#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/98/2019877.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_2019877
loop_
_publ_author_name
'Hützler, Wilhelm Maximilian'
'Egert, Ernst'
_publ_section_title
;
 Cocrystals of 6-methyl-2-thiouracil: presence of the
 acceptor--donor--acceptor/donor--acceptor--donor synthon
;
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2053229615002867
_journal_volume                  71
_journal_year                    2015
_chemical_formula_iupac          'C5 H6 N2 O S, C4 H6 N4'
_chemical_formula_moiety         'C5 H6 N2 O S, C4 H6 N4'
_chemical_formula_sum            'C9 H12 N6 O S'
_chemical_formula_weight         252.31
_chemical_name_systematic
;
6-Methyl-2-thiouracil--2,4-diaminopyrimidine (1/1)
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_Hall           '-P 2ac 2n'
_space_group_name_H-M_alt        'P n m a'
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_space_group_name_H-M   'P n m a'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-1997
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   6.9996(8)
_cell_length_b                   19.223(2)
_cell_length_c                   17.143(2)
_cell_measurement_reflns_used    4338
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.93
_cell_measurement_theta_min      3.32
_cell_volume                     2306.6(4)
_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
;
SHELXL2013 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXD (Sheldrick, 2008)
;
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.989
_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  0.1032
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            11786
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.645
_diffrn_reflns_theta_min         3.318
_exptl_absorpt_coefficient_mu    0.275
_exptl_absorpt_correction_T_max  0.977
_exptl_absorpt_correction_T_min  0.965
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(X-AREA; Stoe & Cie, 2001)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.453
_exptl_crystal_description       plate
_exptl_crystal_F_000             1056
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.090
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.230
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.928
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     197
_refine_ls_number_reflns         2234
_refine_ls_number_restraints     8
_refine_ls_restrained_S_all      0.927
_refine_ls_R_factor_all          0.1100
_refine_ls_R_factor_gt           0.0522
_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)+(0.0416P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0951
_refine_ls_wR_factor_ref         0.1113
_reflns_number_gt                1279
_reflns_number_total             2234
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sk3578sup1.cif
_cod_data_source_block           II
_cod_database_code               2019877
_cod_database_fobs_code          2019877
#BEGIN Tags that were not found in dictionaries:
_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   0.963
_shelx_estimated_absorpt_t_max   0.976
_shelxl_version_number           2.013
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z'
'-x-1/2, y-1/2, z-1/2'
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 0.2237(4) 0.44072(12) 0.55117(17) 0.0328(7) Uani d 1 . .
H H1A 0.218(5) 0.4007(11) 0.5768(17) 0.039 Uiso d 1 . .
C C2A 0.2346(4) 0.49946(16) 0.59457(17) 0.0310(6) Uani d 1 . .
S S21A 0.21417(15) 0.49976(5) 0.69140(5) 0.0503(3) Uani d 1 . .
N N3A 0.2653(4) 0.55891(12) 0.55375(16) 0.0279(6) Uani d 1 . .
H H3A 0.283(4) 0.5981(11) 0.5821(16) 0.033 Uiso d 1 . .
C C4A 0.2883(5) 0.56398(14) 0.4742(2) 0.0314(7) Uani d 1 . .
O O41A 0.3216(3) 0.62137(10) 0.44443(12) 0.0399(6) Uani d 1 . .
C C5A 0.2679(5) 0.49955(17) 0.43221(17) 0.0327(7) Uani d 1 . .
H H5A 0.2757 0.4992 0.3769 0.039 Uiso calc 1 . .
C C6A 0.2378(4) 0.43998(15) 0.4713(2) 0.0301(8) Uani d 1 . .
C C61A 0.2194(5) 0.37000(15) 0.4343(2) 0.0403(9) Uani d 1 . .
H H61A 0.2278 0.3747 0.3775 0.061 Uiso calc 1 . .
H H61B 0.0957 0.3496 0.4483 0.061 Uiso calc 1 . .
H H61C 0.3225 0.3397 0.4529 0.061 Uiso calc 1 . .
C C2B 0.2918(6) 0.7500 0.6008(3) 0.0280(10) Uani d 1 . .
