#------------------------------------------------------------------------------
#$Date: 2016-07-21 04:10:48 +0300 (Thu, 21 Jul 2016) $
#$Revision: 184562 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/05/2020562.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_2020562
loop_
_publ_author_name
'Hützler, Wilhelm Maximilian'
'Egert, Ernst'
'Bolte, Michael'
_publ_section_title
;
 6-Propyl-2-thiouracil versus 6-methoxymethyl-2-thiouracil:
 enhancing the hydrogen-bonded synthon motif by replacement of a methylene
 group with an O atom
;
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2053229616011281
_journal_volume                  72
_journal_year                    2016
_chemical_formula_iupac          'C4 H8 N5 +, C6 H7 N2 O2 S -, C6 H8 N2 O2 S'
_chemical_formula_moiety         'C4 H8 N5 +, C6 H7 N2 O2 S -, C6 H8 N2 O2 S'
_chemical_formula_sum            'C16 H23 N9 O4 S2'
_chemical_formula_weight         469.55
_chemical_name_systematic
;
2,4,6-Triaminopyrimidinium
6-methoxymethyl-2-thiouracilate--6-methoxymethyl-2-thiouracil (1/1)
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           17
_space_group_name_Hall           'P 2c 2'
_space_group_name_H-M_alt        'P 2 2 21'
_symmetry_space_group_name_Hall  'P 2c 2'
_symmetry_space_group_name_H-M   'P 2 2 21'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.8086(4)
_cell_length_b                   8.1414(5)
_cell_length_c                   18.6651(14)
_cell_measurement_reflns_used    41700
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.27
_cell_measurement_theta_min      3.32
_cell_volume                     1034.64(12)
_computing_cell_refinement
;
X-AREA (Stoe & Cie, 2001)
;
_computing_data_collection
;
X-AREA (Stoe & Cie, 2001)
;
_computing_data_reduction
;
X-AREA (Stoe & Cie, 2001)
;
_computing_molecular_graphics
;
Mercury (Macrae et al.,  2008) and XP in SHELXTL-Plus (Sheldrick,
2008)
;
_computing_publication_material
;
publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Stoe IPDS II two-circle'
_diffrn_measurement_method       ω
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0246
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            17255
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.902
_diffrn_reflns_theta_min         3.321
_exptl_absorpt_coefficient_mu    0.303
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.566
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(X-AREA; Stoe & Cie, 2001)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.507
_exptl_crystal_description       block
_exptl_crystal_F_000             492
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.110
_refine_diff_density_max         0.177
_refine_diff_density_min         -0.180
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.66(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.128
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     162
_refine_ls_number_reflns         1999
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.128
_refine_ls_R_factor_all          0.0244
_refine_ls_R_factor_gt           0.0239
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0300P)²+0.3621P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0620
_refine_ls_wR_factor_ref         0.0623
_reflns_number_gt                1975
_reflns_number_total             1999
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            sk3632sup1.cif
_cod_data_source_block           VII
_cod_database_code               2020562
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.956
_shelx_estimated_absorpt_t_max   0.967
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x, y, -z+1/2'
'x, -y, -z'
loop_
_atom_site_type_symbol
_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_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N N1A 0.2088(3) 0.5028(2) 0.08899(10) 0.0194(4) Uani d 1 . .
H H1A 0.115(3) 0.548(3) 0.0638(13) 0.023 Uiso d 1 . .
C C2A 0.3466(3) 0.6089(3) 0.11521(11) 0.0186(4) Uani d 1 . .
S S21A 0.31890(9) 0.81098(7) 0.10002(3) 0.02424(15) Uani d 1 . .
N N3A 0.5000(3) 0.5441(2) 0.15099(10) 0.0224(4) Uani d 1 . .
H H3A 0.590(7) 0.602(6) 0.171(3) 0.027 Uiso d 0.5 A 1
C C4A 0.5234(3) 0.3777(3) 0.16050(11) 0.0224(5) Uani d 1 . .
