data_2007021
_journal_name_full  'Acta Crystallographica'
_journal_year  1998
_journal_volume  C54
_journal_page_first  249
_journal_page_last  250
_publ_section_title
;
5,5-Dihydroxyethylbarbituric Acid
;
loop_
_publ_author_name
  'Irles, Nuria'
  'Subirana, J.Antoni'
  'Solans, Xavier'
_chemical_formula_moiety  'C8 H12 N2 O5'
_chemical_formula_sum  'C8 H12 N2 O5'
_chemical_formula_structural  'C8 H12 N2 O5'
_chemical_formula_analytical  'C8 H12 N2 O5'
_chemical_formula_weight  216.20
_symmetry_cell_setting  monoclinic
_symmetry_space_group_name_H-M  'P 21/c'
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  12.117(2)
_cell_length_b  12.324(2)
_cell_length_c  13.508(3)
_cell_angle_alpha  90.00
_cell_angle_beta  108.83(3)
_cell_angle_gamma  90.00
_cell_volume  1909.2(6)
_cell_formula_units_Z  8
_cell_measurement_temperature  293(2)
_exptl_crystal_density_diffrn  1.504
_diffrn_ambient_temperature  293(2)
_refine_ls_R_factor_obs  .0683
_refine_ls_wR_factor_obs  .1951
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_group
_atom_site_type_symbol
  O1A  .55672(14)  .22839(13)  .68239(11)  .0376(4) Uani d . 1 . O
  O2A  .71917(14)  .52938(14)  .85908(12)  .0386(4) Uani d . 1 . O
  O3A  .41008(13)  .39333(12)  .93254(11)  .0315(4) Uani d . 1 . O
  O4A  .6732(2)  .1729(2)  .92704(14)  .0549(5) Uani d . 1 . O
  O5A  .3394(2)  .49433(14)  .70816(14)  .0425(4) Uani d . 1 . O
  N1A  .6284(2)  .38389(15)  .76454(13)  .0315(4) Uani d . 1 . N
  HN1A  .6698(2)  .39121(15)  .72384(13)  .063(2) Uiso calc R 1 . H
  N2A  .56789(14)  .45559(14)  .89811(12)  .0268(4) Uani d . 1 . N
  C1A  .5539(2)  .2966(2)  .74574(14)  .0248(4) Uani d . 1 . C
  C2A  .6437(2)  .4606(2)  .84139(14)  .0241(4) Uani d . 1 . C
  C3A  .4757(2)  .3851(2)  .88107(14)  .0238(4) Uani d . 1 . C
  C4A  .4623(2)  .29509(15)  .80115(13)  .0230(4) Uani d . 1 . C
  C5A  .4666(2)  .1852(2)  .8583(2)  .0309(4) Uani d . 1 . C
  H5A  .3966(2)  .1788(2)  .8779(2)  .063(2) Uiso calc R 1 . H
  H5A'  .4650(2)  .1271(2)  .8094(2)  .063(2) Uiso calc R 1 . H
  C6A  .5708(2)  .1685(2)  .9549(2)  .0455(6) Uani d . 1 . C
  H6A  .5729(2)  .2245(2) 1.0059(2)  .063(2) Uiso calc R 1 . H
  H6A'  .5653(2)  .0986(2)  .9859(2)  .063(2) Uiso calc R 1 . H
  C7A  .3411(2)  .3023(2)  .7157(2)  .0292(4) Uani d . 1 . C
  C8A  .3235(2)  .4011(2)  .6455(2)  .0395(5) Uani d . 1 . C
  H8A  .3792(2)  .4004(2)  .6075(2)  .063(2) Uiso calc R 1 . H
  H8A'  .2456(2)  .4005(2)  .5950(2)  .063(2) Uiso calc R 1 . H
  O1B  .0591(2)  .2452(2)  .67122(12)  .0433(4) Uani d . 1 . O
  O2B  .21929(14)  -.04677(13)  .86470(12)  .0354(4) Uani d . 1 . O