N N21B 0.2073(6) 0.7500 0.5310(2) 0.0319(9) Uani d 1 . .
H H21B 0.217(5) 0.7139(12) 0.5017(16) 0.038 Uiso d 1 . .
N N3B 0.3282(4) 0.68777(11) 0.63403(15) 0.0317(6) Uani d 1 . .
C C4B 0.4142(5) 0.68906(17) 0.7040(2) 0.0388(8) Uani d 1 . .
H H4B 0.4431 0.6461 0.7287 0.047 Uiso calc 0.5 A 2
N N41B 0.4704(9) 0.6345(3) 0.7398(4) 0.0409(14) Uani d 0.5 B 1
H H41B 0.446(10) 0.5924(17) 0.724(4) 0.049 Uiso d 0.5 C 1
H H42B 0.534(9) 0.635(4) 0.783(2) 0.049 Uiso d 0.5 D 1
C C5B 0.4626(7) 0.7500 0.7420(3) 0.0461(13) Uani d 1 B .
H H5B 0.5253 0.7500 0.7911 0.055 Uiso calc 1 . .
C C2C 0.2411(6) 0.2500 0.6172(3) 0.0271(10) Uani d 1 . .
N N21C 0.4098(6) 0.2500 0.5813(3) 0.0402(11) Uani d 1 . .
H H21C 0.474(5) 0.2879(12) 0.590(2) 0.048 Uiso d 1 . .
N N3C 0.1610(4) 0.31182(11) 0.63317(17) 0.0370(7) Uani d 1 . .
C C4C -0.0051(5) 0.31044(17) 0.6716(2) 0.0449(9) Uani d 1 . .
H H4C -0.0613 0.3535 0.6864 0.054 Uiso calc 0.5 E 2
N N41C -0.0641(8) 0.3658(3) 0.7131(4) 0.0402(15) Uani d 0.5 F 1
H H41C 0.014(8) 0.402(2) 0.713(4) 0.048 Uiso d 0.5 G 1
H H42C -0.169(7) 0.369(3) 0.742(4) 0.048 Uiso d 0.5 H 1
C C5C -0.0986(7) 0.2500 0.6909(3) 0.0393(11) Uani d 1 F .
H H5C -0.2197 0.2500 0.7159 0.047 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
C2A N1A C6A . . 123.5(2)
C2A N1A H1A . . 117(2)
C6A N1A H1A . . 119(2)
N1A C2A N3A . . 115.3(3)
N1A C2A S21A . . 123.0(2)
N3A C2A S21A . . 121.6(2)
C2A N3A C4A . . 126.1(2)
C2A N3A H3A . . 117(2)
C4A N3A H3A . . 117(2)
O41A C4A N3A . . 119.6(3)
O41A C4A C5A . . 125.4(3)
N3A C4A C5A . . 115.0(3)
C6A C5A C4A . . 120.0(3)
C6A C5A H5A . . 120.0
C4A C5A H5A . . 120.0
C5A C6A N1A . . 120.0(3)
C5A C6A C61A . . 124.8(3)
N1A C6A C61A . . 115.2(3)
C6A C61A H61A . . 109.5
C6A C61A H61B . . 109.5
H61A C61A H61B . . 109.5
C6A C61A H61C . . 109.5
H61A C61A H61C . . 109.5
H61B C61A H61C . . 109.5
N21B C2B N3B . 7_575 117.5(2)
N21B C2B N3B . . 117.5(2)
N3B C2B N3B 7_575 . 125.0(4)
C2B N21B H21B . . 119(2)
C4B N3B C2B . . 116.4(3)
N41B C4B N3B . . 123.5(4)
N41B C4B C5B . . 113.2(4)
N3B C4B C5B . . 123.1(3)
N3B C4B H4B . . 118.5
C5B C4B H4B . . 118.5
C4B N41B H41B . . 123(5)
C4B N41B H42B . . 124(5)
H41B N41B H42B . . 112(7)
C4B C5B C4B . 7_575 115.9(5)
C4B C5B H5B . . 122.0
C4B C5B H5B 7_575 . 122.0
N21C C2C N3C . 7_565 117.7(2)
N21C C2C N3C . . 117.7(2)
