#------------------------------------------------------------------------------
#$Date: 2011-09-28 17:24:46 +0300 (Wed, 28 Sep 2011) $
#$Revision: 26848 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/27/2012716.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_2012716
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2002
_journal_volume  58
_journal_page_first  o284
_journal_page_last  o286
_publ_section_title
;
4-Amino-6-benzyloxy-2-(methylsulfanyl)-5-nitrosopyrimidine: hydrogen-bonded
dimers linked into \p-stacked chains
;
_space_group_IT_number           14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_[local]_cod_cif_authors_sg_H-M  'P 21/c'
loop_
_publ_author_name
  'Low, John N.'
  'Quesada, Antonio'
  'Marchal, Antonio'
  'Nogueras, Manuel'
  'S\'anchez, Adolfo'
  'Glidewell, Christopher'
_chemical_formula_moiety  'C12 H12 N4 O2 S'
_chemical_formula_sum  'C12 H12 N4 O2 S'
_chemical_formula_iupac  'C12 H12 N4 O2 S'
_chemical_formula_weight  276.32
_symmetry_cell_setting  monoclinic
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  15.6152(10)
_cell_length_b  9.1842(6)
_cell_length_c  17.7920(11)
_cell_angle_alpha  90.00
_cell_angle_beta  90.830(2)
_cell_angle_gamma  90.00
_cell_volume  2551.3(3)
_cell_formula_units_Z  8
_cell_measurement_temperature  120(2)
_exptl_crystal_density_diffrn  1.439
_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
  N11 0.26619(7) 0.57631(12) 0.38289(6) 0.0256(2) Uani d . 1 . . N
  C12 0.34204(8) 0.50920(15) 0.39377(7) 0.0251(3) Uani d . 1 . . C
  S12 0.37614(2) 0.38279(4) 0.32777(2) 0.03292(10) Uani d . 1 . . S
  C121 0.29268(10) 0.3893(2) 0.25706(9) 0.0404(4) Uani d . 1 . . C
  N13 0.39803(7) 0.52625(12) 0.45058(6) 0.0253(2) Uani d . 1 . . N
  C14 0.37771(8) 0.62629(15) 0.50305(7) 0.0250(3) Uani d . 1 . . C
  N14 0.43291(7) 0.64343(14) 0.55976(7) 0.0315(3) Uani d . 1 . . N
  C15 0.29961(8) 0.70870(15) 0.49700(8) 0.0261(3) Uani d . 1 . . C
  N15 0.27135(8) 0.81465(14) 0.54536(7) 0.0363(3) Uani d . 1 . . N
  O15 0.31865(7) 0.84115(13) 0.60181(6) 0.0432(3) Uani d . 1 . . O
  C16 0.24639(8) 0.67458(15) 0.43399(8) 0.0255(3) Uani d . 1 . . C
  O16 0.17207(6) 0.74563(11) 0.42737(6) 0.0298(2) Uani d . 1 . . O
  C167 0.11727(9) 0.70483(16) 0.36374(8) 0.0312(3) Uani d . 1 . . C
  C161 0.04088(9) 0.80449(16) 0.36150(8) 0.0288(3) Uani d . 1 . . C
  C162 0.00075(10) 0.85356(16) 0.42541(8) 0.0330(3) Uani d . 1 . . C
