#------------------------------------------------------------------------------
#$Date: 2015-01-27 21:58:39 +0200 (Tue, 27 Jan 2015) $
#$Revision: 130149 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/08/4020878.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_4020878
loop_
_publ_author_name
'Sidika Polat Cakir'
'Keith T. Mead'
_publ_section_title
;
 Stereoselective Approach to C-Aryl Pyranoside Synthesis
 Which Addresses the Problem of C7-Substitution in Blepharocalyxin E
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2203
_journal_page_last               2205
_journal_paper_doi               10.1021/jo0355909
_journal_volume                  69
_journal_year                    2004
_chemical_formula_sum            'C20 H20 O4'
_chemical_formula_weight         324.36
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_cell_angle_alpha                84.948(4)
_cell_angle_beta                 80.144(4)
_cell_angle_gamma                87.036(4)
_cell_formula_units_Z            2
_cell_length_a                   6.3446(14)
_cell_length_b                   11.258(3)
_cell_length_c                   11.961(3)
_cell_measurement_temperature    296(2)
_cell_volume                     837.9(3)
_diffrn_ambient_temperature      296(2)
_exptl_crystal_density_diffrn    1.286
_cod_database_code               4020878
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O2 O 0.17048(19) 1.07506(11) 0.08256(11) 0.0556(4) Uani 1 1 d . . .
O3 O 0.2967(2) 0.94838(12) -0.04702(12) 0.0598(4) Uani 1 1 d . . .
O4 O 0.5822(2) 0.42230(12) 0.17499(13) 0.0749(5) Uani 1 1 d . . .
C15 C 0.2689(3) 0.75482(15) 0.14857(15) 0.0432(4) Uani 1 1 d . . .
C9 C 0.3847(3) 0.84020(15) 0.37793(15) 0.0437(4) Uani 1 1 d . . .
C16 C 0.4765(3) 0.73957(18) 0.09309(16) 0.0493(5) Uani 1 1 d . . .
C18 C 0.4899(3) 0.53396(17) 0.16157(16) 0.0537(5) Uani 1 1 d . . .
C17 C 0.5872(3) 0.63034(17) 0.09863(17) 0.0531(5) Uani 1 1 d . . .
O1 O 0.1099(2) 1.16956(12) 0.24984(13) 0.0724(4) Uani 1 1 d . . .
C4 C 0.3483(3) 0.94737(15) 0.29642(16) 0.0444(5) Uani 1 1 d . . .
C7 C 0.1465(3) 0.87310(15) 0.14801(15) 0.0449(5) Uani 1 1 d . . .
C8 C 0.2173(3) 0.96467(18) 0.04989(17) 0.0483(5) Uani 1 1 d . . .
C5 C 0.1364(3) 0.94697(15) 0.25180(16) 0.0456(5) Uani 1 1 d . . .
C14 C 0.2334(4) 0.8073(2) 0.47173(18) 0.0626(6) Uani 1 1 d . . .
C20 C 0.1741(4) 0.65580(18) 0.21066(18) 0.0565(5) Uani 1 1 d . . .
C6 C 0.0645(4) 1.06946(18) 0.20186(17) 0.0566(5) Uani 1 1 d . . .
C3 C 0.3665(5) 1.06282(18) 0.3517(2) 0.0609(6) Uani 1 1 d . . .
C10 C 0.5768(3) 0.77630(18) 0.36492(18) 0.0569(5) Uani 1 1 d . . .
C19 C 0.2807(4) 0.5477(2) 0.21774(19) 0.0626(6) Uani 1 1 d . . .
C11 C 0.6159(4) 0.6814(2) 0.4417(2) 0.0718(7) Uani 1 1 d . . .
C2 C 0.3261(5) 1.1693(2) 0.2722(2) 0.0732(7) Uani 1 1 d . . .
C13 C 0.2727(5) 0.7128(2) 0.5485(2) 0.0747(7) Uani 1 1 d . . .
C21 C 0.7908(5) 0.4001(3) 0.1140(3) 0.0773(7) Uani 1 1 d . . .
C12 C 0.4627(5) 0.6501(2) 0.5328(2) 0.0738(7) Uani 1 1 d . . .
H5 H 0.020(3) 0.9183(13) 0.3141(15) 0.045(5) Uiso 1 1 d . . .
H6 H -0.088(3) 1.0733(15) 0.1969(15) 0.056(5) Uiso 1 1 d . . .
H7 H -0.002(3) 0.8586(13) 0.1389(14) 0.047(5) Uiso 1 1 d . . .
H16 H 0.546(3) 0.8049(16) 0.0516(16) 0.058(6) Uiso 1 1 d . . .
H4 H 0.466(3) 0.9445(13) 0.2338(15) 0.043(5) Uiso 1 1 d . . .
H17 H 0.736(3) 0.6253(15) 0.0570(16) 0.059(5) Uiso 1 1 d . . .
H10 H 0.683(3) 0.7948(16) 0.2980(18) 0.066(6) Uiso 1 1 d . . .
H3B H 0.505(3) 1.0660(15) 0.3682(15) 0.052(6) Uiso 1 1 d . . .
H3A H 0.262(3) 1.0645(16) 0.4220(18) 0.065(6) Uiso 1 1 d . . .
H2A H 0.324(3) 1.2394(19) 0.3087(18) 0.076(7) Uiso 1 1 d . . .
H20 H 0.033(3) 0.6645(16) 0.2469(17) 0.064(6) Uiso 1 1 d . . .
H14 H 0.107(3) 0.8509(17) 0.4831(17) 0.068(6) Uiso 1 1 d . . .
H19 H 0.217(3) 0.4851(18) 0.2608(18) 0.070(6) Uiso 1 1 d . . .
H12 H 0.492(3) 0.585(2) 0.587(2) 0.093(7) Uiso 1 1 d . . .
H2B H 0.425(4) 1.166(2) 0.195(2) 0.090(8) Uiso 1 1 d . . .
H21B H 0.891(4) 0.455(2) 0.140(2) 0.110(9) Uiso 1 1 d . . .
H21A H 0.791(4) 0.417(2) 0.034(2) 0.101(9) Uiso 1 1 d . . .
H11 H 0.754(4) 0.636(2) 0.430(2) 0.098(8) Uiso 1 1 d . . .
H13 H 0.166(4) 0.696(2) 0.607(2) 0.089(8) Uiso 1 1 d . . .
H21C H 0.822(4) 0.319(2) 0.130(2) 0.106(9) Uiso 1 1 d . . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C8 1.339(2) . ?
O2 C6 1.467(2) . ?
O3 C8 1.208(2) . ?
O4 C18 1.367(2) . ?
O4 C21 1.419(3) . ?
C15 C16 1.379(3) . ?
C15 C20 1.388(2) . ?
C15 C7 1.507(2) . ?
C9 C10 1.375(3) . ?
C9 C14 1.383(3) . ?
C9 C4 1.517(2) . ?
C16 C17 1.386(3) . ?
C18 C17 1.375(3) . ?
C18 C19 1.389(3) . ?
O1 C6 1.374(2) . ?
O1 C2 1.441(3) . ?
C4 C3 1.527(3) . ?
C4 C5 1.530(3) . ?
C7 C8 1.515(2) . ?
C7 C5 1.545(2) . ?
C5 C6 1.533(3) . ?
C14 C13 1.384(3) . ?
C20 C19 1.364(3) . ?
C3 C2 1.503(3) . ?
C10 C11 1.387(3) . ?
C11 C12 1.364(3) . ?
C13 C12 1.358(3) . ?
