##############################################################################
#                                                                            #
# 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_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
6-amino-1,3-dimethyl-5-[(E)-2-
(methylsulfanyl)benzylideneamino]pyrimidine-2,4(1H,3H)-dione
;
_chemical_name_common     ?
_chemical_formula_moiety     'C14 H16 N4 O2 S'
_chemical_formula_sum     'C14 H16 N4 O2 S'
_chemical_formula_iupac     'C14 H16 N4 O2 S'
_chemical_formula_weight     304.37
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/c'
_symmetry_space_group_name_Hall     '-P 2ybc'
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'
_cell_length_a     13.5230(2)
_cell_length_b     13.8520(3)
_cell_length_c     7.51800(10)
_cell_angle_alpha     90.00
_cell_angle_beta     101.0680(10)
_cell_angle_gamma     90.00
_cell_volume     1382.08(4)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     9061
_cell_measurement_theta_min     3.07
_cell_measurement_theta_max     28.33
_cell_measurement_temperature     100(2)
_exptl_crystal_description     'rod'
_exptl_crystal_colour     'orange'
_exptl_crystal_size_max     0.463
_exptl_crystal_size_mid     0.290
_exptl_crystal_size_min     0.142
_exptl_crystal_density_diffrn     1.463
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     640
_exptl_absorpt_coefficient_mu     0.245
_exptl_absorpt_correction_type     none
_exptl_absorpt_process_details     ?
_exptl_absorpt_correction_T_min     ?
_exptl_absorpt_correction_T_max     ?
_exptl_special_details
;
;
_diffrn_ambient_temperature     100(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker APEXII CCD'
_diffrn_measurement_device     ?
_diffrn_measurement_method     'φ and ω'
_diffrn_reflns_number     13030
_diffrn_reflns_av_R_equivalents     0.0288
_diffrn_reflns_av_sigmaI/netI     0.0200
_diffrn_reflns_theta_min     2.13
_diffrn_reflns_theta_max     28.37
_diffrn_reflns_theta_full     28.37
_diffrn_measured_fraction_theta_max     0.991
_diffrn_measured_fraction_theta_full     0.991
_diffrn_reflns_limit_h_min     -17
_diffrn_reflns_limit_h_max     18
_diffrn_reflns_limit_k_min     -18
_diffrn_reflns_limit_k_max     18
_diffrn_reflns_limit_l_min     -10
_diffrn_reflns_limit_l_max     10
_refine_special_details
;
;
_reflns_number_total     3420
_reflns_number_gt     3112
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0327
_refine_ls_R_factor_gt     0.0291
_refine_ls_wR_factor_gt     0.0786
_refine_ls_wR_factor_ref     0.0808
_refine_ls_goodness_of_fit_ref     1.024
_refine_ls_restrained_S_all     1.024
_refine_ls_number_reflns     3420
_refine_ls_number_parameters     201
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0421P)²+0.5901P] 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     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.330
_refine_diff_density_min     -0.237
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
_refine_ls_abs_structure_Flack     ?
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, 2010)'
_computing_cell_refinement     'SAINT (Bruker, 2010)'
_computing_data_reduction     'SAINT (Bruker, 2010)'
_computing_structure_solution     'SIR97 (Altomare et al., 1999)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics
             'ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2008)'
_computing_publication_material
                            'SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009)'
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 0.78695(2) -0.045540(19) 0.18639(4) 0.01558(9) Uani d . 1 1 . .
    O O1 0.51894(6) 0.21801(5) 0.44986(11) 0.01675(17) Uani d . 1 1 . .
    O O2 0.23379(6) 0.03778(6) 0.29316(11) 0.01758(17) Uani d . 1 1 . .
    N N1 0.37683(7) 0.12677(6) 0.36962(12) 0.01399(18) Uani d . 1 1 . .
    N N2 0.38044(7) -0.02607(7) 0.23551(12) 0.01352(18) Uani d . 1 1 . .
    N N3 0.63701(7) 0.06360(7) 0.31269(12) 0.01372(18) Uani d . 1 1 . .
    N N4 0.52995(7) -0.08772(7) 0.17260(13) 0.01549(19) Uani d . 1 1 . .
    H H741 0.5910(12) -0.0762(11) 0.181(2) 0.023(4) Uiso d . 1 1 . .
    H H742 0.5004(12) -0.1407(12) 0.134(2) 0.026(4) Uiso d . 1 1 . .
