##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
##############################################################################
#                                                                            #
# 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 2.1.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
# cif/home.html                                                              #
#                                                                            #
#            Copyright International Union of Crystallography                #
#                                                                            #
##############################################################################
                                             
data_global
_audit_creation_method     'from SHELXL97 CIF and IUCr SHELXL97-template'
_journal_date_recd_electronic     2005-02-16
_journal_date_accepted     2005-02-21
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2005
_journal_volume     61
_journal_issue      4
_journal_page_first     o799
_journal_page_last     o800
_journal_paper_category     EO
_publ_contact_author_name     'William Lewis'
_publ_contact_author_address
;
Chemistry Department
University of Canterbury
P.O. Box 4800
Christchurch
New Zealand
8004
;
_publ_contact_author_email     wle11@student.canterbury.ac.nz
_publ_contact_author_fax      64E306(3)
_publ_contact_author_phone     +64(3)3642987x7437
_publ_section_title
;
(+-)-5-Ethyl-1-methyl-5-phenylpyrimidine-2,4,6-trione at 163 K
;
loop_
    _publ_author_name
    _publ_author_address
    'Lewis, William'
;
Chemistry Department
University of Canterbury
PO Box 4800
Christchurch 8004
New Zealand
;
    'McKeown, Robert H.'
;
Chemistry Department
University of Canterbury
PO Box 4800
Christchurch 8004
New Zealand
;
    'Robinson, Ward T.'
;
Chemistry Department
University of Canterbury
P.O. Box 4800
Christchurch 8004
New Zealand
;
data_I
_chemical_name_systematic
;
(+-)-5-Ethyl-1-methyl-5-phenylpyrimidine-2,4,6-trione
;
_chemical_name_common
;
(+-)-5-Ethyl-1-methyl-5-phenylpyrimidine-2,4,6-trione
;
_chemical_formula_moiety     'C13 H14 N2 O3'
_chemical_formula_sum     'C13 H14 N2 O3'
_chemical_formula_iupac     'C13 H14 N2 O3'
_chemical_formula_weight     246.26
_chemical_melting_point     452
_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     13.636(6)
_cell_length_b     7.218(3)
_cell_length_c     12.467(6)
_cell_angle_alpha     90.00
_cell_angle_beta     105.398(6)
_cell_angle_gamma     90.00
_cell_volume     1183.1(9)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     3964
_cell_measurement_theta_min     6.198
_cell_measurement_theta_max     54.540
_cell_measurement_temperature     163(2)
_exptl_crystal_description     'Plate'
_exptl_crystal_colour     'Colourless'
_exptl_crystal_size_max     0.80
_exptl_crystal_size_mid     0.50
_exptl_crystal_size_min     0.10
_exptl_crystal_density_diffrn     1.383
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     520
_exptl_absorpt_coefficient_mu     0.100
_exptl_absorpt_correction_type     'multi-scan'
_exptl_absorpt_process_details     '(SADABS; Bruker, 1999)'
_exptl_absorpt_correction_T_min     0.883683
_exptl_absorpt_correction_T_max     1.000000
_exptl_special_details
;
;
_diffrn_ambient_temperature     163(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 CCD'
_diffrn_measurement_method     'φ and ω'
_diffrn_detector_area_resol_mean     8.192
_diffrn_reflns_number     15219
_diffrn_reflns_av_R_equivalents     0.0576
_diffrn_reflns_av_sigmaI/netI     0.0889
_diffrn_reflns_theta_min     3.10
_diffrn_reflns_theta_max     27.87
_diffrn_reflns_theta_full     25.00
_diffrn_measured_fraction_theta_max     0.947
_diffrn_measured_fraction_theta_full     1.000
_diffrn_reflns_limit_h_min     -17
_diffrn_reflns_limit_h_max     17
_diffrn_reflns_limit_k_min     -9
_diffrn_reflns_limit_k_max     5
_diffrn_reflns_limit_l_min     -16
_diffrn_reflns_limit_l_max     16