O O41A 0.6737(2) 0.32473(19) 0.19069(9) 0.0275(4) Uani d 1 . .
C C5A 0.3714(3) 0.2718(3) 0.13413(13) 0.0246(5) Uani d 1 . .
H H5A 0.3788 0.1565 0.1417 0.029 Uiso calc 1 . .
C C6A 0.2178(3) 0.3373(3) 0.09853(11) 0.0192(4) Uani d 1 . .
C C7A 0.0527(3) 0.2359(3) 0.06922(12) 0.0220(5) Uani d 1 . .
H H7A1 0.1056 0.1376 0.0446 0.026 Uiso calc 1 . .
H H7A2 -0.0338 0.1988 0.1087 0.026 Uiso calc 1 . .
O O8A -0.0544(2) 0.3329(2) 0.02058(9) 0.0281(4) Uani d 1 . .
C C9A -0.2150(4) 0.2467(4) -0.01019(15) 0.0360(6) Uani d 1 . .
H H9A1 -0.1654 0.1566 -0.0400 0.054 Uiso calc 1 . .
H H9A2 -0.2925 0.3220 -0.0398 0.054 Uiso calc 1 . .
H H9A3 -0.2980 0.2019 0.0280 0.054 Uiso calc 1 . .
C C2B 1.0000 0.6519(4) 0.2500 0.0181(6) Uani d 1 . .
N N21B 1.0000 0.4893(3) 0.2500 0.0209(5) Uani d 1 . .
H H22B 0.901(3) 0.436(3) 0.2300(13) 0.025 Uiso d 1 . .
N N3B 0.8501(3) 0.7307(2) 0.21802(10) 0.0189(4) Uani d 1 . .
H H3B 0.749(6) 0.677(6) 0.204(3) 0.023 Uiso d 0.5 B 2
C C4B 0.8477(3) 0.8980(3) 0.21894(11) 0.0198(5) Uani d 1 . .
N N41B 0.6963(3) 0.9717(2) 0.18818(12) 0.0303(5) Uani d 1 . .
H H41B 0.600(4) 0.918(4) 0.1688(15) 0.036 Uiso d 1 . .
H H42B 0.682(5) 1.074(3) 0.1932(15) 0.036 Uiso d 1 . .
C C5B 1.0000 0.9848(4) 0.2500 0.0204(6) Uani d 1 . .
H H5B 1.0000 1.1015 0.2500 0.024 Uiso calc 1 . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
C6A N1A C2A . . 123.27(18)
C6A N1A H1A . . 121.3(18)
C2A N1A H1A . . 115.4(18)
N3A C2A N1A . . 117.53(19)
N3A C2A S21A . . 123.65(17)
N1A C2A S21A . . 118.81(16)
C2A N3A C4A . . 122.7(2)
C2A N3A H3A . . 123(4)
C4A N3A H3A . . 114(4)
O41A C4A N3A . . 119.7(2)
O41A C4A C5A . . 122.7(2)
N3A C4A C5A . . 117.7(2)
C6A C5A C4A . . 119.4(2)
C6A C5A H5A . . 120.3
C4A C5A H5A . . 120.3
C5A C6A N1A . . 119.4(2)
C5A C6A C7A . . 122.9(2)
N1A C6A C7A . . 117.66(18)
O8A C7A C6A . . 108.38(18)
O8A C7A H7A1 . . 110.0
C6A C7A H7A1 . . 110.0
O8A C7A H7A2 . . 110.0
C6A C7A H7A2 . . 110.0
H7A1 C7A H7A2 . . 108.4
C7A O8A C9A . . 112.49(18)
O8A C9A H9A1 . . 109.5
O8A C9A H9A2 . . 109.5
H9A1 C9A H9A2 . . 109.5
O8A C9A H9A3 . . 109.5
H9A1 C9A H9A3 . . 109.5
H9A2 C9A H9A3 . . 109.5
N21B C2B N3B . 3_755 118.50(14)
