##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
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#                                                                            #
# 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 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. The current version number is 2.4.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
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data_global
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2009-07-04
_journal_date_accepted     2009-07-05
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2009
_journal_volume     65
_journal_issue      8
_journal_page_first     o1820
_journal_page_last     o1820
_journal_paper_category     QO
_journal_coeditor_code     XU2548
_publ_contact_author
;
     Dr. Seik Weng Ng
     Department of Chemistry
     University of Malaya
     50603 Kuala Lumpur
     Malaysia
;
_publ_contact_author_email     seikweng@um.edu.my
_publ_contact_author_fax     '03 7967 4193'
_publ_contact_author_phone     '03 7967 6778'
_publ_section_title
;\
5-[3-(2,5-Dimethoxyphenyl)prop-2-enylidene]-1,3-diethyl-2-\
thioxohexahydropyrimidine-4,6-dione
;
loop_
    _publ_author_name
    _publ_author_address
    'Asiri, Abdullah Mohamed'
;
Chemistry Department
Faculty of Science
King Abdul Aziz University
Jeddah
Saudi Arabia
;
    'Khan, Salman A.'
;
Chemistry Department
Faculty of Science
King Abdul Aziz University
Jeddah
Saudi Arabia
;
    'Ng, Seik Weng'
;
Department of Chemistry
University of Malaya
50603 Kuala Lumpur
Malaysia
;
_publ_section_synopsis     .
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
5-[3-(2,5-Dimethoxyphenyl)prop-2-enylidene]-1,3-diethyl-2-
thioxohexahydropyrimidine-4,6-dione
;
_chemical_name_common     ?
_chemical_formula_moiety     'C19 H22 N2 O4 S'
_chemical_formula_sum     'C19 H22 N2 O4 S'
_chemical_formula_iupac     'C19 H22 N2 O4 S'
_chemical_formula_weight     374.45
_chemical_melting_point     ?
_symmetry_cell_setting     Monoclinic
_symmetry_space_group_name_H-M     'P 21/n'
_symmetry_space_group_name_Hall     '-P 2yn'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x+1/2, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x-1/2, -y-1/2, z-1/2'
_cell_length_a     10.0519(2)
_cell_length_b     15.5942(3)
_cell_length_c     11.5920(2)
_cell_angle_alpha     90.00
_cell_angle_beta     90.8130(10)
_cell_angle_gamma     90.00
_cell_volume     1816.88(6)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     4985
_cell_measurement_theta_min     2.2
_cell_measurement_theta_max     28.3
_cell_measurement_temperature     140(2)
_exptl_crystal_description     Irregular
_exptl_crystal_colour     Gold--green
_exptl_crystal_size_max     0.35
_exptl_crystal_size_mid     0.25
_exptl_crystal_size_min     0.15
_exptl_crystal_density_diffrn     1.369
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     792
_exptl_absorpt_coefficient_mu     0.206
_exptl_absorpt_correction_type     Multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_correction_T_min     0.9315
_exptl_absorpt_correction_T_max     0.9698
_diffrn_ambient_temperature     140(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker SMART APEX'
_diffrn_measurement_method     ω
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     12384
_diffrn_reflns_av_R_equivalents     0.0207
_diffrn_reflns_av_sigmaI/netI     0.0238
_diffrn_reflns_theta_min     2.19
_diffrn_reflns_theta_max     27.50
_diffrn_reflns_theta_full     27.50
_diffrn_measured_fraction_theta_max     0.990
_diffrn_measured_fraction_theta_full     0.990
_diffrn_reflns_limit_h_min     -12
_diffrn_reflns_limit_h_max     13
_diffrn_reflns_limit_k_min     -20
_diffrn_reflns_limit_k_max     19
_diffrn_reflns_limit_l_min     -15
_diffrn_reflns_limit_l_max     15
_diffrn_standards_number     0
_diffrn_standards_interval_count     0
_diffrn_standards_interval_time     0
_diffrn_standards_decay_%     0
_reflns_number_total     4124
_reflns_number_gt     3351
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0510
_refine_ls_R_factor_gt     0.0392
_refine_ls_wR_factor_gt     0.1071
_refine_ls_wR_factor_ref     0.1191
_refine_ls_goodness_of_fit_ref     1.016
_refine_ls_restrained_S_all     1.016
_refine_ls_number_reflns     4124
_refine_ls_number_parameters     239
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0635P)²+0.8319P] 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     0.001
_refine_diff_density_max     0.379
_refine_diff_density_min     -0.314
_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, 2008)'
_computing_cell_refinement     'SAINT (Bruker, 2008)'
_computing_data_reduction     'SAINT (Bruker, 2008)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'X-SEED (Barbour, 2001)'
_computing_publication_material     'publCIF (Westrip, 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_disorder_assembly
    _atom_site_disorder_group
    S S1 0.45514(5) 0.17006(3) 0.48043(5) 0.04028(15) Uani d . 1 . .
