##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in          #
# Acta Crystallographica Section E. It conforms to the requirements of       #
# Notes for Authors for Acta Crystallographica Section E, and has been       #
# peer reviewed under the auspices of the IUCr Commission on Journals.       #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_global
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2014-05-26
_journal_date_accepted     2014-05-29
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2014
_journal_volume     70
_journal_issue      7
_journal_page_first     o747
_journal_page_last     o748
_journal_paper_category     QO
_journal_paper_doi     10.1107/S1600536814012513
_journal_coeditor_code     BG2531
_publ_contact_author_name     'Cherif Ben Nasr'
_publ_contact_author_address
; Laboratoire de Chimie des Matériaux
  Faculté des Sciences de Bizerte
  7021 Zarzouna
  Tunisie
;
_publ_contact_author_email     cherif_bennasr@yahoo.fr
_publ_contact_author_fax     ?
_publ_contact_author_phone     ?
_publ_section_title
;
Bis(2-amino-4-methyl-6-oxo-3,6-dihydropyrimidin-1-ium) sulfate monohydrate
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Soudani, Sarra' .
;
Laboratoire de Chimie des Matériaux
Faculté des Sciences de Bizerte
7021 Zarzouna
Tunisia
;
    'Wenger, Emmanuel' .
;
Cristallographie, Résonance Magnétique et Modélisations (CRM2)
UMR CNRS 7036
Institut Jean Barriol
Université de Lorraine
BP 70239
Bd des Aiguillettes
54506 Vandoeuvre-les-Nancy
France
;
    'Jelsch, Christian' .
;
Cristallographie, Résonance Magnétique et Modélisations (CRM2)
UMR CNRS 7036
Institut Jean Barriol
Université de Lorraine
BP 70239
Bd des Aiguillettes
54506 Vandoeuvre-les-Nancy
France
;
    'Ben Nasr, Cherif' .
;
Laboratoire de Chimie des Matériaux
Faculté des sciences de Bizerte
7021 Zarzouna
Tunisia
;
_chemical_name_systematic
;
bis(2-amino-6-methylpyrimidin-4(1H)-one)Sulfate monohydrate
;
data_I
_audit_creation_method     SHELXL-97
_database_code_depnum_ccdc_archive     'CCDC 1005732'
_chemical_name_systematic
;
Bis(2-amino-4-methyl-6-oxo-3,6-dihydropyrimidin-1-ium) sulfate monohydrate
;
_chemical_name_common     ?
_chemical_formula_moiety     '2(C5 H8 N3 O +), O4 S 2-, H2 O'
_chemical_formula_sum     'C10 H18 N6 O7 S'
_chemical_formula_iupac     '2C5 H8 N3 O +, S O4 2-, H2 O'
_chemical_formula_weight     366.36
_chemical_melting_point     ?
_symmetry_cell_setting     triclinic
_symmetry_space_group_name_H-M     'P -1'
_symmetry_space_group_name_Hall     '-P 1'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     6.797(5)
_cell_length_b     10.339(6)
_cell_length_c     12.110(7)
_cell_angle_alpha     113.480(5)
_cell_angle_beta     91.009(7)
_cell_angle_gamma     98.906(5)
_cell_volume     768.2(8)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     ?
_cell_measurement_theta_min     2.19
_cell_measurement_theta_max     33.44
_cell_measurement_temperature     100(2)
_exptl_crystal_description     prism
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.27
_exptl_crystal_size_mid     0.19
_exptl_crystal_size_min     0.12
_exptl_crystal_density_diffrn     1.584
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     384
_exptl_absorpt_coefficient_mu     0.261
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 2008)'
_exptl_absorpt_correction_T_min     0.92
_exptl_absorpt_correction_T_max     0.97
_exptl_special_details     ?
_diffrn_ambient_temperature     100(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     'mirror'
_diffrn_measurement_device_type     'Bruker APEXII CCD'
_diffrn_measurement_method     'ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     5784
_diffrn_reflns_av_R_equivalents     0.0000
_diffrn_reflns_av_sigmaI/netI     0.0428
_diffrn_reflns_theta_min     3.05
_diffrn_reflns_theta_max     33.05
_diffrn_reflns_theta_full     33.05
_diffrn_measured_fraction_theta_max     0.995
_diffrn_measured_fraction_theta_full     0.995
_diffrn_reflns_limit_h_min     0
_diffrn_reflns_limit_h_max     10
_diffrn_reflns_limit_k_min     -15
_diffrn_reflns_limit_k_max     15
_diffrn_reflns_limit_l_min     -18
_diffrn_reflns_limit_l_max     18
_diffrn_standards_number     ?