  C163 -0.07137(10) 0.94235(17) 0.42015(9) 0.0355(3) Uani d . 1 . . C
  C164 -0.10439(10) 0.98162(19) 0.35154(9) 0.0410(4) Uani d . 1 . . C
  C165 -0.06544(12) 0.9315(2) 0.28700(10) 0.0558(5) Uani d . 1 . . C
  C166 0.00637(11) 0.8434(2) 0.29205(9) 0.0479(5) Uani d . 1 . . C
  N21 0.23421(7) 0.27186(13) 0.50043(6) 0.0264(2) Uani d . 1 . . N
  C22 0.15755(8) 0.30913(15) 0.46994(7) 0.0261(3) Uani d . 1 . . C
  S22 0.12166(2) 0.21882(4) 0.38943(2) 0.03311(10) Uani d . 1 . . S
  C221 0.20532(10) 0.09006(17) 0.37297(10) 0.0390(4) Uani d . 1 . . C
  N23 0.10250(7) 0.40863(13) 0.49387(6) 0.0273(3) Uani d . 1 . . N
  C24 0.12322(8) 0.47877(16) 0.55858(8) 0.0281(3) Uani d . 1 . . C
  N24 0.06825(8) 0.57627(15) 0.58339(7) 0.0383(3) Uani d . 1 . . N
  C25 0.20171(9) 0.44616(16) 0.59792(8) 0.0293(3) Uani d . 1 . . C
  N25 0.22988(8) 0.50434(16) 0.66500(7) 0.0407(3) Uani d . 1 . . N
  O25 0.18349(8) 0.60084(15) 0.69388(7) 0.0528(3) Uani d . 1 . . O
  C26 0.25442(8) 0.34040(15) 0.56363(8) 0.0270(3) Uani d . 1 . . C
  O26 0.32842(6) 0.31138(11) 0.59831(5) 0.0303(2) Uani d . 1 . . O
  C267 0.38374(9) 0.20328(17) 0.56463(9) 0.0335(3) Uani d . 1 . . C
  C261 0.45856(9) 0.18088(17) 0.61798(9) 0.0337(3) Uani d . 1 . . C
  C262 0.50491(11) 0.0520(2) 0.61235(12) 0.0511(5) Uani d . 1 . . C
  C263 0.57526(12) 0.0281(2) 0.65882(14) 0.0668(6) Uani d . 1 . . C
  C264 0.60074(11) 0.1306(2) 0.71148(13) 0.0611(6) Uani d . 1 . . C
  C265 0.55452(10) 0.2569(2) 0.71799(10) 0.0480(5) Uani d . 1 . . C
  C266 0.48365(9) 0.28248(19) 0.67110(9) 0.0389(4) Uani d . 1 . . C
  H12A 0.2367 0.3832 0.2812 0.061 Uiso calc R 1 . . H
  H12B 0.2992 0.3072 0.2224 0.061 Uiso calc R 1 . . H
  H12C 0.2966 0.4809 0.2291 0.061 Uiso calc R 1 . . H
  H14A 0.4800 0.5909 0.5618 0.038 Uiso calc R 1 . . H
  H14B 0.4224 0.7073 0.5953 0.038 Uiso calc R 1 . . H
  H16A 0.0983 0.6026 0.3692 0.037 Uiso calc R 1 . . H
  H16B 0.1494 0.7133 0.3164 0.037 Uiso calc R 1 . . H
  H162 0.0226 0.8264 0.4735 0.040 Uiso calc R 1 . . H
  H163 -0.0979 0.9759 0.4647 0.043 Uiso calc R 1 . . H
  H164 -0.1534 1.0426 0.3481 0.049 Uiso calc R 1 . . H
  H165 -0.0881 0.9576 0.2391 0.067 Uiso calc R 1 . . H
  H166 0.0323 0.8092 0.2474 0.058 Uiso calc R 1 . . H
  H22A 0.2597 0.1417 0.3671 0.059 Uiso calc R 1 . . H
  H22B 0.1922 0.0349 0.3271 0.059 Uiso calc R 1 . . H
  H22C 0.2099 0.0230 0.4157 0.059 Uiso calc R 1 . . H
