#------------------------------------------------------------------------------
#$Date: 2011-09-17 21:27:16 +0100 (Sat, 17 Sep 2011) $
#$Revision: 26029 $
#$URL: svn://www.crystallography.net/cod/cif/2/2200569.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_2200569
loop_
_publ_author_name
'Shi, Hao'
'Pan, Yuan Jiang'
'Jin, Zhi Min'
_publ_section_title
;
Natural diterpenoid ludongnin,
octahydro-5'-hydroxy-7a-methyl-8'-methylenespiro[isobenzofuran-4(1H),4'(3'H)-
[1H-7,9a]methanocyclohepta[c]pyran]-1',3,9'(3aH,4'aH)-trione
;
_journal_name_full               'Acta Crystallographica, Section E'
_journal_page_first              o685
_journal_page_last               o687
_journal_volume                  57
_journal_year                    2001
_chemical_formula_iupac          'C20 H24 O6'
_chemical_formula_moiety         'C20 H24 O6'
_chemical_formula_sum            'C20 H24 O6'
_chemical_formula_weight         360.39
_chemical_melting_point          539.0(10)
_chemical_name_common            Ludongnin
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_cell_angle_alpha                90.00
_cell_angle_beta                 115.69(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.2397(13)
_cell_length_b                   36.724(8)
_cell_length_c                   7.304(2)
_cell_measurement_temperature    291(2)
_cell_volume                     1749.9(7)
_diffrn_ambient_temperature      291(2)
_exptl_crystal_density_diffrn    1.368
_[local]_cod_cif_authors_sg_H-M  'P 21'
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_chemical_melting_point' value '538-540' was changed to '539.0(10)'
- the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_database_code               2200569
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
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 .3281(4) .21845(8) .3993(4) .0600(7) Uani d . 1 . . O
H1A .3138 .2270 .2902 .090 Uiso calc R 1 . . H
O2 .6199(4) .25371(7) 1.1879(3) .0514(7) Uani d . 1 . . O
O3 .1614(4) .24262(8) .9923(4) .0585(7) Uani d . 1 . . O
O4 .0682(3) .26942(7) .7008(4) .0479(6) Uani d . 1 . . O
O5 .3429(5) .38238(7) .8393(5) .0696(8) Uani d . 1 . . O
O6 .0656(4) .35278(8) .6352(5) .0805(10) Uani d . 1 . . O
C1 .3685(5) .30797(10) .4311(5) .0439(9) Uani d . 1 . . C
H1B .3496 .2888 .3333 .053 Uiso calc R 1 . . H
H1C .2632 .3262 .3653 .053 Uiso calc R 1 . . H
C2 .5779(6) .32529(10) .4931(5) .0502(9) Uani d . 1 . . C
H2A .6835 .3070 .5546 .060 Uiso calc R 1 . . H
H2B .5878 .3346 .3734 .060 Uiso calc R 1 . . H
C3 .6129(6) .35612(10) .6426(6) .0508(10) Uani d . 1 . . C
H3A .5105 .3749 .5790 .061 Uiso calc R 1 . . H
