#------------------------------------------------------------------------------
#$Date: 2008-01-14 00:15:36 +0200 (Mon, 14 Jan 2008) $
#$Revision: 14 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2011976.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_2011976
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2001
_journal_volume  57
_journal_page_first  608
_journal_page_last  610
_publ_section_title
;
Methyl
7-hydroxy-1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydropteridine-6-carboxylate--
dimethyl sulfoxide (1/1) forms chains containing O---H...O and C---H...O
hydrogen bonds and aromatic \p--\p stacking interactions
;
loop_
_publ_author_name
  'Cannon, Debbie'
  'Low, John N.'
  'Cobo, Justo'
  "Molina, Sebasti\'an"
  'Nogueras, Manuel'
  "S\'anchez, Adolfo"
  'Glidewell, Christopher'
_chemical_formula_moiety  'C11 H12 N4 O5, C2 H6 O S'
_chemical_formula_sum  'C13 H18 N4 O6 S'
_chemical_formula_iupac  'C11 H12 N4 O5, C2 H6 O S'
_chemical_formula_weight  358.37
_symmetry_cell_setting  triclinic
_symmetry_space_group_name_H-M  'P -1'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x, -y, -z'
_cell_length_a  8.8926(2)
_cell_length_b  10.2539(2)
_cell_length_c  10.8500(4)
_cell_angle_alpha  62.2233(10)
_cell_angle_beta  82.4797(10)
_cell_angle_gamma  69.1050(14)
_cell_volume  817.03(4)
_cell_formula_units_Z  2
_cell_measurement_temperature  150(2)
_exptl_crystal_density_diffrn  1.457
_diffrn_ambient_temperature  150(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  .20984(17)  .78664(15)  .49222(15)  .0223(3) Uani d . 1 . . N
  C11  .2364(2)  .62775(19)  .6044(2)  .0315(4) Uani d . 1 . . C
  C2  .19117(19)  .81001(19)  .35871(19)  .0225(4) Uani d . 1 . . C
  O2  .19373(15)  .70316(14)  .33631(14)  .0311(3) Uani d . 1 . . O
  N3  .16521(17)  .96046(16)  .25231(15)  .0228(3) Uani d . 1 . . N
  C31  .1448(2)  .9872(2)  .1094(2)  .0312(4) Uani d . 1 . . C
  C4  .1674(2) 1.08632(19)  .26898(19)  .0230(4) Uani d . 1 . . C
  C4a  .18943(19) 1.05304(18)  .41223(18)  .0197(4) Uani d . 1 . . C
  O4  .14977(17) 1.21352(14)  .16784(13)  .0344(3) Uani d . 1 . . O
  N5  .18648(16) 1.17123(15)  .43783(15)  .0216(3) Uani d . 1 . . N
  C6  .20671(19) 1.13969(18)  .56744(18)  .0203(4) Uani d . 1 . . C
  C61  .1968(2) 1.26821(19)  .60216(19)  .0241(4) Uani d . 1 . . C
  O61  .47876(16) 1.17528(19)  .65920(17)  .0440(4) Uani d . 1 . . O
  C62  .3422(2) 1.23076(19)  .68481(19)  .0249(4) Uani d . 1 . . C
  O62  .30103(14) 1.27098(14)  .78809(13)  .0270(3) Uani d . 1 . . O
  C63  .4326(3) 1.2460(2)  .8712(2)  .0394(5) Uani d . 1 . . C
  C7  .2319(2)  .98491(19)  .67638(18)  .0215(4) Uani d . 1 . . C
  O7  .25198(16)  .95999(14)  .80495(13)  .0288(3) Uani d . 1 . . O
  N8  .23388(17)  .86859(16)  .65320(15)  .0220(3) Uani d . 1 . . N
  C8a  .21190(19)  .90451(18)  .51996(18)  .0190(4) Uani d . 1 . . C
  S1  .25987(6)  .54432(5) 1.05050(5)  .02738(16) Uani d . 1 . . S
  C71  .0732(2)  .5694(2) 1.1328(2)  .0313(4) Uani d . 1 . . C
  C72  .3856(2)  .4063(2) 1.2018(2)  .0391(5) Uani d . 1 . . C
  O1  .29834(17)  .69205(14) 1.00686(13)  .0348(3) Uani d . 1 . . O
  H111  .1554  .5883  .5948  .047 Uiso calc R 1 . . H
  H112  .2274  .6293  .6947  .047 Uiso calc R 1 . . H
  H113  .3442  .5593  .5987  .047 Uiso calc R 1 . . H
  H311  .1745  .8864  .1078  .047 Uiso calc R 1 . . H
  H312  .2142 1.0451  .0482  .047 Uiso calc R 1 . . H
