#------------------------------------------------------------------------------
#$Date: 2008-01-26 15:05:32 +0200 (Sat, 26 Jan 2008) $
#$Revision: 19 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2014409.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_2014409
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2006
_journal_volume  62
_journal_page_first  o107
_journal_page_last  o110
_publ_section_title
;
Hydrogen-bonding patterns in trimethoprim picolinate and
2-amino-4,6-dimethylpyrimidinium picolinate hemihydrate
;
loop_
_publ_author_name
  'Madhukar Hemamalini'
  'Packianathan Thomas Muthiah'
  'Daniel E. Lynch'
_chemical_name_common
;
2-amino-4,6-dimethylpyrimidinium picolinate hemihydrate
;
_chemical_formula_moiety  'C6 H10 N3 + , C6 H4 N O2 - , 0.5H2 O'
_chemical_formula_sum  'C12 H15 N4 O2.50'
_chemical_formula_structural  'C6 H10 N3 + , C6 H4 N O2 - , 0.5H2 O'
_chemical_formula_iupac  'C6 H10 N3 + , C6 H4 N O2 - , 0.5H2 O'
_chemical_formula_weight  255.28
_symmetry_cell_setting  Monoclinic
_symmetry_space_group_name_H-M  'C 2/c'
_symmetry_space_group_name_Hall  '-C 2yc'
loop_
_symmetry_equiv_pos_as_xyz
  x,y,z
  -x,y,1/2-z
  -x,-y,-z
  x,-y,1/2+z
  1/2+x,1/2+y,z
  1/2-x,1/2+y,1/2-z
  1/2-x,1/2-y,-z
  1/2+x,1/2-y,1/2+z
_cell_length_a  15.7666(4)
_cell_length_b  8.79800(10)
_cell_length_c  18.5038(4)
_cell_angle_alpha  90
_cell_angle_beta  102.7400(10)
_cell_angle_gamma  90
_cell_volume  2503.55(9)
_cell_formula_units_Z  8
_cell_measurement_temperature  120
_exptl_crystal_density_diffrn  1.355
_diffrn_ambient_temperature  120
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_type_symbol
  N1 -0.00471(7) 0.71894(12) 0.48590(6) 0.0174(3) Uani . . 1.000 N
  N2 0.13114(7) 0.79667(13) 0.54980(6) 0.0195(3) Uani . . 1.000 N
  N3 0.01063(8) 0.89924(13) 0.58351(6) 0.0190(3) Uani . . 1.000 N
  C2 0.04584(9) 0.80507(14) 0.54005(7) 0.0172(4) Uani . . 1.000 C
  C4 -0.07541(9) 0.90978(15) 0.56940(8) 0.0197(4) Uani . . 1.000 C
  C5 -0.13012(9) 0.82756(16) 0.51217(8) 0.0208(4) Uani . . 1.000 C
  C6 -0.09286(9) 0.72949(15) 0.47096(8) 0.0189(4) Uani . . 1.000 C
  C7 -0.11364(10) 1.01425(18) 0.61770(8) 0.0251(4) Uani . . 1.000 C
  C8 -0.14136(9) 0.63004(17) 0.41025(8) 0.0233(4) Uani . . 1.000 C
  O1 0.06155(6) 0.55173(12) 0.39158(6) 0.0251(3) Uani . . 1.000 O
  O2 0.19643(7) 0.59392(13) 0.45783(6) 0.0264(3) Uani . . 1.000 O
  N4 0.26418(7) 0.48590(13) 0.34444(6) 0.0192(3) Uani . . 1.000 N
  C9 0.17995(9) 0.46233(15) 0.34366(7) 0.0176(4) Uani . . 1.000 C
  C10 0.12663(10) 0.37113(17) 0.29108(8) 0.0227(4) Uani . . 1.000 C
  C11 0.16146(11) 0.30355(17) 0.23621(8) 0.0260(5) Uani . . 1.000 C
  C12 0.24774(11) 0.32921(16) 0.23601(8) 0.0259(5) Uani . . 1.000 C
  C13 0.29686(10) 0.41996(16) 0.29116(8) 0.0227(4) Uani . . 1.000 C
  C14 0.14375(9) 0.54243(15) 0.40325(8) 0.0183(4) Uani . . 1.000 C
  O1W 0.00000 0.7153(2) 0.25000 0.0556(7) Uani . . 1.000 O
  H1 0.02020 0.65550 0.46020 0.0210 Uiso . R 1.000 H