H3B .7467 .3668 .6781 .061 Uiso calc R 1 . . H
C4 .6011(5) .34284(9) .8365(5) .0429(9) Uani d . 1 . . C
C5 .4000(5) .32149(9) .7821(5) .0375(8) Uani d . 1 . . C
H5A .4122 .3093 .9061 .045 Uiso calc R 1 . . H
C6 .2460(7) .35231(10) .7390(7) .0535(10) Uani d . 1 . . C
C7 .2028(5) .24993(10) .8529(5) .0408(8) Uani d . 1 . . C
C8 .3906(5) .23568(9) .8393(4) .0339(7) Uani d . 1 . . C
C9 .4739(5) .25749(9) .7041(4) .0330(7) Uani d . 1 . . C
H9A .6088 .2666 .7991 .040 Uiso calc R 1 . . H
C10 .3422(5) .29189(9) .6134(5) .0336(7) Uani d . 1 . . C
C11 .5155(6) .23190(9) .5589(5) .0421(8) Uani d . 1 . . C
H11A .5906 .2455 .4972 .051 Uiso calc R 1 . . H
C12 .6456(6) .19966(10) .6745(5) .0516(10) Uani d . 1 . . C
H12A .7875 .2074 .7439 .062 Uiso calc R 1 . . H
H12B .6374 .1808 .5781 .062 Uiso calc R 1 . . H
C13 .5798(5) .18343(9) .8314(5) .0473(9) Uani d . 1 . . C
H13A .5937 .1569 .8375 .057 Uiso calc R 1 . . H
C14 .3601(5) .19488(9) .7802(5) .0428(8) Uani d . 1 . . C
H14A .3053 .1815 .8602 .051 Uiso calc R 1 . . H
H14B .2707 .1916 .6369 .051 Uiso calc R 1 . . H
C15 .5757(5) .23262(9) 1.0485(5) .0373(8) Uani d . 1 . . C
C16 .6929(5) .20013(10) 1.0379(5) .0457(9) Uani d . 1 . . C
C17 .8627(6) .18976(12) 1.1911(7) .0714(13) Uani d . 1 . . C
H17A .9138 .2029 1.3119 .086 Uiso calc R 1 . . H
H17B .9321 .1693 1.1790 .086 Uiso calc R 1 . . H
C18 .8024(6) .32473(11) .9816(6) .0596(11) Uani d . 1 . . C
H18A .9047 .3431 1.0455 .089 Uiso calc R 1 . . H
H18B .8477 .3084 .9066 .089 Uiso calc R 1 . . H
H18C .7809 .3113 1.0836 .089 Uiso calc R 1 . . H
C19 .5605(7) .37542(11) .9432(7) .0649(12) Uani d . 1 . . C
H19A .6004 .3699 1.0853 .078 Uiso calc R 1 . . H
H19B .6373 .3965 .9347 .078 Uiso calc R 1 . . H
C20 .1186(5) .27993(10) .5349(5) .0440(9) Uani d . 1 . . C
H20A .0298 .2997 .4590 .053 Uiso calc R 1 . . H
H20B .0939 .2595 .4433 .053 Uiso calc R 1 . . H
O1' -.3955(3) .58886(7) .1686(4) .0527(7) Uani d . 1 . . O
H1'A -.5010 .5770 .1377 .079 Uiso calc R 1 . . H
O2' .3896(3) .54835(7) .4384(3) .0478(6) Uani d . 1 . . O
O3' .1919(4) .56283(8) -.0129(4) .0552(7) Uani d . 1 . . O
O4' -.1052(3) .53694(7) -.1068(3) .0463(6) Uani d . 1 . . O
O5' .0239(5) .42278(7) .1509(4) .0660(8) Uani d . 1 . . O
O6' -.1798(5) .45366(8) -.1190(4) .0742(9) Uani d . 1 . . O
C1' -.3756(5) .49813(10) .1919(5) .0405(8) Uani d . 1 . . C
H1'B -.4719 .5176 .1758 .049 Uiso calc R 1 . . H
H1'C -.4449 .4803 .0861 .049 Uiso calc R 1 . . H
C2' -.3138(5) .48014(9) .3990(5) .0449(9) Uani d . 1 . . C
H2'A -.2480 .4979 .5059 .054 Uiso calc R 1 . . H
H2'B -.4350 .4712 .4092 .054 Uiso calc R 1 . . H
C3' -.1683(5) .44896(9) .4252(5) .0449(9) Uani d . 1 . . C
