#------------------------------------------------------------------------------
#$Date: 2011-09-17 23:27:16 +0300 (Sat, 17 Sep 2011) $
#$Revision: 26029 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2013182.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_2013182
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2003
_journal_volume  59
_journal_page_first  o9
_journal_page_last  o13
_publ_section_title
;
Hydrogen bonding in 2-amino-4-methoxy-6-methylpyrimidine,
2-benzylamino-4-benzyloxy-6-methylpyrimidine and
4-benzylamino-2,6-bis(benzyloxy)pyrimidine: \p-stacked chains of fused
R^2^~2~(8) rings, and centrosymmetric R^2^~2~(8) dimers
;
loop_
_publ_author_name
  'Glidewell, Christopher'
  'Low, John N.'
  'Melguizo, Manuel'
  'Quesada, Antonio'
_chemical_formula_moiety  'C6 H9 N3 O'
_chemical_formula_sum  'C6 H9 N3 O'
_chemical_formula_iupac  'C6 H9 N3 O'
_chemical_formula_weight  139.16
_symmetry_cell_setting  orthorhombic
_symmetry_space_group_name_H-M  'P n m a'
_symmetry_space_group_name_Hall  '-P 2ac 2n'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x+1/2, -y, z+1/2'
  'x+1/2, -y+1/2, -z+1/2'
  '-x, y+1/2, -z'
  '-x, -y, -z'
  'x+1/2, y, -z+1/2'
  '-x+1/2, y+1/2, z+1/2'
  'x, -y+1/2, z'
_cell_length_a  8.1442(17)
_cell_length_b  6.5456(11)
_cell_length_c  12.285(2)
_cell_angle_alpha  90.00
_cell_angle_beta  90.00
_cell_angle_gamma  90.00
_cell_volume  654.9(2)
_cell_formula_units_Z  4
_cell_measurement_temperature  120(2)
_exptl_crystal_density_diffrn  1.411
_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 0.6539(2) 0.2500 0.38300(14) 0.0247(5) Uani d S 1 . . N
  N2 0.50228(17) 0.2500 0.22581(14) 0.0303(6) Uani d S 1 . . N
  C2 0.5046(2) 0.2500 0.33456(18) 0.0234(5) Uani d S 1 . . C
  N3 0.3588(2) 0.2500 0.38607(13) 0.0246(5) Uani d S 1 . . N
  C4 0.3649(2) 0.2500 0.49404(18) 0.0234(6) Uani d S 1 . . C
  O4 0.21476(15) 0.2500 0.54049(11) 0.0277(5) Uani d S 1 . . O
  C41 0.2082(2) 0.2500 0.65685(16) 0.0301(6) Uani d S 1 . . C
  C5 0.5107(2) 0.2500 0.55251(18) 0.0245(6) Uani d S 1 . . C
  C6 0.6537(3) 0.2500 0.49193(18) 0.0248(6) Uani d S 1 . . C
  C61 0.8176(2) 0.2500 0.54723(17) 0.0300(6) Uani d S 1 . . C
  H1 0.4080 0.2500 0.1909 0.036 Uiso calc SR 1 . . H
  H2 0.5951 0.2500 0.1891 0.036 Uiso calc SR 1 . . H
  H41A 0.0936 0.2399 0.6806 0.045 Uiso calc PR 0.50 . . H
  H41B 0.2562 0.3770 0.6846 0.045 Uiso calc PR 0.50 . . H
  H41C 0.2703 0.1331 0.6850 0.045 Uiso calc PR 0.50 . . H
  H5 0.5122 0.2500 0.6298 0.029 Uiso calc SR 1 . . H
  H61A 0.8982 0.3195 0.5009 0.045 Uiso calc PR 0.50 . . H
  H61B 0.8529 0.1088 0.5599 0.045 Uiso calc PR 0.50 . . H
  H61C 0.8090 0.3217 0.6170 0.045 Uiso calc PR 0.50 . . 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 0.0185(10) 0.0332(11) 0.0223(12) 0.000 -0.0014(7) 0.000
  N2 0.0215(11) 0.0485(13) 0.0209(13) 0.000 0.0003(7) 0.000
  C2 0.0202(12) 0.0267(13) 0.0234(14) 0.000 -0.0007(8) 0.000
  N3 0.0212(10) 0.0323(11) 0.0204(13) 0.000 0.0006(7) 0.000
  C4 0.0163(12) 0.0283(13) 0.0257(14) 0.000 0.0015(8) 0.000
  O4 0.0186(8) 0.0438(10) 0.0206(9) 0.000 0.0025(6) 0.000
  C41 0.0239(12) 0.0445(15) 0.0218(14) 0.000 0.0044(9) 0.000
  C5 0.0223(12) 0.0310(13) 0.0200(14) 0.000 -0.0010(8) 0.000
  C6 0.0220(12) 0.0256(13) 0.0269(14) 0.000 -0.0014(9) 0.000
  C61 0.0186(12) 0.0424(15) 0.0289(15) 0.000 -0.0027(9) 0.000
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 . 1.354(2) y
  N2 C2 . 1.336(3) no
  N2 H1 . 0.8800 no
  N2 H2 . 0.8800 no
  C2 N3 . 1.346(2) y
  N3 C4 . 1.327(3) y
  C4 O4 . 1.349(2) no
  C4 C5 . 1.388(3) y
  O4 C41 . 1.430(2) no
  C41 H41A . 0.9800 no
  C41 H41B . 0.9800 no
  C41 H41C . 0.9800 no
  C5 C6 . 1.382(3) y
  C5 H5 . 0.9500 no
  C6 N1 . 1.338(3) y
  C6 C61 . 1.498(3) no
  C61 H61A . 0.9800 no
  C61 H61B . 0.9800 no
  C61 H61C . 0.9800 no
_cod_database_code 2013182