  O3B  -.08750(13)  .10525(13)  .93045(12)  .0351(4) Uani d . 1 . O
  O4B  .2016(2)  .2707(2)  .92661(14)  .0565(6) Uani d . 1 . O
  HO4B  .2126(2)  .3098(2)  .88164(14)  .063(2) Uiso calc R 1 . H
  O5B  -.1621(2)  .0007(2)  .6956(2)  .0492(5) Uani d . 1 . O
  HO5B  -.2020(2)  -.0042(2)  .7342(2)  .063(2) Uiso calc R 1 . H
  N1B  .1282(2)  .09240(15)  .75974(13)  .0309(4) Uani d . 1 . N
  HN1B  .1663(2)  .07880(15)  .71741(13)  .063(2) Uiso calc R 1 . H
  N2B  .06723(15)  .03416(14)  .89765(12)  .0277(4) Uani d . 1 . N
  C1B  .0566(2)  .1821(2)  .73859(14)  .0272(4) Uani d . 1 . C
  C2B  .1439(2)  .0230(2)  .84219(14)  .0252(4) Uani d . 1 . C
  C3B  -.0212(2)  .1074(2)  .87906(14)  .0245(4) Uani d . 1 . C
  C4B  -.0300(2)  .19472(15)  .79789(13)  .0234(4) Uani d . 1 . C
  C5B  -.0069(2)  .3061(2)  .8559(2)  .0356(5) Uani d . 1 . C
  H5B  -.0003(2)  .3617(2)  .8073(2)  .063(2) Uiso calc R 1 . H
  H5B'  -.0733(2)  .3241(2)  .8779(2)  .063(2) Uiso calc R 1 . H
  C6B  .1022(3)  .3077(3)  .9506(2)  .0484(7) Uani d . 1 . C
  C7B  -.1544(2)  .1960(2)  .71821(15)  .0301(4) Uani d . 1 . C
  H7B  -.2098(2)  .1974(2)  .75639(15)  .063(2) Uiso calc R 1 . H
  H7B'  -.1644(2)  .2626(2)  .67798(15)  .063(2) Uiso calc R 1 . H
  C8B  -.1837(2)  .1013(2)  .6430(2)  .0432(6) Uani d . 1 . C
  H8B  -.2653(2)  .1054(2)  .6008(2)  .063(2) Uiso calc R 1 . H
  H8B'  -.1375(2)  .1062(2)  .5964(2)  .063(2) Uiso calc R 1 . H
  HO4A  .714(3)  .231(3)  .983(2)  .063(2) Uiso d . 1 . H
  HO5A  .343(3)  .577(3)  .688(2)  .063(2) Uiso d . 1 . H
  HN2A  .561(3)  .511(3)  .940(3)  .063(2) Uiso d . 1 . H
  H7A  .332(3)  .237(3)  .677(2)  .063(2) Uiso d . 1 . H
  H7A'  .285(3)  .296(3)  .749(2)  .063(2) Uiso d . 1 . H
  HN2B  .071(3)  -.017(3)  .941(3)  .063(2) Uiso d . 1 . H
  H6B  .095(3)  .248(3)  1.007(2)  .063(2) Uiso d . 1 . H
  H6B'  .105(3)  .374(3)  .972(2)  .063(2) 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
  O1A  .0483(9)  .0409(9)  .0336(7)  -.0022(7)  .0272(7)  -.0109(6)
  O2A  .0404(9)  .0453(9)  .0414(8)  -.0142(7)  .0291(7)  -.0069(7)
  O3A  .0344(8)  .0382(8)  .0336(7)  -.0080(6)  .0272(6)  -.0124(6)
  O4A  .0475(10)  .0698(14)  .0454(10)  .0184(9)  .0123(8)  -.0110(9)
  O5A  .0565(11)  .0320(8)  .0433(9)  .0027(7)  .0222(8)  .0016(7)
  N1A  .0378(9)  .0390(10)  .0306(8)  -.0058(7)  .0290(7)  -.0066(7)
  N2A  .0293(8)  .0336(9)  .0251(7)  -.0072(7)  .0195(7)  -.0091(6)
  C1A  .0246(9)  .0314(9)  .0230(8)  .0027(7)  .0141(7)  -.0017(7)
  C2A  .0253(9)  .0292(9)  .0225(8)  .0008(7)  .0142(7)  .0002(7)
  C3A  .0242(8)  .0302(9)  .0232(8)  .0019(7)  .0164(7)  -.0012(7)