H3'A -.2368 .4310 .3203 .054 Uiso calc R 1 . . H
H3'B -.1330 .4375 .5558 .054 Uiso calc R 1 . . H
C4' .0288(5) .46125(9) .4137(5) .0427(8) Uani d . 1 . . C
C5' -.0268(5) .48378(9) .2165(5) .0366(8) Uani d . 1 . . C
H5'A .0991 .4958 .2294 .044 Uiso calc R 1 . . H
C6' -.0730(6) .45338(10) .0600(6) .0513(10) Uani d . 1 . . C
C7' .0517(5) .55599(9) .0281(5) .0400(8) Uani d . 1 . . C
C8' .0432(4) .56942(9) .2179(4) .0327(7) Uani d . 1 . . C
C9' -.0943(4) .54763(8) .3002(5) .0318(7) Uani d . 1 . . C
H9'A .0014 .5378 .4321 .038 Uiso calc R 1 . . H
C10' -.1931(5) .51372(8) .1640(5) .0319(7) Uani d . 1 . . C
C11' -.2352(5) .57350(9) .3464(5) .0404(8) Uani d . 1 . . C
H11B -.2980 .5598 .4200 .048 Uiso calc R 1 . . H
C12' -.1095(5) .60452(9) .4824(6) .0463(9) Uani d . 1 . . C
H12C -.0376 .5956 .6205 .056 Uiso calc R 1 . . H
H12D -.2021 .6236 .4825 .056 Uiso calc R 1 . . H
C13' .0478(5) .62090(9) .4159(5) .0422(8) Uani d . 1 . . C
H13B .0567 .6474 .4337 .051 Uiso calc R 1 . . H
C14' -.0106(5) .61039(9) .1943(5) .0406(8) Uani d . 1 . . C
H14C .0700 .6237 .1396 .049 Uiso calc R 1 . . H
H14D -.1552 .6144 .1088 .049 Uiso calc R 1 . . H
C15' .2536(5) .57060(9) .3983(5) .0360(7) Uani d . 1 . . C
C16' .2567(5) .60343(10) .5193(5) .0439(9) Uani d . 1 . . C
C17' .4243(6) .61465(11) .6755(6) .0631(11) Uani d . 1 . . C
H17C .5464 .6019 .7136 .076 Uiso calc R 1 . . H
H17D .4202 .6353 .7474 .076 Uiso calc R 1 . . H
C18' .1781(6) .47852(11) .6149(5) .0597(11) Uani d . 1 . . C
H18D .2360 .4599 .7160 .090 Uiso calc R 1 . . H
H18E .1060 .4958 .6587 .090 Uiso calc R 1 . . H
H18F .2857 .4907 .5958 .090 Uiso calc R 1 . . H
C19' .1308(6) .42868(11) .3676(6) .0606(11) Uani d . 1 . . C
H19C .2747 .4336 .4071 .073 Uiso calc R 1 . . H
H19D .1200 .4074 .4408 .073 Uiso calc R 1 . . H
C20' -.2718(5) .52686(10) -.0559(5) .0436(9) Uani d . 1 . . C
H20C -.3524 .5077 -.1468 .052 Uiso calc R 1 . . H
H20D -.3607 .5477 -.0760 .052 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 .0748(19) .0685(18) .0303(13) -.0124(15) .0169(14) -.0058(13)
O2 .0602(16) .0631(17) .0293(13) -.0091(14) .0180(12) -.0050(13)
O3 .0533(16) .083(2) .0500(15) -.0010(14) .0324(13) .0143(14)
O4 .0352(13) .0572(16) .0518(14) .0037(12) .0194(12) .0180(12)
O5 .077(2) .0399(16) .107(2) .0044(15) .054(2) -.0053(16)
O6 .0490(18) .0619(19) .136(3) .0156(16) .0452(19) .017(2)
C1 .052(2) .047(2) .0352(19) .0036(18) .0210(17) .0121(16)
C2 .057(2) .054(2) .051(2) .0043(19) .033(2) .0153(19)
C3 .045(2) .046(2) .067(3) .0016(18) .030(2) .014(2)
C4 .044(2) .0344(19) .048(2) -.0049(16) .0175(18) .0012(16)
C5 .0406(19) .0372(19) .0410(19) .0003(16) .0237(16) .0070(15)
C6 .058(3) .037(2) .085(3) .005(2) .049(2) .010(2)
