#------------------------------------------------------------------------------
#$Date: 2010-01-30 14:59:17 +0100 (Sat, 30 Jan 2010) $
#$Revision: 966 $
#$URL: svn://www.crystallography.net/cod/cif/2/2008153.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_2008153
_journal_name_full 'Acta Crystallographica Section C'
_journal_year  1999
_journal_volume 55
_journal_page_first  254
_journal_page_last  256
_publ_section_title
;
A 1-alkylated pteridine
;
_space_group_IT_number           14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_[local]_cod_cif_authors_sg_H-M  'P 21/n'
loop_
_publ_author_name
  'Helliwell, Madeleine'
  'Dinsmore, Andrew'
  'Garner, C. David'
  'Joule, John A.'
_chemical_formula_sum  'C15 H19 Cl N6 O3'
_chemical_formula_weight  366.81
_symmetry_cell_setting  monoclinic
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x+1/2, y+1/2, -z+1/2'
  '-x, -y, -z'
  'x-1/2, -y-1/2, z-1/2'
_cell_length_a  11.7770(11)
_cell_length_b  9.3742(5)
_cell_length_c  17.0675(15)
_cell_angle_alpha  90.00
_cell_angle_beta  106.623(7)
_cell_angle_gamma  90.00
_cell_volume  1805.5(3)
_cell_formula_units_Z  4
_cell_measurement_temperature  296(2)
_exptl_crystal_density_diffrn  1.349
_diffrn_ambient_temperature  296.2
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
  Cl1 0.08434(9) 0.17990(13) 0.82344(7) 0.0867(4) Uani d . 1 . . Cl
  O1 0.5163(2) 0.2705(3) 1.00055(16) 0.0700(8) Uani d . 1 . . O
  O2 0.3302(2) -0.1383(3) 1.21625(14) 0.0597(7) Uani d . 1 . . O
  O3 0.4398(3) -0.3008(3) 1.30057(17) 0.0764(8) Uani d . 1 . . O
  N1 0.4063(2) -0.0556(3) 1.11305(16) 0.0494(7) Uani d . 1 . . N
  N2 0.5475(2) 0.1248(3) 1.11056(16) 0.0495(7) Uani d . 1 . . N
  N3 0.2870(2) 0.1705(3) 0.93634(16) 0.0519(7) Uani d . 1 . . N
  N4 0.2243(3) -0.0702(3) 1.01207(18) 0.0600(8) Uani d . 1 . . N
  N5 0.5766(2) -0.0386(3) 1.21891(16) 0.0519(7) Uani d . 1 . . N
  N6 0.7560(2) -0.0240(3) 1.31793(17) 0.0567(8) Uani d . 1 . . N
  C1 0.5131(3) 0.0151(4) 1.14651(19) 0.0472(8) Uani d . 1 . . C
  C2 0.4803(3) 0.1765(4) 1.0375(2) 0.0500(8) Uani d . 1 . . C
  C3 0.3610(3) 0.1138(4) 1.00385(18) 0.0455(8) Uani d . 1 . . C
  C4 0.1843(3) 0.1059(4) 0.9084(2) 0.0577(10) Uani d . 1 . . C
  C5 0.1530(3) -0.0139(4) 0.9445(2) 0.0648(11) Uani d . 1 . . C
  H5 0.0798 -0.0563 0.9209 0.078 Uiso calc R 1 . . H
  C6 0.3286(3) -0.0033(4) 1.04180(19) 0.0482(8) Uani d . 1 . . C
  C7 0.6858(3) 0.0088(4) 1.2468(2) 0.0551(9) Uani d . 1 . . C
  H7 0.7143 0.0693 1.2135 0.066 Uiso calc R 1 . . H
  C8 0.8783(3) 0.0270(5) 1.3453(3) 0.0806(13) Uani d . 1 . . C
  H8A 0.8948 0.0834 1.3029 0.121 Uiso calc R 1 . . H
  H8B 0.9313 -0.0530 1.3574 0.121 Uiso calc R 1 . . H
  H8C 0.8891 0.0841 1.3935 0.121 Uiso calc R 1 . . H
  C9 0.7174(4) -0.1125(6) 1.3747(3) 0.0910(16) Uani d . 1 . . C
  H9A 0.6995 -0.0535 1.4156 0.136 Uiso calc R 1 . . H
  H9B 0.7792 -0.1784 1.4005 0.136 Uiso calc R 1 . . H
  H9C 0.6478 -0.1645 1.3458 0.136 Uiso calc R 1 . . H
  C10 0.3790(3) -0.1824(4) 1.1519(2) 0.0586(9) Uani d . 1 . . C
  H10A 0.3221 -0.2406 1.1125 0.070 Uiso calc R 1 . . H
  H10B 0.4502 -0.2383 1.1743 0.070 Uiso calc R 1 . . H
  C11 0.3754(3) -0.1999(4) 1.2901(2) 0.0545(9) Uani d . 1 . . C
  C12 0.3328(3) -0.1250(4) 1.3547(2) 0.0588(10) Uani d . 1 . . C
  C13 0.3673(4) 0.0329(5) 1.3575(3) 0.0841(13) Uani d . 1 . . C
  H13A 0.4512 0.0409 1.3656 0.126 Uiso calc R 1 . . H
