#------------------------------------------------------------------------------
#$Date: 2025-08-19 00:52:38 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301791 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/99/2009951.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_2009951
loop_
_publ_author_name
'Low, John N.'
'Scrimgeour, Sheelagh N.'
'Egglishaw, Clare'
'Howie, R. Alan'
'Moreno-Carretero, Miguel N.'
'Hueso-Ure\~na, Francisco'
_publ_section_title
;
 4-Amino-2-methylthio-6-oxo-1,6-dihydropyrimidine and its 1-methyl
 derivative and 4-amino-2-methoxy-1-methyl-6-oxo-1,6-dihydropyrimidine
 and its 5-nitroso derivative
;
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1329
_journal_page_last               1333
_journal_paper_doi               10.1107/S0108270194000946
_journal_volume                  50
_journal_year                    1994
_chemical_formula_moiety         'C5 H7 N3 O S, 3(H2 O)'
_chemical_formula_sum            'C5 H13 N3 O4 S'
_chemical_formula_weight         211.23
_chemical_name_systematic
;
4-amino-1,6-dihydro-2-methylthio-6-oxopyrimidine trihydrate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_cell_angle_alpha                76.880(2)
_cell_angle_beta                 98.86(3)
_cell_angle_gamma                111.50(3)
_cell_formula_units_Z            2
_cell_length_a                   6.848(4)
_cell_length_b                   6.865(2)
_cell_length_c                   11.763(4)
_cell_measurement_reflns_used    14
_cell_measurement_temperature    293
_cell_measurement_theta_max      10.50
_cell_measurement_theta_min      8.00
_cell_volume                     499.6(4)
_computing_cell_refinement       'Nicolet P3 software'
_computing_data_collection       'Nicolet P3 software'
_computing_data_reduction        'NRCVAX DATRD2'
_computing_molecular_graphics    PLUTON-92
_computing_publication_material  'NRCVAX TABLES'
_computing_structure_refinement  'NRCVAX LSTSQ'
_computing_structure_solution    SHELX86
_diffrn_ambient_temperature      293
_diffrn_measurement_device       'Nicolet P3 four circle diffractometer'
_diffrn_measurement_method       '\w scan b/P/b'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'xray tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.019
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            1741
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         0.00
_diffrn_standards_decay_%        2.2
_diffrn_standards_interval_count 50
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.26
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  1.0000
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_description       prism
_exptl_crystal_F_000             224
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.16
_refine_diff_density_min         -0.25
_refine_ls_goodness_of_fit_obs   2.80
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     118
