#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/33/2223300.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_2223300
loop_
_publ_author_name
'Panchatcharam, R.'
'Dhayalan, V.'
'Mohanakrishnan, A. K.'
'Chakkaravarthi, G.'
'Manivannan, V.'
_publ_section_title
1,3-Dimethyl-5-(2-methylbenzylidene)pyrimidine-2,4,6(1H,3H,5H)-trione
_journal_coeditor_code           BT5051
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2394
_journal_paper_doi               10.1107/S1600536809035521
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C14 H14 N2 O3'
_chemical_formula_moiety         'C14 H14 N2 O3'
_chemical_formula_sum            'C14 H14 N2 O3'
_chemical_formula_weight         258.27
_chemical_name_systematic
;
1,3-Dimethyl-5-(2-methylbenzylidene)pyrimidine-
2,4,6(1H,3H,5H)trione
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 94.267(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.182(5)
_cell_length_b                   8.334(4)
_cell_length_c                   18.202(5)
_cell_measurement_reflns_used    6022
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      29.8
_cell_measurement_theta_min      2.24
_cell_volume                     1237.7(10)
_computing_cell_refinement       'SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT (Bruker, 2004)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker Kappa APEXII'
_diffrn_measurement_method       'ω and φ'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0237
_diffrn_reflns_av_sigmaI/netI    0.0244
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            16198
_diffrn_reflns_theta_full        30.71
_diffrn_reflns_theta_max         30.71
_diffrn_reflns_theta_min         2.24
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  0.9824
_exptl_absorpt_correction_T_min  0.9709
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.386
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.517
_refine_diff_density_min         -0.338
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         3837
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.1031
_refine_ls_R_factor_gt           0.0716
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1214P)²+0.5641P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2077
_refine_ls_wR_factor_ref         0.2375
_reflns_number_gt                2517
_reflns_number_total             3837
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt5051.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2223300
_cod_database_fobs_code          2223300
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'
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
C C1 0.0138(2) 0.2553(2) 0.49118(10) 0.0391(4) Uani d . 1 . .
C C2 -0.1183(3) 0.2104(3) 0.44177(12) 0.0547(6) Uani d . 1 . .
H H2 -0.1974 0.1406 0.4573 0.066 Uiso calc R 1 . .
C C3 -0.1326(3) 0.2681(4) 0.37060(12) 0.0589(6) Uani d . 1 . .
H H3 -0.2205 0.2370 0.3384 0.071 Uiso calc R 1 . .
C C4 -0.0168(3) 0.3713(3) 0.34746(12) 0.0548(6) Uani d . 1 . .
H H4 -0.0285 0.4147 0.3003 0.066 Uiso calc R 1 . .
C C5 0.1166(3) 0.4106(3) 0.39422(12) 0.0519(5) Uani d . 1 . .
H H5 0.1961 0.4785 0.3775 0.062 Uiso calc R 1 . .
C C6 0.1363(2) 0.3521(3) 0.46527(11) 0.0424(5) Uani d . 1 . .
C C7 0.2861(3) 0.4007(4) 0.51198(15) 0.0714(8) Uani d . 1 . .
H H7A 0.3586 0.3105 0.5188 0.107 Uiso calc R 1 . .
H H7B 0.2552 0.4370 0.5590 0.107 Uiso calc R 1 . .
H H7C 0.3408 0.4859 0.4881 0.107 Uiso calc R 1 . .
C C8 0.0343(3) 0.2024(3) 0.56714(11) 0.0447(5) Uani d . 1 . .
H H8 0.1412 0.2161 0.5873 0.054 Uiso calc R 1 . .
C C9 -0.0641(2) 0.1379(2) 0.61602(10) 0.0390(4) Uani d . 1 . .
C C10 0.0217(3) 0.0920(3) 0.68754(10) 0.0429(5) Uani d . 1 . .
C C11 -0.2160(2) -0.0676(2) 0.71455(10) 0.0396(4) Uani d . 1 . .