    O O1 0.65557(12) 0.44794(7) 0.58487(12) 0.0369(3) Uani d . 1 . .
    O O2 0.88016(13) 0.19441(7) 0.68934(12) 0.0368(3) Uani d . 1 . .
    O O3 1.30863(11) 0.51465(7) 0.76778(11) 0.0323(3) Uani d . 1 . .
    O O4 1.02427(13) 0.79694(8) 0.61792(13) 0.0412(3) Uani d . 1 . .
    N N1 0.57177(12) 0.31723(8) 0.53660(11) 0.0229(3) Uani d . 1 . .
    N N2 0.67570(13) 0.19089(8) 0.60462(11) 0.0238(3) Uani d . 1 . .
    C C1 0.67099(15) 0.37060(9) 0.58438(13) 0.0242(3) Uani d . 1 . .
    C C2 0.78972(15) 0.32772(9) 0.63022(13) 0.0229(3) Uani d . 1 . .
    C C3 0.78870(16) 0.23434(9) 0.64445(13) 0.0250(3) Uani d . 1 . .
    C C4 0.57229(15) 0.22878(10) 0.54306(14) 0.0248(3) Uani d . 1 . .
    C C5 0.45950(15) 0.36105(10) 0.47751(14) 0.0265(3) Uani d . 1 . .
    H H5A 0.4319 0.3274 0.4088 0.032 Uiso calc R 1 . .
    H H5B 0.4890 0.4182 0.4508 0.032 Uiso calc R 1 . .
    C C6 0.34165(17) 0.37168(11) 0.55619(16) 0.0341(4) Uani d . 1 . .
    H H6A 0.2705 0.4026 0.5152 0.051 Uiso calc R 1 . .
    H H6B 0.3690 0.4042 0.6249 0.051 Uiso calc R 1 . .
    H H6C 0.3092 0.3151 0.5794 0.051 Uiso calc R 1 . .
    C C7 0.67507(17) 0.09673(10) 0.62395(15) 0.0303(4) Uani d . 1 . .
    H H7A 0.5820 0.0766 0.6301 0.036 Uiso calc R 1 . .
    H H7B 0.7216 0.0837 0.6977 0.036 Uiso calc R 1 . .
    C C8 0.7422(2) 0.04915(11) 0.52713(19) 0.0415(4) Uani d . 1 . .
    H H8A 0.7466 -0.0121 0.5458 0.062 Uiso calc R 1 . .
    H H8B 0.8325 0.0715 0.5175 0.062 Uiso calc R 1 . .
    H H8C 0.6911 0.0572 0.4553 0.062 Uiso calc R 1 . .
    C C9 0.90368(16) 0.36954(10) 0.66047(13) 0.0250(3) Uani d . 1 . .
    H H9 0.9718 0.3342 0.6923 0.030 Uiso calc R 1 . .
    C C10 0.93689(16) 0.45823(10) 0.65184(13) 0.0254(3) Uani d . 1 . .
    H H10 0.8741 0.4981 0.6216 0.031 Uiso calc R 1 . .