_refine_ls_number_reflns         1438
_refine_ls_R_factor_all          0.053
_refine_ls_R_factor_obs          0.036
_refine_ls_shift/esd_max         <0.001
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'w = 1/\s^2^(F)'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.042
_refine_ls_wR_factor_obs         0.041
_reflns_number_observed          1438
_reflns_number_total             1738
_reflns_observed_criterion       Inet>2.5\s(Inet)
_cod_data_source_file            ha1089.cif
_cod_data_source_block           AMT
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value '1/\s^2^(F)' was changed to
'calc'. New tag '_refine_ls_weighting_details' was created. The value
of the new tag was set to 'w = 1/\s^2^(F)'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_formula_sum        'C5 H13 N3 O4 S '
_cod_database_code               2009951
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
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
_atom_site_aniso_type_symbol
N1 0.0383(12) 0.0317(11) 0.0285(11) 0.0167(18) -0.0015(18) -0.0160(18) N
C2 0.0313(13) 0.0336(13) 0.0286(13) 0.023(2) 0.004(2) -0.010(2) C
S2 0.0505(4) 0.0392(4) 0.0273(3) 0.0175(6) 0.0012(6) -0.0143(5) S
C21 0.078(2) 0.0416(17) 0.0382(16) 0.025(3) 0.014(3) 0.001(3) C
N3 0.0364(12) 0.0339(12) 0.0318(12) 0.0201(19) 0.0015(19) -0.0142(19) N
C4 0.0334(13) 0.0332(13) 0.0321(13) 0.024(2) 0.000(2) -0.020(2) C
N4 0.0751(17) 0.0308(12) 0.0331(12) 0.019(2) 0.006(2) -0.0174(19) N
C5 0.0400(15) 0.0363(14) 0.0281(13) 0.026(2) 0.000(2) -0.015(2) C
C6 0.0345(14) 0.0337(14) 0.0293(13) 0.022(2) 0.002(2) -0.007(2) C
O6 0.0661(13) 0.0314(10) 0.0324(10) 0.0113(18) -0.0047(18) -0.0079(16) O
O1W 0.0560(12) 0.0482(11) 0.0333(10) 0.0370(18) 0.0070(17) -0.0174(16) O
O2W 0.0482(11) 0.0399(11) 0.0504(12) 0.0049(17) 0.0100(18) -0.0206(17) O
O3W 0.0516(12) 0.0414(11) 0.0509(12) 0.0258(18) -0.0115(19) -0.0105(18) O
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_type_symbol
N1 0.3550(3) 0.7087(3) 0.02900(16) 0.0339(12) Uani d . N
C2 0.2674(4) 0.5046(4) 0.0875(2) 0.0312(15) Uani d . C
S2 0.28555(11) 0.48164(11) 0.23947(5) 0.0411(4) Uani d . S
C21 0.1773(5) 0.1970(4) 0.2879(2) 0.056(2) Uani d . C
N3 0.1784(3) 0.3392(3) 0.03780(16) 0.0347(13) Uani d . N
C4 0.1781(4) 0.3828(4) -0.0825(2) 0.0324(14) Uani d . C
N4 0.0877(4) 0.2130(3) -0.13393(18) 0.0485(16) Uani d . N
C5 0.2626(4) 0.5866(4) -0.1483(2) 0.0349(15) Uani d . C
C6 0.3561(4) 0.7583(4) -0.0917(2) 0.0333(15) Uani d . C
O6 0.4422(3) 0.9518(3) -0.14049(14) 0.0476(12) Uani d . O
O1W 0.3796(3) 0.0738(3) 0.62784(14) 0.0455(12) Uani d . O
O2W 0.2708(3) 0.7495(3) 0.50653(16) 0.0494(12) Uani d . O
O3W 0.1255(3) 0.3147(3) 0.60304(16) 0.0505(12) Uani d . O
H1 0.426 0.835 0.079 0.0498 Uiso d R H
H211 0.193 0.170 0.382 0.0725 Uiso d R H
H212 0.263 0.116 0.258 0.0725 Uiso d R H
H213 0.013 0.136 0.258 0.0725 Uiso d R H
H41 0.100 0.242 -0.217 0.0493 Uiso d R H
H42 0.048 0.075 -0.095 0.0493 Uiso d R H