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_refine_special_details
;
Refinement of F² against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F², conventional
R-factors R are based on F, with F set to zero for
negative F². The threshold expression of F² >
σ(F²) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F² are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger.
;
_reflns_number_total     5784
_reflns_number_gt     5347
_reflns_threshold_expression     I>2sigma(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0920
_refine_ls_R_factor_gt     0.0806
_refine_ls_wR_factor_gt     0.1276
_refine_ls_wR_factor_ref     0.1313
_refine_ls_goodness_of_fit_ref     1.354
_refine_ls_restrained_S_all     1.352
_refine_ls_number_reflns     5784
_refine_ls_number_parameters     289
_refine_ls_number_restraints     15
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0440P)²+0.4148P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.643
_refine_diff_density_min     -0.383
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
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'
_computing_data_collection     'APEX2 (Bruker, 2007)'
_computing_cell_refinement     'SAINT (Bruker, 2012)'
_computing_data_reduction     'SAINT (Bruker, 2012)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material     'SHELXL97 (Sheldrick, 2008)'
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
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    S S1 0.32594(6) 0.79761(4) 0.06036(4) 0.00888(9) Uani d . 1 1 . .
    O O4 0.10950(17) 0.75634(13) 0.01545(11) 0.0129(2) Uani d . 1 1 . .
    O O5 0.39545(18) 0.67318(13) 0.06868(11) 0.0136(2) Uani d . 1 1 . .
    O O6 0.44256(18) 0.84309(13) -0.02448(11) 0.0137(2) Uani d . 1 1 . .
    O O7 0.34949(19) 0.91648(13) 0.18190(11) 0.0161(3) Uani d . 1 1 . .
    C C1 -0.1015(2) 0.07187(17) 0.18509(14) 0.0097(3) Uani d . 1 1 . .
    N N1 -0.1580(2) -0.04398(16) 0.08537(13) 0.0125(3) Uani d . 1 1 . .
    N N2 -0.2110(2) 0.17792(15) 0.22132(13) 0.0113(3) Uani d . 1 1 . .
    C C3 -0.1599(2) 0.30560(18) 0.32540(15) 0.0121(3) Uani d . 1 1 . .
    O O3 -0.2627(2) 0.39938(14) 0.34694(12) 0.0188(3) Uani d . 1 1 . .
    C C4 0.0171(3) 0.31382(18) 0.39715(15) 0.0128(3) Uani d . 1 1 . .
    C C5 0.1275(2) 0.20844(17) 0.35890(15) 0.0109(3) Uani d D 1 1 . .
    C C6 0.3178(3) 0.2130(2) 0.42459(17) 0.0171(3) Uani d . 1 1 . .
    N N7 0.0687(2) 0.08908(15) 0.25224(13) 0.0108(3) Uani d . 1 1 . .
    C C11 -0.0959(2) 0.61151(17) 0.19155(15) 0.0113(3) Uani d . 1 1 . .
    N N11 -0.2643(2) 0.58800(17) 0.12550(14) 0.0145(3) Uani d . 1 1 . .
    N N12 -0.0358(2) 0.73732(16) 0.28733(13) 0.0138(3) Uani d . 1 1 . .
    C C13 0.1415(3) 0.76947(19) 0.36118(16) 0.0151(3) Uani d . 1 1 . .
    O O13 0.1845(2) 0.88853(14) 0.44418(12) 0.0226(3) Uani d . 1 1 . .
    C C14 0.2552(3) 0.65558(19) 0.33060(16) 0.0153(3) Uani d . 1 1 . .
    C C15 0.1953(2) 0.53064(18) 0.23358(15) 0.0119(3) Uani d D 1 1 . .
    C C16 0.3067(3) 0.4085(2) 0.18954(17) 0.0149(3) Uani d . 1 1 . .
    N N17 0.0195(2) 0.51065(15) 0.16497(13) 0.0111(3) Uani d . 1 1 . .
    O O8 0.6783(2) 0.91155(15) 0.32711(12) 0.0190(3) Uani d . 1 1 . .
