#------------------------------------------------------------------------------
#$Date: 2008-01-26 13:05:32 +0000 (Sat, 26 Jan 2008) $
#$Revision: 19 $
#$URL: svn://www.crystallography.net/cod/cif/2/2011658.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_2011658
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2000
_journal_volume  56
_journal_page_first  e598
_journal_page_last  e599
_publ_section_title
;
2-(4-Acetyl-3,5-dihydroxy-2-methylphenoxy)-4,6-dimethoxy-3-methylbenzoic acid
;
loop_
_publ_author_name
  'Chantrapromma, Suchada'
  'Fun, Hoong-Kun'
  'Razak, Ibrahim Abdul'
  'Saewon, Nisakorn'
  'Karalai, Chatchanok'
  'Chantrapromma, Kan'
_chemical_formula_sum  'C19 H20 O8'
_chemical_formula_weight  376.35
_chemical_melting_point  '174-176'
_symmetry_cell_setting  monoclinic
_symmetry_space_group_name_H-M  'P 21/n'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x+1/2, y+1/2, -z+1/2'
  '-x, -y, -z'
  'x-1/2, -y-1/2, z-1/2'
_cell_length_a  6.0228(3)
_cell_length_b  24.7920(10)
_cell_length_c  12.1890(10)
_cell_angle_alpha  90.00
_cell_angle_beta  100.9280(10)
_cell_angle_gamma  90.00
_cell_volume  1787.1(2)
_cell_formula_units_Z  4
_cell_measurement_temperature  293(2)
_exptl_crystal_density_diffrn  1.399
_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 1.1912(5)  .58748(10)  .2336(2)  .0408(8) Uani d . 1 . . O
  O2  .5518(6)  .65014(13)  -.0280(3)  .0714(12) Uani d . 1 . . O
  H2A  .5548  .6186  -.0477  .107 Uiso calc R 1 . . H
  O3  .6996(7)  .80722(13)  .0786(3)  .0742(12) Uani d . 1 . . O
  O4 1.0595(7)  .77311(12)  .1958(3)  .0718(12) Uani d . 1 . . O
  H4A  .9642  .7950  .1667  .108 Uiso calc R 1 . . H
  O5  .6954(6)  .48547(12)  .4075(3)  .0585(10) Uani d . 1 . . O
  O6 1.1350(5)  .39835(11)  .1675(3)  .0469(9) Uani d . 1 . . O
  O7 1.4470(5)  .46170(12)  .1015(3)  .0482(9) Uani d . 1 . . O
  O8 1.2700(6)  .53787(13)  .0455(3)  .0613(10) Uani d . 1 . . O
  H8A 1.3684  .5390  .0074  .092 Uiso calc R 1 . . H
  C1  .8631(8)  .61821(17)  .1042(4)  .0462(12) Uani d . 1 . . C
  H1A  .8223  .5829  .0843  .055 Uiso calc R 1 . . H
  C2  .7321(8)  .66010(17)  .0563(4)  .0486(13) Uani d . 1 . . C
  C3  .7823(8)  .71442(16)  .0875(4)  .0422(12) Uani d . 1 . . C
  C4  .9890(8)  .72245(16)  .1640(4)  .0442(12) Uani d . 1 . . C
  C5 1.1305(8)  .68091(16)  .2101(4)  .0425(12) Uani d . 1 . . C
  C6 1.0567(8)  .62856(16)  .1827(4)  .0402(11) Uani d . 1 . . C
  C7 1.0854(7)  .53831(15)  .2480(4)  .0336(10) Uani d . 1 . . C
  C8  .9357(7)  .53618(16)  .3208(4)  .0400(11) Uani d . 1 . . C
  C9  .8464(7)  .48542(17)  .3387(4)  .0396(11) Uani d . 1 . . C
  C10  .9128(7)  .43905(16)  .2901(4)  .0402(11) Uani d . 1 . . C
  H10A  .8545  .4057  .3052  .048 Uiso calc R 1 . . H
  C11 1.0657(7)  .44248(16)  .2190(4)  .0359(10) Uani d . 1 . . C
  C12 1.1536(7)  .49248(15)  .1943(3)  .0323(10) Uani d . 1 . . C
  C13  .6371(9)  .76068(18)  .0483(4)  .0543(14) Uani d . 1 . . C
  C14  .4080(10)  .7549(2)  -.0252(5)  .0721(17) Uani d . 1 . . C
  H14A  .3408  .7899  -.0401  .108 Uiso calc R 1 . . H
  H14B  .3133  .7330  .0119  .108 Uiso calc R 1 . . H
  H14C  .4236  .7381  -.0943  .108 Uiso calc R 1 . . H
  C15 1.3484(9)  .6915(2)  .2918(5)  .0708(17) Uani d . 1 . . C
  H15A 1.3722  .7297  .2999  .106 Uiso calc R 1 . . H
  H15B 1.4723  .6755  .2643  .106 Uiso calc R 1 . . H
  H15C 1.3389  .6760  .3630  .106 Uiso calc R 1 . . H
  C16  .8672(9)  .58493(18)  .3812(4)  .0535(13) Uani d . 1 . . C
  H16A  .9421  .6164  .3601  .080 Uiso calc R 1 . . H
