#------------------------------------------------------------------------------
#$Date: 2016-03-21 02:20:25 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178382 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/04/4020444.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_4020444
loop_
_publ_author_name
'Thomas D. Avery'
'Daniela Caiazza'
'Julie A. Culbert'
'Dennis K. Taylor'
'Edward R. T. Tiekink'
_publ_section_title
;
 1,2-Dioxines Containing Tethered Hydroxyl Functionality
 as Convenient Precursors for Pyran Syntheses
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8344
_journal_page_last               8351
_journal_paper_doi               10.1021/jo050806n
_journal_volume                  70
_journal_year                    2005
_chemical_formula_moiety         'C19 H20 O4'
_chemical_formula_sum            'C19 H20 O4'
_chemical_formula_weight         312.35
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_cell_angle_alpha                90
_cell_angle_beta                 96.181(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   35.331(3)
_cell_length_b                   10.4015(8)
_cell_length_c                   8.7744(7)
_cell_measurement_temperature    223(2)
_cell_volume                     3205.8(4)
_diffrn_ambient_temperature      223(2)
_exptl_crystal_density_diffrn    1.294
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4020444
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
O1 O 0.65927(4) 0.03256(16) 0.27676(18) 0.0404(4) Uani 1 1 d . . .
O22 O 0.59299(5) 0.22602(16) 0.1902(2) 0.0473(4) Uani 1 1 d . . .
O31 O 0.66647(4) -0.04628(14) 0.59027(17) 0.0382(4) Uani 1 1 d . . .
O32 O 0.68708(6) 0.0035(2) 0.8338(2) 0.0626(6) Uani 1 1 d . . .
C2 C 0.64544(6) 0.1072(2) 0.3951(2) 0.0339(5) Uani 1 1 d . . .
H2 H 0.6473 0.1988 0.3665 0.041 Uiso 1 1 calc R . .
C3 C 0.66977(7) 0.0878(2) 0.5462(3) 0.0361(5) Uani 1 1 d . . .
H3 H 0.6606 0.1441 0.6254 0.043 Uiso 1 1 calc R . .
C4 C 0.71114(7) 0.1188(2) 0.5279(3) 0.0414(6) Uani 1 1 d . . .
H4A H 0.7272 0.0955 0.6220 0.050 Uiso 1 1 calc R . .
H4B H 0.7138 0.2114 0.5116 0.050 Uiso 1 1 calc R . .
C5 C 0.72438(7) 0.0460(2) 0.3932(3) 0.0434(6) Uani 1 1 d . . .
H5A H 0.7258 -0.0461 0.4167 0.052 Uiso 1 1 calc R . .
H5B H 0.7499 0.0753 0.3751 0.052 Uiso 1 1 calc R . .
C6 C 0.69710(7) 0.0682(3) 0.2514(3) 0.0456(6) Uani 1 1 d . . .
H6A H 0.6976 0.1592 0.2228 0.055 Uiso 1 1 calc R . .
H6B H 0.7052 0.0175 0.1665 0.055 Uiso 1 1 calc R . .
C21 C 0.60382(6) 0.0752(2) 0.3935(3) 0.0348(5) Uani 1 1 d . . .
H21A H 0.5950 0.1024 0.4907 0.042 Uiso 1 1 calc R . .
H21B H 0.6005 -0.0182 0.3848 0.042 Uiso 1 1 calc R . .
C22 C 0.57964(6) 0.1402(2) 0.2618(3) 0.0338(5) Uani 1 1 d . . .
C31 C 0.67757(7) -0.0754(3) 0.7375(3) 0.0449(6) Uani 1 1 d . . .
C32 C 0.67751(8) -0.2166(3) 0.7632(3) 0.0604(8) Uani 1 1 d . . .
H32A H 0.7035 -0.2482 0.7749 0.091 Uiso 1 1 calc R . .
H32B H 0.6634 -0.2585 0.6761 0.091 Uiso 1 1 calc R . .
H32C H 0.6656 -0.2354 0.8553 0.091 Uiso 1 1 calc R . .
C41 C 0.53888(6) 0.10315(19) 0.2270(2) 0.0296(5) Uani 1 1 d . . .
C42 C 0.52069(7) 0.0116(2) 0.3132(2) 0.0348(5) Uani 1 1 d . . .
H42 H 0.5348 -0.0318 0.3943 0.042 Uiso 1 1 calc R . .
C43 C 0.48289(7) -0.0147(2) 0.2803(3) 0.0357(5) Uani 1 1 d . . .
H43 H 0.4714 -0.0762 0.3389 0.043 Uiso 1 1 calc R . .
C44 C 0.46069(6) 0.04884(19) 0.1598(2) 0.0314(5) Uani 1 1 d . . .
