#------------------------------------------------------------------------------
#$Date: 2009-11-16 03:43:51 +0200 (Mon, 16 Nov 2009) $
#$Revision: 853 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2011751.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_2011751
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2001
_journal_volume  57
_journal_page_first  170
_journal_page_last  171
_publ_section_title
;
Sipeimine, a steroidal alkaloid from Fritillaria roylei Hooker
;
_space_group_IT_number           4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_[local]_cod_cif_authors_sg_H-M  'P 21'
loop_
_publ_author_name
  'Jiang, Ren-Wang'
  'Ma, Shuang-Cheng'
  'But, Paul P. H.'
  'Dong, Hui'
  'Mak, Thomas C. W.'
_chemical_name_common  'sipeimine'
_chemical_formula_moiety  'C27 H43 N O3'
_chemical_formula_sum  'C27 H43 N O3'
_chemical_formula_weight  429.62
_symmetry_cell_setting  monoclinic
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x, y+1/2, -z'
_cell_length_a  6.6185(5)
_cell_length_b  12.3948(8)
_cell_length_c  14.5069(10)
_cell_angle_alpha  90.00
_cell_angle_beta  90.8220(10)
_cell_angle_gamma  90.00
_cell_volume  1189.95(14)
_cell_formula_units_Z  2
_cell_measurement_temperature  293(2)
_exptl_crystal_density_diffrn  1.199
_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  .6837(6)  .7650(3)  .78059(17)  .1145(12) Uani d . 1 . . O
  H1  .7191  .8207  .8067  .172 Uiso calc R 1 . . H
  O2  .0921(5)  .9253(2)  .59128(19)  .1042(10) Uani d . 1 . . O
  O3  .1456(4)  .40336(18)  .09243(16)  .0795(7) Uani d . 1 . . O
  H3  .2577  .4221  .0751  .119 Uiso calc R 1 . . H
  N1  .2739(3)  .5855(2)  .00561(14)  .0462(6) Uani d . 1 . . N
  C1  .6414(5)  .6826(3)  .53240(19)  .0614(9) Uani d . 1 . . C
  H1A  .6618  .6115  .5063  .074 Uiso calc R 1 . . H
  H1B  .7309  .7323  .5014  .074 Uiso calc R 1 . . H
  C2  .6965(5)  .6798(4)  .6355(2)  .0740(11) Uani d . 1 . . C
  H2A  .6187  .6235  .6650  .089 Uiso calc R 1 . . H
  H2B  .8384  .6616  .6427  .089 Uiso calc R 1 . . H
  C3  .6575(6)  .7854(4)  .6835(2)  .0823(12) Uani d . 1 . . C
  H3A  .7572  .8388  .6639  .099 Uiso calc R 1 . . H
  C4  .4469(6)  .8279(3)  .6636(2)  .0722(10) Uani d . 1 . . C
  H4A  .4349  .9002  .6886  .087 Uiso calc R 1 . . H
  H4B  .3489  .7824  .6939  .087 Uiso calc R 1 . . H
  C5  .3998(5)  .8306(3)  .5601(2)  .0591(8) Uani d . 1 . . C
  H5  .5064  .8749  .5332  .071 Uiso calc R 1 . . H
  C6  .2024(6)  .8869(3)  .5342(2)  .0725(10) Uani d . 1 . . C
  C7  .1509(6)  .8910(3)  .4326(2)  .0749(10) Uani d . 1 . . C
  H7A  .2422  .9399  .4017  .090 Uiso calc R 1 . . H
  H7B  .0141  .9175  .4236  .090 Uiso calc R 1 . . H
  C8  .1696(4)  .7782(2)  .39169(19)  .0501(7) Uani d . 1 . . C
  H8  .0740  .7328  .4251  .060 Uiso calc R 1 . . H
  C9  .3800(4)  .7311(2)  .41165(17)  .0437(6) Uani d . 1 . . C
  H9  .4784  .7835  .3890  .052 Uiso calc R 1 . . H
  C10  .4213(4)  .7175(2)  .51475(18)  .0458(7) Uani d . 1 . . C
  C11  .3838(4)  .6352(2)  .34595(17)  .0442(6) Uani d . 1 . . C
  H11A  .2967  .5774  .3668  .053 Uiso calc R 1 . . H
  H11B  .5199  .6076  .3387  .053 Uiso calc R 1 . . H
  C12  .3029(4)  .6862(2)  .25628(17)  .0438(6) Uani d . 1 . . C