_diffrn_standards_number     0
_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 > 2sigma(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     2670
_reflns_number_gt     1969
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0669
_refine_ls_R_factor_gt     0.0421
_refine_ls_wR_factor_gt     0.1092
_refine_ls_wR_factor_ref     0.1273
_refine_ls_goodness_of_fit_ref     1.084
_refine_ls_restrained_S_all     1.084
_refine_ls_number_reflns     2670
_refine_ls_number_parameters     216
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     refxyz
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
                  'calc w = 1/[σ²(Fo²)+0.1704P] 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     0.317
_refine_diff_density_min     -0.192
_refine_ls_extinction_method     SHELXTL
_refine_ls_extinction_coef     0.028(4)
_refine_ls_extinction_expression
                                  'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
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'
_computing_data_collection     'SMART (Bruker, 1999)'
_computing_cell_refinement     'SAINT-Plus (Bruker, 1999)'
_computing_data_reduction     'SAINT-Plus'
_computing_structure_solution     'SHELXTL (Sheldrick, 2001)'
_computing_structure_refinement     'SHELXTL'
_computing_molecular_graphics     'SHELXTL'
_computing_publication_material     'SHELXTL'
loop_
    _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
    _atom_site_type_symbol
    N1 0.65348(10) 0.07027(18) 0.33475(10) 0.0254(3) Uani d . 1 . . N
    C1 0.65070(18) 0.1255(3) 0.44783(16) 0.0385(5) Uani d . 1 . . C
    H1A 0.602(4) 0.220(8) 0.440(4) 0.058 Uiso d P 0.55(4) A 1 H
    H1B 0.727(4) 0.157(7) 0.490(4) 0.058 Uiso d P 0.55(4) A 1 H
    H1C 0.629(4) 0.010(7) 0.489(4) 0.058 Uiso d P 0.55(4) A 1 H
    H1D 0.714(5) 0.086(9) 0.502(5) 0.058 Uiso d P 0.45(4) A 2 H
    H1E 0.586(5) 0.092(10) 0.456(5) 0.058 Uiso d P 0.45(4) A 2 H
    H1F 0.653(5) 0.268(9) 0.445(4) 0.058 Uiso d P 0.45(4) A 2 H
    C2 0.57740(11) 0.1397(2) 0.24633(13) 0.0237(4) Uani d . 1 . . C
    O2 0.51654(8) 0.25406(16) 0.25880(10)
                                        0.0329(3) Uani d . 1 . . O
    N3 0.57365(10) 0.06980(18) 0.14236(11) 0.0228(3) Uani d . 1 . . N
    H3A 0.5184(14) 0.097(2) 0.0901(15) 0.027 Uiso d . 1 . . H
    C4 0.63173(11) -0.0714(2) 0.11971(12) 0.0220(3) Uani d . 1 . . C
    O4 0.60741(8) -0.15259(16) 0.03090(9) 0.0305(3) Uani d . 1 . . O
    C5 0.73205(11) -0.1082(2) 0.20687(12) 0.0224(3) Uani d . 1 . . C
    C6 0.72608(12) -0.0576(2) 0.32398(13) 0.0250(4) Uani d . 1 . . C
    O6 0.78634(9) -0.12010(17) 0.40561(9) 0.0353(3) Uani d . 1 . . O
    C7 0.81121(11) 0.0195(2) 0.17474(13) 0.0230(4) Uani d . 1 . . C
    C8 0.86655(12) 0.1522(2) 0.24645(15) 0.0292(4) Uani d . 1 . . C
    H8A 0.8597(14) 0.168(3) 0.3228(16) 0.035 Uiso d . 1 . . H
    C9 0.93700(13) 0.2632(3) 0.21351(17) 0.0377(5) Uani d . 1 . . C
    H9A 0.9758(16) 0.353(3) 0.2670(17) 0.045 Uiso d . 1 . . H
    C10 0.95306(13) 0.2430(3) 0.10971(17) 0.0384(5) Uani d . 1 . . C
    H10A 1.0011(16) 0.323(3) 0.0815(17) 0.046 Uiso d . 1 . . H
    C11 0.89899(13) 0.1096(3) 0.03816(16) 0.0345(4) Uani d . 1 . . C
    H11A 0.9099(14) 0.088(3) -0.0339(16) 0.041 Uiso d . 1 . . H
    C12 0.82846(12) -0.0014(2) 0.06987(14) 0.0291(4) Uani d . 1 . . C
    H12A 0.7939(14) -0.096(3) 0.0196(15) 0.035 Uiso d . 1 . . H
    C13 0.76509(12) -0.3121(2) 0.20458(15) 0.0267(4) Uani d . 1 . . C
    H13A 0.7730(13) -0.332(2) 0.1261(16) 0.032 Uiso d . 1 . . H
    H13B 0.8342(15) -0.326(2) 0.2599(15) 0.032 Uiso d . 1 . . H
    C14 0.69212(14) -0.4507(2) 0.23351(17) 0.0333(4) Uani d . 1 . . C
    H14A 0.7204(16) -0.568(3) 0.2292(16) 0.050 Uiso d . 1 . . H
    H14B 0.6232(18) -0.441(3) 0.1783(18) 0.050 Uiso d . 1 . . H
    H14C 0.6850(16) -0.428(3) 0.3103(19) 0.050 Uiso d . 1 . . H
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds 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
    N1 C6 . 1.386(2) ?