H5 0.255 0.610 -0.243 0.0508 Uiso d R H
H1W1 0.297 0.166 0.621 0.0678 Uiso d R H
H2W1 0.382 0.045 0.705 0.0678 Uiso d R H
H1W2 0.381 0.801 0.452 0.0702 Uiso d R H
H2W2 0.294 0.867 0.547 0.0702 Uiso d R H
H1W3 0.195 0.458 0.578 0.0709 Uiso d R H
H2W3 0.001 0.277 0.567 0.0709 Uiso d R H
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C 0.002 0.002 'International Tables Vol. IV Table 2.2B'
H 0.000 0.000 'International Tables Vol. IV Table 2.2B'
N 0.004 0.003 'International Tables Vol. IV Table 2.2B'
O 0.008 0.006 'International Tables Vol. IV Table 2.2B'
S 0.110 0.124 'International Tables Vol. IV Table 2.2B'
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
0 2 -2
1 -1 -6
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 122.20(19) yes
C2 N1 H1 118.86(18) no
C6 N1 H1 118.93(18) no
N1 C2 S2 113.82(17) yes
N1 C2 N3 124.7(2) yes
S2 C2 N3 121.52(18) yes
C2 S2 C21 102.08(12) yes
S2 C21 H211 106.1(2) no
S2 C21 H212 111.3(2) no
S2 C21 H213 111.0(2) no
H211 C21 H212 109.5(3) no
H211 C21 H213 109.5(3) no
H212 C21 H213 109.5(3) no
C2 N3 C4 114.65(19) yes
N3 C4 N4 114.8(2) yes
N3 C4 C5 124.0(2) yes
N4 C4 C5 121.2(2) yes
C4 N4 H41 114.7(2) no
C4 N4 H42 124.5(2) no
H41 N4 H42 118.9(2) no
C4 C5 C6 119.4(2) yes
C4 C5 H5 120.2(2) no
C6 C5 H5 120.4(2) no
N1 C6 C5 115.1(2) yes
N1 C6 O6 118.9(2) yes
C5 C6 O6 126.0(2) yes
H1W1 O1W H2W1 92.62(15) no
H1W2 O2W H2W2 105.58(16) no
H1W3 O3W H2W3 109.22(18) no
O1W H1W1 H2W1 40.91(10) no
O1W H2W1 H1W1 46.47(11) no
O2W H1W2 H2W2 37.22(10) no
O2W H2W2 H1W2 37.19(10) no
O3W H1W3 H2W3 34.16(11) no
O3W H2W3 H1W3 36.62(11) no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C2 ? ? 1.368(3) yes
N1 C6 ? ? 1.383(3) yes
N1 H1 ? ? 1.0800(19) no
C2 S2 ? ? 1.747(2) yes
C2 N3 ? ? 1.299(3) yes
S2 C21 ? ? 1.804(3) yes
C21 H211 ? ? 1.080(3) no
C21 H212 ? ? 1.080(3) no
C21 H213 ? ? 1.081(3) no
N3 C4 ? ? 1.379(3) yes
C4 N4 ? ? 1.335(3) yes
C4 C5 ? ? 1.394(3) yes
N4 H41 ? ? 0.960(2) no
N4 H42 ? ? 0.911(2) no
C5 C6 ? ? 1.384(3) yes
C5 H5 ? ? 1.080(2) no
C6 O6 ? ? 1.275(3) yes
O1W H1W1 ? ? 0.9777(17) no
O1W H2W1 ? ? 0.8832(16) no
O2W H1W2 ? ? 0.9725(18) no
O2W H2W2 ? ? 0.9732(17) no
O3W H1W3 ? ? 0.9222(17) no
O3W H2W3 ? ? 0.8680(18) no
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
N1 O6 2.745(3) 2_675 yes
OW2 OW1 2.729(3) 1_565 yes
OW2 OW1 2.805(3) 2_666 yes
OW3 OW2 2.797(3) 1_555 yes
OW3 OW2 2.743(3) 2_566 yes
OW1 OW3 2.753(3) 1_555 yes
OW1 O6 2.679(3) 1_546 yes
N4 OW3 3.043(3) 1_554 yes
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 S2 179.9(2) no
C6 N1 C2 N3 0.20(10) no
C2 N1 C6 C5 -0.10(10) no
C2 N1 C6 O6 -179.4(3) no
N1 C2 S2 C21 -175.5(2) no
N3 C2 S2 C21 4.20(10) no
N1 C2 N3 C4 0.20(10) no
S2 C2 N3 C4 -179.4(2) no
C2 N3 C4 N4 179.7(3) no
C2 N3 C4 C5 -0.80(10) no
N3 C4 C5 C6 0.90(10) no
N4 C4 C5 C6 -179.6(3) no
C4 C5 C6 N1 -0.40(10) no
C4 C5 C6 O6 178.8(3) no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139057264
