Electronic Supplementary Material for CrystEngComm This Journal is © The Royal Society of Chemistry 2005 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Prof S Price' _publ_contact_author_address ; Dept of Chemistry University College London 20 Gordon Street LONDON WC1H 0AJ UNITED KINGDOM ; _publ_contact_author_email S.L.PRICE@UCL.AC.UK _publ_section_title ; Computational prediction and X-ray determination of the crystal structures of 3-oxauracil and 5-hydroxyuracil - an informal blind test. ; loop_ _publ_author_name 'S. Price' 'Royston C. B. Copley' 'Lucie S. Deprez' 'Thomas Lewis' data_3oxauracil _database_code_depnum_ccdc_archive 'CCDC 267948' _audit_creation_method SHELXL-97 _chemical_name_common 3-Oxauracil _chemical_melting_point ? _chemical_formula_moiety 'C4 H3 N O3' _chemical_formula_sum 'C4 H3 N O3' _chemical_formula_weight 113.07 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 7.7407(2) _cell_length_b 5.54050(10) _cell_length_c 10.4926(2) _cell_angle_alpha 90.00 _cell_angle_beta 103.6430(10) _cell_angle_gamma 90.00 _cell_volume 437.303(16) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.717 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 232 _exptl_absorpt_coefficient_mu 1.323 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3872 _diffrn_reflns_av_R_equivalents 0.0200 _diffrn_reflns_av_sigmaI/netI 0.0177 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 5.88 _diffrn_reflns_theta_max 72.48 _reflns_number_total 852 _reflns_number_gt 783 _reflns_threshold_expression >2sigma(I) _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0475P)^2^+0.1476P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 852 _refine_ls_number_parameters 77 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0324 _refine_ls_R_factor_gt 0.0299 _refine_ls_wR_factor_ref 0.0849 _refine_ls_wR_factor_gt 0.0822 _refine_ls_goodness_of_fit_ref 1.067 _refine_ls_restrained_S_all 1.067 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.34147(14) 0.28064(19) 0.48351(10) 0.0220(3) Uani 1 1 d . . . H1 H 0.400(2) 0.186(3) 0.5452(19) 0.040(5) Uiso 1 1 d . . . C2 C 0.34752(15) 0.2136(2) 0.36019(11) 0.0196(3) Uani 1 1 d . . . O3 O 0.25732(10) 0.35568(15) 0.26087(8) 0.0206(3) Uani 1 1 d . . . C4 C 0.15709(15) 0.5601(2) 0.27810(11) 0.0200(3) Uani 1 1 d . . . C5 C 0.16533(16) 0.6255(2) 0.41136(12) 0.0205(3) Uani 1 1 d . . . H5 H 0.1082 0.7679 0.4308 0.025 Uiso 1 1 calc R . . C6 C 0.25421(15) 0.4843(2) 0.50823(11) 0.0211(3) Uani 1 1 d . . . H6 H 0.2569 0.5262 0.5965 0.025 Uiso 1 1 calc R . . O7 O 0.42643(12) 0.03986(17) 0.33256(8) 0.0271(3) Uani 1 1 d . . . O8 O 0.07715(12) 0.65607(17) 0.17900(9) 0.0281(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0249(5) 0.0237(5) 0.0166(5) 0.0032(4) 0.0031(4) 0.0031(4) C2 0.0182(5) 0.0213(6) 0.0190(6) 0.0013(5) 0.0037(4) -0.0007(4) O3 0.0225(4) 0.0241(5) 0.0159(4) 0.0017(3) 0.0060(3) 0.0031(3) C4 0.0196(5) 0.0199(6) 0.0214(6) 0.0024(4) 0.0067(5) -0.0010(5) C5 0.0223(5) 0.0186(6) 0.0221(6) -0.0001(4) 0.0082(5) 0.0000(4) C6 0.0234(6) 0.0227(6) 0.0181(6) -0.0018(5) 0.0064(5) -0.0030(5) O7 0.0303(5) 0.0270(5) 0.0238(5) -0.0013(4) 0.0058(4) 0.0083(4) O8 0.0328(5) 0.0300(5) 0.0209(5) 0.0074(4) 0.0053(4) 0.0068(4) _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_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C2 1.3576(16) . yes N1 C6 1.3709(16) . yes N1 H1 0.87(2) . ? C2 O7 1.2115(15) . yes C2 O3 1.3600(14) . yes O3 C4 1.4085(14) . yes C4 O8 1.2013(15) . yes C4 C5 1.4312(17) . yes C5 C6 1.3373(17) . yes C5 H5 0.9500 . ? C6 H6 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 N1 C6 122.32(10) . . yes C2 N1 H1 114.3(12) . . ? C6 N1 H1 123.4(12) . . ? O7 C2 N1 125.32(11) . . yes O7 C2 O3 118.24(10) . . yes N1 C2 O3 116.44(10) . . yes C2 O3 C4 124.46(9) . . yes O8 C4 O3 115.57(11) . . yes O8 C4 C5 128.96(12) . . yes O3 C4 C5 115.46(10) . . yes C6 C5 C4 119.40(11) . . yes C6 C5 H5 120.3 . . ? C4 C5 H5 120.3 . . ? C5 C6 N1 121.72(11) . . yes C5 C6 H6 119.1 . . ? N1 C6 H6 119.1 . . ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 N1 C2 O7 177.83(11) . . . . yes C6 N1 C2 O3 -1.97(17) . . . . yes O7 C2 O3 C4 178.68(10) . . . . yes N1 C2 O3 C4 -1.50(16) . . . . yes C2 O3 C4 O8 -175.64(10) . . . . yes C2 O3 C4 C5 4.66(16) . . . . yes O8 C4 C5 C6 175.82(12) . . . . yes O3 C4 C5 C6 -4.52(16) . . . . yes C4 C5 C6 N1 1.51(18) . . . . yes C2 N1 C6 C5 1.96(18) . . . . yes 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_site_symmetry_A N1 H1 O7 0.87(2) 2.05(2) 2.9103(14) 168.9(17) 3_656 C6 H6 O7 0.95 2.54 3.3520(14) 143.4 4_566 C6 H6 O8 0.95 2.52 3.1965(15) 128.2 4_576 _diffrn_measured_fraction_theta_max 0.978 _diffrn_reflns_theta_full 72.48 _diffrn_measured_fraction_theta_full 0.978 _refine_diff_density_max 0.240 _refine_diff_density_min -0.172 _refine_diff_density_rms 0.043 _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/c' _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.7771 _exptl_absorpt_correction_T_max 0.9503 loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 1.00 0.00 0.00 0.0200 -1.00 0.00 0.00 0.0200 1.00 0.00 -2.00 0.0800 -1.00 0.00 2.00 0.0800 0.00 1.00 0.00 0.1100 0.00 -1.00 0.00 0.1100 _exptl_crystal_description plate _exptl_crystal_colour colourless _chemical_name_systematic ; 3-Oxauracil ; _computing_data_merging 'SHELXTL V6.10 UNIX (Bruker, 2001)' _computing_structure_solution 'SHELXTL V6.10 UNIX (Bruker, 2001)' _computing_structure_refinement 'SHELXTL V6.10 UNIX (Bruker, 2001)' _computing_molecular_graphics 'SHELXTL V5.10 UNIX (Bruker, 1997)' _computing_publication_material 'SHELXTL V6.10 UNIX (Bruker, 2001)' _atom_sites_solution_primary direct _atom_sites_solution_secondary ? _atom_sites_solution_hydrogens mixed _refine_ls_hydrogen_treatment mixed _computing_data_collection 'SMART V5.604 [NT] (Bruker, 2000)' _computing_cell_refinement 'SMART V5.604 [NT] (Bruker, 2000)' _computing_data_reduction 'SAINT+ V6.02A [NT] (Bruker, 1999)' _diffrn_measurement_device_type 'Bruker AXS SMART 6000' _diffrn_measurement_method \w _diffrn_radiation_collimation '0.8 mm double-pinhole' _diffrn_radiation_monochromator 'graphite - parallel geometry' _diffrn_radiation_source 'normal focus sealed tube' #===END data_3oxauracilmonohydrate _database_code_depnum_ccdc_archive 'CCDC 267949' _audit_creation_method SHELXL-97 _chemical_name_common '3-Oxauracil monohydrate' _chemical_melting_point ? _chemical_formula_moiety 'C4 H3 N O3, H2 O' _chemical_formula_sum 'C4 H5 N O4' _chemical_formula_weight 131.09 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z' 'x+1/2, -y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z' '-x-1/2, y-1/2, z-1/2' _cell_length_a 14.4737(3) _cell_length_b 6.00300(10) _cell_length_c 6.36260(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 552.818(17) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.575 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 272 _exptl_absorpt_coefficient_mu 1.268 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4664 _diffrn_reflns_av_R_equivalents 0.0150 _diffrn_reflns_av_sigmaI/netI 0.0088 