C C12 -0.2395(3) 0.1068(3) 0.60570(11) 0.0449(5) Uani d . 1 . .
C C13 0.0281(3) -0.0647(3) 0.79980(12) 0.0584(6) Uani d . 1 . .
H H13A 0.1247 -0.1223 0.7885 0.088 Uiso calc R 1 . .
H H13B -0.0416 -0.1340 0.8257 0.088 Uiso calc R 1 . .
H H13C 0.0589 0.0263 0.8300 0.088 Uiso calc R 1 . .
C C14 -0.4706(3) -0.0581(4) 0.63701(16) 0.0715(8) Uani d . 1 . .
H H14A -0.4822 -0.1675 0.6524 0.107 Uiso calc R 1 . .
H H14B -0.5004 -0.0496 0.5851 0.107 Uiso calc R 1 . .
H H14C -0.5409 0.0093 0.6636 0.107 Uiso calc R 1 . .
N N1 -0.3007(2) -0.0073(2) 0.65217(9) 0.0433(4) Uani d . 1 . .
N N2 -0.0600(2) -0.0100(2) 0.73120(8) 0.0397(4) Uani d . 1 . .
O O1 0.1595(2) 0.1369(3) 0.70726(9) 0.0682(6) Uani d . 1 . .
O O2 -0.3317(2) 0.1744(3) 0.56044(11) 0.0748(6) Uani d . 1 . .
O O3 -0.2774(2) -0.1642(2) 0.75393(10) 0.0587(5) Uani d . 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'
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 C1 C2 . . 118.38(18) ?
C6 C1 C8 . . 117.61(18) ?
C2 C1 C8 . . 123.97(19) ?
C3 C2 C1 . . 121.1(2) ?
C3 C2 H2 . . 119.5 ?
C1 C2 H2 . . 119.5 ?
C4 C3 C2 . . 119.7(2) ?
C4 C3 H3 . . 120.1 ?
C2 C3 H3 . . 120.1 ?
C3 C4 C5 . . 119.7(2) ?
C3 C4 H4 . . 120.1 ?
C5 C4 H4 . . 120.1 ?
C4 C5 C6 . . 121.9(2) ?
C4 C5 H5 . . 119.0 ?
C6 C5 H5 . . 119.0 ?
C5 C6 C1 . . 118.95(19) ?
C5 C6 C7 . . 118.1(2) ?
C1 C6 C7 . . 122.9(2) ?
C6 C7 H7A . . 109.5 ?
C6 C7 H7B . . 109.5 ?
H7A C7 H7B . . 109.5 ?
C6 C7 H7C . . 109.5 ?
H7A C7 H7C . . 109.5 ?
H7B C7 H7C . . 109.5 ?
C9 C8 C1 . . 135.66(19) ?
C9 C8 H8 . . 112.2 ?
C1 C8 H8 . . 112.2 ?
C8 C9 C12 . . 127.86(18) ?
C8 C9 C10 . . 114.43(18) ?
C12 C9 C10 . . 117.69(17) ?
O1 C10 N2 . . 120.04(18) ?
O1 C10 C9 . . 123.19(19) ?
N2 C10 C9 . . 116.74(18) ?
O3 C11 N2 . . 121.34(19) ?
O3 C11 N1 . . 121.6(2) ?
N2 C11 N1 . . 117.08(17) ?
O2 C12 N1 . . 119.8(2) ?
O2 C12 C9 . . 124.2(2) ?
N1 C12 C9 . . 116.06(17) ?
N2 C13 H13A . . 109.5 ?
N2 C13 H13B . . 109.5 ?
H13A C13 H13B . . 109.5 ?
N2 C13 H13C . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 109.5 ?
N1 C14 H14A . . 109.5 ?
N1 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
N1 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
C11 N1 C12 . . 124.58(17) ?
C11 N1 C14 . . 117.58(19) ?
C12 N1 C14 . . 117.7(2) ?
C10 N2 C11 . . 124.92(16) ?
C10 N2 C13 . . 117.15(18) ?
