#------------------------------------------------------------------------------
#$Date: 2011-09-10 05:16:28 +0200 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: svn://www.crystallography.net/cod/cif/2/2009073.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2009073
loop_
_publ_author_name
'Low, J. N.'
'Godino, M. L.'
'L\'opez, R.'
'P\'erez, A.'
'Melguizo, M.'
'Cobo, J.'
_publ_section_title
;
 <i>N</i>-(6-Amino-3,4-dihydro-3-methyl-5-nitroso-4-oxopyrimidin-2-yl)methionine
;
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1727
_journal_page_last               1730
_journal_volume                  55
_journal_year                    1999
_chemical_formula_moiety         'C10 H15 N5 O4 S '
_chemical_formula_sum            'C10 H15 N5 O4 S'
_chemical_formula_weight         301.33
_chemical_name_systematic
;
N-(6-amino-3,4-dihydro-3-methyl-5-nitroso-4-oxopyrimidin-2-yl)
methionine
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.0165(4)
_cell_length_b                   11.3057(3)
_cell_length_c                   13.4155(6)
_cell_measurement_reflns_used    all
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26.27
_cell_measurement_theta_min      2.35
_cell_volume                     1367.55(9)
_computing_cell_refinement       COLLECT
_computing_data_collection       'COLLECT (Enraf-Nonius, 1998)'
_computing_data_reduction
'COLLECT and DATRD2 in NRCVAX94 (Gabe et al., 1989)'
_computing_molecular_graphics    'PLATON (Spek, 1998) and PLUTON (Spek, 1995)'
_computing_publication_material
'NRCVAX94, SHELX97, WordPerfect and PREP8 (Ferguson, 19??)'
_computing_structure_refinement  'NRCVAX94 and SHELXL97'
_computing_structure_solution    'SOLVER in NRCVAX'
_diffrn_ambient_temperature      150.0(10)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Kappa CCD area detector'
_diffrn_measurement_method       \f+\w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'X-ray tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.051
_diffrn_reflns_av_sigmaI/netI    0.048
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            10372
_diffrn_reflns_theta_full        26.27
_diffrn_reflns_theta_max         26.27
_diffrn_reflns_theta_min         2.35
_exptl_absorpt_coefficient_mu    0.260
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  1.0000
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.464
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.521
_refine_diff_density_min         -0.369
_refine_ls_abs_structure_details 'Flack (1983)'
_refine_ls_abs_structure_Flack   -0.07(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.208
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         2778
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.208
_refine_ls_R_factor_all          0.061
_refine_ls_R_factor_gt           0.047
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme
'calc w = 1/[\s^2^(Fo^2^)+(0.0679P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_wR_factor_ref         0.128
