#------------------------------------------------------------------------------
#$Date: 2008-01-14 00:15:36 +0200 (Mon, 14 Jan 2008) $
#$Revision: 14 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2014733.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_2014733
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2005
_journal_volume  61
_journal_page_first  o15
_journal_page_last  o20
_publ_section_title
;
5-(1-Hydroxyethylidene)-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione
and four amino derivatives
;
loop_
_publ_author_name
  'da Silva, Emerson T.'
  'Ribiero, Rodrigo S.'
  'Lima, Edson L. S.'
  'Wardell, James L.'
  'Skakle, Janet M. S.'
  'Low, John N.'
  'Glidewell, Christopher'
_chemical_formula_moiety  'C12 H19 N3 O5'
_chemical_formula_sum  'C12 H19 N3 O5'
_chemical_formula_iupac  'C12 H19 N3 O5'
_chemical_formula_weight  285.30
_symmetry_cell_setting  trigonal
_symmetry_space_group_name_H-M  'R -3'
_symmetry_space_group_name_Hall  '-R 3'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-y, x-y, z'
  '-x+y, -x, z'
  'x+2/3, y+1/3, z+1/3'
  '-y+2/3, x-y+1/3, z+1/3'
  '-x+y+2/3, -x+1/3, z+1/3'
  'x+1/3, y+2/3, z+2/3'
  '-y+1/3, x-y+2/3, z+2/3'
  '-x+y+1/3, -x+2/3, z+2/3'
  '-x, -y, -z'
  'y, -x+y, -z'
  'x-y, x, -z'
  '-x+2/3, -y+1/3, -z+1/3'
  'y+2/3, -x+y+1/3, -z+1/3'
  'x-y+2/3, x+1/3, -z+1/3'
  '-x+1/3, -y+2/3, -z+2/3'
  'y+1/3, -x+y+2/3, -z+2/3'
  'x-y+1/3, x+2/3, -z+2/3'
_cell_length_a  18.4577(4)
_cell_length_b  18.4577(4)
_cell_length_c  19.7736(4)
_cell_angle_alpha  90.00
_cell_angle_beta  90.00
_cell_angle_gamma  120.00
_cell_volume  5834.1(2)
_cell_formula_units_Z  18
_cell_measurement_temperature  120(2)
_exptl_crystal_density_diffrn  1.462
_diffrn_ambient_temperature  120(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
  O2 -0.15632(6) 0.33916(6) 0.09144(5) 0.0206(2) Uani d . 1 . . O
  O4 -0.05233(6) 0.61636(6) 0.05752(5) 0.0193(2) Uani d . 1 . . O
  O6 0.12518(6) 0.50353(6) 0.09788(5) 0.0216(3) Uani d . 1 . . O
  O51 0.08471(6) 0.83411(6) -0.02294(5) 0.0182(2) Uani d . 1 . . O
  O52 0.08356(6) 0.85482(6) 0.09012(5) 0.0205(2) Uani d . 1 . . O
  N1 -0.01542(7) 0.42417(7) 0.09841(6) 0.0149(3) Uani d . 1 . . N
  N3 -0.10321(7) 0.47955(7) 0.07858(6) 0.0152(3) Uani d . 1 . . N
  N51 0.10694(7) 0.71932(7) 0.06069(6) 0.0159(3) Uani d . 1 . . N
  C1 -0.00815(9) 0.35043(8) 0.11368(7) 0.0187(3) Uani d . 1 . . C
  C2 -0.09556(8) 0.40959(8) 0.08972(7) 0.0154(3) Uani d . 1 . . C
  C3 -0.18752(8) 0.46736(9) 0.07052(7) 0.0203(3) Uani d . 1 . . C
  C4 -0.03586(8) 0.56031(8) 0.07096(6) 0.0143(3) Uani d . 1 . . C
  C5 0.04738(8) 0.57301(8) 0.07892(7) 0.0142(3) Uani d . 1 . . C
  C6 0.05812(8) 0.50185(8) 0.09210(7) 0.0147(3) Uani d . 1 . . C
  C51 0.11810(8) 0.65554(8) 0.07353(7) 0.0145(3) Uani d . 1 . . C
  C52 0.20607(8) 0.67348(9) 0.08217(7) 0.0181(3) Uani d . 1 . . C
  C53 0.17286(8) 0.80644(8) 0.05238(8) 0.0185(3) Uani d . 1 . . C
  C54 0.13520(8) 0.86096(8) 0.03604(7) 0.0173(3) Uani d . 1 . . C
  C55 0.13239(9) 0.85833(9) -0.08419(7) 0.0225(3) Uani d . 1 . . C
  C56 0.05569(10) 0.91427(9) 0.08661(8) 0.0245(3) Uani d . 1 . . C
  H1A -0.0514 0.3150 0.1464 0.028 Uiso calc R 1 . . H
  H1B 0.0472 0.3682 0.1329 0.028 Uiso calc R 1 . . H