  H313  .0321 1.0482  .0767  .047 Uiso calc R 1 . . H
  H611  .1847 1.3658  .5145  .029 Uiso calc R 1 . . H
  H612  .0997 1.2871  .6561  .029 Uiso calc R 1 . . H
  H631  .4952 1.1340  .9178  .059 Uiso calc R 1 . . H
  H632  .3894 1.2830  .9413  .059 Uiso calc R 1 . . H
  H633  .5023 1.3039  .8107  .059 Uiso calc R 1 . . H
  H7  .2670  .8445  .8803  .035 Uiso d . 1 . . H
  H711  -.0141  .6436 1.0621  .047 Uiso calc R 1 . . H
  H712  .0746  .6102 1.1981  .047 Uiso calc R 1 . . H
  H713  .0558  .4684 1.1836  .047 Uiso calc R 1 . . H
  H721  .4984  .3812 1.1759  .059 Uiso calc R 1 . . H
  H722  .3572  .3108 1.2460  .059 Uiso calc R 1 . . H
  H723  .3709  .4505 1.2672  .059 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  .0283(8)  .0203(7)  .0226(8)  -.0112(6)  .0017(6)  -.0111(6)
  C11  .0483(12)  .0204(9)  .0274(11)  -.0163(8)  .0001(9)  -.0082(8)
  C2  .0200(9)  .0252(8)  .0273(10)  -.0091(7)  .0015(7)  -.0150(8)
  O2  .0406(8)  .0296(7)  .0345(8)  -.0168(6)  .0033(6)  -.0204(6)
  N3  .0257(8)  .0239(7)  .0220(8)  -.0077(6)  -.0024(6)  -.0127(6)
  C31  .0385(11)  .0335(10)  .0263(10)  -.0093(9)  -.0037(8)  -.0180(9)
  C4  .0244(9)  .0217(8)  .0243(10)  -.0075(7)  -.0014(7)  -.0110(8)
  C4a  .0203(8)  .0197(8)  .0211(9)  -.0075(7)  .0000(7)  -.0099(7)
  O4  .0549(9)  .0244(7)  .0222(7)  -.0137(6)  -.0056(6)  -.0073(6)
  N5  .0225(7)  .0207(7)  .0234(8)  -.0085(6)  .0012(6)  -.0106(6)
  C6  .0191(8)  .0201(8)  .0230(9)  -.0064(7)  .0005(7)  -.0107(7)
  C61  .0281(9)  .0212(8)  .0258(10)  -.0082(7)  .0005(7)  -.0128(7)
  O61  .0260(8)  .0636(10)  .0617(11)  -.0150(7)  .0093(7)  -.0457(9)
  C62  .0288(10)  .0219(8)  .0297(10)  -.0123(7)  .0050(8)  -.0145(8)
  O62  .0300(7)  .0289(6)  .0283(7)  -.0099(5)  -.0016(5)  -.0172(6)
  C63  .0417(12)  .0438(12)  .0398(13)  -.0138(10)  -.0104(9)  -.0218(10)
  C7  .0224(8)  .0237(8)  .0219(9)  -.0097(7)  .0037(7)  -.0124(7)
  O7  .0462(8)  .0245(6)  .0192(7)  -.0150(6)  .0012(6)  -.0103(5)
  N8  .0259(8)  .0221(7)  .0212(8)  -.0107(6)  .0020(6)  -.0106(6)
  C8a  .0174(8)  .0212(8)  .0228(9)  -.0087(7)  .0025(6)  -.0122(7)
  S1  .0375(3)  .0246(2)  .0236(3)  -.0140(2)  .00578(19)  -.0123(2)
  C71  .0286(10)  .0290(9)  .0352(11)  -.0074(8)  .0011(8)  -.0153(9)
  C72  .0287(10)  .0299(10)  .0411(13)  -.0105(8)  .0020(9)  -.0019(9)
  O1  .0563(9)  .0267(7)  .0234(7)  -.0239(6)  .0003(6)  -.0054(6)
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 . 1.376(2) y
  C2 N3 . 1.386(2) y
  N3 C4 . 1.391(2) y
  C4 C4a . 1.452(2) y
  N5 C4a . 1.355(2) y
  N5 C6 . 1.310(2) y
  C6 C7 . 1.426(2) y
  C7 N8 . 1.323(2) y
  N1 C8a . 1.381(2) y
  N8 C8a . 1.338(2) y
  C4a C8a . 1.382(2) y
  C2 O2 . 1.220(2) y
  C4 O4 . 1.223(2) y
  C62 O61 . 1.200(2) y
  C62 O62 . 1.332(2) y
  C7 O7 . 1.320(2) y
  N1 C11 . 1.464(2) no
  C11 H111 .  .9800 no
  C11 H112 .  .9800 no
  C11 H113 .  .9800 no
  N3 C31 . 1.467(2) no
  C31 H311 .  .9800 no
  C31 H312 .  .9800 no
  C31 H313 .  .9800 no
  C6 C61 . 1.502(2) no
  C61 C62 . 1.501(2) no
  C61 H611 .  .9900 no
  C61 H612 .  .9900 no
  O62 C63 . 1.447(2) no
  C63 H631 .  .9800 no
  C63 H632 .  .9800 no
  C63 H633 .  .9800 no
  O7 H7 . 1.050 no
  S1 O1 . 1.5148(13) no
  S1 C72 . 1.770(2) no
  S1 C71 . 1.7723(19) no
  C71 H711 .  .9800 no
  C71 H712 .  .9800 no
  C71 H713 .  .9800 no
  C72 H721 .  .9800 no
  C72 H722 .  .9800 no
  C72 H723 .  .9800 no