  H16B  .9095  .5796  .4604  .080 Uiso calc R 1 . . H
  H16C  .7064  .5898  .3614  .080 Uiso calc R 1 . . H
  C17  .5833(9)  .43585(19)  .4250(5)  .0658(16) Uani d . 1 . . C
  H17A  .4812  .4420  .4754  .099 Uiso calc R 1 . . H
  H17B  .6937  .4094  .4564  .099 Uiso calc R 1 . . H
  H17C  .5001  .4230  .3549  .099 Uiso calc R 1 . . H
  C18 1.0217(9)  .34841(17)  .1762(5)  .0560(14) Uani d . 1 . . C
  H18A 1.0858  .3210  .1362  .084 Uiso calc R 1 . . H
  H18B  .8639  .3524  .1449  .084 Uiso calc R 1 . . H
  H18C 1.0393  .3383  .2534  .084 Uiso calc R 1 . . H
  C19 1.3050(8)  .49644(16)  .1123(4)  .0384(11) Uani d . 1 . . C
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  .0546(18)  .0297(16)  .038(2)  -.0020(13)  .0086(15)  .0020(13)
  O2  .093(3)  .0396(18)  .070(3)  .0101(18)  -.013(2)  -.0040(17)
  O3  .104(3)  .032(2)  .084(3)  .0077(18)  .011(2)  .0013(18)
  O4  .100(3)  .0298(18)  .082(3)  -.0069(18)  .008(2)  -.0062(17)
  O5  .079(2)  .047(2)  .061(3)  .0046(17)  .042(2)  .0006(16)
  O6  .067(2)  .0329(17)  .048(2)  .0005(14)  .0296(17)  -.0024(14)
  O7  .066(2)  .0402(17)  .045(2)  .0076(16)  .0263(17)  .0050(14)
  O8  .084(2)  .054(2)  .057(2)  .0194(18)  .041(2)  .0228(17)
  C1  .073(3)  .025(2)  .037(3)  .003(2)  .005(3)  -.0011(19)
  C2  .067(3)  .036(3)  .039(3)  -.001(2)  .001(3)  -.002(2)
  C3  .069(3)  .029(2)  .035(3)  .002(2)  .023(3)  .0003(18)
  C4  .075(3)  .026(2)  .037(3)  -.009(2)  .022(3)  -.0035(18)
  C5  .063(3)  .031(2)  .036(3)  -.006(2)  .016(2)  -.0018(19)
  C6  .060(3)  .032(2)  .032(3)  .002(2)  .017(2)  .0013(19)
  C7  .043(2)  .032(2)  .026(3)  .0014(19)  .005(2)  .0047(17)
  C8  .056(3)  .031(2)  .034(3)  .006(2)  .013(2)  .0014(19)
  C9  .051(3)  .042(3)  .032(3)  .010(2)  .023(2)  .0045(19)
  C10  .056(3)  .032(2)  .036(3)  .000(2)  .019(2)  .0052(19)
  C11  .052(2)  .034(2)  .025(3)  .0054(19)  .016(2)  .0004(18)
  C12  .043(2)  .036(2)  .021(3)  .0034(18)  .014(2)  .0046(17)
  C13  .091(4)  .036(3)  .042(3)  .010(3)  .026(3)  .008(2)
  C14  .088(4)  .051(3)  .076(4)  .018(3)  .012(3)  .012(3)
  C15  .079(4)  .054(3)  .076(4)  -.011(3)  .006(3)  -.009(3)
  C16  .078(3)  .043(3)  .045(3)  .007(2)  .025(3)  -.001(2)
  C17  .077(4)  .053(3)  .078(4)  -.004(3)  .043(3)  .009(3)
  C18  .072(3)  .039(3)  .065(4)  -.001(2)  .034(3)  -.004(2)
  C19  .061(3)  .030(2)  .025(3)  -.001(2)  .012(2)  -.0003(19)
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 C6 . 1.374(5) yes
  O1 C7 . 1.402(5) yes
  O2 C2 . 1.369(6) yes
  O2 H2A .  .8200 ?
  O3 C13 . 1.248(5) yes
  O4 C4 . 1.358(5) yes
  O4 H4A .  .8200 ?
  O5 C9 . 1.349(5) yes
  O5 C17 . 1.438(5) yes
  O6 C11 . 1.366(5) yes
  O6 C18 . 1.427(5) yes
  O7 C19 . 1.239(5) yes
  O8 C19 . 1.303(5) yes
  O8 H8A .  .8200 ?
  C1 C2 . 1.366(6) ?
  C1 C6 . 1.385(6) ?
  C1 H1A .  .9300 ?
  C2 C3 . 1.416(6) ?
  C3 C4 . 1.421(7) ?
  C3 C13 . 1.466(6) ?
  C4 C5 . 1.386(6) ?
  C5 C6 . 1.392(6) ?
  C5 C15 . 1.512(7) ?
  C7 C8 . 1.381(6) ?
  C7 C12 . 1.411(6) ?
  C8 C9 . 1.402(6) ?
  C8 C16 . 1.512(6) ?
  C9 C10 . 1.387(6) ?
  C10 C11 . 1.381(6) ?
  C10 H10A .  .9300 ?
  C11 C12 . 1.403(6) ?
  C12 C19 . 1.478(6) ?
  C13 C14 . 1.503(8) ?
  C14 H14A .  .9600 ?
  C14 H14B .  .9600 ?
  C14 H14C .  .9600 ?
  C15 H15A .  .9600 ?
  C15 H15B .  .9600 ?
  C15 H15C .  .9600 ?
  C16 H16A .  .9600 ?
  C16 H16B .  .9600 ?
  C16 H16C .  .9600 ?
  C17 H17A .  .9600 ?
  C17 H17B .  .9600 ?
  C17 H17C .  .9600 ?
  C18 H18A .  .9600 ?
  C18 H18B .  .9600 ?
  C18 H18C .  .9600 ?