    N1 C2 . 1.391(2) ?
    N1 C1 . 1.475(2) ?
    C1 H1A . 0.94(5) ?
    C1 H1B . 1.06(5) ?
    C1 H1C . 1.06(5) ?
    C1 H1D . 0.99(7) ?
    C1 H1E . 0.95(6) ?
    C1 H1F . 1.03(6) ?
    C2 O2 . 1.2095(19) ?
    C2 N3 . 1.379(2) ?
    N3 C4 . 1.365(2) ?
    N3 H3A . 0.876(18) ?
    C4 O4 . 1.2184(19) ?
    C4 C5 . 1.528(2) ?
    C5 C6 . 1.528(2) ?
    C5 C13 . 1.541(2) ?
    C5 C7 . 1.551(2) ?
    C6 O6 . 1.2126(19) ?
    C7 C8 . 1.389(2) ?
    C7 C12 . 1.397(2) ?
    C8 C9 . 1.394(2) ?
    C8 H8A . 0.988(19) ?
    C9 C10 . 1.376(3) ?
    C9 H9A . 0.98(2) ?
    C10 C11 . 1.385(3) ?
    C10 H10A . 1.00(2) ?
    C11 C12 . 1.387(2) ?
    C11 H11A . 0.962(19) ?
    C12 H12A . 0.963(19) ?
    C13 C14 . 1.520(2) ?
    C13 H13A . 1.023(18) ?
    C13 H13B . 1.014(19) ?
    C14 H14A . 0.94(2) ?
    C14 H14B . 1.01(2) ?
    C14 H14C . 1.00(2) ?
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
    C6 N1 C2 . . 124.39(13) ?
    C6 N1 C1 . . 118.22(14) ?
    C2 N1 C1 . . 117.19(15) ?
    N1 C1 H1A . . 107(3) ?
    N1 C1 H1B . . 105(3) ?
    H1A C1 H1B . . 118(4) ?
    N1 C1 H1C . . 109(2) ?
    H1A C1 H1C . . 110(4) ?
    H1B C1 H1C . . 107(3) ?
    N1 C1 H1D . . 110(3) ?
    N1 C1 H1E . . 107(3) ?
    H1D C1 H1E . . 121(5) ?
    N1 C1 H1F . . 103(3) ?
    H1D C1 H1F . . 107(5) ?
    H1E C1 H1F . . 107(5) ?
    O2 C2 N3 . . 121.00(14) ?
    O2 C2 N1 . . 122.47(15) ?
    N3 C2 N1 . . 116.52(13) ?
    C4 N3 C2 . . 126.06(13) ?
    C4 N3 H3A . . 116.2(12) ?
    C2 N3 H3A . . 115.3(11) ?
    O4 C4 N3 . . 120.94(14) ?
    O4 C4 C5 . . 122.61(14) ?
    N3 C4 C5 . . 116.23(13) ?
    C4 C5 C6 . . 111.91(13) ?
    C4 C5 C13 . . 111.34(12) ?
    C6 C5 C13 . . 109.63(13) ?
    C4 C5 C7 . . 105.43(12) ?
    C6 C5 C7 . . 108.79(12) ?
    C13 C5 C7 . . 109.62(12) ?
    O6 C6 N1 . . 120.59(14) ?
    O6 C6 C5 . . 121.11(14) ?
    N1 C6 C5 . . 118.20(13) ?
    C8 C7 C12 . . 118.64(15) ?
    C8 C7 C5 . . 122.71(14) ?
    C12 C7 C5 . . 118.65(14) ?
    C7 C8 C9 . . 120.40(16) ?
    C7 C8 H8A . . 121.8(11) ?
    C9 C8 H8A . . 117.7(11) ?