N21B C2B N3B . . 118.50(14)
N3B C2B N3B 3_755 . 123.0(3)
C2B N21B H22B . . 119.3(18)
C2B N3B C4B . . 118.7(2)
C2B N3B H3B . . 120(4)
C4B N3B H3B . . 120(4)
N41B C4B N3B . . 117.2(2)
N41B C4B C5B . . 122.3(2)
N3B C4B C5B . . 120.5(2)
C4B N41B H41B . . 123(2)
C4B N41B H42B . . 119(2)
H41B N41B H42B . . 117(3)
C4B C5B C4B . 3_755 118.5(3)
C4B C5B H5B . . 120.8
C4B C5B H5B 3_755 . 120.8
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
N1A C6A . 1.361(3)
N1A C2A . 1.366(3)
N1A H1A . 0.88(2)
C2A N3A . 1.347(3)
C2A S21A . 1.680(2)
N3A C4A . 1.375(3)
N3A H3A . 0.86(3)
C4A O41A . 1.245(3)
C4A C5A . 1.435(3)
C5A C6A . 1.349(3)
C5A H5A . 0.9500
C6A C7A . 1.498(3)
C7A O8A . 1.407(3)
C7A H7A1 . 0.9900
C7A H7A2 . 0.9900
O8A C9A . 1.421(3)
C9A H9A1 . 0.9800
C9A H9A2 . 0.9800
C9A H9A3 . 0.9800
C2B N21B . 1.323(4)
C2B N3B 3_755 1.345(2)
C2B N3B . 1.345(2)
N21B H22B . 0.88(2)
N3B C4B . 1.362(3)
N3B H3B . 0.86(3)
C4B N41B . 1.324(3)
C4B C5B . 1.382(3)
N41B H41B . 0.87(2)
N41B H42B . 0.84(2)
C5B C4B 3_755 1.382(3)
C5B H5B . 0.9500
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
N1A H1A O8A 4_565 0.88(2) 2.18(2) 3.031(2) 164(2)
N21B H22B O41A . 0.88(2) 1.94(2) 2.821(2) 176(3)
N3A H3A N3B . 0.86(3) 2.24(3) 3.091(3) 173(5)
N3B H3B N3A . 0.86(3) 2.24(3) 3.091(3) 172(5)
N41B H41B S21A . 0.87(2) 2.46(2) 3.320(2) 169(3)
N41B H42B O41A 1_565 0.84(2) 2.04(2) 2.879(3) 171(3)
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_site_symmetry_1
_geom_torsion_site_symmetry_4
_geom_torsion
C6A N1A C2A N3A . . 1.3(3)
C6A N1A C2A S21A . . -179.87(17)
N1A C2A N3A C4A . . 1.2(3)
S21A C2A N3A C4A . . -177.52(17)
C2A N3A C4A O41A . . 176.1(2)
C2A N3A C4A C5A . . -3.3(3)
O41A C4A C5A C6A . . -176.4(2)
N3A C4A C5A C6A . . 3.1(3)
C4A C5A C6A N1A . . -0.7(3)
C4A C5A C6A C7A . . -180.0(2)
C2A N1A C6A C5A . . -1.5(3)
C2A N1A C6A C7A . . 177.77(19)
C5A C6A C7A O8A . . -165.2(2)
N1A C6A C7A O8A . . 15.5(3)
C6A C7A O8A C9A . . -180.0(2)
N21B C2B N3B C4B . . 178.90(15)
N3B C2B N3B C4B 3_755 . -1.10(15)
C2B N3B C4B N41B . . -178.75(18)
C2B N3B C4B C5B . . 2.2(3)
N41B C4B C5B C4B . 3_755 179.9(3)
N3B C4B C5B C4B . 3_755 -1.12(15)

_cod_database_fobs_code 2020562