  H12  .4087  .7353  .2351  .053 Uiso calc R 1 . . H
  C13  .2594(4)  .6081(2)  .17582(16)  .0440(6) Uani d . 1 . . C
  H13  .3503  .5463  .1839  .053 Uiso calc R 1 . . H
  C14  .1264(4)  .7587(2)  .28844(19)  .0503(7) Uani d . 1 . . C
  H14  .1306  .8277  .2555  .060 Uiso calc R 1 . . H
  C15  -.0821(4)  .7082(3)  .2756(2)  .0668(9) Uani d . 1 . . C
  H15A  -.1025  .6555  .3240  .080 Uiso calc R 1 . . H
  H15B  -.1838  .7639  .2822  .080 Uiso calc R 1 . . H
  C16  -.1116(5)  .6539(3)  .1835(2)  .0630(9) Uani d . 1 . . C
  H16A  -.0954  .7063  .1345  .076 Uiso calc R 1 . . H
  H16B  -.2471  .6245  .1789  .076 Uiso calc R 1 . . H
  C17  .0430(4)  .5635(2)  .17314(18)  .0490(7) Uani d . 1 . . C
  H17  .0293  .5160  .2267  .059 Uiso calc R 1 . . H
  C18  .3075(4)  .6586(3)  .08329(18)  .0501(7) Uani d . 1 . . C
  H18A  .2242  .7223  .0746  .060 Uiso calc R 1 . . H
  H18B  .4476  .6816  .0840  .060 Uiso calc R 1 . . H
  C19  .2773(5)  .6351(2)  .5569(2)  .0544(7) Uani d . 1 . . C
  H19A  .1406  .6599  .5495  .082 Uiso calc R 1 . . H
  H19B  .3085  .6269  .6214  .082 Uiso calc R 1 . . H
  H19C  .2924  .5669  .5264  .082 Uiso calc R 1 . . H
  C20  .0089(5)  .4937(2)  .0870(2)  .0569(8) Uani d . 1 . . C
  C21  -.2041(7)  .4472(4)  .0837(3)  .0983(15) Uani d . 1 . . C
  H21A  -.2108  .3902  .0389  .147 Uiso calc R 1 . . H
  H21B  -.2984  .5029  .0668  .147 Uiso calc R 1 . . H
  H21C  -.2374  .4191  .1432  .147 Uiso calc R 1 . . H
  C22  .0597(4)  .5548(3)  -.00137(19)  .0490(7) Uani d . 1 . . C
  H22  -.0224  .6205  -.0045  .059 Uiso calc R 1 . . H
  C23  .0190(5)  .4881(3)  -.0879(2)  .0660(9) Uani d . 1 . . C
  H23A  .0860  .4188  -.0817  .079 Uiso calc R 1 . . H
  H23B  -.1250  .4749  -.0940  .079 Uiso calc R 1 . . H
  C24  .0930(5)  .5442(3)  -.17424(19)  .0671(9) Uani d . 1 . . C
  H24A  .0708  .4977  -.2272  .081 Uiso calc R 1 . . H
  H24B  .0168  .6101  -.1841  .081 Uiso calc R 1 . . H
  C25  .3144(6)  .5704(3)  -.1651(2)  .0708(10) Uani d . 1 . . C
  H25  .3490  .6163  -.2176  .085 Uiso calc R 1 . . H
  C26  .3466(6)  .6372(3)  -.0786(2)  .0745(11) Uani d . 1 . . C
  H26A  .4898  .6520  -.0712  .089 Uiso calc R 1 . . H
  H26B  .2778  .7058  -.0865  .089 Uiso calc R 1 . . H
  C27  .4472(7)  .4725(5)  -.1692(3)  .1074(17) Uani d . 1 . . C
  H27A  .4263  .4288  -.1155  .161 Uiso calc R 1 . . H
  H27B  .5862  .4945  -.1711  .161 Uiso calc R 1 . . H
  H27C  .4142  .4316  -.2235  .161 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  .158(3)  .145(3)  .0399(14)  -.073(3)  -.0098(15)  -.0106(17)
  O2  .140(2)  .098(2)  .0756(19)  .0266(19)  .0348(16)  -.0260(16)
  O3  .142(2)  .0497(13)  .0462(13)  .0046(15)  -.0053(14)  .0065(11)
  N1  .0510(13)  .0560(14)  .0315(12)  -.0114(12)  .0010(9)  -.0005(10)
  C1  .0572(18)  .091(2)  .0366(16)  -.0072(17)  .0049(13)  -.0103(16)
  C2  .063(2)  .121(3)  .0386(17)  -.013(2)  -.0052(14)  -.0098(19)
  C3  .101(3)  .108(3)  .0381(18)  -.053(2)  -.0003(17)  -.0101(18)
  C4  .110(3)  .066(2)  .0409(18)  -.029(2)  .0179(17)  -.0216(15)
  C5  .084(2)  .0530(18)  .0411(16)  -.0164(17)  .0158(14)  -.0134(14)
  C6  .107(3)  .0494(19)  .062(2)  -.0023(19)  .0224(19)  -.0194(17)
  C7  .101(3)  .064(2)  .060(2)  .022(2)  .0052(18)  -.0133(17)