_reflns_number_gt                2331
_reflns_number_total             2778
_reflns_threshold_expression     I>2\s(I)
_[local]_cod_data_source_file    sk1287.cif
_[local]_cod_data_source_block   HL
_cod_database_code               2009073
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'
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_type_symbol
N1 0.2739(3) 0.04658(17) 0.03525(18) 0.0227(5) Uani d . 1 N
C2 0.3681(3) 0.0895(2) 0.1005(2) 0.0195(6) Uani d . 1 C
N2 0.3641(2) 0.20587(16) 0.11709(17) 0.0214(5) Uani d . 1 N
C21 0.2658(3) 0.2805(2) 0.0579(2) 0.0238(6) Uani d . 1 C
C22 0.3342(3) 0.4034(2) 0.0507(2) 0.0218(6) Uani d . 1 C
O21 0.2520(3) 0.47330(16) -0.00295(19) 0.0402(6) Uani d . 1 O
O22 0.4503(2) 0.42879(16) 0.09130(16) 0.0282(5) Uani d . 1 O
C23 0.1071(3) 0.2824(2) 0.0985(2) 0.0303(7) Uani d . 1 C
C24 0.0891(3) 0.3499(3) 0.1950(3) 0.0399(8) Uani d . 1 C
S2 -0.09168(9) 0.32937(8) 0.25138(8) 0.0496(3) Uani d . 1 S
C25 -0.0622(5) 0.1884(4) 0.3029(3) 0.0565(10) Uani d . 1 C
N3 0.4725(2) 0.02325(18) 0.15143(19) 0.0222(5) Uani d . 1 N
C3 0.5843(3) 0.0824(2) 0.2139(2) 0.0273(6) Uani d . 1 C
C4 0.4820(3) -0.0992(2) 0.1365(2) 0.0215(6) Uani d . 1 C
O4 0.5725(2) -0.15844(16) 0.18275(15) 0.0276(5) Uani d . 1 O
C5 0.3787(3) -0.1486(2) 0.0630(2) 0.0212(6) Uani d . 1 C
N5 0.3858(2) -0.26479(18) 0.05386(19) 0.0245(5) Uani d . 1 N
O5 0.2997(2) -0.31171(14) -0.01405(15) 0.0277(5) Uani d . 1 O
C6 0.2765(3) -0.0684(2) 0.0130(2) 0.0212(6) Uani d . 1 C
N6 0.1807(3) -0.10606(17) -0.05300(19) 0.0261(6) Uani d . 1 N
H2 0.4193 0.2367 0.1625 0.026 Uiso calc R 1 H
H21 0.2622 0.2474 -0.0096 0.029 Uiso calc R 1 H
H21A 0.2909 0.5388 -0.0061 0.060 Uiso calc R 1 H
H23A 0.0427 0.3174 0.0486 0.036 Uiso calc R 1 H
H23B 0.0746 0.2015 0.1089 0.036 Uiso calc R 1 H
H24A 0.1044 0.4335 0.1823 0.048 Uiso calc R 1 H
H24B 0.1648 0.3242 0.2416 0.048 Uiso calc R 1 H
H25A -0.1500 0.1633 0.3374 0.085 Uiso calc R 1 H
H25B 0.0193 0.1917 0.3488 0.085 Uiso calc R 1 H
H25C -0.0398 0.1333 0.2506 0.085 Uiso calc R 1 H
H3A 0.6506 0.0244 0.2412 0.041 Uiso calc R 1 H
H3B 0.5357 0.1238 0.2671 0.041 Uiso calc R 1 H
H3C 0.6394 0.1375 0.1741 0.041 Uiso calc R 1 H
H6A 0.1196 -0.0573 -0.0800 0.031 Uiso calc R 1 H
H6B 0.1789 -0.1796 -0.0694 0.031 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 0.0253(12) 0.0123(10) 0.0306(13) 0.0017(8) -0.0039(11) 0.0005(9)
C2 0.0229(14) 0.0134(12) 0.0222(14) -0.0011(9) 0.0017(12) 0.0008(10)
N2 0.0252(12) 0.0139(10) 0.0252(13) 0.0006(8) -0.0055(10) -0.0004(9)
C21 0.0278(15) 0.0141(12) 0.0297(15) -0.0004(10) -0.0070(13) -0.0015(11)
C22 0.0287(16) 0.0099(11) 0.0267(15) 0.0032(10) 0.0001(13) -0.0026(11)
O21 0.0479(14) 0.0145(9) 0.0583(16) -0.0063(9) -0.0236(12) 0.0071(10)
O22 0.0295(12) 0.0180(9) 0.0370(12) -0.0033(8) -0.0006(9) 0.0019(8)
C23 0.0251(15) 0.0207(13) 0.0452(18) -0.0025(11) -0.0048(14) 0.0001(12)
C24 0.0286(17) 0.0353(17) 0.056(2) -0.0071(13) 0.0070(16) -0.0150(15)
