#------------------------------------------------------------------------------
#$Date: 2011-09-17 21:27:16 +0100 (Sat, 17 Sep 2011) $
#$Revision: 26029 $
#$URL: svn://www.crystallography.net/cod/cif/2/2202271.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_2202271
_journal_name_full  'Acta Crystallographica, Section E'
_journal_year  2003
_journal_volume  59
_journal_page_first  o1575
_journal_page_last  o1577
_publ_section_title
;
3-(5,7-Dimethoxy-2,2-dimethyl-2H-benzo[b]pyran-6-yl)propionic acid
;
_space_group_IT_number           15
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_[local]_cod_cif_authors_sg_H-M  'C 2/c'
loop_
_publ_author_name
  'Silva, M.'
  'Napolitano, H. B.'
  'Ellena, J.'
  'Rocha, W. C.'
  'Vieira, P. C.'
  'Oliva, G.'
  'Thiemann, O. H.'
_chemical_formula_moiety  'C16 H20 O5'
_chemical_formula_sum  'C16 H20 O5'
_chemical_formula_iupac  'C16 H20 O5'
_chemical_formula_weight  292.32
_symmetry_cell_setting  monoclinic
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x, y, -z+1/2'
  'x+1/2, y+1/2, z'
  '-x+1/2, y+1/2, -z+1/2'
  '-x, -y, -z'
  'x, -y, z-1/2'
  '-x+1/2, -y+1/2, -z'
  'x+1/2, -y+1/2, z-1/2'
_cell_length_a  23.3022(3)
_cell_length_b  10.2248(2)
_cell_length_c  15.0785(3)
_cell_angle_alpha  90
_cell_angle_beta  122.2730(10)
_cell_angle_gamma  90
_cell_volume  3037.60(9)
_cell_formula_units_Z  8
_cell_measurement_temperature  120(2)
_exptl_crystal_density_diffrn  1.278
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
  C13 -0.17318(8) 0.34247(15) -0.33222(12) 0.0334(3) Uani d . 1 . . C
  C15 -0.05400(8) 0.52785(13) 0.08274(13) 0.0337(3) Uani d . 1 . . C
  O20 0.19639(4) 0.32730(9) 0.38925(7) 0.0278(2) Uani d . 1 . . O
  C16 0.11583(7) 0.05665(14) 0.00327(12) 0.0311(3) Uani d . 1 . . C
  O19 0.10000(4) 0.14355(9) 0.06192(7) 0.0295(2) Uani d . 1 . . O
  C10 0.08016(7) 0.30486(13) 0.18803(10) 0.0255(3) Uani d . 1 . . C
  C7 0.03408(6) 0.18379(12) 0.01653(10) 0.0238(3) Uani d . 1 . . C
  C8 0.02258(6) 0.26705(12) 0.08000(9) 0.0228(3) Uani d . 1 . . C
  C6 -0.01759(6) 0.14873(12) -0.08405(10) 0.0251(3) Uani d . 1 . . C
  C1 -0.19220(6) 0.23845(13) -0.28030(10) 0.0266(3) Uani d . 1 . . C
  C9 -0.04311(6) 0.31305(12) 0.03743(9) 0.0225(3) Uani d . 1 . . C
  O18 -0.05724(4) 0.39039(9) 0.09929(7) 0.0264(2) Uani d . 1 . . O
  C12 0.16551(6) 0.22373(12) 0.37012(10) 0.0237(3) Uani d . 1 . . C
  C5 -0.08228(6) 0.19751(12) -0.12295(9) 0.0241(3) Uani d . 1 . . C
  C4 -0.09670(6) 0.28131(12) -0.06393(9) 0.0232(3) Uani d . 1 . . C
  C2 -0.21218(7) 0.30046(13) -0.20982(10) 0.0279(3) Uani d . 1 . . C
  O17 -0.13316(4) 0.15304(8) -0.21922(7) 0.0281(2) Uani d . 1 . . O
  C3 -0.16684(6) 0.32264(13) -0.10918(10) 0.0264(3) Uani d . 1 . . C
  C11 0.10199(6) 0.19405(13) 0.26714(10) 0.0255(3) Uani d . 1 . . C
  C14 -0.24721(8) 0.14828(15) -0.36001(12) 0.0365(4) Uani d . 1 . . C
  O21 0.18620(5) 0.12654(9) 0.43794(7) 0.0310(3) Uani d . 1 . . O
  H15A -0.0075(8) 0.5516(15) 0.0955(12) 0.043(4) Uiso d . 1 . . H
  H13B -0.1350(9) 0.3943(16) -0.2781(13) 0.046(4) Uiso d . 1 . . H
  H13C -0.2115(9) 0.4033(16) -0.3742(13) 0.048(4) Uiso d . 1 . . H
  H13A -0.1610(8) 0.3016(16) -0.3807(13) 0.044(4) Uiso d . 1 . . H
  H15C -0.0874(9) 0.5523(16) 0.0104(14) 0.048(5) Uiso d . 1 . . H
  H16C 0.1074(7) 0.0998(15) -0.0635(13) 0.039(4) Uiso d . 1 . . H
  H10B 0.1197(8) 0.3351(14) 0.1849(11) 0.033(4) Uiso d . 1 . . H