N3C C2C N3C 7_565 . 124.6(4)
C2C N21C H21C . . 112(2)
C4C N3C C2C . . 116.5(3)
N3C C4C N41C . . 120.8(4)
N3C C4C C5C . . 123.3(3)
N41C C4C C5C . . 113.3(4)
N3C C4C H4C . . 118.3
C5C C4C H4C . . 118.3
C4C N41C H41C . . 116(5)
C4C N41C H42C . . 127(4)
H41C N41C H42C . . 117(6)
C4C C5C C4C . 7_565 115.5(4)
C4C C5C H5C . . 122.3
C4C C5C H5C 7_565 . 122.3
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
N1A C2A . 1.354(4)
N1A C6A . 1.373(5)
N1A H1A . 0.887(18)
C2A N3A . 1.357(4)
C2A S21A . 1.666(3)
N3A C4A . 1.376(4)
N3A H3A . 0.904(17)
C4A O41A . 1.238(4)
C4A C5A . 1.440(4)
C5A C6A . 1.343(4)
C5A H5A . 0.9500
C6A C61A . 1.493(4)
C61A H61A . 0.9800
C61A H61B . 0.9800
C61A H61C . 0.9800
C2B N21B . 1.336(6)
C2B N3B 7_575 1.349(3)
C2B N3B . 1.349(3)
N21B H21B . 0.859(17)
N3B C4B . 1.343(4)
C4B N41B . 1.277(6)
C4B C5B . 1.382(4)
C4B H4B . 0.9500
N41B H41B . 0.87(2)
N41B H42B . 0.87(2)
C5B C4B 7_575 1.382(4)
C5B H5B . 0.9500
C2C N21C . 1.331(6)
C2C N3C 7_565 1.342(3)
C2C N3C . 1.342(3)
N21C H21C . 0.870(18)
N3C C4C . 1.337(4)
C4C N41C . 1.346(6)
C4C C5C . 1.374(4)
C4C H4C . 0.9500
N41C H41C . 0.89(2)
N41C H42C . 0.89(2)
C5C C4C 7_565 1.374(4)
C5C H5C . 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 N3C . 0.887(18) 2.003(19) 2.883(4) 171(3)
N3A H3A N3B . 0.904(17) 1.966(18) 2.868(3) 174(3)
N21B H21B O41A . 0.859(17) 2.159(19) 2.993(3) 164(3)
N41B H41B S21A . 0.87(2) 2.47(4) 3.258(6) 150(6)
N21C H21C O41A 5_666 0.870(18) 2.33(2) 3.137(3) 154(3)
N41C H41C S21A . 0.89(2) 2.37(2) 3.250(6) 170(6)
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 . . -1.5(5)
C6A N1A C2A S21A . . 179.1(2)
N1A C2A N3A C4A . . -0.9(5)
S21A C2A N3A C4A . . 178.5(3)
C2A N3A C4A O41A . . -177.7(3)
C2A N3A C4A C5A . . 3.1(5)
O41A C4A C5A C6A . . 177.9(3)
N3A C4A C5A C6A . . -3.0(5)
C4A C5A C6A N1A . . 0.9(5)
C4A C5A C6A C61A . . -178.4(3)
C2A N1A C6A C5A . . 1.4(5)
C2A N1A C6A C61A . . -179.2(3)
N21B C2B N3B C4B . . 179.7(4)
N3B C2B N3B C4B 7_575 . -2.8(6)
C2B N3B C4B N41B . . -174.6(4)
C2B N3B C4B C5B . . 0.7(5)
N41B C4B C5B C4B . 7_575 176.8(4)
N3B C4B C5B C4B . 7_575 1.1(7)
N21C C2C N3C C4C . . -177.8(4)
N3C C2C N3C C4C 7_565 . 3.9(6)
C2C N3C C4C N41C . . 157.1(5)
C2C N3C C4C C5C . . -3.6(6)
N3C C4C C5C C4C . 7_565 3.3(7)
N41C C4C C5C C4C . 7_565 -158.7(4)