  C4A  .0252(8)  .0288(9)  .0203(8)  .0006(7)  .0148(7)  -.0035(6)
  C5A  .0349(10)  .0303(10)  .0326(10)  .0027(8)  .0182(8)  .0066(8)
  C6A  .064(2)  .0499(14)  .0250(10)  .0203(12)  .0175(10)  .0055(9)
  C7A  .0293(10)  .0300(10)  .0300(9)  -.0005(8)  .0120(8)  -.0019(8)
  C8A  .0432(13)  .0452(13)  .0286(10)  .0058(10)  .0092(9)  .0023(9)
  O1B  .0547(10)  .0525(10)  .0360(8)  .0080(8)  .0332(8)  .0162(7)
  O2B  .0379(8)  .0370(8)  .0400(8)  .0083(6)  .0246(7)  .0021(6)
  O3B  .0366(8)  .0448(9)  .0369(8)  .0090(6)  .0295(7)  .0152(6)
  O4B  .0494(11)  .0790(15)  .0449(9)  -.0191(10)  .0203(8)  .0018(9)
  O5B  .0525(11)  .0415(9)  .0629(12)  -.0083(8)  .0313(9)  -.0134(8)
  N1B  .0345(9)  .0414(10)  .0274(8)  .0062(7)  .0249(7)  .0046(7)
  N2B  .0318(9)  .0326(9)  .0267(8)  .0066(7)  .0208(7)  .0099(6)
  C1B  .0287(9)  .0366(10)  .0222(8)  -.0019(8)  .0162(7)  .0031(7)
  C2B  .0252(9)  .0288(9)  .0270(9)  .0011(7)  .0158(7)  -.0019(7)
  C3B  .0249(9)  .0310(9)  .0243(8)  -.0002(7)  .0171(7)  .0050(7)
  C4B  .0285(9)  .0263(8)  .0218(8)  .0008(7)  .0168(7)  .0046(6)
  C5B  .0491(13)  .0336(11)  .0302(10)  -.0062(9)  .0211(9)  -.0039(8)
  C6B  .063(2)  .057(2)  .0322(11)  -.0194(13)  .0249(11)  -.0076(11)
  C7B  .0291(10)  .0318(10)  .0302(9)  .0019(8)  .0104(8)  .0065(8)
  C8B  .0450(13)  .0495(14)  .0332(11)  -.0038(11)  .0098(10)  -.0019(10)
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
  O1A C1A . 1.208(2) ?
  O2A C2A . 1.213(2) ?
  O3A C3A . 1.217(2) ?
  O4A C6A . 1.408(3) ?
  O4A HO4A . 1.05(4) ?
  O5A C8A . 1.404(3) ?
  O5A HO5A . 1.06(4) ?
  N1A C2A . 1.372(2) yes
  N1A C1A . 1.374(3) yes
  N1A HN1A .  .86 ?
  N2A C2A . 1.374(2) yes
  N2A C3A . 1.375(2) yes
  N2A HN2A .  .90(4) ?
  C1A C4A . 1.527(2) yes
  C3A C4A . 1.519(2) yes
  C4A C7A . 1.549(3) ?
  C4A C5A . 1.552(3) ?
  C5A C6A . 1.509(3) ?
  C5A H5A .  .97 ?
  C5A H5A' .  .97 ?
  C6A H6A .  .97 ?
  C6A H6A' .  .97 ?
  C7A C8A . 1.515(3) ?
  C7A H7A .  .95(3) ?
  C7A H7A' .  .93(3) ?
  C8A H8A .  .97 ?
  C8A H8A' .  .97 ?
  O1B C1B . 1.205(2) ?
  O2B C2B . 1.220(2) ?
  O3B C3B . 1.220(2) ?
  O4B C6B . 1.419(4) ?
  O4B HO4B .  .82 ?
  O5B C8B . 1.410(3) ?
  O5B HO5B .  .82 ?
  N1B C2B . 1.368(2) yes
  N1B C1B . 1.377(3) yes
  N1B HN1B .  .86 ?
  N2B C3B . 1.361(2) yes
  N2B C2B . 1.375(2) yes
  N2B HN2B .  .86(4) ?
  C1B C4B . 1.520(2) yes
  C3B C4B . 1.516(2) yes
  C4B C7B . 1.544(3) ?
  C4B C5B . 1.560(3) ?
  C5B C6B . 1.514(4) ?
  C5B H5B .  .97 ?
  C5B H5B' .  .97 ?
  C6B H6B . 1.09(3) ?
  C6B H6B' .  .87(3) ?
  C7B C8B . 1.512(3) ?
  C7B H7B .  .97 ?
  C7B H7B' .  .97 ?
  C8B H8B .  .97 ?
  C8B H8B' .  .97 ?