data_2013195
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2003
_journal_volume  59
_journal_page_first  o4
_journal_page_last  o8
_publ_section_title
;
Two polymorphs of 2-amino-4-chloro-6-morpholinopyrimidine in P2~1~/c
with Z' = 1 and Z' = 2, and 2-amino-4-chloro-6-piperidinopyrimidine,
isomorphous and almost isostructural with the Z' = 2 polymorph
;
loop_
_publ_author_name
  'Bowes, Katharine F.'
  'Glidewell, Christopher'
  'Low, John N.'
  'Melguizo, Manuel'
  'Quesada, Antonio'
_chemical_formula_moiety  'C8 H11 Cl N4 O'
_chemical_formula_sum  'C8 H11 Cl N4 O'
_chemical_formula_iupac  'C8 H11 Cl N4 O'
_chemical_formula_weight  214.66
_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  9.4143(4)
_cell_length_b  13.0869(4)
_cell_length_c  7.5774(2)
_cell_angle_alpha  90.00
_cell_angle_beta  96.4260(13)
_cell_angle_gamma  90.00
_cell_volume  927.70(5)
_cell_formula_units_Z  4
_cell_measurement_temperature  120(2)
_exptl_crystal_density_diffrn  1.537
_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 0.71414(14) 0.68239(10) 0.31515(17) 0.0145(3) Uani d . 1 . . N
  C2 0.61611(17) 0.61494(13) 0.3565(2) 0.0153(3) Uani d . 1 . . C
  N2 0.64679(15) 0.51494(11) 0.33258(19) 0.0210(3) Uani d . 1 . . N
  N3 0.48967(14) 0.63653(10) 0.41696(17) 0.0162(3) Uani d . 1 . . N
  C4 0.46540(16) 0.73618(13) 0.4275(2) 0.0151(3) Uani d . 1 . . C
  Cl4 0.29987(4) 0.76873(3) 0.49579(5) 0.02164(14) Uani d . 1 . . Cl
  C5 0.55396(16) 0.81388(12) 0.3899(2) 0.0146(3) Uani d . 1 . . C
  C6 0.68472(17) 0.78156(12) 0.3325(2) 0.0133(3) Uani d . 1 . . C
  N61 0.78585(14) 0.84916(10) 0.28931(18) 0.0148(3) Uani d . 1 . . N
  C62 0.78964(18) 0.95378(13) 0.3586(2) 0.0184(4) Uani d . 1 . . C
  C63 0.88104(18) 1.02158(13) 0.2538(2) 0.0208(4) Uani d . 1 . . C
  O64 1.01967(12) 0.97951(9) 0.24329(15) 0.0205(3) Uani d . 1 . . O
  C65 1.00464(18) 0.88308(13) 0.1556(2) 0.0191(4) Uani d . 1 . . C
  C66 0.92618(17) 0.80832(13) 0.2607(2) 0.0190(4) Uani d . 1 . . C
  H1 0.7274 0.4976 0.2920 0.025 Uiso calc R 1 . . H
  H2 0.5861 0.4674 0.3577 0.025 Uiso calc R 1 . . H
  H51 0.5298 0.8839 0.4012 0.017 Uiso calc R 1 . . H
  H3 0.8293 0.9535 0.4852 0.022 Uiso calc R 1 . . H
  H4 0.6913 0.9815 0.3504 0.022 Uiso calc R 1 . . H
  H5 0.8323 1.0311 0.1323 0.025 Uiso calc R 1 . . H
  H6 0.8911 1.0896 0.3111 0.025 Uiso calc R 1 . . H
  H7 1.1004 0.8555 0.1401 0.023 Uiso calc R 1 . . H
  H8 0.9515 0.8922 0.0363 0.023 Uiso calc R 1 . . H
  H9 0.9142 0.7427 0.1957 0.023 Uiso calc R 1 . . H
  H10 0.9827 0.7952 0.3767 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 0.0145(6) 0.0133(7) 0.0159(7) -0.0003(5) 0.0025(5) 0.0019(5)
  C2 0.0160(8) 0.0151(8) 0.0146(8) -0.0018(6) 0.0001(6) 0.0012(6)
  N2 0.0217(8) 0.0125(7) 0.0298(8) -0.0013(6) 0.0081(6) 0.0009(6)
  N3 0.0142(7) 0.0163(7) 0.0182(7) -0.0019(5) 0.0017(5) 0.0035(5)
  C4 0.0121(7) 0.0207(9) 0.0126(8) 0.0006(6) 0.0019(6) 0.0019(6)
  Cl4 0.0133(2) 0.0262(3) 0.0268(2) 0.00021(16) 0.00769(15) 0.00222(17)
  C5 0.0147(8) 0.0139(8) 0.0151(8) 0.0008(6) 0.0017(6) 0.0011(6)
  C6 0.0139(8) 0.0147(8) 0.0110(7) -0.0002(6) 0.0002(6) 0.0024(6)
  N61 0.0130(7) 0.0124(7) 0.0198(7) -0.0011(5) 0.0054(5) 0.0001(5)
  C62 0.0192(8) 0.0146(8) 0.0225(9) -0.0022(7) 0.0075(6) -0.0032(7)
  C63 0.0189(8) 0.0155(9) 0.0288(9) -0.0026(7) 0.0064(7) -0.0009(7)
  O64 0.0169(6) 0.0189(6) 0.0263(6) -0.0054(5) 0.0053(5) -0.0027(5)
  C65 0.0176(8) 0.0185(9) 0.0225(9) -0.0027(7) 0.0077(6) -0.0010(7)
  C66 0.0144(8) 0.0163(8) 0.0272(9) 0.0014(7) 0.0071(6) 0.0021(7)
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 C6 . 1.337(2) no
  N1 C2 . 1.339(2) no
  C2 N3 . 1.352(2) no
  C2 N2 . 1.357(2) no
  N2 H1 . 0.88 no
  N2 H2 . 0.88 no
  N3 C4 . 1.328(2) no
  C4 C5 . 1.365(2) no
  C4 Cl4 . 1.7489(16) no
  C5 C6 . 1.415(2) no
  C5 H51 . 0.95 no
  C6 N61 . 1.366(2) no
  N61 C66 . 1.464(2) no
  N61 C62 . 1.465(2) no
  C62 C63 . 1.520(2) no
  C62 H3 . 0.99 no
  C62 H4 . 0.99 no
  C63 O64 . 1.427(2) no
  C63 H5 . 0.99 no
  C63 H6 . 0.99 no
  O64 C65 . 1.426(2) no
  C65 C66 . 1.506(2) no
  C65 H7 . 0.99 no
  C65 H8 . 0.99 no
  C66 H9 . 0.99 no
  C66 H10 . 0.99 no