#------------------------------------------------------------------------------
#$Date: 2008-11-20 19:58:43 +0000 (Thu, 20 Nov 2008) $
#$Revision: 481 $
#$URL: svn://www.crystallography.net/cod/cif/2/2008223.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_2008223
_journal_name_full 'Acta Crystallographica Section C'
_journal_year  1999
_journal_volume 55
_journal_page_first  436
_journal_page_last  439
_publ_section_title
;
 Two dioxane derivatives of anthraquinone
;
loop_
_publ_author_name
  'Cambie, Richard C.'
  'Lorimer, Rachel M.'
  'Rickard, Clifton E. F.'
  'Rutledge, P. Stewart'
_chemical_formula_sum  'C25 H26 O5'
_chemical_formula_weight  406.46
_symmetry_cell_setting  Orthorhombic
_symmetry_space_group_name_H-M  'P 21 21 21'
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  6.79300(10)
_cell_length_b  14.0076(2)
_cell_length_c  22.27700(10)
_cell_angle_alpha  90.00
_cell_angle_beta  90.00
_cell_angle_gamma  90.00
_cell_volume  2119.77(4)
_cell_formula_units_Z  4
_cell_measurement_temperature  203(2)
_exptl_crystal_density_diffrn  1.274
_diffrn_ambient_temperature  203(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
  O4 0.1205(2) 0.19020(9) 0.17708(5) 0.0540(4) Uani d . 1 . . O
  H4 0.1108 0.2450 0.1632 0.065 Uiso calc R 1 . . H
  O9 0.0796(2) 0.05196(9) -0.07789(6) 0.0609(4) Uani d . 1 . . O
  O10 0.0978(2) 0.31883(8) 0.09559(6) 0.0550(3) Uani d . 1 . . O
  C1 0.1239(2) -0.01045(11) 0.04125(7) 0.0381(4) Uani d . 1 . . C
  H1A 0.1198 -0.0572 0.0110 0.046 Uiso calc R 1 . . H
  C2 0.1462(2) -0.03813(11) 0.10127(8) 0.0380(4) Uani d . 1 . . C
  C3 0.1468(2) 0.02940(12) 0.14734(8) 0.0407(4) Uani d . 1 . . C
  C4 0.1232(3) 0.12653(12) 0.13163(8) 0.0411(4) Uani d . 1 . . C
  C4A 0.1084(2) 0.15508(11) 0.07146(7) 0.0370(4) Uani d . 1 . . C
  C5 0.1047(3) 0.38136(12) -0.02293(9) 0.0460(4) Uani d . 1 . . C
  H5A 0.1066 0.4277 0.0076 0.055 Uiso calc R 1 . . H
  C6 0.1065(3) 0.40919(13) -0.08199(9) 0.0520(5) Uani d . 1 . . C
  H6A 0.1092 0.4744 -0.0918 0.062 Uiso calc R 1 . . H
  C7 0.1042(3) 0.34116(14) -0.12708(9) 0.0528(5) Uani d . 1 . . C
  H7A 0.1061 0.3605 -0.1675 0.063 Uiso calc R 1 . . H
  C8 0.0991(3) 0.24471(13) -0.11301(8) 0.0476(4) Uani d . 1 . . C
  H8A 0.0968 0.1990 -0.1439 0.057 Uiso calc R 1 . . H
  C8A 0.0973(3) 0.21551(11) -0.05344(8) 0.0397(4) Uani d . 1 . . C
  C9 0.0928(3) 0.11175(11) -0.03844(8) 0.0417(4) Uani d . 1 . . C
  C9A 0.1078(3) 0.08448(11) 0.02611(7) 0.0362(4) Uani d . 1 . . C
