#------------------------------------------------------------------------------
#$Date: 2008-01-14 00:15:36 +0200 (Mon, 14 Jan 2008) $
#$Revision: 14 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2013199.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_2013199
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2003
_journal_volume  59
_journal_page_first  o14
_journal_page_last  o18
_publ_section_title
;
Hydrogen bonding in nitroaniline analogues: hydrogen-bonded sheets in
2-amino-4,6-dimethoxy-5-nitropyrimidine and \p-stacked hydrogen-bonded sheets
in 4-amino-2,6-dimethoxy-5-nitropyrimidine
;
loop_
_publ_author_name
  'Glidewell, Christopher'
  'Low, John N.'
  'Melguizo, Manuel'
  'Quesada, Antonio'
_chemical_formula_moiety  'C6 H8 N4 O4'
_chemical_formula_sum  'C6 H8 N4 O4'
_chemical_formula_weight  200.16
_symmetry_cell_setting  monoclinic
_symmetry_space_group_name_H-M  'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
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  7.3443(2)
_cell_length_b  7.8437(2)
_cell_length_c  14.9129(4)
_cell_angle_alpha  90
_cell_angle_beta  109.9470(13)
_cell_angle_gamma  90
_cell_volume  807.54(4)
_cell_formula_units_Z  4
_cell_measurement_temperature  120(2)
_exptl_crystal_density_diffrn  1.646
_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
  N1 0.22558(15) 0.10695(13) 0.46351(7) 0.0133(3) Uani d . 1 . . N
  C2 0.21598(18) 0.02873(16) 0.38128(9) 0.0131(3) Uani d . 1 . . C
  N2 0.37375(15) -0.04917(15) 0.37713(8) 0.0164(3) Uani d . 1 . . N
  N3 0.06003(15) 0.02311(14) 0.30037(7) 0.0136(2) Uani d . 1 . . N
  C4 -0.09743(18) 0.10148(16) 0.30191(9) 0.0127(3) Uani d . 1 . . C
  O4 -0.25573(13) 0.09551(12) 0.22500(6) 0.0150(2) Uani d . 1 . . O
  C41 -0.24346(19) -0.00391(18) 0.14537(9) 0.0176(3) Uani d . 1 . . C
  C5 -0.10622(17) 0.18542(16) 0.38375(9) 0.0130(3) Uani d . 1 . . C
  N5 -0.27988(15) 0.26800(14) 0.38510(8) 0.0140(3) Uani d . 1 . . N
  O51 -0.39187(13) 0.32829(12) 0.30986(7) 0.0193(2) Uani d . 1 . . O
  O52 -0.31205(14) 0.27579(13) 0.46063(7) 0.0206(3) Uani d . 1 . . O
  C6 0.06565(18) 0.18391(15) 0.46433(9) 0.0127(3) Uani d . 1 . . C
  O6 0.06585(13) 0.26712(12) 0.54186(6) 0.0164(2) Uani d . 1 . . O
  C61 0.24604(19) 0.27703(18) 0.62109(9) 0.0172(3) Uani d . 1 . . C
  H2A 0.4808 -0.0489 0.4271 0.020 Uiso calc R 1 . . H
  H2B 0.3711 -0.1010 0.3244 0.020 Uiso calc R 1 . . H
  H41A -0.1467 0.0468 0.1216 0.026 Uiso calc R 1 . . H
  H41B -0.3699 -0.0047 0.0943 0.026 Uiso calc R 1 . . H
  H41C -0.2054 -0.1210 0.1664 0.026 Uiso calc R 1 . . H
  H61A 0.2902 0.1617 0.6435 0.026 Uiso calc R 1 . . H
  H61B 0.2263 0.3422 0.6731 0.026 Uiso calc R 1 . . H
  H61C 0.3439 0.3338 0.6005 0.026 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
  N1 0.0123(5) 0.0131(5) 0.0131(5) 0.0007(4) 0.0025(4) 0.0004(4)
  C2 0.0129(6) 0.0120(6) 0.0134(6) -0.0009(4) 0.0030(5) 0.0019(5)
  N2 0.0123(5) 0.0226(6) 0.0120(5) 0.0035(4) 0.0009(4) -0.0042(4)
  N3 0.0124(5) 0.0145(5) 0.0125(5) 0.0007(4) 0.0026(4) -0.0003(4)
  C4 0.0121(6) 0.0114(6) 0.0129(6) -0.0013(4) 0.0020(5) 0.0024(5)
  O4 0.0121(5) 0.0175(5) 0.0124(5) 0.0012(3) 0.0004(4) -0.0025(4)
  C41 0.0161(6) 0.0222(7) 0.0130(6) 0.0001(5) 0.0030(5) -0.0039(5)
  C5 0.0118(6) 0.0118(6) 0.0146(6) 0.0014(4) 0.0035(5) 0.0010(5)
  N5 0.0134(5) 0.0130(5) 0.0145(5) 0.0000(4) 0.0034(4) -0.0011(4)
  O51 0.0177(5) 0.0224(5) 0.0153(5) 0.0074(4) 0.0024(4) 0.0047(4)
  O52 0.0178(5) 0.0303(6) 0.0145(5) 0.0048(4) 0.0065(4) -0.0006(4)
  C6 0.0142(6) 0.0102(6) 0.0129(6) -0.0009(4) 0.0037(5) 0.0005(5)
  O6 0.0133(5) 0.0204(5) 0.0129(5) 0.0020(3) 0.0010(4) -0.0051(4)
  C61 0.0138(6) 0.0215(7) 0.0136(6) -0.0015(5) 0.0014(5) -0.0056(5)
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 . 1.3515(17) y
  C2 N3 . 1.3515(16) y
  N3 C4 . 1.3167(16) y
  C4 C5 . 1.4076(18) y
  C5 C6 . 1.4151(17) y
  C6 N1 . 1.3244(16) y
  C2 N2 . 1.3299(16) y
  C5 N5 . 1.4367(16) y
  N5 O51 . 1.2368(14) y
  N5 O52 . 1.2287(14) y
  C4 O4 . 1.3265(15) y
  C6 O6 . 1.3273(15) y
  N2 H2A . 0.88 no
  N2 H2B . 0.88 no
  O4 C41 . 1.4490(15) no
  C41 H41A . 0.98 no
  C41 H41B . 0.98 no
  C41 H41C . 0.98 no
  O6 C61 . 1.4445(15) no
  C61 H61A . 0.98 no
  C61 H61B . 0.98 no
  C61 H61C . 0.98 no