    C C1 0.53409(8) 0.06569(7) 0.31391(14) 0.0131(2) Uani d . 1 1 . .
    C C2 0.48115(8) 0.14156(8) 0.38191(14) 0.0131(2) Uani d . 1 1 . .
    C C3 0.32410(8) 0.04571(8) 0.29933(14) 0.0140(2) Uani d . 1 1 . .
    C C4 0.48168(8) -0.01659(8) 0.23983(13) 0.0128(2) Uani d . 1 1 . .
    C C5 0.69984(8) 0.12764(8) 0.38818(14) 0.0144(2) Uani d . 1 1 . .
    H H5 0.6751 0.1802 0.4481 0.017 Uiso calc R 1 1 . .
    C C6 0.80731(8) 0.12361(8) 0.38633(14) 0.0145(2) Uani d . 1 1 . .
    C C7 0.85605(8) 0.05250(8) 0.29813(14) 0.0147(2) Uani d . 1 1 . .
    C C8 0.95997(9) 0.06045(8) 0.30539(16) 0.0182(2) Uani d . 1 1 . .
    H H8 0.9931 0.0137 0.2453 0.022 Uiso calc R 1 1 . .
    C C9 1.01545(9) 0.13518(9) 0.39841(16) 0.0203(2) Uani d . 1 1 . .
    H H9 1.0858 0.1393 0.4006 0.024 Uiso calc R 1 1 . .
    C C10 0.96888(9) 0.20383(9) 0.48817(16) 0.0195(2) Uani d . 1 1 . .
    H H10 1.0070 0.2545 0.5535 0.023 Uiso calc R 1 1 . .
    C C11 0.86603(8) 0.19752(8) 0.48140(15) 0.0170(2) Uani d . 1 1 . .
    H H11 0.8342 0.2447 0.5430 0.020 Uiso calc R 1 1 . .
    C C12 0.31814(9) 0.20105(8) 0.44153(16) 0.0183(2) Uani d . 1 1 . .
    H H121 0.2763 0.2358 0.3408 0.027 Uiso calc R 1 1 . .
    H H122 0.3640 0.2465 0.5159 0.027 Uiso calc R 1 1 . .
    H H123 0.2748 0.1705 0.5160 0.027 Uiso calc R 1 1 . .
    C C13 0.32800(8) -0.11442(8) 0.16217(15) 0.0166(2) Uani d . 1 1 . .
    H H131 0.3329 -0.1216 0.0345 0.025 Uiso calc R 1 1 . .
    H H132 0.2569 -0.1104 0.1722 0.025 Uiso calc R 1 1 . .
    H H133 0.3591 -0.1703 0.2309 0.025 Uiso calc R 1 1 . .
    C C14 0.87950(9) -0.10803(9) 0.08635(16) 0.0199(2) Uani d . 1 1 . .
    H H141 0.9071 -0.0639 0.0063 0.030 Uiso calc R 1 1 . .
    H H142 0.8478 -0.1632 0.0160 0.030 Uiso calc R 1 1 . .
    H H143 0.9340 -0.1310 0.1823 0.030 Uiso calc R 1 1 . .
_geom_special_details
;
;
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 C7 . 1.7669(11) ?
    S1 C14 . 1.8008(11) ?
    O1 C2 . 1.2423(13) ?
    O2 C3 . 1.2182(13) ?
    N1 C3 . 1.3799(14) ?
    N1 C2 . 1.4108(13) ?
    N1 C12 . 1.4648(13) ?
    N2 C4 . 1.3694(13) ?
    N2 C3 . 1.3927(13) ?
    N2 C13 . 1.4679(13) ?
    N3 C5 . 1.2829(14) ?
    N3 C1 . 1.3940(13) ?
    N4 C4 . 1.3339(14) ?
    N4 H741 . 0.832(16) ?
    N4 H742 . 0.859(16) ?
    C1 C4 . 1.3999(14) ?
    C1 C2 . 1.4209(14) ?
    C5 C6 . 1.4572(15) ?
    C5 H5 . 0.95 ?
    C6 C11 . 1.4041(15) ?
    C6 C7 . 1.4184(15) ?
    C7 C8 . 1.4003(15) ?
    C8 C9 . 1.3863(17) ?
    C8 H8 . 0.95 ?
    C9 C10 . 1.3856(17) ?
    C9 H9 . 0.95 ?
    C10 C11 . 1.3847(15) ?
    C10 H10 . 0.95 ?
    C11 H11 . 0.95 ?
    C12 H121 . 0.98 ?