S2 0.0339(5) 0.0487(5) 0.0664(7) 0.0030(4) 0.0125(5) -0.0064(5)
C25 0.053(2) 0.066(2) 0.051(2) -0.005(2) 0.005(2) 0.0056(19)
N3 0.0225(12) 0.0159(10) 0.0283(14) -0.0013(9) -0.0025(10) 0.0011(9)
C3 0.0308(16) 0.0202(13) 0.0308(16) 0.0015(12) -0.0107(13) 0.0006(11)
C4 0.0234(14) 0.0145(12) 0.0264(16) 0.0025(10) 0.0020(12) 0.0021(11)
O4 0.0296(11) 0.0201(9) 0.0330(12) 0.0035(8) -0.0065(9) 0.0000(8)
C5 0.0211(14) 0.0158(13) 0.0266(15) -0.0013(9) -0.0002(12) 0.0030(10)
N5 0.0266(13) 0.0153(11) 0.0317(13) 0.0009(9) -0.0003(11) 0.0001(9)
O5 0.0344(11) 0.0140(9) 0.0348(12) -0.0017(8) -0.0078(9) -0.0028(8)
C6 0.0210(14) 0.0165(12) 0.0263(15) 0.0019(10) 0.0012(12) 0.0007(11)
N6 0.0293(13) 0.0099(10) 0.0390(15) 0.0030(9) -0.0105(12) -0.0007(10)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C2 N1 C6 119.9(2) n
N1 C2 N2 117.3(2) n
N1 C2 N3 124.7(2) n
N2 C2 N3 118.0(2) n
C2 N2 C21 119.7(2) n
N2 C21 C22 108.4(2) n
N2 C21 C23 112.5(2) n
C22 C21 C23 112.8(2) n
O22 C22 O21 126.5(2) n
O22 C22 C21 122.5(2) n
O21 C22 C21 111.0(2) n
C24 C23 C21 114.3(2) n
C23 C24 S2 112.9(2) n
C25 S2 C24 98.28(18) n
C2 N3 C4 120.4(2) n
C2 N3 C3 120.1(2) n
C4 N3 C3 119.2(2) n
O4 C4 N3 120.6(2) n
O4 C4 C5 123.7(2) n
N3 C4 C5 115.7(2) n
N5 C5 C6 127.3(2) n
N5 C5 C4 114.2(2) n
C6 C5 C4 118.3(2) n
O5 N5 C5 116.0(2) n
N6 C6 N1 117.2(2) n
N6 C6 C5 121.8(2) n
N1 C6 C5 121.0(2) n
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C2 1.313(4) n
N1 C6 1.334(3) n
C2 N2 1.335(3) n
C2 N3 1.384(3) n
N2 C21 1.459(3) n
C21 C22 1.523(3) n
C21 C23 1.531(4) n
C22 O22 1.214(3) n
C22 O21 1.301(3) n
C23 C24 1.512(5) n
C24 S2 1.812(3) n
S2 C25 1.757(4) n
N3 C4 1.401(3) n
N3 C3 1.471(3) n
C4 O4 1.224(3) n
C4 C5 1.467(4) n
C5 N5 1.321(3) n
C5 C6 1.456(4) n
N5 O5 1.309(3) n
C6 N6 1.308(4) n
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N2 H2 O4 3_655 0.86 2.39 3.145(3) 146.5 y
O21 H21A O5 1_565 0.82 1.70 2.473(2) 157.4 y
N6 H6A O22 2_455 0.86 2.11 2.932(3) 159.1 y
N6 H6B O5 1_555 0.86 1.99 2.613(3) 128.3 y
N6 H6B O4 2_445 0.86 2.57 3.327(3) 148.0 y
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_publ_flag
C6 N1 C2 N2 177.6(2) n
C6 N1 C2 N3 -1.1(4) n
N1 C2 N2 C21 -4.7(4) n
N3 C2 N2 C21 174.0(2) n
C2 N2 C21 C22 -151.1(2) n
C2 N2 C21 C23 83.5(3) n
N2 C21 C22 O22 -1.3(4) n
C23 C21 C22 O22 124.0(3) n
N2 C21 C22 O21 178.9(2) n
C23 C21 C22 O21 -55.9(3) n
N2 C21 C23 C24 71.5(3) n
C22 C21 C23 C24 -51.5(3) n
C21 C23 C24 S2 -170.2(2) n
C23 C24 S2 C25 77.8(3) n
N1 C2 N3 C4 -1.1(4) n
N2 C2 N3 C4 -179.7(2) n
N1 C2 N3 C3 172.7(3) n
N2 C2 N3 C3 -5.9(4) n
C2 N3 C4 O4 -178.7(3) n
C3 N3 C4 O4 7.5(4) n
C2 N3 C4 C5 1.7(4) n
C3 N3 C4 C5 -172.2(2) n
O4 C4 C5 N5 3.2(4) n
N3 C4 C5 N5 -177.2(2) n
O4 C4 C5 C6 -179.9(3) n
N3 C4 C5 C6 -0.3(4) n
C6 C5 N5 O5 6.3(4) n
C4 C5 N5 O5 -177.2(2) n
C2 N1 C6 N6 -179.6(3) n
C2 N1 C6 C5 2.5(4) n
N5 C5 C6 N6 -3.3(4) n
C4 C5 C6 N6 -179.6(2) n
N5 C5 C6 N1 174.6(3) n
C4 C5 C6 N1 -1.8(4) n