C45 C 0.42108(7) 0.0252(2) 0.1237(3) 0.0401(6) Uani 1 1 d . . .
H45 H 0.4087 -0.0345 0.1818 0.048 Uiso 1 1 calc R . .
C46 C 0.40104(7) 0.0882(3) 0.0062(3) 0.0461(6) Uani 1 1 d . . .
H46 H 0.3750 0.0709 -0.0177 0.055 Uiso 1 1 calc R . .
C47 C 0.41892(7) 0.1790(3) -0.0803(3) 0.0476(7) Uani 1 1 d . . .
H47 H 0.4046 0.2232 -0.1604 0.057 Uiso 1 1 calc R . .
C48 C 0.45665(7) 0.2036(2) -0.0493(3) 0.0385(6) Uani 1 1 d . . .
H48 H 0.4683 0.2639 -0.1089 0.046 Uiso 1 1 calc R . .
C49 C 0.47859(6) 0.13949(19) 0.0713(2) 0.0296(5) Uani 1 1 d . . .
C50 C 0.51781(6) 0.16284(19) 0.1066(2) 0.0306(5) Uani 1 1 d . . .
H50 H 0.5299 0.2211 0.0460 0.037 Uiso 1 1 calc R . .
O1A O 0.91510(5) 0.40898(16) 0.57016(18) 0.0447(4) Uani 1 1 d . . .
O22A O 0.83058(5) 0.39219(16) 0.2026(2) 0.0556(5) Uani 1 1 d . . .
O31A O 0.94018(5) 0.41821(16) 0.26818(18) 0.0428(4) Uani 1 1 d . . .
O32A O 0.93373(7) 0.5056(3) 0.0349(2) 0.0860(7) Uani 1 1 d . . .
C2A C 0.89037(7) 0.4265(2) 0.4319(3) 0.0363(5) Uani 1 1 d . . .
H2A H 0.8680 0.4769 0.4561 0.044 Uiso 1 1 calc R . .
C3A C 0.91000(7) 0.4999(2) 0.3140(3) 0.0377(5) Uani 1 1 d . . .
H3A H 0.8915 0.5186 0.2237 0.045 Uiso 1 1 calc R . .
C4A C 0.92691(8) 0.6249(2) 0.3796(3) 0.0477(6) Uani 1 1 d . . .
H4A1 H 0.9063 0.6863 0.3906 0.057 Uiso 1 1 calc R . .
H4A2 H 0.9434 0.6618 0.3081 0.057 Uiso 1 1 calc R . .
C5A C 0.94973(7) 0.6052(3) 0.5340(3) 0.0495(7) Uani 1 1 d . . .
H5A1 H 0.9733 0.5588 0.5205 0.059 Uiso 1 1 calc R . .
H5A2 H 0.9566 0.6889 0.5804 0.059 Uiso 1 1 calc R . .
C6A C 0.92668(8) 0.5296(3) 0.6383(3) 0.0540(7) Uani 1 1 d . . .
H6A1 H 0.9420 0.5146 0.7366 0.065 Uiso 1 1 calc R . .
H6A2 H 0.9041 0.5792 0.6580 0.065 Uiso 1 1 calc R . .
C21A C 0.87697(6) 0.2935(2) 0.3815(3) 0.0361(5) Uani 1 1 d . . .
H21C H 0.8979 0.2485 0.3398 0.043 Uiso 1 1 calc R . .
H21D H 0.8707 0.2455 0.4715 0.043 Uiso 1 1 calc R . .
C22A C 0.84273(6) 0.2929(2) 0.2625(3) 0.0370(5) Uani 1 1 d . . .
C31A C 0.94868(8) 0.4293(3) 0.1240(3) 0.0528(7) Uani 1 1 d . . .
C32A C 0.97844(8) 0.3354(3) 0.0901(4) 0.0672(9) Uani 1 1 d . . .
H32D H 0.9666 0.2642 0.0316 0.101 Uiso 1 1 calc R . .
H32E H 0.9915 0.3035 0.1855 0.101 Uiso 1 1 calc R . .
H32F H 0.9966 0.3774 0.0311 0.101 Uiso 1 1 calc R . .
C41A C 0.82489(6) 0.1675(2) 0.2174(2) 0.0338(5) Uani 1 1 d . . .
C42A C 0.79491(7) 0.1650(2) 0.0966(3) 0.0408(6) Uani 1 1 d . . .
H42A H 0.7870 0.2422 0.0473 0.049 Uiso 1 1 calc R . .
C43A C 0.77749(7) 0.0535(3) 0.0508(3) 0.0465(6) Uani 1 1 d . . .