  H13B 0.3467 0.0788 1.4018 0.126 Uiso calc R 1 . . H
  H13C 0.3258 0.0779 1.3069 0.126 Uiso calc R 1 . . H
  C14 0.3916(4) -0.1932(5) 1.4373(3) 0.0866(14) Uani d . 1 . . C
  H14A 0.3738 -0.2933 1.4347 0.130 Uiso calc R 1 . . H
  H14B 0.3622 -0.1492 1.4784 0.130 Uiso calc R 1 . . H
  H14C 0.4758 -0.1800 1.4507 0.130 Uiso calc R 1 . . H
  C15 0.1988(4) -0.1399(7) 1.3344(3) 0.1033(18) Uani d . 1 . . C
  H15A 0.1621 -0.0919 1.2838 0.155 Uiso calc R 1 . . H
  H15B 0.1722 -0.0980 1.3773 0.155 Uiso calc R 1 . . H
  H15C 0.1778 -0.2391 1.3293 0.155 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
  Cl1 0.0707(6) 0.0874(8) 0.0753(7) 0.0066(6) -0.0219(5) 0.0030(6)
  O1 0.0592(15) 0.0805(19) 0.0625(16) -0.0131(14) 0.0048(12) 0.0178(15)
  O2 0.0500(13) 0.0728(18) 0.0541(15) 0.0051(12) 0.0112(11) 0.0181(13)
  O3 0.089(2) 0.0612(18) 0.0729(18) 0.0175(16) 0.0144(15) 0.0172(15)
  N1 0.0479(15) 0.0514(18) 0.0438(16) -0.0056(13) 0.0049(12) -0.0019(13)
  N2 0.0408(14) 0.0592(18) 0.0445(16) -0.0014(13) 0.0060(12) 0.0033(14)
  N3 0.0494(15) 0.0560(18) 0.0450(16) 0.0032(14) 0.0049(12) -0.0055(14)
  N4 0.0523(17) 0.0592(19) 0.0595(19) -0.0097(15) 0.0016(14) -0.0087(16)
  N5 0.0434(15) 0.064(2) 0.0443(16) 0.0025(14) 0.0055(12) 0.0005(14)
  N6 0.0425(15) 0.071(2) 0.0489(17) 0.0091(14) 0.0000(13) 0.0015(15)
  C1 0.0432(17) 0.055(2) 0.0422(18) 0.0042(16) 0.0101(14) -0.0056(16)
  C2 0.0487(18) 0.054(2) 0.0455(19) 0.0001(16) 0.0111(15) -0.0003(17)
  C3 0.0424(17) 0.055(2) 0.0361(17) 0.0028(15) 0.0056(13) -0.0080(16)
  C4 0.054(2) 0.058(2) 0.053(2) 0.0034(18) 0.0007(16) -0.0120(18)
  C5 0.052(2) 0.068(3) 0.062(2) -0.0082(19) -0.0048(18) -0.013(2)
  C6 0.0497(18) 0.051(2) 0.0412(18) -0.0026(16) 0.0081(15) -0.0094(16)
  C7 0.054(2) 0.057(2) 0.051(2) 0.0037(18) 0.0094(16) 0.0010(18)
  C8 0.055(2) 0.091(3) 0.079(3) -0.008(2) -0.008(2) -0.001(3)
  C9 0.059(2) 0.147(5) 0.060(3) 0.016(3) 0.008(2) 0.032(3)
  C10 0.062(2) 0.052(2) 0.056(2) -0.0058(19) 0.0082(17) 0.0021(18)
  C11 0.0436(18) 0.052(2) 0.061(2) -0.0064(17) 0.0036(16) 0.0145(18)
  C12 0.0463(19) 0.071(3) 0.058(2) 0.0003(18) 0.0129(16) 0.014(2)
  C13 0.093(3) 0.075(3) 0.088(3) 0.006(3) 0.031(3) 0.001(3)
  C14 0.089(3) 0.103(4) 0.069(3) 0.007(3) 0.023(2) 0.020(3)
  C15 0.053(2) 0.165(5) 0.096(4) -0.004(3) 0.027(2) 0.014(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
  Cl1 C4 . 1.730(4) no
  O1 C2 . 1.228(4) no
  O2 C11 . 1.349(4) no
  O2 C10 . 1.438(4) no
  O3 C11 . 1.194(4) no
  N1 C6 . 1.386(4) no
  N1 C1 . 1.392(4) no
  N1 C10 . 1.442(4) no
  N2 C1 . 1.318(4) no
  N2 C2 . 1.361(4) no
  N3 C4 . 1.314(4) no
  N3 C3 . 1.340(4) no
  N4 C5 . 1.326(4) no
  N4 C6 . 1.342(4) no
  N5 C7 . 1.314(4) no
  N5 C1 . 1.346(4) no
  N6 C7 . 1.296(4) no
  N6 C9 . 1.445(5) no
  N6 C8 . 1.461(4) no
  C2 C3 . 1.479(4) no
  C3 C6 . 1.383(5) no
  C4 C5 . 1.382(5) no
  C5 H5 . 0.9300 no
  C7 H7 . 0.9300 no
  C8 H8A . 0.9600 no
  C8 H8B . 0.9600 no
  C8 H8C . 0.9600 no
  C9 H9A . 0.9600 no
  C9 H9B . 0.9600 no
  C9 H9C . 0.9600 no
  C10 H10A . 0.9700 no
  C10 H10B . 0.9700 no
  C11 C12 . 1.509(5) no
  C12 C14 . 1.522(5) no
  C12 C15 . 1.522(5) no
  C12 C13 . 1.532(6) no
  C13 H13A . 0.9600 no
  C13 H13B . 0.9600 no
  C13 H13C . 0.9600 no
  C14 H14A . 0.9600 no
  C14 H14B . 0.9600 no
  C14 H14C . 0.9600 no
  C15 H15A . 0.9600 no
  C15 H15B . 0.9600 no
  C15 H15C . 0.9600 no
_cod_database_code 2008153