#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/86/2018666.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_2018666
loop_
_publ_author_name
'Zhang, Zhenfeng'
'Xian, Dong'
'Glidewell, Christopher'
_publ_section_title
;
 4,6-Diaminopyrimidine-2(1H)-thione hemihydrate: a
 three-dimensional hydrogen-bonded framework
;
_journal_coeditor_code           SK3446
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o377
_journal_page_last               o380
_journal_paper_doi               10.1107/S0108270112036359
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C4 H6 N4 S , 0.5H2 O'
_chemical_formula_moiety         'C4 H6 N4 S, 0.5(H2 O)'
_chemical_formula_sum            'C4 H7 N4 O0.5 S'
_chemical_formula_weight         151.20
_chemical_name_systematic
;
4,6-Diaminopyrimidine-2(1H)-thione hemihydrate
;
_space_group_IT_number           64
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-C 2ac 2'
_symmetry_space_group_name_H-M   'C m c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            16
_cell_length_a                   9.7274(19)
_cell_length_b                   13.259(3)
_cell_length_c                   19.982(4)
_cell_measurement_reflns_used    1701
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.46
_cell_measurement_theta_min      2.04
_cell_volume                     2577.2(9)
_computing_cell_refinement       'SMART (Bruker, 1997)'
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        'SAINT (Bruker, 1997)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material
;
SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1115
_diffrn_reflns_av_sigmaI/netI    0.0871
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6772
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.79
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.420
_exptl_absorpt_correction_T_max  0.921
_exptl_absorpt_correction_T_min  0.884
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.559
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1264
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.263
_refine_diff_density_min         -0.254
_refine_ls_extinction_coef       0.0025(5)
_refine_ls_extinction_expression
'Fc^*^ = kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   0.957
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     100
_refine_ls_number_reflns         1570
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.957
_refine_ls_R_factor_all          0.0880
_refine_ls_R_factor_gt           0.0458
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0387P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0915
_refine_ls_wR_factor_ref         0.1050
_reflns_number_gt                983
_reflns_number_total             1570
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sk3446.cif
_cod_data_source_block           I
_cod_original_sg_symbol_Hall     '-C 2bc 2'
_cod_original_formula_sum        'C4 H7 N4 O0.5 S1'
_cod_database_code               2018666
_cod_database_fobs_code          2018666
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'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1, z+1/2'
'x+1/2, -y+1/2, -z'
'-x+1/2, y+1, -z+1/2'
'-x, -y, -z'
'x, y-1/2, -z-1/2'
'-x, y, z'
'x, -y-1/2, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, y, -z-1/2'
'-x+1/2, y+1/2, z'
'x+1/2, -y, 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_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