  H24A 0.0205 0.5933 0.5581 0.046 Uiso calc R 1 . . H
  H24B 0.0794 0.6242 0.6252 0.046 Uiso calc R 1 . . H
  H26A 0.4040 0.2378 0.5153 0.040 Uiso calc R 1 . . H
  H26B 0.3523 0.1107 0.5570 0.040 Uiso calc R 1 . . H
  H262 0.4882 -0.0197 0.5765 0.061 Uiso calc R 1 . . H
  H263 0.6066 -0.0601 0.6545 0.080 Uiso calc R 1 . . H
  H264 0.6496 0.1137 0.7427 0.073 Uiso calc R 1 . . H
  H265 0.5708 0.3273 0.7546 0.058 Uiso calc R 1 . . H
  H266 0.4524 0.3707 0.6758 0.047 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
  N11 0.0202(5) 0.0290(6) 0.0275(6) -0.0012(4) -0.0042(4) 0.0013(5)
  C12 0.0214(6) 0.0269(7) 0.0270(6) -0.0037(5) -0.0007(5) 0.0006(5)
  S12 0.02645(18) 0.0395(2) 0.03268(19) 0.00186(15) -0.00430(14) -0.01012(15)
  C121 0.0306(8) 0.0596(11) 0.0308(8) -0.0036(7) -0.0061(6) -0.0118(7)
  N13 0.0195(5) 0.0288(6) 0.0276(6) 0.0006(5) -0.0034(4) -0.0007(5)
  C14 0.0203(6) 0.0276(7) 0.0269(6) -0.0028(5) -0.0033(5) 0.0012(5)
  N14 0.0239(6) 0.0381(7) 0.0324(6) 0.0051(5) -0.0090(5) -0.0083(5)
  C15 0.0212(6) 0.0265(7) 0.0306(7) 0.0000(5) -0.0036(5) -0.0001(5)
  N15 0.0306(7) 0.0371(7) 0.0409(7) 0.0034(5) -0.0065(5) -0.0090(6)
  O15 0.0353(6) 0.0503(7) 0.0437(6) 0.0053(5) -0.0125(5) -0.0178(5)
  C16 0.0193(6) 0.0267(7) 0.0305(7) -0.0018(5) -0.0033(5) 0.0050(5)
  O16 0.0218(5) 0.0331(5) 0.0343(5) 0.0042(4) -0.0099(4) -0.0013(4)
  C167 0.0249(7) 0.0363(8) 0.0320(7) 0.0017(6) -0.0106(6) 0.0006(6)
  C161 0.0205(6) 0.0345(8) 0.0314(7) -0.0026(6) -0.0053(5) 0.0046(6)
  C162 0.0348(8) 0.0348(8) 0.0293(7) -0.0004(6) -0.0072(6) 0.0022(6)
  C163 0.0311(8) 0.0387(8) 0.0367(8) -0.0016(6) 0.0002(6) -0.0033(6)
  C164 0.0260(8) 0.0500(10) 0.0467(9) 0.0080(7) -0.0078(7) -0.0018(7)
  C165 0.0461(10) 0.0865(15) 0.0344(9) 0.0268(10) -0.0097(8) 0.0083(9)
  C166 0.0390(9) 0.0765(13) 0.0283(8) 0.0208(9) 0.0005(7) 0.0071(8)
  N21 0.0193(5) 0.0307(6) 0.0293(6) 0.0015(5) -0.0019(4) 0.0056(5)
  C22 0.0218(6) 0.0307(7) 0.0257(6) -0.0005(5) -0.0009(5) 0.0060(5)
  S22 0.02616(18) 0.0416(2) 0.03141(19) 0.00181(15) -0.00467(14) -0.00393(15)
  C221 0.0344(8) 0.0364(8) 0.0463(9) 0.0017(7) 0.0016(7) -0.0075(7)
  N23 0.0205(5) 0.0354(6) 0.0259(6) 0.0033(5) -0.0050(4) 0.0024(5)
  C24 0.0199(6) 0.0362(8) 0.0281(7) 0.0027(6) -0.0042(5) 0.0029(6)
  N24 0.0266(6) 0.0523(8) 0.0358(7) 0.0138(6) -0.0112(5) -0.0106(6)
  C25 0.0197(6) 0.0397(8) 0.0282(7) 0.0034(6) -0.0057(5) 0.0027(6)