    C C11 1.05873(16) 0.48485(10) 0.68724(14) 0.0258(3) Uani d . 1 . .
    H H11 1.1170 0.4415 0.7155 0.031 Uiso calc R 1 . .
    C C12 1.11166(16) 0.57152(10) 0.68749(13) 0.0246(3) Uani d . 1 . .
    C C13 1.24183(16) 0.58518(10) 0.72991(13) 0.0252(3) Uani d . 1 . .
    C C14 1.29543(16) 0.66804(10) 0.73119(14) 0.0275(3) Uani d . 1 . .
    H H14 1.3836 0.6774 0.7589 0.033 Uiso calc R 1 . .
    C C15 1.21964(17) 0.73610(10) 0.69203(15) 0.0294(4) Uani d . 1 . .
    H H15 1.2566 0.7922 0.6926 0.035 Uiso calc R 1 . .
    C C16 1.08972(17) 0.72399(10) 0.65159(14) 0.0288(3) Uani d . 1 . .
    C C17 1.03685(16) 0.64216(10) 0.64830(14) 0.0262(3) Uani d . 1 . .
    H H17 0.9490 0.6336 0.6192 0.031 Uiso calc R 1 . .
    C C18 1.44150(17) 0.52479(11) 0.81125(16) 0.0328(4) Uani d . 1 . .
    H H18A 1.4763 0.4690 0.8361 0.049 Uiso calc R 1 . .
    H H18B 1.4415 0.5643 0.8770 0.049 Uiso calc R 1 . .
    H H18C 1.4978 0.5481 0.7504 0.049 Uiso calc R 1 . .
    C C19 0.89413(19) 0.78713(12) 0.56997(19) 0.0415(4) Uani d . 1 . .
    H H19A 0.8576 0.8436 0.5503 0.062 Uiso calc R 1 . .
    H H19B 0.8368 0.7592 0.6264 0.062 Uiso calc R 1 . .
    H H19C 0.8983 0.7518 0.5002 0.062 Uiso calc R 1 . .
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 C4 . 1.6516(16) ?
    O1 C1 . 1.2160(19) ?
    O2 C3 . 1.2207(19) ?
    O3 C13 . 1.3582(19) ?
    O3 C18 . 1.430(2) ?
    O4 C16 . 1.368(2) ?
    O4 C19 . 1.422(2) ?
    N1 C4 . 1.3815(19) ?
    N1 C1 . 1.4065(19) ?
    N1 C5 . 1.4791(19) ?
    N2 C4 . 1.385(2) ?
    N2 C3 . 1.396(2) ?
    N2 C7 . 1.4852(19) ?
    C1 C2 . 1.461(2) ?
    C2 C9 . 1.360(2) ?
    C2 C3 . 1.465(2) ?
    C5 C6 . 1.514(2) ?
    C5 H5A . 0.9900 ?
    C5 H5B . 0.9900 ?
    C6 H6A . 0.9800 ?
    C6 H6B . 0.9800 ?
    C6 H6C . 0.9800 ?
    C7 C8 . 1.512(2) ?
    C7 H7A . 0.9900 ?
    C7 H7B . 0.9900 ?
    C8 H8A . 0.9800 ?
    C8 H8B . 0.9800 ?
    C8 H8C . 0.9800 ?
    C9 C10 . 1.427(2) ?
    C9 H9 . 0.9500 ?
    C10 C11 . 1.351(2) ?
    C10 H10 . 0.9500 ?
    C11 C12 . 1.453(2) ?
    C11 H11 . 0.9500 ?
    C12 C17 . 1.405(2) ?
    C12 C13 . 1.407(2) ?
    C13 C14 . 1.400(2) ?
    C14 C15 . 1.379(2) ?
    C14 H14 . 0.9500 ?
    C15 C16 . 1.394(2) ?
    C15 H15 . 0.9500 ?
    C16 C17 . 1.383(2) ?
    C17 H17 . 0.9500 ?
    C18 H18A . 0.9800 ?
    C18 H18B . 0.9800 ?