N N11 0.1197(2) 0.43195(13) 0.59257(10) 0.0293(5) Uani d . 1 1
H H11 0.1958 0.4463 0.6123 0.035 Uiso calc PR 0.50 1
C C12 0.0000 0.4538(2) 0.62198(17) 0.0282(8) Uani d S 1 2
C C14 0.1210(3) 0.38681(16) 0.53110(12) 0.0295(6) Uani d . 1 1
C C15 0.0000 0.3631(2) 0.50014(18) 0.0332(9) Uani d S 1 2
H H15 0.0000 0.3314 0.4586 0.040 Uiso calc SR 1 2
S S12 0.0000 0.51191(7) 0.69803(5) 0.0381(3) Uani d S 1 2
N N14 0.2434(2) 0.36958(15) 0.50452(12) 0.0420(6) Uani d . 1 1
H H14A 0.3264 0.3745 0.5282 0.050 Uiso d R 1 1
H H14B 0.2507 0.3391 0.4667 0.050 Uiso d R 1 1
N N21 0.3805(2) 0.53044(13) 0.63819(10) 0.0301(5) Uani d . 1 1
H H21 0.3042 0.4986 0.6330 0.036 Uiso calc PR 0.50 1
C C22 0.5000 0.4817(2) 0.63050(17) 0.0295(8) Uani d S 1 2
C C24 0.3791(3) 0.62980(16) 0.65421(12) 0.0293(6) Uani d . 1 1
C C25 0.5000 0.6812(2) 0.66219(16) 0.0303(8) Uani d S 1 2
H H25 0.5000 0.7495 0.6728 0.036 Uiso calc SR 1 2
S S22 0.5000 0.35701(6) 0.61298(6) 0.0431(3) Uani d S 1 2
N N24 0.2551(2) 0.67278(14) 0.65822(11) 0.0399(6) Uani d . 1 1
H H24A 0.1736 0.6303 0.6671 0.048 Uiso d R 1 1
H H24B 0.2484 0.7339 0.6816 0.048 Uiso d R 1 1
O O31 0.2500 0.85123(19) 0.7500 0.0473(8) Uani d SD 1 2
H H31 0.185(3) 0.8869(19) 0.7454(17) 0.071 Uiso d D 1 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
C12 N11 C14 . . 119.9(2)
C12 N11 H11 . . 120.1
C14 N11 H11 . . 120.1
N11 C12 N11 11 . 121.3(3)
N11 C12 S12 11 . 119.35(15)
N11 C12 S12 . . 119.36(15)
N14 C14 C15 . . 123.6(2)
N14 C14 N11 . . 116.4(2)
C15 C14 N11 . . 120.0(3)
C14 C15 C14 . 11 119.0(3)
C14 C15 H15 . . 120.5
C14 C15 H15 11 . 120.5
C14 N14 H14A . . 124.0
C14 N14 H14B . . 120.5
H14A N14 H14B . . 113.9
C22 N21 C24 . . 120.3(2)
C22 N21 H21 . . 119.9
C24 N21 H21 . . 119.9
N21 C22 N21 11_655 . 120.6(3)
N21 C22 S22 11_655 . 119.71(14)
N21 C22 S22 . . 119.71(14)
N24 C24 N21 . . 115.9(2)
N24 C24 C25 . . 123.8(2)
N21 C24 C25 . . 120.2(2)
C24 C25 C24 . 11_655 118.4(3)
C24 C25 H25 . . 120.8
C24 C25 H25 11_655 . 120.8
C24 N24 H24A . . 119.4
C24 N24 H24B . . 117.4
H24A N24 H24B . . 110.4
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 . 1.336(2) y
N11 C14 . 1.366(3) y
N11 H11 . 0.8600 ?
C12 N11 11 1.336(2) ?
C12 S12 . 1.704(4) y
C14 N14 . 1.324(3) y
C14 C15 . 1.366(3) y
C15 C14 11 1.366(3) ?
C15 H15 . 0.9300 ?
N14 H14A . 0.9383 ?
N14 H14B . 0.8597 ?
N21 C22 . 1.339(2) y
N21 C24 . 1.356(3) y
N21 H21 . 0.8600 ?
C22 N21 11_655 1.339(2) ?
C22 S22 . 1.690(3) y
C24 N24 . 1.337(3) y
C24 C25 . 1.368(3) y
C25 C24 11_655 1.368(3) ?
C25 H25 . 0.9300 ?
N24 H24A . 0.9880 ?
N24 H24B . 0.9372 ?
O31 H31 . 0.79(3) ?
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
N11 H11 N21 . 0.86 2.18 2.995(3) 159 y
N21 H21 N11 . 0.86 2.16 2.995(3) 165 y
N14 H14A S22 . 0.94 2.40 3.310(2) 162 y
N24 H24A S12 . 0.99 2.39 3.368(2) 171 y
N14 H14B N24 3_566 0.86 2.50 3.302(2) 155 y
N24 H24B O31 . 0.94 2.07 2.994(3) 168 y
O31 H31 S12 4_556 0.79(3) 2.70(3) 3.396(2) 148(3) 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_site_symmetry_4
_geom_torsion
C14 N11 C12 N11 11 0.3(4)
C14 N11 C12 S12 . -178.95(18)
C12 N11 C14 N14 . 178.5(2)
C12 N11 C14 C15 . -0.7(4)
N14 C14 C15 C14 11 -178.09(18)
N11 C14 C15 C14 11 1.1(5)
C24 N21 C22 N21 11_655 -0.3(5)
C24 N21 C22 S22 . 178.0(2)
C22 N21 C24 N24 . 177.5(3)
C22 N21 C24 C25 . 0.4(4)
N24 C24 C25 C24 11_655 -177.32(17)
N21 C24 C25 C24 11_655 -0.6(5)