H43A H 0.7576 0.0543 -0.0294 0.056 Uiso 1 1 calc R . .
C44A C 0.78895(7) -0.0644(2) 0.1226(3) 0.0401(6) Uani 1 1 d . . .
C45A C 0.77169(8) -0.1834(3) 0.0797(3) 0.0546(7) Uani 1 1 d . . .
H45A H 0.7510 -0.1857 0.0028 0.065 Uiso 1 1 calc R . .
C46A C 0.78460(9) -0.2944(3) 0.1480(4) 0.0609(8) Uani 1 1 d . . .
H46A H 0.7730 -0.3728 0.1169 0.073 Uiso 1 1 calc R . .
C47A C 0.81479(8) -0.2936(3) 0.2633(4) 0.0583(8) Uani 1 1 d . . .
H47A H 0.8237 -0.3714 0.3086 0.070 Uiso 1 1 calc R . .
C48A C 0.83158(7) -0.1807(2) 0.3110(3) 0.0490(7) Uani 1 1 d . . .
H48A H 0.8516 -0.1809 0.3909 0.059 Uiso 1 1 calc R . .
C49A C 0.81928(6) -0.0636(2) 0.2416(3) 0.0378(5) Uani 1 1 d . . .
C50A C 0.83643(6) 0.0551(2) 0.2872(3) 0.0356(5) Uani 1 1 d . . .
H50A H 0.8563 0.0564 0.3676 0.043 Uiso 1 1 calc R . .
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
O1 C2 1.424(3) . ?
O1 C6 1.427(3) . ?
O22 C22 1.216(3) . ?
O31 C31 1.344(3) . ?
O31 C3 1.455(3) . ?
O32 C31 1.200(3) . ?
C2 C21 1.507(3) . ?
C2 C3 1.514(3) . ?
C2 H2 0.9900 . ?
C3 C4 1.522(3) . ?
C3 H3 0.9900 . ?
C4 C5 1.519(3) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C5 C6 1.507(3) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C21 C22 1.520(3) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C22 C41 1.490(3) . ?
C31 C32 1.486(4) . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
C32 H32C 0.9700 . ?
C41 C50 1.373(3) . ?
C41 C42 1.413(3) . ?
C42 C43 1.363(3) . ?
C42 H42 0.9400 . ?
C43 C44 1.411(3) . ?
C43 H43 0.9400 . ?
C44 C45 1.423(3) . ?
C44 C49 1.414(3) . ?
C45 C46 1.355(3) . ?
C45 H45 0.9400 . ?
C46 C47 1.404(4) . ?
C46 H46 0.9400 . ?
C47 C48 1.356(3) . ?
C47 H47 0.9400 . ?
C48 C49 1.410(3) . ?
C48 H48 0.9400 . ?
C49 C50 1.408(3) . ?
C50 H50 0.9400 . ?
O1A C2A 1.428(3) . ?
O1A C6A 1.430(3) . ?
O22A C22A 1.216(3) . ?
O31A C31A 1.336(3) . ?
O31A C3A 1.454(3) . ?
O32A C31A 1.196(3) . ?
C2A C3A 1.513(3) . ?
C2A C21A 1.512(3) . ?
C2A H2A 0.9900 . ?
C3A C4A 1.519(3) . ?
C3A H3A 0.9900 . ?
C4A C5A 1.514(3) . ?
C4A H4A1 0.9800 . ?
C4A H4A2 0.9800 . ?
C5A C6A 1.510(4) . ?
C5A H5A1 0.9800 . ?
C5A H5A2 0.9800 . ?
C6A H6A1 0.9800 . ?
C6A H6A2 0.9800 . ?
C21A C22A 1.511(3) . ?
C21A H21C 0.9800 . ?
C21A H21D 0.9800 . ?
C22A C41A 1.483(3) . ?
C31A C32A 1.488(4) . ?
C32A H32D 0.9700 . ?
C32A H32E 0.9700 . ?
C32A H32F 0.9700 . ?
C41A C50A 1.362(3) . ?
C41A C42A 1.416(3) . ?
C42A C43A 1.353(3) . ?
C42A H42A 0.9400 . ?
C43A C44A 1.418(3) . ?
C43A H43A 0.9400 . ?
C44A C49A 1.414(3) . ?
C44A C45A 1.413(3) . ?
C45A C46A 1.358(4) . ?
C45A H45A 0.9400 . ?
C46A C47A 1.389(4) . ?
C46A H46A 0.9400 . ?
C47A C48A 1.361(4) . ?
C47A H47A 0.9400 . ?
C48A C49A 1.409(3) . ?
C48A H48A 0.9400 . ?
C49A C50A 1.414(3) . ?
C50A H50A 0.9400 . ?