C11 N2 C13 . . 117.91(18) ?
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
C1 C6 . 1.396(3) ?
C1 C2 . 1.404(3) ?
C1 C8 . 1.449(3) ?
C2 C3 . 1.379(3) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.369(4) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.373(4) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.380(3) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.495(3) ?
C7 H7A . 0.9600 ?
C7 H7B . 0.9600 ?
C7 H7C . 0.9600 ?
C8 C9 . 1.355(3) ?
C8 H8 . 0.9300 ?
C9 C12 . 1.457(3) ?
C9 C10 . 1.482(3) ?
C10 O1 . 1.217(3) ?
C10 N2 . 1.371(3) ?
C11 O3 . 1.212(2) ?
C11 N2 . 1.376(3) ?
C11 N1 . 1.380(3) ?
C12 O2 . 1.214(3) ?
C12 N1 . 1.391(3) ?
C13 N2 . 1.467(3) ?
C13 H13A . 0.9600 ?
C13 H13B . 0.9600 ?
C13 H13C . 0.9600 ?
C14 N1 . 1.460(3) ?
C14 H14A . 0.9600 ?
C14 H14B . 0.9600 ?
C14 H14C . 0.9600 ?
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
C2 H2 O2 . 0.93 2.26 2.893(3) 125 y
C8 H8 O1 . 0.93 2.28 2.732(3) 110 y
C13 H13B O3 . 0.96 2.26 2.706(4) 107 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_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 C1 C2 C3 . . . . -4.0(4) ?
C8 C1 C2 C3 . . . . 178.4(2) ?
C1 C2 C3 C4 . . . . -0.2(4) ?
C2 C3 C4 C5 . . . . 3.1(4) ?
C3 C4 C5 C6 . . . . -1.7(4) ?
C4 C5 C6 C1 . . . . -2.5(4) ?
C4 C5 C6 C7 . . . . 179.6(3) ?
C2 C1 C6 C5 . . . . 5.2(3) ?
C8 C1 C6 C5 . . . . -177.0(2) ?
C2 C1 C6 C7 . . . . -177.0(3) ?
C8 C1 C6 C7 . . . . 0.7(3) ?
C6 C1 C8 C9 . . . . 164.5(3) ?
C2 C1 C8 C9 . . . . -17.9(4) ?
C1 C8 C9 C12 . . . . -3.4(4) ?
C1 C8 C9 C10 . . . . 175.4(2) ?
C8 C9 C10 O1 . . . . 14.5(3) ?
C12 C9 C10 O1 . . . . -166.7(2) ?
C8 C9 C10 N2 . . . . -163.5(2) ?
C12 C9 C10 N2 . . . . 15.4(3) ?
C8 C9 C12 O2 . . . . -22.1(4) ?
C10 C9 C12 O2 . . . . 159.2(2) ?
C8 C9 C12 N1 . . . . 158.5(2) ?
C10 C9 C12 N1 . . . . -20.2(3) ?
O3 C11 N1 C12 . . . . 178.2(2) ?
N2 C11 N1 C12 . . . . -0.2(3) ?
O3 C11 N1 C14 . . . . 2.9(3) ?
N2 C11 N1 C14 . . . . -175.4(2) ?
O2 C12 N1 C11 . . . . -166.3(2) ?
C9 C12 N1 C11 . . . . 13.1(3) ?
O2 C12 N1 C14 . . . . 8.9(4) ?
C9 C12 N1 C14 . . . . -171.7(2) ?
O1 C10 N2 C11 . . . . 179.7(2) ?
C9 C10 N2 C11 . . . . -2.3(3) ?
O1 C10 N2 C13 . . . . -2.0(3) ?
C9 C10 N2 C13 . . . . 176.01(19) ?
O3 C11 N2 C10 . . . . 176.1(2) ?
N1 C11 N2 C10 . . . . -5.6(3) ?
O3 C11 N2 C13 . . . . -2.2(3) ?
N1 C11 N2 C13 . . . . 176.12(18) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 1710779