  N25 0.0291(7) 0.0567(9) 0.0361(7) 0.0086(6) -0.0080(5) -0.0073(6)
  O25 0.0370(6) 0.0748(9) 0.0460(7) 0.0187(6) -0.0140(5) -0.0226(6)
  C26 0.0192(6) 0.0328(7) 0.0287(7) 0.0000(5) -0.0025(5) 0.0102(6)
  O26 0.0196(5) 0.0387(6) 0.0324(5) 0.0063(4) -0.0053(4) 0.0053(4)
  C267 0.0231(7) 0.0353(8) 0.0420(8) 0.0065(6) -0.0030(6) 0.0043(6)
  C261 0.0173(6) 0.0391(8) 0.0447(8) 0.0025(6) 0.0001(6) 0.0159(7)
  C262 0.0294(8) 0.0452(10) 0.0787(13) 0.0099(7) -0.0015(8) 0.0112(9)
  C263 0.0315(9) 0.0584(13) 0.1103(18) 0.0178(9) -0.0063(11) 0.0271(12)
  C264 0.0215(8) 0.0762(14) 0.0852(15) -0.0004(9) -0.0142(9) 0.0438(12)
  C265 0.0275(8) 0.0641(12) 0.0520(10) -0.0124(8) -0.0118(7) 0.0252(9)
  C266 0.0242(7) 0.0445(9) 0.0476(9) -0.0001(6) -0.0066(6) 0.0177(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
  N11 C12 . 1.347(2) y
  C12 N13 . 1.336(2) y
  N13 C14 . 1.351(2) y
  C14 C15 . 1.438(2) y
  C15 C16 . 1.421(2) y
  C16 N11 . 1.321(2) y
  C12 S12 . 1.740(2) y
  S12 C121 . 1.799(2) y
  C121 H12A . 0.9800 no
  C121 H12B . 0.9800 no
  C121 H12C . 0.9800 no
  C14 N14 . 1.327(2) y
  N14 H14A . 0.8800 no
  N14 H14B . 0.8800 no
  C15 N15 . 1.376(2) y
  N15 O15 . 1.262(2) y
  C16 O16 . 1.335(2) y
  O16 C167 . 1.458(2) no
  C167 C161 . 1.504(2) no
  C167 H16A . 0.9900 no
  C167 H16B . 0.9900 no
  C161 C162 . 1.382(2) no
  C161 C166 . 1.388(2) no
  C162 C163 . 1.392(2) no
  C162 H162 . 0.9500 no
  C163 C164 . 1.367(2) no
  C163 H163 . 0.9500 no
  C164 C165 . 1.386(2) no
  C164 H164 . 0.9500 no
  C165 C166 . 1.384(2) no
  C165 H165 . 0.9500 no
  C166 H166 . 0.9500 no
  N21 C22 . 1.351(2) y
  C22 N23 . 1.329(2) y
  N23 C24 . 1.354(2) y
  C24 C25 . 1.434(2) y
  C25 C26 . 1.417(2) y
  C26 N21 . 1.323(2) y
  C22 S22 . 1.741(2) y
  S22 C221 . 1.789(2) y
  C221 H22A . 0.9800 no
  C221 H22B . 0.9800 no
  C221 H22C . 0.9800 no
  C24 N24 . 1.321(2) y
  N24 H24A . 0.8800 no
  N24 H24B . 0.8800 no
  C25 N25 . 1.374(2) y
  N25 O25 . 1.259(2) y
  C26 O26 . 1.329(2) y
  O26 C267 . 1.451(2) no
  C267 C261 . 1.509(2) no
  C267 H26A . 0.9900 no
  C267 H26B . 0.9900 no
  C261 C266 . 1.381(2) no
  C261 C262 . 1.392(2) no
  C262 C263 . 1.383(3) no
  C262 H262 . 0.9500 no
  C263 C264 . 1.382(3) no
  C263 H263 . 0.9500 no
  C264 C265 . 1.372(3) no
  C264 H264 . 0.9500 no
  C265 C266 . 1.396(2) no
  C265 H265 . 0.9500 no
  C266 H266 . 0.9500 no
_cod_database_code 2012716