    C18 H18C . 0.9800 ?
    C19 H19A . 0.9800 ?
    C19 H19B . 0.9800 ?
    C19 H19C . 0.9800 ?
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
    C13 O3 C18 . . 118.65(12) ?
    C16 O4 C19 . . 117.25(14) ?
    C4 N1 C1 . . 124.56(13) ?
    C4 N1 C5 . . 119.26(13) ?
    C1 N1 C5 . . 116.18(12) ?
    C4 N2 C3 . . 124.38(13) ?
    C4 N2 C7 . . 119.65(13) ?
    C3 N2 C7 . . 115.81(13) ?
    O1 C1 N1 . . 119.92(14) ?
    O1 C1 C2 . . 123.75(14) ?
    N1 C1 C2 . . 116.32(13) ?
    C9 C2 C1 . . 123.71(14) ?
    C9 C2 C3 . . 117.04(14) ?
    C1 C2 C3 . . 119.24(13) ?
    O2 C3 N2 . . 119.86(14) ?
    O2 C3 C2 . . 123.26(14) ?
    N2 C3 C2 . . 116.89(13) ?
    N1 C4 N2 . . 117.14(13) ?
    N1 C4 S1 . . 121.84(12) ?
    N2 C4 S1 . . 121.01(11) ?
    N1 C5 C6 . . 111.71(13) ?
    N1 C5 H5A . . 109.3 ?
    C6 C5 H5A . . 109.3 ?
    N1 C5 H5B . . 109.3 ?
    C6 C5 H5B . . 109.3 ?
    H5A C5 H5B . . 107.9 ?
    C5 C6 H6A . . 109.5 ?
    C5 C6 H6B . . 109.5 ?
    H6A C6 H6B . . 109.5 ?
    C5 C6 H6C . . 109.5 ?
    H6A C6 H6C . . 109.5 ?
    H6B C6 H6C . . 109.5 ?
    N2 C7 C8 . . 111.72(14) ?
    N2 C7 H7A . . 109.3 ?
    C8 C7 H7A . . 109.3 ?
    N2 C7 H7B . . 109.3 ?
    C8 C7 H7B . . 109.3 ?
    H7A C7 H7B . . 107.9 ?
    C7 C8 H8A . . 109.5 ?
    C7 C8 H8B . . 109.5 ?
    H8A C8 H8B . . 109.5 ?
    C7 C8 H8C . . 109.5 ?
    H8A C8 H8C . . 109.5 ?
    H8B C8 H8C . . 109.5 ?
    C2 C9 C10 . . 130.09(15) ?
    C2 C9 H9 . . 115.0 ?
    C10 C9 H9 . . 115.0 ?
    C11 C10 C9 . . 119.24(15) ?
    C11 C10 H10 . . 120.4 ?
    C9 C10 H10 . . 120.4 ?
    C10 C11 C12 . . 128.08(15) ?
    C10 C11 H11 . . 116.0 ?
    C12 C11 H11 . . 116.0 ?
    C17 C12 C13 . . 119.00(14) ?
    C17 C12 C11 . . 122.30(15) ?
    C13 C12 C11 . . 118.70(14) ?
    O3 C13 C14 . . 123.75(15) ?
    O3 C13 C12 . . 116.31(13) ?
    C14 C13 C12 . . 119.94(15) ?
    C15 C14 C13 . . 119.73(15) ?
    C15 C14 H14 . . 120.1 ?
    C13 C14 H14 . . 120.1 ?
    C14 C15 C16 . . 121.12(14) ?
    C14 C15 H15 . . 119.4 ?
    C16 C15 H15 . . 119.4 ?
    O4 C16 C17 . . 125.20(16) ?
    O4 C16 C15 . . 115.32(14) ?
    C17 C16 C15 . . 119.48(15) ?
    C16 C17 C12 . . 120.71(15) ?
    C16 C17 H17 . . 119.6 ?
    C12 C17 H17 . . 119.6 ?
    O3 C18 H18A . . 109.5 ?