    H H1A -0.274(4) -0.063(3) 0.046(2) 0.020(6) Uiso d . 1 1 . .
    H H1B -0.082(4) -0.104(3) 0.064(2) 0.019(6) Uiso d . 1 1 . .
    H H2 -0.310(4) 0.173(3) 0.168(2) 0.028(7) Uiso d . 1 1 . .
    H H4 0.060(4) 0.398(2) 0.472(2) 0.019(6) Uiso d . 1 1 . .
    H H6A 0.344(3) 0.302(3) 0.4979(18) 0.032(7) Uiso d D 1 1 . .
    H H6B 0.425(2) 0.212(3) 0.379(2) 0.031(7) Uiso d D 1 1 . .
    H H6C 0.306(4) 0.130(3) 0.444(2) 0.038(8) Uiso d D 1 1 . .
    H H7 0.143(4) 0.028(3) 0.230(2) 0.029(7) Uiso d . 1 1 . .
    H H11A -0.303(4) 0.505(3) 0.065(3) 0.029(7) Uiso d . 1 1 . .
    H H11B -0.337(4) 0.657(3) 0.143(2) 0.026(6) Uiso d . 1 1 . .
    H H12 -0.118(4) 0.804(3) 0.305(2) 0.027(6) Uiso d . 1 1 . .
    H H14 0.374(4) 0.672(3) 0.378(2) 0.023(6) Uiso d . 1 1 . .
    H H16A 0.417(3) 0.424(3) 0.245(2) 0.031(7) Uiso d D 1 1 . .
    H H16B 0.351(3) 0.397(2) 0.1108(18) 0.024(6) Uiso d D 1 1 . .
    H H16C 0.220(4) 0.3214(14) 0.178(2) 0.021(6) Uiso d D 1 1 . .
    H H17 -0.020(4) 0.432(3) 0.109(3) 0.030(7) Uiso d . 1 1 . .
    H H8A 0.694(5) 0.983(3) 0.396(3) 0.041(8) Uiso d . 1 1 . .
    H H8B 0.577(4) 0.914(3) 0.290(3) 0.030(7) Uiso d . 1 1 . .
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes.
;
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
    S1 O5 . 1.4759(14) ?
    S1 O7 . 1.4805(14) ?
    S1 O6 . 1.4843(14) ?
    S1 O4 . 1.4949(16) ?
    C1 N1 . 1.315(2) ?
    C1 N7 . 1.349(2) ?
    C1 N2 . 1.353(2) ?
    N1 H1A . 0.87(3) ?
    N1 H1B . 0.83(3) ?
    N2 C3 . 1.403(2) ?
    N2 H2 . 0.91(3) ?
    C3 O3 . 1.229(2) ?
    C3 C4 . 1.443(2) ?
    C4 C5 . 1.352(2) ?
    C4 H4 . 0.97(2) ?
    C5 N7 . 1.382(2) ?
    C5 C6 . 1.491(2) ?
    C6 H6A . 0.98(2) ?
    C6 H6B . 0.92(2) ?
    C6 H6C . 0.97(2) ?
    N7 H7 . 0.83(3) ?
    C11 N11 . 1.318(2) ?
    C11 N17 . 1.342(2) ?
    C11 N12 . 1.349(2) ?
    N11 H11A . 0.87(3) ?
    N11 H11B . 0.89(3) ?
    N12 C13 . 1.402(2) ?
    N12 H12 . 0.91(3) ?
    C13 O13 . 1.226(2) ?
    C13 C14 . 1.437(3) ?
    C14 C15 . 1.351(2) ?
    C14 H14 . 0.94(3) ?
    C15 N17 . 1.383(2) ?
    C15 C16 . 1.492(3) ?
    C16 H16A . 0.95(2) ?
    C16 H16B . 0.972(19) ?
    C16 H16C . 0.953(19) ?
    N17 H17 . 0.83(3) ?
    O8 H8A . 0.86(3) ?
    O8 H8B . 0.82(3) ?
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
    _geom_angle_publ_flag
    O5 S1 O7 . . 109.31(8) ?
    O5 S1 O6 . . 109.99(8) ?
    O7 S1 O6 . . 110.24(9) ?
    O5 S1 O4 . . 108.97(8) ?
    O7 S1 O4 . . 108.81(7) ?