  C10 0.1000(3) 0.25659(12) 0.05611(8) 0.0413(4) Uani d . 1 . . C
  C10A 0.1000(3) 0.28464(11) -0.00776(8) 0.0400(4) Uani d . 1 . . C
  O1' 0.1141(2) -0.19900(8) 0.06838(5) 0.0492(3) Uani d . 1 . . O
  C2' 0.1753(3) -0.14243(12) 0.11681(8) 0.0406(4) Uani d . 1 . . C
  H2'A 0.0969 -0.1586 0.1529 0.049 Uiso calc R 1 . . H
  O3' 0.37782(18) -0.15460(8) 0.12930(6) 0.0488(3) Uani d . 1 . . O
  C4' 0.4289(3) -0.25270(14) 0.14563(10) 0.0588(5) Uani d . 1 . . C
  C5' 0.3475(3) -0.31880(13) 0.09782(10) 0.0602(6) Uani d . 1 . . C
  H5'A 0.4260 -0.3118 0.0612 0.072 Uiso calc R 1 . . H
  H5'B 0.3606 -0.3850 0.1115 0.072 Uiso calc R 1 . . H
  C6' 0.1344(3) -0.29931(12) 0.08330(9) 0.0550(5) Uani d . 1 . . C
  H6'A 0.0532 -0.3135 0.1191 0.066 Uiso calc R 1 . . H
  C7' 0.6527(4) -0.2532(2) 0.14624(16) 0.1038(10) Uani d . 1 . . C
  H7'A 0.7016 -0.2335 0.1073 0.156 Uiso calc R 1 . . H
  H7'B 0.6994 -0.3171 0.1551 0.156 Uiso calc R 1 . . H
  H7'C 0.6998 -0.2094 0.1767 0.156 Uiso calc R 1 . . H
  C8' 0.3518(4) -0.27601(16) 0.20825(11) 0.0788(7) Uani d . 1 . . C
  H8'A 0.4020 -0.2296 0.2367 0.118 Uiso calc R 1 . . H
  H8'B 0.3952 -0.3394 0.2198 0.118 Uiso calc R 1 . . H
  H8'C 0.2090 -0.2739 0.2081 0.118 Uiso calc R 1 . . H
  C9' 0.0561(6) -0.35524(16) 0.03065(13) 0.1035(11) Uani d . 1 . . C
  H9'A -0.0747 -0.3325 0.0206 0.155 Uiso calc R 1 . . H
  H9'B 0.0499 -0.4224 0.0411 0.155 Uiso calc R 1 . . H
  H9'C 0.1427 -0.3467 -0.0036 0.155 Uiso calc R 1 . . H
  C1" 0.1772(3) 0.00524(13) 0.21252(8) 0.0497(5) Uani d . 1 . . C
  H1"A 0.2494 0.0579 0.2314 0.060 Uiso calc R 1 . . H
  H1"B 0.2610 -0.0516 0.2148 0.060 Uiso calc R 1 . . H
  C2" -0.0066(3) -0.01324(13) 0.24900(9) 0.0510(5) Uani d . 1 . . C
  C3" -0.1803(4) -0.02816(16) 0.22535(11) 0.0678(6) Uani d . 1 . . C
  H3"1 -0.2891 -0.0404 0.2503 0.081 Uiso calc R 1 . . H
  H3"2 -0.1963 -0.0266 0.1834 0.081 Uiso calc R 1 . . H
  C4" 0.0287(5) -0.01469(19) 0.31559(10) 0.0862(8) Uani d . 1 . . C
  H4"A -0.0923 -0.0316 0.3361 0.129 Uiso calc R 1 . . H
  H4"B 0.0716 0.0480 0.3287 0.129 Uiso calc R 1 . . H
  H4"C 0.1297 -0.0614 0.3249 0.129 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
  O4 0.0703(9) 0.0427(7) 0.0488(7) -0.0008(7) 0.0060(7) -0.0127(5)
  O9 0.0938(11) 0.0421(7) 0.0468(8) -0.0016(7) 0.0001(8) -0.0052(6)
  O10 0.0672(8) 0.0378(7) 0.0601(8) 0.0019(7) 0.0086(7) -0.0130(6)
  C1 0.0367(9) 0.0349(8) 0.0427(9) -0.0009(7) 0.0035(8) -0.0050(7)
  C2 0.0316(9) 0.0356(9) 0.0469(10) 0.0002(7) 0.0019(7) -0.0024(7)