    O3 C18 H18B . . 109.5 ?
    H18A C18 H18B . . 109.5 ?
    O3 C18 H18C . . 109.5 ?
    H18A C18 H18C . . 109.5 ?
    H18B C18 H18C . . 109.5 ?
    O4 C19 H19A . . 109.5 ?
    O4 C19 H19B . . 109.5 ?
    H19A C19 H19B . . 109.5 ?
    O4 C19 H19C . . 109.5 ?
    H19A C19 H19C . . 109.5 ?
    H19B C19 H19C . . 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
    C4 N1 C1 O1 . . . . -172.42(15) ?
    C5 N1 C1 O1 . . . . 6.6(2) ?
    C4 N1 C1 C2 . . . . 8.2(2) ?
    C5 N1 C1 C2 . . . . -172.73(13) ?
    O1 C1 C2 C9 . . . . -11.3(3) ?
    N1 C1 C2 C9 . . . . 167.98(14) ?
    O1 C1 C2 C3 . . . . 169.12(15) ?
    N1 C1 C2 C3 . . . . -11.6(2) ?
    C4 N2 C3 O2 . . . . -173.69(15) ?
    C7 N2 C3 O2 . . . . 1.7(2) ?
    C4 N2 C3 C2 . . . . 6.8(2) ?
    C7 N2 C3 C2 . . . . -177.84(13) ?
    C9 C2 C3 O2 . . . . 5.6(2) ?
    C1 C2 C3 O2 . . . . -174.83(15) ?
    C9 C2 C3 N2 . . . . -174.93(14) ?
    C1 C2 C3 N2 . . . . 4.7(2) ?
    C1 N1 C4 N2 . . . . 2.4(2) ?
    C5 N1 C4 N2 . . . . -176.56(13) ?
    C1 N1 C4 S1 . . . . -177.59(12) ?
    C5 N1 C4 S1 . . . . 3.42(19) ?
    C3 N2 C4 N1 . . . . -10.5(2) ?
    C7 N2 C4 N1 . . . . 174.31(13) ?
    C3 N2 C4 S1 . . . . 169.52(12) ?
    C7 N2 C4 S1 . . . . -5.67(19) ?
    C4 N1 C5 C6 . . . . 82.80(17) ?
    C1 N1 C5 C6 . . . . -96.28(16) ?
    C4 N2 C7 C8 . . . . 88.82(18) ?
    C3 N2 C7 C8 . . . . -86.77(18) ?
    C1 C2 C9 C10 . . . . -2.7(3) ?
    C3 C2 C9 C10 . . . . 176.85(15) ?
    C2 C9 C10 C11 . . . . -179.44(16) ?
    C9 C10 C11 C12 . . . . -179.07(15) ?
    C10 C11 C12 C17 . . . . 0.0(3) ?
    C10 C11 C12 C13 . . . . 179.19(15) ?
    C18 O3 C13 C14 . . . . -0.2(2) ?
    C18 O3 C13 C12 . . . . 179.70(14) ?
    C17 C12 C13 O3 . . . . 179.26(13) ?
    C11 C12 C13 O3 . . . . 0.1(2) ?
    C17 C12 C13 C14 . . . . -0.8(2) ?
    C11 C12 C13 C14 . . . . -179.99(14) ?
    O3 C13 C14 C15 . . . . -179.33(14) ?
    C12 C13 C14 C15 . . . . 0.7(2) ?
    C13 C14 C15 C16 . . . . 0.4(2) ?
    C19 O4 C16 C17 . . . . -3.6(3) ?
    C19 O4 C16 C15 . . . . 176.54(16) ?
    C14 C15 C16 O4 . . . . 178.46(15) ?
    C14 C15 C16 C17 . . . . -1.4(2) ?
    O4 C16 C17 C12 . . . . -178.52(15) ?
    C15 C16 C17 C12 . . . . 1.3(2) ?
    C13 C12 C17 C16 . . . . -0.2(2) ?
    C11 C12 C17 C16 . . . . 178.91(15) ?
