) no C15 H15 . 0.9300 no C16 C17 . 1.387(4) no C17 C18 . 1.393(4) no C17 H17 . 0.9300 no C19 H19 . 0.9800 no C20 C21 . 1.527(5) no C20 H20A . 0.9700 no C20 H20B . 0.9700 no C21 H21A . 0.9600 no C21 H21B . 0.9600 no C21 H21C . 0.9600 no C22 H22A . 0.9600 no C22 H22B . 0.9600 no C22 H22C . 0.9600 no C24 H24A . 0.9600 no C24 H24B . 0.9600 no C24 H24C . 0.9600 no C25 H25A . 0.9600 no C25 H25B . 0.9600 no C25 H25C . 0.9600 no C26 C27 . 1.499(5) no C27 H27A . 0.9600 no C27 H27B . 0.9600 no C27 H27C . 0.9600 no