  H1C -0.0154 0.3187 0.0720 0.028 Uiso calc R 1 . . H
  H3A -0.2289 0.4104 0.0844 0.030 Uiso calc R 1 . . H
  H3B -0.1967 0.4757 0.0230 0.030 Uiso calc R 1 . . H
  H3C -0.1933 0.5078 0.0988 0.030 Uiso calc R 1 . . H
  H51 0.0550 0.7085 0.0567 0.019 Uiso calc R 1 . . H
  H52A 0.2222 0.6523 0.0429 0.027 Uiso calc R 1 . . H
  H52B 0.2100 0.6459 0.1232 0.027 Uiso calc R 1 . . H
  H52C 0.2437 0.7340 0.0861 0.027 Uiso calc R 1 . . H
  H53A 0.2109 0.8105 0.0154 0.022 Uiso calc R 1 . . H
  H53B 0.2060 0.8264 0.0945 0.022 Uiso calc R 1 . . H
  H54 0.1808 0.9204 0.0305 0.021 Uiso calc R 1 . . H
  H55A 0.1735 0.9182 -0.0826 0.034 Uiso calc R 1 . . H
  H55B 0.0949 0.8469 -0.1228 0.034 Uiso calc R 1 . . H
  H55C 0.1615 0.8264 -0.0892 0.034 Uiso calc R 1 . . H
  H56A 0.1042 0.9708 0.0832 0.037 Uiso calc R 1 . . H
  H56B 0.0238 0.9101 0.1275 0.037 Uiso calc R 1 . . H
  H56C 0.0200 0.9027 0.0468 0.037 Uiso calc R 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
  O2 0.0158(5) 0.0150(5) 0.0263(6) 0.0041(4) -0.0012(4) -0.0007(4)
  O4 0.0167(5) 0.0171(5) 0.0272(6) 0.0108(4) -0.0021(4) 0.0001(4)
  O6 0.0149(5) 0.0202(5) 0.0323(6) 0.0108(4) -0.0009(4) 0.0014(4)
  O51 0.0147(5) 0.0192(5) 0.0190(5) 0.0071(4) -0.0007(4) 0.0000(4)
  O52 0.0247(6) 0.0197(5) 0.0199(5) 0.0131(5) 0.0030(4) 0.0026(4)
  N1 0.0144(6) 0.0131(6) 0.0180(6) 0.0075(5) -0.0006(5) -0.0004(4)
  N3 0.0104(5) 0.0154(6) 0.0200(6) 0.0066(5) -0.0006(5) 0.0001(5)
  N51 0.0119(6) 0.0137(6) 0.0209(6) 0.0056(5) -0.0001(5) 0.0004(5)
  C1 0.0201(7) 0.0145(7) 0.0229(7) 0.0096(6) -0.0010(6) 0.0003(6)
  C2 0.0152(7) 0.0167(7) 0.0135(6) 0.0075(6) -0.0002(5) -0.0010(5)
  C3 0.0130(7) 0.0207(7) 0.0273(8) 0.0085(6) -0.0013(6) 0.0012(6)
  C4 0.0144(7) 0.0145(7) 0.0130(6) 0.0064(6) -0.0003(5) -0.0011(5)
  C5 0.0129(7) 0.0145(7) 0.0146(6) 0.0064(5) -0.0006(5) -0.0007(5)
  C6 0.0146(7) 0.0157(7) 0.0132(6) 0.0073(5) -0.0003(5) -0.0017(5)
  C51 0.0154(7) 0.0160(7) 0.0118(6) 0.0076(6) 0.0005(5) -0.0008(5)
  C52 0.0141(7) 0.0175(7) 0.0214(7) 0.0071(6) -0.0004(6) 0.0009(6)
  C53 0.0133(7) 0.0143(7) 0.0243(7) 0.0041(6) -0.0008(6) 0.0031(6)
  C54 0.0149(7) 0.0150(7) 0.0188(7) 0.0052(6) -0.0011(5) 0.0008(6)
  C55 0.0221(8) 0.0239(8) 0.0203(7) 0.0106(7) 0.0014(6) 0.0012(6)
  C56 0.0294(8) 0.0233(8) 0.0263(8) 0.0171(7) 0.0005(6) -0.0005(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
  N1 C2 . 1.3756(17) no
  N1 C6 . 1.4027(17) no
  N1 C1 . 1.4644(17) no
  C1 H1A . 0.98 no
  C1 H1B . 0.98 no
  C1 H1C . 0.98 no
  C2 O2 . 1.2211(16) no
  C2 N3 . 1.3851(17) no
  N3 C4 . 1.3918(16) no
  N3 C3 . 1.4655(17) no
  C3 H3A . 0.98 no
  C3 H3B . 0.98 no
  C3 H3C . 0.98 no
  C4 O4 . 1.2442(16) no
  C4 C5 . 1.4422(18) no
  C5 C51 . 1.4308(18) no
  C5 C6 . 1.4467(18) no
  C51 N51 . 1.3172(17) no
  C51 C52 . 1.4959(18) no
  C52 H52A . 0.98 no
  C52 H52B . 0.98 no
  C52 H52C . 0.98 no
  N51 C53 . 1.4617(16) no
  N51 H51 . 0.88 no
  C53 C54 . 1.5166(19) no
  C53 H53A . 0.99 no
  C53 H53B . 0.99 no
  C54 O52 . 1.3990(17) no
  C54 O51 . 1.4185(16) no
  C54 H54 . 1.00 no
  O51 C55 . 1.4312(17) no
  C55 H55A . 0.98 no
  C55 H55B . 0.98 no
  C55 H55C . 0.98 no
  O52 C56 . 1.4275(17) no
  C56 H56A . 0.98 no
  C56 H56B . 0.98 no
  C56 H56C . 0.98 no
  C6 O6 . 1.2278(16) no