data_2014731 _journal_name_full 'Acta Crystallographica, Section C' _journal_year 2005 _journal_volume 61 _journal_page_first o15 _journal_page_last o20 _publ_section_title ; 5-(1-Hydroxyethylidene)-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione and four amino derivatives ; loop_ _publ_author_name 'da Silva, Emerson T.' 'Ribiero, Rodrigo S.' 'Lima, Edson L. S.' 'Wardell, James L.' 'Skakle, Janet M. S.' 'Low, John N.' 'Glidewell, Christopher' _chemical_formula_moiety 'C8 H10 N2 O4' _chemical_formula_sum 'C8 H10 N2 O4' _chemical_formula_iupac 'C8 H10 N2 O4' _chemical_formula_weight 198.18 _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 8.6066(5) _cell_length_b 9.1751(5) _cell_length_c 11.9799(7) _cell_angle_alpha 90.00 _cell_angle_beta 109.321(2) _cell_angle_gamma 90.00 _cell_volume 892.73(9) _cell_formula_units_Z 4 _cell_measurement_temperature 291(2) _exptl_crystal_density_diffrn 1.475 _diffrn_ambient_temperature 291(2) 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 O2 0.15848(17) 0.66714(19) 0.48681(14) 0.0761(5) Uani d . 1 . . O O4 0.68888(18) 0.78399(16) 0.54571(13) 0.0641(4) Uani d . 1 . . O O6 0.54580(17) 0.41371(16) 0.76817(12) 0.0621(4) Uani d . 1 . . O O51 0.91332(17) 0.66835(18) 0.70291(15) 0.0707(4) Uani d . 1 . . O N1 0.35333(16) 0.53851(16) 0.62581(11) 0.0446(3) Uani d . 1 . . N N3 0.42439(18) 0.72019(15) 0.51240(11) 0.0458(3) Uani d . 1 . . N C1 0.2236(2) 0.4511(2) 0.64934(18) 0.0617(5) Uani d . 1 . . C C2 0.3024(2) 0.64364(19) 0.53906(14) 0.0471(4) Uani d . 1 . . C C3 0.3700(3) 0.8321(2) 0.42007(18) 0.0667(6) Uani d . 1 . . C C4 0.5885(2) 0.70517(18) 0.57344(14) 0.0444(4) Uani d . 1 . . C C5 0.63903(19) 0.59883(17) 0.66653(13) 0.0411(3) Uani d . 1 . . C C6 0.51627(19) 0.51007(18) 0.69328(13) 0.0425(3) Uani d . 1 . . C C51 0.8064(2) 0.5875(2) 0.73124(16) 0.0519(4) Uani d . 1 . . C C52 0.8796(3) 0.4923(3) 0.8341(2) 0.0829(7) Uani d . 1 . . C H1A 0.2426 0.4487 0.7329 0.092 Uiso calc R 1 . . H H1B 0.2258 0.3536 0.6208 0.092 Uiso calc R 1 . . H H1C 0.1181 0.4942 0.6096 0.092 Uiso calc R 1 . . H H3A 0.3564 0.9232 0.4552 0.100 Uiso calc R 1 . . H H3B 0.2670 0.8034 0.3630 0.100 Uiso calc R 1 . . H H3C 0.4511 0.8430 0.3816 0.100 Uiso calc R 1 . . H H51 0.8649 0.7195 0.6459 0.085 Uiso calc R 1 . . H H52A 0.9958 0.5104 0.8662 0.124 Uiso calc R 1 . . H H52B 0.8610 0.3922 0.8100 0.124 Uiso calc R 1 . . H H52C 0.8296 0.5122 0.8933 0.124 Uiso calc R 1 . . H loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O2 0.0438(7) 0.0855(11) 0.0813(10) 0.0029(7) -0.0032(7) 0.0159(8) O4 0.0652(8) 0.0593(9) 0.0717(8) -0.0110(6) 0.0279(7) 0.0061(7) O6 0.0570(8) 0.0644(9) 0.0614(8) 0.0033(6) 0.0148(6) 0.0214(6) O51 0.0449(7) 0.0780(11) 0.0866(11) -0.0101(7) 0.0181(7) -0.0055(8) N1 0.0394(6) 0.0488(8) 0.0436(6) -0.0028(5) 0.0111(5) 0.0003(6) N3 0.0535(8) 0.0400(7) 0.0394(6) 0.0001(6) 0.0093(5) 0.0010(5) C1 0.0452(9) 0.0730(13) 0.0675(11) -0.0100(8) 0.0195(8) 0.0068(10) C2 0.0446(8) 0.0466(9) 0.0433(7) 0.0001(7) 0.0055(6) -0.0022(6) C3 0.0771(13) 0.0550(12) 0.0570(10) 0.0007(10) 0.0074(9) 0.0169(8) C4 0.0495(8) 0.0405(8) 0.0429(7) -0.0026(6) 0.0149(6) -0.0058(6) C5 0.0400(7) 0.0413(8) 0.0406(7) 0.0007(6) 0.0115(6) -0.0063(6) C6 0.0425(7) 0.0449(9) 0.0385(7) 0.0013(6) 0.0111(6) -0.0031(6) C51 0.0418(8) 0.0545(10) 0.0560(9) 0.0021(7) 0.0115(7) -0.0122(7) C52 0.0533(11) 0.0963(19) 0.0807(14) 0.0117(12) -0.0027(10) 0.0147(13) 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 N1 . 1.475(2) no C1 H1A . 0.96 no C1 H1B . 0.96 no C1 H1C . 0.96 no C2 O2 . 1.208(2) no C2 N1 . 1.379(2) no C2 N3 . 1.386(2) no N1 C6 . 1.392(2) no N3 C4 . 1.365(2) no N3 C3 . 1.468(2) no C3 H3A . 0.96 no C3 H3B . 0.96 no C3 H3C . 0.96 no C4 O4 . 1.253(2) no C4 C5 . 1.437(2) no C5 C51 . 1.396(2) no C5 C6 . 1.451(2) no C51 O51 . 1.311(2) no C51 C52 . 1.471(3) no C52 H52A . 0.96 no C52 H52B . 0.96 no C52 H52C . 0.96 no O51 H51 . 0.82 no C6 O6 . 1.225(2) no