data_2012723
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2002
_journal_volume  58
_journal_page_first  o289
_journal_page_last  o294
_publ_section_title
;
Hydrogen bonding in 2-amino-4,6-dimethoxypyrimidine,
2-benzylamino-4,6-bis(benzyloxy)pyrimidine and
2-amino-4,6-bis(N-pyrrolidino)pyrimidine: chains of fused rings and a
centrosymmetric dimer
;
loop_
_publ_author_name
  'Low, John N.'
  'Quesada, Antonio'
  'Marchal, Antonio'
  'Melguizo, Manuel'
  'Nogueras, Manuel'
  'Glidewell, Christopher'
_chemical_formula_moiety  'C12 H19 N5'
_chemical_formula_sum  'C12 H19 N5'
_chemical_formula_weight  233.32
_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, -z+1/2'
  '-x, -y, -z'
  'x, -y, z+1/2'
  'x+1/2, y+1/2, z'
  '-x+1/2, y+1/2, -z+1/2'
  '-x+1/2, -y+1/2, -z'
  'x+1/2, -y+1/2, z+1/2'
_cell_length_a  12.5654(8)
_cell_length_b  13.2735(8)
_cell_length_c  14.2279(9)
_cell_angle_alpha  90
_cell_angle_beta  93.090(2)
_cell_angle_gamma  90
_cell_volume  2369.6(3)
_cell_formula_units_Z  8
_cell_measurement_temperature  120(2)
_exptl_crystal_density_diffrn  1.308
_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 0.14234(7) 0.42768(7) 0.04220(6) 0.0167(2) Uani d . 1 . . N
  C2 0.08934(9) 0.41017(8) 0.12032(8) 0.0169(3) Uani d . 1 . . C
  N2 -0.01134(8) 0.44606(8) 0.12240(7) 0.0226(3) Uani d . 1 . . N
  N3 0.12512(7) 0.36133(7) 0.19908(6) 0.0177(2) Uani d . 1 . . N
  C4 0.22452(9) 0.32333(8) 0.19736(8) 0.0168(3) Uani d . 1 . . C
  N4 0.25920(7) 0.27045(8) 0.27487(7) 0.0210(3) Uani d . 1 . . N
  C41 0.19010(9) 0.24157(9) 0.34986(8) 0.0200(3) Uani d . 1 . . C
  C42 0.25113(10) 0.15405(9) 0.39630(9) 0.0247(3) Uani d . 1 . . C
  C43 0.36722(10) 0.18595(10) 0.38874(9) 0.0248(3) Uani d . 1 . . C
  C44 0.36740(9) 0.23140(9) 0.28994(8) 0.0203(3) Uani d . 1 . . C
  C5 0.28893(9) 0.33753(8) 0.12149(8) 0.0181(3) Uani d . 1 . . C
  C6 0.24377(9) 0.39189(8) 0.04469(8) 0.0163(3) Uani d . 1 . . C
  N6 0.30145(7) 0.41109(7) -0.03098(7) 0.0190(2) Uani d . 1 . . N
  C61 0.41069(9) 0.37530(9) -0.03849(8) 0.0193(3) Uani d . 1 . . C
  C62 0.44028(10) 0.41074(9) -0.13600(8) 0.0228(3) Uani d . 1 . . C
  C63 0.36687(9) 0.50100(9) -0.15631(8) 0.0216(3) Uani d . 1 . . C
  C64 0.26383(9) 0.47094(9) -0.11223(8) 0.0188(3) Uani d . 1 . . C
  H2A -0.0398 0.4794 0.0738 0.027 Uiso calc R 1 . . H
  H2B -0.0484 0.4360 0.1723 0.027 Uiso calc R 1 . . H
  H41A 0.1190 0.2200 0.3240 0.024 Uiso calc R 1 . . H
  H41B 0.1814 0.2976 0.3947 0.024 Uiso calc R 1 . . H
  H42A 0.2360 0.0901 0.3623 0.030 Uiso calc R 1 . . H
  H42B 0.2334 0.1461 0.4628 0.030 Uiso calc R 1 . . H
  H43A 0.4158 0.1273 0.3950 0.030 Uiso calc R 1 . . H
  H43B 0.3885 0.2365 0.4374 0.030 Uiso calc R 1 . . H