C7 .0369(19) .044(2) .0406(19) -.0105(17) .0163(17) .0026(17)
C8 .0353(18) .0375(17) .0287(16) -.0019(15) .0136(15) .0080(14)
C9 .0325(17) .0403(19) .0261(16) -.0039(15) .0125(14) .0015(14)
C10 .0287(17) .0387(18) .0300(18) .0019(15) .0096(15) .0053(14)
C11 .052(2) .042(2) .0359(18) -.0039(18) .0219(17) -.0026(16)
C12 .059(2) .044(2) .054(2) .0054(19) .027(2) -.0071(18)
C13 .051(2) .0302(19) .056(2) .0018(17) .0183(19) .0008(16)
C14 .045(2) .0371(19) .0415(19) -.0080(17) .0139(16) .0028(16)
C15 .038(2) .0417(19) .0315(18) -.0102(16) .0147(15) .0059(16)
C16 .043(2) .042(2) .046(2) -.0008(17) .0135(18) .0128(17)
C17 .058(3) .060(3) .071(3) .006(2) .005(2) .017(2)
C18 .050(2) .052(2) .059(2) -.011(2) .007(2) -.001(2)
C19 .081(3) .045(2) .071(3) -.008(2) .035(3) -.008(2)
C20 .040(2) .049(2) .039(2) .0025(17) .0137(17) .0127(17)
O1' .0290(13) .0479(15) .0725(18) .0016(11) .0138(13) .0106(13)
O2' .0318(13) .0583(16) .0522(15) .0030(13) .0171(12) .0036(13)
O3' .0458(15) .082(2) .0449(14) -.0119(14) .0262(12) .0014(14)
O4' .0484(14) .0579(16) .0319(12) -.0129(13) .0168(11) .0010(11)
O5' .099(2) .0388(15) .076(2) .0060(15) .0525(18) -.0044(15)
O6' .123(3) .0601(18) .0429(16) -.0122(19) .0390(18) -.0123(14)
C1' .0336(18) .0372(18) .046(2) -.0055(16) .0130(16) -.0008(16)
C2' .049(2) .042(2) .054(2) -.0097(18) .0333(19) -.0002(17)
C3' .063(2) .0356(19) .040(2) -.0060(18) .0262(18) .0029(15)
C4' .047(2) .0353(19) .044(2) -.0023(17) .0178(18) .0042(16)
C5' .0383(19) .0343(18) .0414(19) -.0041(15) .0214(16) -.0005(15)
C6' .071(3) .036(2) .061(3) -.008(2) .042(2) -.0043(19)
C7' .0353(19) .045(2) .0391(19) -.0038(16) .0158(17) .0084(16)
C8' .0291(17) .0338(17) .0347(17) -.0040(15) .0136(14) .0015(15)
C9' .0275(16) .0315(17) .0368(17) -.0020(14) .0144(14) .0043(14)
C10' .0301(17) .0323(17) .0322(17) -.0023(14) .0125(14) .0026(14)
C11' .0353(18) .0374(19) .051(2) .0007(16) .0213(17) .0038(17)
C12' .047(2) .0371(19) .058(2) -.0004(17) .0250(19) -.0022(18)
C13' .041(2) .0291(17) .054(2) -.0029(15) .0178(18) -.0007(16)
C14' .0357(18) .0378(19) .046(2) -.0049(16) .0158(16) .0096(16)
C15' .0270(17) .0389(18) .0454(19) .0005(16) .0189(15) .0068(16)
C16' .040(2) .042(2) .042(2) -.0050(17) .0112(17) -.0020(16)
C17' .062(3) .049(2) .057(2) .004(2) .005(2) -.006(2)
C18' .064(3) .050(2) .044(2) .002(2) .004(2) .0097(19)
C19' .061(3) .045(2) .074(3) .013(2) .028(2) .008(2)
C20' .0348(18) .053(2) .0358(18) -.0054(17) .0087(15) .0053(17)
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 C11 . 1.439(4) ?
O1 H1A . .8200 ?
O2 C15 . 1.207(4) yes
O3 C7 . 1.210(4) yes
O4 C7 . 1.326(4) ?
O4 C20 . 1.461(4) ?