  C8  .0536(16)  .0511(17)  .0458(16)  .0029(14)  .0109(13)  -.0032(13)
  C9  .0501(15)  .0467(16)  .0345(14)  -.0063(13)  .0094(11)  -.0036(12)
  C10  .0513(16)  .0522(17)  .0341(14)  -.0082(13)  .0094(11)  -.0108(12)
  C11  .0452(14)  .0539(16)  .0334(14)  .0051(13)  .0006(11)  -.0073(12)
  C12  .0443(15)  .0511(16)  .0360(15)  -.0011(12)  .0040(11)  -.0030(12)
  C13  .0464(15)  .0529(16)  .0327(14)  .0042(13)  .0003(11)  -.0007(12)
  C14  .0561(17)  .0524(17)  .0424(16)  .0087(14)  .0063(12)  .0011(13)
  C15  .0457(16)  .099(3)  .056(2)  .0103(17)  .0044(14)  -.0094(19)
  C16  .0432(16)  .089(2)  .0571(19)  .0029(16)  .0008(13)  -.0058(18)
  C17  .0590(17)  .0563(18)  .0318(14)  -.0117(14)  .0021(12)  .0044(12)
  C18  .0523(16)  .0623(18)  .0357(15)  -.0129(14)  .0031(12)  -.0056(13)
  C19  .0650(18)  .0594(18)  .0390(15)  -.0132(15)  .0070(13)  -.0051(13)
  C20  .074(2)  .0506(19)  .0458(17)  -.0174(16)  -.0009(14)  .0041(14)
  C21  .111(3)  .118(4)  .067(3)  -.069(3)  .018(2)  -.016(2)
  C22  .0548(17)  .0547(17)  .0375(15)  -.0056(13)  -.0064(12)  .0027(12)
  C23  .069(2)  .083(2)  .0463(18)  -.0199(19)  -.0107(15)  -.0088(17)
  C24  .091(2)  .079(2)  .0308(16)  .0031(19)  -.0131(15)  -.0005(15)
  C25  .094(3)  .086(3)  .0327(16)  -.026(2)  .0056(15)  -.0043(16)
  C26  .107(3)  .080(2)  .0372(17)  -.038(2)  .0121(16)  -.0059(16)
  C27  .089(3)  .154(5)  .079(3)  .014(3)  -.002(2)  -.047(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 C3 . 1.439(4) ?
  O1 H1 .  .8200 ?
  O2 C6 . 1.209(4) ?
  O3 C20 . 1.441(4) ?
  O3 H3 .  .8200 ?
  N1 C18 . 1.461(4) ?
  N1 C26 . 1.467(4) ?
  N1 C22 . 1.470(3) ?
  C1 C2 . 1.536(4) ?
  C1 C10 . 1.537(4) ?
  C1 H1A .  .9700 ?
  C1 H1B .  .9700 ?
  C2 C3 . 1.506(6) ?
  C2 H2A .  .9700 ?
  C2 H2B .  .9700 ?
  C3 C4 . 1.514(5) ?
  C3 H3A .  .9800 ?
  C4 C5 . 1.529(4) ?
  C4 H4A .  .9700 ?
  C4 H4B .  .9700 ?
  C5 C6 . 1.523(5) ?
  C5 C10 . 1.557(4) ?
  C5 H5 .  .9800 ?
  C6 C7 . 1.510(5) ?
  C7 C8 . 1.524(5) ?
  C7 H7A .  .9700 ?
  C7 H7B .  .9700 ?
  C8 C9 . 1.534(4) ?
  C8 C14 . 1.540(4) ?
  C8 H8 .  .9800 ?
  C9 C11 . 1.524(4) ?
  C9 C10 . 1.526(3) ?
  C9 H9 .  .9800 ?
  C10 C19 . 1.530(4) ?
  C11 C12 . 1.536(4) ?
  C11 H11A .  .9700 ?
  C11 H11B .  .9700 ?
  C12 C13 . 1.540(4) ?
  C12 C14 . 1.551(4) ?
  C12 H12 .  .9800 ?
  C13 C18 . 1.519(4) ?
  C13 C17 . 1.535(4) ?
  C13 H13 .  .9800 ?
  C14 C15 . 1.524(4) ?
  C14 H14 .  .9800 ?
  C15 C16 . 1.506(4) ?
  C15 H15A .  .9700 ?
  C15 H15B .  .9700 ?
  C16 C17 . 1.526(4) ?
  C16 H16A .  .9700 ?
  C16 H16B .  .9700 ?
  C17 C20 . 1.534(4) ?
  C17 H17 .  .9800 ?
  C18 H18A .  .9700 ?
  C18 H18B .  .9700 ?
  C19 H19A .  .9600 ?
  C19 H19B .  .9600 ?
  C19 H19C .  .9600 ?
  C20 C21 . 1.524(5) ?
  C20 C22 . 1.530(4) ?
  C21 H21A .  .9600 ?
  C21 H21B .  .9600 ?
  C21 H21C .  .9600 ?
  C22 C23 . 1.523(4) ?
  C22 H22 .  .9800 ?
  C23 C24 . 1.520(5) ?
  C23 H23A .  .9700 ?
  C23 H23B .  .9700 ?
  C24 C25 . 1.505(5) ?
  C24 H24A .  .9700 ?
  C24 H24B .  .9700 ?
  C25 C27 . 1.500(6) ?
  C25 C26 . 1.515(4) ?
  C25 H25 .  .9800 ?
  C26 H26A .  .9700 ?
  C26 H26B .  .9700 ?
  C27 H27A .  .9600 ?
  C27 H27B .  .9600 ?
  C27 H27C .  .9600 ?