    C10 C9 C8 . . 120.68(17) ?
    C10 C9 H9A . . 121.2(12) ?
    C8 C9 H9A . . 118.1(12) ?
    C9 C10 C11 . . 119.27(17) ?
    C9 C10 H10A . . 123.4(12) ?
    C11 C10 H10A . . 117.3(12) ?
    C10 C11 C12 . . 120.59(17) ?
    C10 C11 H11A . . 121.9(12) ?
    C12 C11 H11A . . 117.5(12) ?
    C11 C12 C7 . . 120.41(17) ?
    C11 C12 H12A . . 118.8(11) ?
    C7 C12 H12A . . 120.7(11) ?
    C14 C13 C5 . . 114.26(14) ?
    C14 C13 H13A . . 112.0(10)
                            ?
    C5 C13 H13A . . 105.0(10)
                           ?
    C14 C13 H13B . . 108.8(10) ?
    C5 C13 H13B . . 107.7(10) ?
    H13A C13 H13B . . 108.8(14) ?
    C13 C14 H14A . . 105.9(13) ?
    C13 C14 H14B . . 110.1(12) ?
    H14A C14 H14B . . 110.2(17) ?
    C13 C14 H14C . . 110.8(13) ?
    H14A C14 H14C . . 110.3(17) ?
    H14B C14 H14C . . 109.4(17) ?
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
    C6 N1 C2 O2 . . . . -178.51(14) ?
    C1 N1 C2 O2 . . . . 6.8(2) ?
    C6 N1 C2 N3 . . . . 2.2(2) ?
    C1 N1 C2 N3 . . . . -172.47(15) ?
    O2 C2 N3 C4 . . . . -173.37(14) ?
    N1 C2 N3 C4 . . . . 5.9(2) ?
    C2 N3 C4 O4 . . . . 162.33(15) ?
    C2 N3 C4 C5 . . . . -23.0(2) ?
    O4 C4 C5 C6 . . . . -155.56(14) ?
    N3 C4 C5 C6 . . . . 29.84(18) ?
    O4 C4 C5 C13 . . . . -32.5(2) ?
    N3 C4 C5 C13 . . . . 152.93(14) ?
    O4 C4 C5 C7 . . . . 86.33(17) ?
    N3 C4 C5 C7 . . . . -88.27(15) ?
    C2 N1 C6 O6 . . . . -175.56(14) ?
    C1 N1 C6 O6 . . . . -0.9(2) ?
    C2 N1 C6 C5 . . . . 8.1(2) ?
    C1 N1 C6 C5 . . . . -177.30(15) ?
    C4 C5 C6 O6 . . . . 160.39(14) ?
    C13 C5 C6 O6 . . . . 36.3(2) ?
    C7 C5 C6 O6 . . . . -83.52(18) ?
    C4 C5 C6 N1 . . . . -23.27(19) ?
    C13 C5 C6 N1 . . . . -147.32(14) ?
    C7 C5 C6 N1 . . . . 92.82(16) ?
    C4 C5 C7 C8 . . . . 121.60(15) ?
    C6 C5 C7 C8 . . . . 1.41(19) ?
    C13 C5 C7 C8 . . . . -118.46(16) ?
    C4 C5 C7 C12 . . . . -59.21(17) ?
    C6 C5 C7 C12 . . . . -179.40(13) ?
    C13 C5 C7 C12 . . . . 60.73(18) ?
    C12 C7 C8 C9 . . . . 0.7(2) ?
    C5 C7 C8 C9 . . . . 179.84(14) ?
    C7 C8 C9 C10 . . . . -0.1(3) ?
    C8 C9 C10 C11 . . . . -0.6(3) ?
    C9 C10 C11 C12 . . . . 0.7(3) ?
    C10 C11 C12 C7 . . . . -0.2(3) ?
    C8 C7 C12 C11 . . . . -0.5(2) ?
    C5 C7 C12 C11 . . . . -179.71(14) ?
    C4 C5 C13 C14 . . . . -63.03(19) ?
    C6 C5 C13 C14 . . . . 61.36(18) ?
    C7 C5 C13 C14 . . . . -179.29(14) ?
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
    N3 H3A O4 3_655 0.876(18) 2.003(19) 2.8787(19) 178.8(17) yes
    C12 H12A O6 4_555 0.963(19) 2.48(2) 3.371(2) 154.1(15) yes