    O6 S1 O4 . . 109.49(8) ?
    N1 C1 N7 . . 120.88(15) ?
    N1 C1 N2 . . 120.63(15) ?
    N7 C1 N2 . . 118.48(15) ?
    C1 N1 H1A . . 122.7(16) ?
    C1 N1 H1B . . 117.4(17) ?
    H1A N1 H1B . . 120(2) ?
    C1 N2 C3 . . 124.22(14) ?
    C1 N2 H2 . . 116.8(17) ?
    C3 N2 H2 . . 118.0(17) ?
    O3 C3 N2 . . 119.39(15) ?
    O3 C3 C4 . . 125.98(16) ?
    N2 C3 C4 . . 114.61(14) ?
    C5 C4 C3 . . 120.56(15) ?
    C5 C4 H4 . . 120.1(14) ?
    C3 C4 H4 . . 119.2(14) ?
    C4 C5 N7 . . 120.36(15) ?
    C4 C5 C6 . . 123.67(15) ?
    N7 C5 C6 . . 115.96(15) ?
    C5 C6 H6A . . 108.6(13) ?
    C5 C6 H6B . . 112.1(14) ?
    H6A C6 H6B . . 108(2) ?
    C5 C6 H6C . . 109.4(14) ?
    H6A C6 H6C . . 111(2) ?
    H6B C6 H6C . . 108(2) ?
    C1 N7 C5 . . 121.60(14) ?
    C1 N7 H7 . . 120.5(19) ?
    C5 N7 H7 . . 117.9(19) ?
    N11 C11 N17 . . 120.64(15) ?
    N11 C11 N12 . . 120.77(16) ?
    N17 C11 N12 . . 118.59(15) ?
    C11 N11 H11A . . 119.9(18) ?
    C11 N11 H11B . . 119.6(17) ?
    H11A N11 H11B . . 120(2) ?
    C11 N12 C13 . . 123.73(15) ?
    C11 N12 H12 . . 117.5(17) ?
    C13 N12 H12 . . 118.8(17) ?
    O13 C13 N12 . . 118.40(17) ?
    O13 C13 C14 . . 126.54(17) ?
    N12 C13 C14 . . 115.06(15) ?
    C15 C14 C13 . . 120.77(16) ?
    C15 C14 H14 . . 121.2(15) ?
    C13 C14 H14 . . 118.0(15) ?
    C14 C15 N17 . . 119.59(16) ?
    C14 C15 C16 . . 125.40(16) ?
    N17 C15 C16 . . 115.00(15) ?
    C15 C16 H16A . . 110.6(13) ?
    C15 C16 H16B . . 109.0(12) ?
    H16A C16 H16B . . 111(2) ?
    C15 C16 H16C . . 110.2(12) ?
    H16A C16 H16C . . 110(2) ?
    H16B C16 H16C . . 106(2) ?
    C11 N17 C15 . . 122.20(15) ?
    C11 N17 H17 . . 119.0(19) ?
    C15 N17 H17 . . 118.7(19) ?
    H8A O8 H8B . . 108(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
    N1 H1A O6 1_445 0.87(3) 2.02(3) 2.856(3) 161(3)
    N1 H1B O4 1_545 0.83(3) 2.01(3) 2.847(4) 178(2)
    N2 H2 O6 2_565 0.91(3) 1.88(2) 2.749(4) 161(2)
    N7 H7 O7 1_545 0.83(3) 1.91(3) 2.730(4) 170(3)
    N11 H11A O5 2_565 0.87(3) 1.91(3) 2.782(6) 178(3)
    N11 H11B O5 1_455 0.89(3) 2.07(3) 2.767(3) 134(2)
    N12 H12 O8 1_455 0.92(3) 1.87(3) 2.771(4) 170(3)
    N17 H17 O4 2_565 0.82(3) 1.92(3) 2.746(6) 177(3)
    O8 H8A O13 2_676 0.86(3) 1.94(3) 2.750(5) 158(3)
    O8 H8B O7 1_555 0.83(3) 2.02(3) 2.839(4) 173(3)
    C4 H4 O3 2_566 0.97(2) 2.54(2) 3.485(3) 165(2)
    C6 H6C O13 1_545 0.968 2.51 3.440(3) 162(2)
    C16 H16A O3 1_655 0.946 2.583 3.499(5) 163(2)
