#------------------------------------------------------------------------------
#$Date: 2009-11-16 01:43:51 +0000 (Mon, 16 Nov 2009) $
#$Revision: 853 $
#$URL: svn://www.crystallography.net/cod/cif/2/2202335.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_2202335
_journal_name_full  'Acta Crystallographica, Section E'
_journal_year  2003
_journal_volume  59
_journal_page_first  o1196
_journal_page_last  o1198
_publ_section_title
;
3-Ethoxycarbonyl-4-hydroxy-6-methoxymethyleneoxy-1-methyl-2-quinolone
;
_space_group_IT_number           14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_[local]_cod_cif_authors_sg_H-M  'P 21/c'
loop_
_publ_author_name
  'Pozzi, C. Gustavo'
  "Goeta, Andr\'es E."
  'Autino, Juan C.'
  'Punte, Graciela'
_chemical_formula_moiety  'C15 H17 N O6'
_chemical_formula_sum  'C15 H17 N O6'
_chemical_formula_iupac  'C15 H17 N O6'
_chemical_formula_weight  307.30
_symmetry_cell_setting  monoclinic
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'
_cell_length_a  11.558(3)
_cell_length_b  10.476(2)
_cell_length_c  11.750(2)
_cell_angle_alpha  90.00
_cell_angle_beta  98.823(3)
_cell_angle_gamma  90.00
_cell_volume  1405.9(5)
_cell_formula_units_Z  4
_cell_measurement_temperature  100(2)
_exptl_crystal_density_diffrn  1.445
_diffrn_ambient_temperature  100(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
  N1 -0.10217(9) 0.49877(10) 0.31837(9) 0.0167(2) Uani d . 1 . . N
  C2 -0.17015(11) 0.41122(12) 0.36837(10) 0.0170(2) Uani d . 1 . . C
  C3 -0.10626(11) 0.31269(12) 0.44051(10) 0.0162(2) Uani d . 1 . . C
  C4A 0.08094(10) 0.39480(12) 0.39502(10) 0.0159(2) Uani d . 1 . . C
  C4 0.01511(11) 0.30558(12) 0.45308(10) 0.0156(2) Uani d . 1 . . C
  C5 0.20385(11) 0.38476(12) 0.40468(10) 0.0172(2) Uani d . 1 . . C
  H5 0.2407(14) 0.3171(16) 0.4490(13) 0.020(4) Uiso d . 1 . . H
  C6 0.26489(11) 0.47201(13) 0.34883(11) 0.0185(3) Uani d . 1 . . C
  C7 0.20362(12) 0.56976(13) 0.28376(11) 0.0204(3) Uani d . 1 . . C
  H7 0.2476(16) 0.6305(16) 0.2434(15) 0.030(4) Uiso d . 1 . . H
  C8A 0.01903(10) 0.49094(12) 0.32839(10) 0.0162(2) Uani d . 1 . . C
  C8 0.08353(11) 0.57944(13) 0.27316(11) 0.0192(3) Uani d . 1 . . C
  H8 0.0435(14) 0.6471(16) 0.2291(14) 0.024(4) Uiso d . 1 . . H
  C9 -0.16595(11) 0.21633(12) 0.50186(10) 0.0172(2) Uani d . 1 . . C
  O10 -0.28169(8) 0.22102(9) 0.48625(8) 0.0201(2) Uani d . 1 . . O
  C11 -0.34014(12) 0.12130(14) 0.54398(12) 0.0219(3) Uani d . 1 . . C
  H11B -0.2986(14) 0.1111(15) 0.6211(14) 0.021(4) Uiso d . 1 . . H
  H11A -0.4156(15) 0.1570(16) 0.5453(13) 0.023(4) Uiso d . 1 . . H
  C12 -0.34791(13) -0.00083(14) 0.47535(13) 0.0259(3) Uani d . 1 . . C
  H12C -0.3935(16) 0.0134(17) 0.3985(16) 0.031(4) Uiso d . 1 . . H
  H12B -0.3837(16) -0.0683(18) 0.5173(15) 0.034(5) Uiso d . 1 . . H
  H12A -0.2683(17) -0.0352(18) 0.4637(15) 0.035(5) Uiso d . 1 . . H
  O13 -0.11068(8) 0.13483(9) 0.56458(8) 0.0225(2) Uani d . 1 . . O
  O14 0.07756(8) 0.21692(9) 0.51637(8) 0.0200(2) Uani d . 1 . . O
  H14 0.025(2) 0.172(2) 0.5492(18) 0.051(6) Uiso d . 1 . . H
  O15 -0.27786(8) 0.42042(10) 0.35004(8) 0.0245(2) Uani d . 1 . . O
  C16 -0.16336(12) 0.60044(13) 0.24695(12) 0.0202(3) Uani d . 1 . . C
  H16C -0.1358(15) 0.6839(17) 0.2792(14) 0.025(4) Uiso d . 1 . . H