  H2A 0.16470 0.85190 0.58430 0.0230 Uiso . R 1.000 H
  H2B 0.15450 0.73580 0.52180 0.0230 Uiso . R 1.000 H
  H5 -0.19140 0.84000 0.50250 0.0250 Uiso . R 1.000 H
  H7A -0.13480 0.95450 0.65480 0.0300 Uiso . R 1.000 H
  H7B -0.16210 1.07090 0.58720 0.0300 Uiso . R 1.000 H
  H7C -0.06900 1.08570 0.64270 0.0300 Uiso . R 1.000 H
  H8A -0.11540 0.63850 0.36690 0.0280 Uiso . R 1.000 H
  H8B -0.20230 0.66210 0.39680 0.0280 Uiso . R 1.000 H
  H8C -0.13820 0.52430 0.42720 0.0280 Uiso . R 1.000 H
  H10 0.06750 0.35530 0.29270 0.0270 Uiso . R 1.000 H
  H11 0.12650 0.24090 0.19960 0.0310 Uiso . R 1.000 H
  H12 0.27310 0.28560 0.19880 0.0310 Uiso . R 1.000 H
  H13 0.35640 0.43610 0.29110 0.0270 Uiso . R 1.000 H
  H1W 0.01610 0.64410 0.29200 0.0670 Uiso . R 1.000 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 0.0181(6) 0.0184(6) 0.0161(6) 0.0009(4) 0.0048(5) -0.0014(4)
  N2 0.0178(6) 0.0228(6) 0.0180(6) -0.0007(4) 0.0043(5) -0.0047(4)
  N3 0.0214(6) 0.0192(6) 0.0173(6) 0.0005(5) 0.0065(5) -0.0002(4)
  C2 0.0217(7) 0.0156(7) 0.0146(7) 0.0000(5) 0.0049(5) 0.0029(5)
  C4 0.0235(7) 0.0180(7) 0.0197(7) 0.0010(5) 0.0091(6) 0.0043(5)
  C5 0.0181(7) 0.0219(7) 0.0231(7) 0.0004(5) 0.0060(6) 0.0026(6)
  C6 0.0196(7) 0.0187(7) 0.0182(7) -0.0004(5) 0.0038(5) 0.0046(5)
  C7 0.0260(7) 0.0266(8) 0.0257(8) 0.0018(6) 0.0121(6) -0.0033(6)
  C8 0.0217(7) 0.0241(8) 0.0228(7) -0.0015(6) 0.0024(6) -0.0014(6)
  O1 0.0182(5) 0.0321(6) 0.0247(6) 0.0019(4) 0.0040(4) -0.0080(4)
  O2 0.0205(5) 0.0359(6) 0.0224(6) -0.0001(4) 0.0038(4) -0.0115(4)
  N4 0.0223(6) 0.0184(6) 0.0180(6) 0.0009(5) 0.0065(5) -0.0003(4)
  C9 0.0208(7) 0.0169(7) 0.0148(7) 0.0020(5) 0.0031(5) 0.0012(5)
  C10 0.0228(7) 0.0239(7) 0.0201(7) 0.0002(6) 0.0018(6) -0.0016(5)
  C11 0.0358(9) 0.0229(8) 0.0179(7) -0.0016(6) 0.0027(6) -0.0044(5)
  C12 0.0399(9) 0.0212(7) 0.0199(8) 0.0010(6) 0.0139(6) -0.0017(6)
  C13 0.0269(8) 0.0205(7) 0.0237(7) 0.0004(6) 0.0119(6) 0.0013(5)
  C14 0.0196(7) 0.0174(7) 0.0176(7) 0.0009(5) 0.0036(5) 0.0005(5)
  O1W 0.0824(16) 0.0339(10) 0.0387(11) 0.0000 -0.0120(10) 0.0000
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
  O1 C14 . . 1.2687(18) yes
  O2 C14 . . 1.2430(18) yes
  O1W H1W . . 0.9868 no
  O1W H1W . 2_555 0.9868 no
  N1 C2 . . 1.3642(17) yes
  N1 C6 . . 1.3591(18) yes
  N2 C2 . . 1.3190(18) yes
  N3 C4 . . 1.3270(19) yes
  N3 C2 . . 1.3558(18) yes
  N1 H1 . . 0.8799 no
  N2 H2A . . 0.8801 no
  N2 H2B . . 0.8804 no
  N4 C13 . . 1.3409(19) yes
  N4 C9 . . 1.3410(18) yes
  C4 C5 . . 1.409(2) no
  C4 C7 . . 1.498(2) no
  C5 C6 . . 1.367(2) no
  C6 C8 . . 1.494(2) no
  C5 H5 . . 0.9493 no
  C7 H7C . . 0.9803 no
  C7 H7A . . 0.9798 no
  C7 H7B . . 0.9801 no
  C8 H8A . . 0.9805 no
  C8 H8C . . 0.9795 no
  C8 H8B . . 0.9794 no
  C9 C14 . . 1.5218(19) no
  C9 C10 . . 1.392(2) no
  C10 C11 . . 1.390(2) no
  C11 C12 . . 1.380(2) no
  C12 C13 . . 1.389(2) no
  C10 H10 . . 0.9496 no
  C11 H11 . . 0.9497 no
  C12 H12 . . 0.9500 no
  C13 H13 . . 0.9497 no