#------------------------------------------------------------------------------ #$Date: 2013-12-28 15:58:47 +0200 (Sat, 28 Dec 2013) $ #$Revision: 91933 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/01/47/2014731.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_2014731 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' _publ_section_title ;5-(1-Hydroxyethylidene)-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione and four amino derivatives ; _journal_issue 1 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first o15 _journal_page_last o20 _journal_volume 61 _journal_year 2005 _chemical_formula_iupac 'C8 H10 N2 O4' _chemical_formula_moiety 'C8 H10 N2 O4' _chemical_formula_sum 'C8 H10 N2 O4' _chemical_formula_weight 198.18 _chemical_name_systematic ; 5-(1-hydroxyethylidene)-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 90.00 _cell_angle_beta 109.321(2) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 8.6066(5) _cell_length_b 9.1751(5) _cell_length_c 11.9799(7) _cell_measurement_reflns_used 3198 _cell_measurement_temperature 291(2) _cell_measurement_theta_max 32.54 _cell_measurement_theta_min 2.86 _cell_volume 892.73(9) _computing_cell_refinement 'SAINT (Bruker, 2000)' _computing_data_collection 'SMART (Bruker, 2000)' _computing_data_reduction SAINT _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material 'SHELXL97 and PRPKAPPA (Ferguson, 1999)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 291(2) _diffrn_measured_fraction_theta_full 0.989 _diffrn_measured_fraction_theta_max 0.989 _diffrn_measurement_device_type 'Bruker SMART 1000 CCD area detector' _diffrn_measurement_method \f-\w _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed X-ray tube' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0222 _diffrn_reflns_av_sigmaI/netI 0.0263 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_number 7606 _diffrn_reflns_theta_full 32.54 _diffrn_reflns_theta_max 32.54 _diffrn_reflns_theta_min 2.86 _diffrn_standards_decay_% nil _exptl_absorpt_coefficient_mu 0.120 _exptl_absorpt_correction_T_max 0.976 _exptl_absorpt_correction_T_min 0.934 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Bruker, 2000)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.475 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 416 _exptl_crystal_size_max 0.52 _exptl_crystal_size_mid 0.33 _exptl_crystal_size_min 0.20 _refine_diff_density_max 0.302 _refine_diff_density_min -0.221 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 131 _refine_ls_number_reflns 3198 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.033 _refine_ls_R_factor_all 0.1017 _refine_ls_R_factor_gt 0.0635 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.102P)^2^+0.1435P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1799 _refine_ls_wR_factor_ref 0.2070 _reflns_number_gt 1926 _reflns_number_total 3198 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file sk1792.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M 'P 21/c' _cod_depositor_comments ; The following automatic conversions were performed: '_exptl_absorpt_correction_type' value 'Multi-scan' changed to 'multi-scan' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_database_code 2014731 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' 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 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 _geom_angle_publ_flag N1 C1 H1A 109.5 no N1 C1 H1B 109.5 no H1A C1 H1B 109.5 no N1 C1 H1C 109.5 no H1A C1 H1C 109.5 no H1B C1 H1C 109.5 no O2 C2 N1 122.10(17) no O2 C2 N3 121.02(16) no N1 C2 N3 116.87(14) no C2 N1 C6 125.24(14) no C2 N1 C1 116.88(14) no C6 N1 C1 117.88(14) no C4 N3 C2 123.62(14) no C4 N3 C3 119.31(16) no C2 N3 C3 116.83(15) no N3 C3 H3A 109.5 no N3 C3 H3B 109.5 no H3A C3 H3B 109.5 no N3 C3 H3C 109.5 no H3A C3 H3C 109.5 no H3B C3 H3C 109.5 no O4 C4 N3 118.79(16) no O4 C4 C5 122.64(16) no N3 C4 C5 118.58(14) no C51 C5 C4 118.29(15) no C51 C5 C6 121.90(15) no C4 C5 C6 119.79(14) no O51 C51 C5 119.85(17) no O51 C51 C52 114.22(17) no C5 C51 C52 125.93(19) no C51 C52 H52A 109.5 no C51 C52 H52B 109.5 no H52A C52 H52B 109.5 no C51 C52 H52C 109.5 no H52A C52 H52C 109.5 no H52B C52 H52C 109.5 no C51 O51 H51 109.5 no O6 C6 N1 119.06(15) no O6 C6 C5 125.24(15) no N1 C6 C5 115.70(14) no loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag O51 H51 O4 0.82 1.70 2.450(2) 151 no 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 _geom_torsion_publ_flag O2 C2 N1 C6 -176.89(16) no N3 C2 N1 C6 4.3(2) no O2 C2 N1 C1 2.3(3) no N3 C2 N1 C1 -176.53(15) no O2 C2 N3 C4 175.60(17) no N1 C2 N3 C4 -5.6(2) no O2 C2 N3 C3 1.2(3) no N1 C2 N3 C3 -179.98(15) no C2 N3 C4 O4 -176.93(15) no C3 N3 C4 O4 -2.7(2) no C2 N3 C4 C5 3.4(2) no C3 N3 C4 C5 177.67(15) no O4 C4 C5 C51 2.5(2) no N3 C4 C5 C51 -177.85(14) no O4 C4 C5 C6 -179.38(15) no N3 C4 C5 C6 0.2(2) no C4 C5 C51 O51 -2.9(2) no C6 C5 C51 O51 179.03(15) no C4 C5 C51 C52 175.76(19) no C6 C5 C51 C52 -2.3(3) no C2 N1 C6 O6 179.79(15) no C1 N1 C6 O6 0.7(2) no C2 N1 C6 C5 -1.0(2) no C1 N1 C6 C5 179.91(15) no C51 C5 C6 O6 -4.2(3) no C4 C5 C6 O6 177.80(15) no C51 C5 C6 N1 176.61(14) no C4 C5 C6 N1 -1.4(2) no _cod_database_fobs_code 2014731 _journal_paper_doi 10.1107/S0108270104028859