    C12 H122 . 0.98 ?
    C12 H123 . 0.98 ?
    C13 H131 . 0.98 ?
    C13 H132 . 0.98 ?
    C13 H133 . 0.98 ?
    C14 H141 . 0.98 ?
    C14 H142 . 0.98 ?
    C14 H143 . 0.98 ?
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
    C7 S1 C14 . . 102.80(5) ?
    C3 N1 C2 . . 125.45(9) ?
    C3 N1 C12 . . 115.86(9) ?
    C2 N1 C12 . . 118.66(9) ?
    C4 N2 C3 . . 122.27(9) ?
    C4 N2 C13 . . 119.84(9) ?
    C3 N2 C13 . . 117.89(9) ?
    C5 N3 C1 . . 124.05(9) ?
    C4 N4 H741 . . 112.5(11) ?
    C4 N4 H742 . . 122.0(10) ?
    H741 N4 H742 . . 125.4(15) ?
    N3 C1 C4 . . 114.23(9) ?
    N3 C1 C2 . . 126.19(10) ?
    C4 C1 C2 . . 119.58(10) ?
    O1 C2 N1 . . 118.55(9) ?
    O1 C2 C1 . . 125.63(10) ?
    N1 C2 C1 . . 115.82(9) ?
    O2 C3 N1 . . 121.91(10) ?
    O2 C3 N2 . . 122.23(10) ?
    N1 C3 N2 . . 115.86(9) ?
    N4 C4 N2 . . 118.68(10) ?
    N4 C4 C1 . . 120.32(10) ?
    N2 C4 C1 . . 121.00(9) ?
    N3 C5 C6 . . 123.11(10) ?
    N3 C5 H5 . . 118.4 ?
    C6 C5 H5 . . 118.4 ?
    C11 C6 C7 . . 118.44(10) ?
    C11 C6 C5 . . 115.77(9) ?
    C7 C6 C5 . . 125.79(10) ?
    C8 C7 C6 . . 118.69(10) ?
    C8 C7 S1 . . 120.94(8) ?
    C6 C7 S1 . . 120.35(8) ?
    C9 C8 C7 . . 121.35(10) ?
    C9 C8 H8 . . 119.3 ?
    C7 C8 H8 . . 119.3 ?
    C10 C9 C8 . . 120.37(10) ?
    C10 C9 H9 . . 119.8 ?
    C8 C9 H9 . . 119.8 ?
    C11 C10 C9 . . 119.08(11) ?
    C11 C10 H10 . . 120.5 ?
    C9 C10 H10 . . 120.5 ?
    C10 C11 C6 . . 122.05(10) ?
    C10 C11 H11 . . 119.0 ?
    C6 C11 H11 . . 119.0 ?
    N1 C12 H121 . . 109.5 ?
    N1 C12 H122 . . 109.5 ?
    H121 C12 H122 . . 109.5 ?
    N1 C12 H123 . . 109.5 ?
    H121 C12 H123 . . 109.5 ?
    H122 C12 H123 . . 109.5 ?
    N2 C13 H131 . . 109.5 ?
    N2 C13 H132 . . 109.5 ?
    H131 C13 H132 . . 109.5 ?
    N2 C13 H133 . . 109.5 ?
    H131 C13 H133 . . 109.5 ?
    H132 C13 H133 . . 109.5 ?
    S1 C14 H141 . . 109.5 ?
    S1 C14 H142 . . 109.5 ?
    H141 C14 H142 . . 109.5 ?
    S1 C14 H143 . . 109.5 ?
    H141 C14 H143 . . 109.5 ?
    H142 C14 H143 . . 109.5 ?
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_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    C5 N3 C1 C4 . . . . -173.63(10) ?
    C5 N3 C1 C2 . . . . 6.25(17) ?
    C3 N1 C2 O1 . . . . -179.44(9) ?
    C12 N1 C2 O1 . . . . -1.49(14) ?
    C3 N1 C2 C1 . . . . 0.49(15) ?
    C12 N1 C2 C1 . . . . 178.43(9) ?
    N3 C1 C2 O1 . . . . 0.43(17) ?
    C4 C1 C2 O1 . . . . -179.68(10) ?
    N3 C1 C2 N1 . . . . -179.49(9) ?
    C4 C1 C2 N1 . . . . 0.40(14) ?
    C2 N1 C3 O2 . . . . 179.92(9) ?
    C12 N1 C3 O2 . . . . 1.93(15) ?