  H16B -0.2440(17) 0.5932(17) 0.2538(15) 0.032(5) Uiso d . 1 . . H
  H16A -0.1508(14) 0.5914(16) 0.1674(14) 0.023(4) Uiso d . 1 . . H
  O17 0.38414(8) 0.47260(9) 0.35095(8) 0.0215(2) Uani d . 1 . . O
  C18 0.45109(12) 0.37448(13) 0.41508(12) 0.0218(3) Uani d . 1 . . C
  H18B 0.4336(14) 0.3724(15) 0.4930(14) 0.019(4) Uiso d . 1 . . H
  H18A 0.5313(15) 0.4014(16) 0.4119(14) 0.026(4) Uiso d . 1 . . H
  O19 0.42767(8) 0.25349(9) 0.36709(8) 0.0225(2) Uani d . 1 . . O
  C20 0.46905(14) 0.23784(16) 0.25916(13) 0.0278(3) Uani d . 1 . . C
  H20C 0.4628(15) 0.1462(18) 0.2392(15) 0.028(4) Uiso d . 1 . . H
  H20B 0.4212(17) 0.2879(18) 0.2002(16) 0.034(5) Uiso d . 1 . . H
  H20A 0.552(2) 0.2680(19) 0.2675(17) 0.045(6) 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
  N1 0.0153(5) 0.0181(5) 0.0166(5) 0.0004(4) 0.0021(4) 0.0023(4)
  C2 0.0154(6) 0.0192(6) 0.0161(5) -0.0016(4) 0.0019(4) -0.0008(4)
  C3 0.0160(6) 0.0165(6) 0.0162(5) -0.0010(4) 0.0031(4) -0.0002(4)
  C4A 0.0161(6) 0.0159(6) 0.0158(5) -0.0012(4) 0.0031(4) -0.0010(4)
  C4 0.0165(6) 0.0155(6) 0.0146(5) -0.0002(4) 0.0018(4) -0.0010(4)
  C5 0.0161(6) 0.0171(6) 0.0182(5) -0.0003(5) 0.0024(4) -0.0003(5)
  C6 0.0142(6) 0.0214(6) 0.0200(6) -0.0018(5) 0.0032(4) -0.0023(5)
  C7 0.0206(6) 0.0206(6) 0.0206(6) -0.0032(5) 0.0056(5) 0.0012(5)
  C8A 0.0154(6) 0.0175(6) 0.0157(5) -0.0013(4) 0.0021(4) -0.0022(4)
  C8 0.0188(6) 0.0198(6) 0.0191(6) 0.0000(5) 0.0033(5) 0.0025(5)
  C9 0.0150(6) 0.0193(6) 0.0172(5) -0.0021(5) 0.0027(4) -0.0013(4)
  O10 0.0148(4) 0.0218(5) 0.0239(4) -0.0023(3) 0.0040(3) 0.0041(4)
  C11 0.0156(6) 0.0264(7) 0.0243(6) -0.0024(5) 0.0047(5) 0.0078(5)
  C12 0.0226(7) 0.0257(7) 0.0286(7) -0.0062(6) 0.0012(5) 0.0047(6)
  O13 0.0172(5) 0.0234(5) 0.0264(5) -0.0014(4) 0.0022(4) 0.0073(4)
  O14 0.0159(4) 0.0199(5) 0.0241(5) 0.0000(4) 0.0026(3) 0.0059(4)
  O15 0.0138(4) 0.0290(5) 0.0300(5) -0.0002(4) 0.0006(4) 0.0086(4)
  C16 0.0178(6) 0.0201(6) 0.0224(6) 0.0016(5) 0.0021(5) 0.0046(5)
  O17 0.0137(4) 0.0215(5) 0.0298(5) -0.0016(3) 0.0051(4) 0.0039(4)
  C18 0.0157(6) 0.0249(7) 0.0243(6) -0.0017(5) 0.0013(5) 0.0019(5)
  O19 0.0190(5) 0.0223(5) 0.0269(5) -0.0005(4) 0.0057(4) 0.0030(4)
  C20 0.0247(7) 0.0289(8) 0.0311(7) 0.0017(6) 0.0085(6) 0.0001(6)
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
  O13 C9 . 1.2392(16) ?
  C9 C3 . 1.4721(17) ?
  C3 C4 . 1.3899(17) ?
  C4 O14 . 1.3312(15) ?
  N1 C8A . 1.3901(16) ?
  N1 C2 . 1.3948(16) ?
  N1 C16 . 1.4686(16) ?
  C2 O15 . 1.2342(15) ?
  C2 C3 . 1.4619(17) ?
  C4A C8A . 1.4027(17) ?
  C4A C5 . 1.4116(17) ?
  C4A C4 . 1.4412(17) ?
  C5 C6 . 1.3805(18) ?
  C5 H5 . 0.941(17) ?
  C6 O17 . 1.3747(15) ?
  C6 C7 . 1.4030(19) ?
  C7 C8 . 1.3782(19) ?
  C7 H7 . 0.981(18) ?
  C8A C8 . 1.4088(17) ?
  C8 H8 . 0.955(17) ?
  C9 O10 . 1.3230(15) ?
  O10 C11 . 1.4657(15) ?
  C11 C12 . 1.508(2) ?
  C11 H11B . 0.964(16) ?
  C11 H11A . 0.951(17) ?
  C12 H12C . 0.984(18) ?
  C12 H12B . 0.988(19) ?
  C12 H12A . 1.016(19) ?
  O14 H14 . 0.90(2) ?
  C16 H16C . 0.986(18) ?
  C16 H16B . 0.95(2) ?
  C16 H16A . 0.972(16) ?
  O17 C18 . 1.4298(16) ?
  C18 O19 . 1.3968(17) ?
  C18 H18B . 0.967(16) ?
  C18 H18A . 0.975(17) ?
  O19 C20 . 1.4318(17) ?
  C20 H20C . 0.988(18) ?
  C20 H20B . 0.971(19) ?
  C20 H20A . 1.00(2) ?