  H15B -0.0607(8) 0.5762(17) 0.1354(13) 0.051(5) Uiso d . 1 . . H
  H16B 0.1651(9) 0.0324(16) 0.0529(12) 0.045(4) Uiso d . 1 . . H
  H10A 0.0662(7) 0.3796(14) 0.2119(11) 0.029(4) Uiso d . 1 . . H
  H6 -0.0088(7) 0.0894(14) -0.1260(11) 0.027(3) Uiso d . 1 . . H
  H16A 0.0867(7) -0.0216(15) -0.0184(11) 0.032(4) Uiso d . 1 . . H
  H14B -0.2889(9) 0.1962(16) -0.4113(14) 0.049(4) Uiso d . 1 . . H
  H2 -0.2618(8) 0.3299(14) -0.2456(12) 0.036(4) Uiso d . 1 . . H
  H14A -0.2314(8) 0.1021(16) -0.4013(13) 0.046(4) Uiso d . 1 . . H
  H3 -0.1779(7) 0.3663(14) -0.0630(12) 0.034(4) Uiso d . 1 . . H
  H21 0.2319(10) 0.1540(19) 0.5044(16) 0.071(6) Uiso d . 1 . . H
  H11B 0.1105(7) 0.1106(15) 0.2426(11) 0.037(4) Uiso d . 1 . . H
  H11A 0.0669(8) 0.1733(14) 0.2818(11) 0.037(4) Uiso d . 1 . . H
  H14C -0.2578(9) 0.0818(18) -0.3218(13) 0.055(5) Uiso d . 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
  C13 0.0360(8) 0.0343(8) 0.0309(8) -0.0002(7) 0.0185(7) 0.0030(7)
  C15 0.0415(9) 0.0255(7) 0.0368(8) 0.0071(6) 0.0227(7) -0.0003(6)
  O20 0.0253(5) 0.0259(5) 0.0261(5) -0.0027(4) 0.0096(4) 0.0019(4)
  C16 0.0290(8) 0.0293(8) 0.0369(8) 0.0038(6) 0.0189(7) -0.0045(6)
  O19 0.0224(5) 0.0316(5) 0.0309(5) 0.0049(4) 0.0118(4) -0.0041(4)
  C10 0.0250(7) 0.0239(7) 0.0250(7) 0.0004(5) 0.0116(6) -0.0006(5)
  C7 0.0220(6) 0.0213(6) 0.0264(7) 0.0020(5) 0.0119(6) 0.0018(5)
  C8 0.0237(7) 0.0210(6) 0.0222(7) 0.0000(5) 0.0112(6) 0.0011(5)
  C6 0.0268(7) 0.0217(7) 0.0263(7) 0.0012(5) 0.0139(6) -0.0018(5)
  C1 0.0218(6) 0.0264(7) 0.0244(7) 0.0013(5) 0.0075(6) 0.0019(5)
  C9 0.0272(7) 0.0205(6) 0.0233(7) 0.0013(5) 0.0158(6) 0.0016(5)
  O18 0.0305(5) 0.0274(5) 0.0254(5) 0.0030(4) 0.0177(4) 0.0002(4)
  C12 0.0236(6) 0.0259(7) 0.0247(7) 0.0020(5) 0.0149(6) 0.0013(5)
  C5 0.0246(7) 0.0219(6) 0.0218(6) -0.0012(5) 0.0097(6) 0.0004(5)
  C4 0.0226(7) 0.0221(7) 0.0249(7) 0.0000(5) 0.0127(6) 0.0032(5)
  C2 0.0224(7) 0.0301(7) 0.0293(7) 0.0011(6) 0.0126(6) 0.0038(6)
  O17 0.0242(5) 0.0265(5) 0.0240(5) 0.0021(4) 0.0064(4) -0.0027(4)
  C3 0.0248(7) 0.0283(7) 0.0278(7) 0.0025(5) 0.0151(6) 0.0028(6)
  C11 0.0236(7) 0.0260(7) 0.0249(7) -0.0021(5) 0.0115(6) -0.0005(5)
  C14 0.0274(8) 0.0342(8) 0.0320(8) -0.0024(6) 0.0053(7) -0.0027(7)
  O21 0.0317(5) 0.0276(5) 0.0242(5) -0.0041(4) 0.0086(4) 0.0043(4)
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
  C13 C1 . 1.5202(18) ?
  C13 H13B . 0.982(17) ?
  C13 H13C . 0.991(17) ?
  C13 H13A . 1.005(17) ?
  C15 O18 . 1.4365(16) ?
  C15 H15A . 1.024(16) ?
  C15 H15C . 0.976(18) ?
  C15 H15B . 1.016(18) ?
  O20 C12 . 1.2252(15) y
  C16 O19 . 1.4338(15) ?
  C16 H16C . 1.018(16) ?
  C16 H16B . 1.011(17) ?
  C16 H16A . 0.985(15) ?
  O19 C7 . 1.3692(15) ?
  C10 C8 . 1.5063(17) ?
  C10 C11 . 1.5223(18) ?
  C10 H10B . 0.996(15) ?
  C10 H10A . 0.972(14) ?
  C7 C6 . 1.3886(18) ?
  C7 C8 . 1.4095(17) ?
  C8 C9 . 1.3882(17) ?
  C6 C5 . 1.3859(18) ?
  C6 H6 . 0.974(14) ?
  C1 O17 . 1.4664(15) ?
  C1 C2 . 1.5089(18) ?
  C1 C14 . 1.5140(19) ?
  C9 O18 . 1.3899(14) ?
  C9 C4 . 1.4009(17) ?
  C12 O21 . 1.3188(15) y
  C12 C11 . 1.4965(17) ?
  C5 O17 . 1.3717(15) ?
  C5 C4 . 1.3995(17) ?
  C4 C3 . 1.4575(17) ?
  C2 C3 . 1.3261(19) ?
  C2 H2 . 1.025(16) ?
  C3 H3 . 0.971(15) ?
  C11 H11B . 0.991(15) ?
  C11 H11A . 0.978(16) ?
  C14 H14B . 0.990(18) ?
  C14 H14A . 0.994(17) ?
  C14 H14C . 1.004(18) ?
  O21 H21 . 1.04(2) ?
_cod_database_code 2202271