  C3 0.0365(9) 0.0413(9) 0.0442(9) -0.0012(8) 0.0016(7) -0.0036(8)
  C4 0.0374(9) 0.0393(9) 0.0465(10) -0.0008(8) 0.0038(8) -0.0095(8)
  C4A 0.0299(8) 0.0348(8) 0.0464(9) -0.0004(7) 0.0059(8) -0.0057(7)
  C5 0.0353(9) 0.0348(9) 0.0678(12) 0.0004(8) 0.0038(10) -0.0009(8)
  C6 0.0411(10) 0.0392(9) 0.0756(14) 0.0022(9) 0.0039(10) 0.0111(9)
  C7 0.0454(10) 0.0520(11) 0.0608(12) 0.0022(10) 0.0022(10) 0.0128(9)
  C8 0.0449(10) 0.0445(10) 0.0534(11) 0.0025(9) 0.0027(9) 0.0039(8)
  C8A 0.0320(8) 0.0383(9) 0.0489(10) 0.0000(8) 0.0038(8) 0.0001(7)
  C9 0.0401(10) 0.0385(9) 0.0466(10) 0.0002(8) 0.0023(8) -0.0041(7)
  C9A 0.0307(8) 0.0345(8) 0.0436(9) 0.0006(7) 0.0029(8) -0.0045(7)
  C10 0.0320(8) 0.0362(9) 0.0557(10) 0.0014(8) 0.0059(8) -0.0054(8)
  C10A 0.0276(8) 0.0378(9) 0.0545(10) 0.0012(7) 0.0058(8) -0.0004(7)
  O1' 0.0629(8) 0.0326(6) 0.0520(7) 0.0028(6) -0.0113(7) -0.0012(5)
  C2' 0.0382(9) 0.0386(9) 0.0451(10) 0.0000(7) -0.0003(8) 0.0008(7)
  O3' 0.0393(7) 0.0433(7) 0.0639(8) 0.0033(6) -0.0030(6) 0.0082(6)
  C4' 0.0489(12) 0.0489(11) 0.0786(14) 0.0082(9) -0.0025(10) 0.0163(10)
  C5' 0.0726(14) 0.0410(11) 0.0670(13) 0.0151(10) 0.0145(11) 0.0094(9)
  C6' 0.0741(14) 0.0313(9) 0.0596(12) 0.0037(10) -0.0040(11) 0.0021(8)
  C7' 0.0529(15) 0.0803(18) 0.178(3) 0.0175(13) -0.0101(17) 0.037(2)
  C8' 0.106(2) 0.0617(13) 0.0687(14) 0.0014(14) -0.0183(15) 0.0190(11)
  C9' 0.175(3) 0.0398(12) 0.096(2) 0.0063(16) -0.053(2) -0.0121(12)
  C1" 0.0575(12) 0.0452(10) 0.0464(10) 0.0023(9) -0.0044(9) -0.0044(8)
  C2" 0.0730(14) 0.0327(9) 0.0473(10) 0.0065(9) 0.0097(10) 0.0051(8)
  C3" 0.0646(15) 0.0686(14) 0.0704(15) 0.0082(12) 0.0180(12) 0.0137(12)
  C4" 0.134(2) 0.0729(16) 0.0512(13) -0.0148(16) 0.0089(14) 0.0092(12)
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
  O4 C4 . 1.3493(19) ?
  O9 C9 . 1.217(2) ?
  O10 C10 . 1.238(2) ?
  C1 C9A . 1.376(2) ?
  C1 C2 . 1.400(2) ?
  C2 C3 . 1.396(2) ?
  C2 C2' . 1.514(2) n
  C3 C4 . 1.414(2) ?
  C3 C1" . 1.505(2) n
  C4 C4A . 1.403(2) ?
  C4A C9A . 1.414(2) ?
  C4A C10 . 1.463(2) ?
  C5 C6 . 1.372(3) ?
  C5 C10A . 1.397(2) ?
  C6 C7 . 1.385(3) ?
  C7 C8 . 1.387(3) ?
  C8 C8A . 1.389(2) ?
  C8A C10A . 1.405(2) ?
  C8A C9 . 1.492(2) ?
  C9 C9A . 1.491(2) ?
  C10 C10A . 1.476(3) ?
  O1' C2' . 1.402(2) n
  O1' C6' . 1.451(2) n
  C2' O3' . 1.414(2) n
  O3' C4' . 1.463(2) n
  C4' C5' . 1.516(3) n
  C4' C7' . 1.520(3) n
  C4' C8' . 1.526(3) n
  C5' C6' . 1.508(3) n
  C6' C9' . 1.508(3) n
  C1" C2" . 1.512(3) n
  C2" C3" . 1.309(3) n
  C2" C4" . 1.503(3) n