#------------------------------------------------------------------------------
#$Date: 2008-01-26 15:05:32 +0200 (Sat, 26 Jan 2008) $
#$Revision: 19 $
#$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