    C2 N1 C3 N2 . . . . -0.31(15) ?
    C12 N1 C3 N2 . . . . -178.30(9) ?
    C4 N2 C3 O2 . . . . 178.97(10) ?
    C13 N2 C3 O2 . . . . -1.22(15) ?
    C4 N2 C3 N1 . . . . -0.80(14) ?
    C13 N2 C3 N1 . . . . 179.01(9) ?
    C3 N2 C4 N4 . . . . -178.61(9) ?
    C13 N2 C4 N4 . . . . 1.58(14) ?
    C3 N2 C4 C1 . . . . 1.70(15) ?
    C13 N2 C4 C1 . . . . -178.11(9) ?
    N3 C1 C4 N4 . . . . -1.25(14) ?
    C2 C1 C4 N4 . . . . 178.85(9) ?
    N3 C1 C4 N2 . . . . 178.43(9) ?
    C2 C1 C4 N2 . . . . -1.47(15) ?
    C1 N3 C5 C6 . . . . 179.53(9) ?
    N3 C5 C6 C11 . . . . -177.63(10) ?
    N3 C5 C6 C7 . . . . 2.35(17) ?
    C11 C6 C7 C8 . . . . -1.72(15) ?
    C5 C6 C7 C8 . . . . 178.31(10) ?
    C11 C6 C7 S1 . . . . 176.75(8) ?
    C5 C6 C7 S1 . . . . -3.23(15) ?
    C14 S1 C7 C8 . . . . -5.40(10) ?
    C14 S1 C7 C6 . . . . 176.17(9) ?
    C6 C7 C8 C9 . . . . 0.86(16) ?
    S1 C7 C8 C9 . . . . -177.60(9) ?
    C7 C8 C9 C10 . . . . 0.49(17) ?
    C8 C9 C10 C11 . . . . -0.93(17) ?
    C9 C10 C11 C6 . . . . 0.01(17) ?
    C7 C6 C11 C10 . . . . 1.31(16) ?
    C5 C6 C11 C10 . . . . -178.71(10) ?
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
    N4 H741 S1 . 0.83(2) 2.675(17) 3.5060(10) 176.0(10)
    N4 H742 O1 2_645 0.86(2) 2.058(16) 2.8797(12) 160.0(10)
data_global
_journal_date_recd_electronic     2011-06-16
_journal_date_accepted     2011-07-07
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2011
_journal_volume     67
_journal_issue      8
_journal_page_first     o2025
_journal_page_last     o2026
_journal_paper_category     QO
_journal_coeditor_code     CI5192
_publ_contact_author_name     'Dr Richard Betz'
_publ_contact_author_address
;
Department of Chemistry
Nelson Mandela Metropolitan University
Summerstrand Campus (South)
University Way
Summerstrand
PO Box 77000
Port Elizabeth 6031
South Africa
;
_publ_contact_author_email     richard.betz@webmail.co.za
_publ_contact_author_fax     '+27-41-504-4236'
_publ_contact_author_phone     '+27-41-504-4285'
_publ_section_title
;\
A second monoclinic polymorph of
6-amino-1,3-dimethyl-5-[(E)-2-(methylsulfanyl)benzylideneamino]\
pyrimidine-2,4(1H,3H)-dione
;
loop_
    _publ_author_name
    _publ_author_address
    'Booysen, Irvin'
;
University of Kwazulu-Natal
School of Chemistry
Private Bag X01
Scottsville 3209
Pietermaritzburg
South Africa
;
    'Muhammed, Ismail'
;
University of Kwazulu-Natal
School of Chemistry
Private Bag X01
Scottsville 3209
Pietermaritzburg
South Africa
;
    'Soares, Anna'
;
University of Kwazulu-Natal
School of Chemistry
Private Bag X01
Scottsville 3209
Pietermaritzburg
South Africa
;
    'Gerber, Thomas'
;
Nelson Mandela Metropolitan University
Summerstrand Campus
Department of Chemistry
University Way
Summerstrand
PO Box 77000
Port Elizabeth 6031
South Africa
;
    'Hosten, Eric'
;
Nelson Mandela Metropolitan University
Summerstrand Campus
Department of Chemistry
University Way
Summerstrand
PO Box 77000
Port Elizabeth 6031
South Africa
;
    'Betz, Richard'
;
Nelson Mandela Metropolitan University
Summerstrand Campus
Department of Chemistry
University Way
Summerstrand
PO Box 77000
Port Elizabeth 6031
South Africa
;