  H44A 0.4207 0.2861 0.2871 0.024 Uiso calc R 1 . . H
  H44B 0.3827 0.1794 0.2426 0.024 Uiso calc R 1 . . H
  H5 0.3595 0.3118 0.1218 0.022 Uiso calc R 1 . . H
  H61A 0.4142 0.3010 -0.0336 0.023 Uiso calc R 1 . . H
  H61B 0.4589 0.4051 0.0114 0.023 Uiso calc R 1 . . H
  H62A 0.4272 0.3570 -0.1835 0.027 Uiso calc R 1 . . H
  H62B 0.5161 0.4311 -0.1355 0.027 Uiso calc R 1 . . H
  H63A 0.3970 0.5631 -0.1270 0.026 Uiso calc R 1 . . H
  H63B 0.3550 0.5120 -0.2249 0.026 Uiso calc R 1 . . H
  H64A 0.2238 0.5309 -0.0926 0.023 Uiso calc R 1 . . H
  H64B 0.2178 0.4305 -0.1565 0.023 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 0.0156(5) 0.0198(5) 0.0148(5) 0.0000(4) 0.0009(4) 0.0007(4)
  C2 0.0159(5) 0.0186(5) 0.0161(6) -0.0027(4) 0.0003(4) -0.0009(4)
  N2 0.0161(5) 0.0349(6) 0.0172(5) 0.0040(4) 0.0034(4) 0.0079(4)
  N3 0.0152(5) 0.0231(5) 0.0147(5) -0.0005(4) 0.0009(4) 0.0016(4)
  C4 0.0182(6) 0.0173(5) 0.0148(5) -0.0023(4) -0.0007(4) -0.0001(4)
  N4 0.0162(5) 0.0288(5) 0.0183(5) 0.0021(4) 0.0023(4) 0.0070(4)
  C41 0.0205(6) 0.0244(6) 0.0149(6) -0.0020(5) 0.0005(4) 0.0031(4)
  C42 0.0292(7) 0.0246(6) 0.0203(6) -0.0008(5) -0.0002(5) 0.0053(5)
  C43 0.0252(7) 0.0264(6) 0.0225(6) 0.0037(5) -0.0027(5) 0.0047(5)
  C44 0.0176(6) 0.0234(6) 0.0197(6) 0.0029(5) -0.0001(4) 0.0005(5)
  C5 0.0154(5) 0.0210(6) 0.0179(6) 0.0024(4) 0.0017(4) 0.0011(4)
  C6 0.0175(6) 0.0162(5) 0.0151(6) -0.0011(4) 0.0016(4) -0.0020(4)
  N6 0.0173(5) 0.0249(5) 0.0152(5) 0.0049(4) 0.0038(4) 0.0037(4)
  C61 0.0163(6) 0.0237(6) 0.0181(6) 0.0033(4) 0.0040(4) 0.0004(4)
  C62 0.0215(6) 0.0283(6) 0.0191(6) 0.0021(5) 0.0068(5) 0.0009(5)
  C63 0.0203(6) 0.0282(6) 0.0166(6) 0.0001(5) 0.0028(4) 0.0028(5)
  C64 0.0190(6) 0.0229(6) 0.0144(6) 0.0002(4) -0.0004(4) 0.0016(4)
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 . 1.3464(15) y
  C2 N3 . 1.3506(14) y
  N3 C4 . 1.3484(15) y
  C4 C5 . 1.3965(16) y
  C5 C6 . 1.4035(15) y
  C6 N1 . 1.3588(14) y
  C2 N2 . 1.3537(15) y
  N2 H2A . 0.8800 no
  N2 H2B . 0.8800 no
  C4 N4 . 1.3590(14) y
  N4 C44 . 1.4601(14) no
  N4 C41 . 1.4625(15) no
  C41 C42 . 1.5230(16) no
  C41 H41A . 0.9900 no
  C41 H41B . 0.9900 no
  C42 C43 . 1.5283(18) no
  C42 H42A . 0.9900 no
  C42 H42B . 0.9900 no
  C43 C44 . 1.5298(16) no
  C43 H43A . 0.9900 no
  C43 H43B . 0.9900 no
  C44 H44A . 0.9900 no
  C44 H44B . 0.9900 no
  C5 H5 . 0.9500 no
  C6 N6 . 1.3540(15) y
  N6 C64 . 1.4602(14) no
  N6 C61 . 1.4619(14) no
  C61 C62 . 1.5296(16) no
  C61 H61A . 0.9900 no
  C61 H61B . 0.9900 no
  C62 C63 . 1.5300(16) no
  C62 H62A . 0.9900 no
  C62 H62B . 0.9900 no
  C63 C64 . 1.5219(16) no
  C63 H63A . 0.9900 no
  C63 H63B . 0.9900 no
  C64 H64A . 0.9900 no
  C64 H64B . 0.9900 no