O5 C6 . 1.343(5) ?
O5 C19 . 1.444(5) ?
O6 C6 . 1.193(5) yes
C1 C2 . 1.521(5) ?
C1 C10 . 1.542(4) ?
C1 H1B . .9700 ?
C1 H1C . .9700 ?
C2 C3 . 1.516(5) ?
C2 H2A . .9700 ?
C2 H2B . .9700 ?
C3 C4 . 1.535(5) ?
C3 H3A . .9700 ?
C3 H3B . .9700 ?
C4 C19 . 1.524(5) ?
C4 C18 . 1.533(5) ?
C4 C5 . 1.546(5) ?
C5 C6 . 1.523(5) ?
C5 C10 . 1.558(5) ?
C5 H5A . .9800 ?
C7 C8 . 1.499(5) ?
C8 C15 . 1.539(4) ?
C8 C14 . 1.549(5) ?
C8 C9 . 1.581(4) ?
C9 C11 . 1.541(4) ?
C9 C10 . 1.548(4) ?
C9 H9A . .9800 ?
C10 C20 . 1.528(4) ?
C11 C12 . 1.521(5) ?
C11 H11A . .9800 ?
C12 C13 . 1.539(5) ?
C12 H12A . .9700 ?
C12 H12B . .9700 ?
C13 C16 . 1.500(5) ?
C13 C14 . 1.527(5) ?
C13 H13A . .9800 ?
C14 H14A . .9700 ?
C14 H14B . .9700 ?
C15 C16 . 1.486(5) ?
C16 C17 . 1.310(5) yes
C17 H17A . .9300 ?
C17 H17B . .9300 ?
C18 H18A . .9600 ?
C18 H18B . .9600 ?
C18 H18C . .9600 ?
C19 H19A . .9700 ?
C19 H19B . .9700 ?
C20 H20A . .9700 ?
C20 H20B . .9700 ?
O1' C11' . 1.430(4) ?
O1' H1'A . .8200 ?
O2' C15' . 1.213(4) yes
O3' C7' . 1.204(4) yes
O4' C7' . 1.334(4) ?
O4' C20' . 1.456(4) ?
O5' C6' . 1.339(5) ?
O5' C19' . 1.445(4) ?
O6' C6' . 1.196(5) yes
C1' C2' . 1.529(5) ?
C1' C10' . 1.532(4) ?
C1' H1'B . .9700 ?
C1' H1'C . .9700 ?
C2' C3' . 1.511(5) ?
C2' H2'A . .9700 ?
C2' H2'B . .9700 ?
C3' C4' . 1.533(5) ?
C3' H3'A . .9700 ?
C3' H3'B . .9700 ?
C4' C19' . 1.519(5) ?
C4' C18' . 1.534(5) ?
C4' C5' . 1.556(5) ?
C5' C6' . 1.527(5) ?
C5' C10' . 1.551(4) ?
C5' H5'A . .9800 ?
C7' C8' . 1.497(5) ?
C8' C15' . 1.523(4) ?
C8' C14' . 1.545(5) ?
C8' C9' . 1.585(4) ?
C9' C11' . 1.535(4) ?
C9' C10' . 1.560(4) ?
C9' H9'A . .9800 ?
C10' C20' . 1.531(4) ?
C11' C12' . 1.526(5) ?
C11' H11B . .9800 ?
C12' C13' . 1.541(5) ?
C12' H12C . .9700 ?
C12' H12D . .9700 ?
C13' C16' . 1.510(5) ?
C13' C14' . 1.534(5) ?
C13' H13B . .9800 ?
C14' H14C . .9700 ?
C14' H14D . .9700 ?
C15' C16' . 1.489(5) ?
C16' C17' . 1.320(5) yes
C17' H17C . .9300 ?
C17' H17D . .9300 ?
C18' H18D . .9600 ?
C18' H18E . .9600 ?
C18' H18F . .9600 ?
C19' H19C . .9700 ?
C19' H19D . .9700 ?
C20' H20C . .9700 ?
C20' H20D . .9700 ?