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 6 _diffrn_reflns_theta_min 6.11 _diffrn_reflns_theta_max 72.78 _reflns_number_total 596 _reflns_number_gt 593 _reflns_threshold_expression >2sigma(I) _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0620P)^2^+0.0637P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 596 _refine_ls_number_parameters 70 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0298 _refine_ls_R_factor_gt 0.0298 _refine_ls_wR_factor_ref 0.0819 _refine_ls_wR_factor_gt 0.0818 _refine_ls_goodness_of_fit_ref 1.083 _refine_ls_restrained_S_all 1.083 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.29810(7) 0.2500 0.12634(17) 0.0220(3) Uani 1 2 d S . . H1 H 0.2563(14) 0.2500 0.035(3) 0.032(4) Uiso 1 2 d S . . C2 C 0.26795(8) 0.2500 0.32735(19) 0.0215(3) Uani 1 2 d S . . O3 O 0.33353(5) 0.2500 0.48092(13) 0.0220(3) Uani 1 2 d S . . C4 C 0.42863(8) 0.2500 0.4419(2) 0.0224(3) Uani 1 2 d S . . C5 C 0.45590(8) 0.2500 0.2256(2) 0.0247(3) Uani 1 2 d S . . H5 H 0.5195(13) 0.2500 0.198(3) 0.028(4) Uiso 1 2 d S . . C6 C 0.39028(9) 0.2500 0.0766(2) 0.0237(3) Uani 1 2 d S . . H6 H 0.4014(13) 0.2500 -0.073(3) 0.033(5) Uiso 1 2 d S . . O7 O 0.18733(6) 0.2500 0.37884(15) 0.0295(3) Uani 1 2 d S . . O8 O 0.47658(6) 0.2500 0.59703(15) 0.0286(3) Uani 1 2 d S . . O9 O 0.16617(7) 0.2500 0.82028(15) 0.0272(3) Uani 1 2 d S . . H9A H 0.1712(14) 0.2500 0.673(4) 0.049(6) Uiso 1 2 d S . . H9B H 0.1061(18) 0.2500 0.848(3) 0.048(6) Uiso 1 2 d S . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0213(6) 0.0287(6) 0.0162(6) 0.000 -0.0025(4) 0.000 C2 0.0194(6) 0.0258(6) 0.0193(6) 0.000 0.0000(4) 0.000 O3 0.0192(5) 0.0320(5) 0.0149(5) 0.000 0.0004(3) 0.000 C4 0.0187(6) 0.0257(6) 0.0227(7) 0.000 -0.0003(5) 0.000 C5 0.0201(6) 0.0328(7) 0.0214(7) 0.000 0.0023(5) 0.000 C6 0.0251(7) 0.0280(6) 0.0182(6) 0.000 0.0044(5) 0.000 O7 0.0191(5) 0.0472(6) 0.0221(5) 0.000 -0.0007(3) 0.000 O8 0.0213(5) 0.0436(6) 0.0209(5) 0.000 -0.0033(3) 0.000 O9 0.0205(5) 0.0414(6) 0.0196(5) 0.000 -0.0010(3) 0.000 _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_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C2 1.3513(16) . yes N1 C6 1.3713(16) . yes N1 H1 0.84(2) . ? C2 O7 1.2121(15) . yes C2 O3 1.3622(14) . yes O3 C4 1.3986(14) . yes C4 O8 1.2065(16) . yes C4 C5 1.4321(19) . yes C5 C6 1.3418(19) . yes C5 H5 0.936(18) . ? C6 H6 0.97(2) . ? O9 H9A 0.94(2) . ? O9 H9B 0.89(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 N1 C6 122.18(11) . . yes C2 N1 H1 115.1(14) . . ? C6 N1 H1 122.7(14) . . ? O7 C2 N1 124.52(12) . . yes O7 C2 O3 118.49(11) . . yes N1 C2 O3 117.00(10) . . yes C2 O3 C4 123.95(9) . . yes O8 C4 O3 114.90(11) . . yes O8 C4 C5 128.88(11) . . yes O3 C4 C5 116.22(11) . . yes C6 C5 C4 118.94(11) . . yes C6 C5 H5 124.3(12) . . ? C4 C5 H5 116.8(12) . . ? C5 C6 N1 121.71(12) . . yes C5 C6 H6 125.4(11) . . ? N1 C6 H6 112.9(12) . . ? H9A O9 H9B 105.7(19) . . ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 N1 C2 O7 180.0 . . . . yes C6 N1 C2 O3 0.0 . . . . yes O7 C2 O3 C4 180.0 . . . . yes N1 C2 O3 C4 0.0 . . . . yes C2 O3 C4 O8 180.0 . . . . yes C2 O3 C4 C5 0.0 . . . . yes O8 C4 C5 C6 180.0 . . . . yes O3 C4 C5 C6 0.0 . . . . yes C4 C5 C6 N1 0.0 . . . . yes C2 N1 C6 C5 0.0 . . . . yes 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_site_symmetry_A N1 H1 O9 0.84(2) 1.89(2) 2.7273(14) 178(2) 1_554 O9 H9A O7 0.94(2) 1.88(2) 2.8253(14) 177.3(19) . O9 H9B O8 0.89(3) 1.91(3) 2.7940(14) 179(2) 6_557 C5 H5 O7 0.936(18) 2.478(18) 3.4149(15) 179.4(16) 6_656 C6 H6 O8 0.97(2) 2.36(2) 3.2970(16) 162.2(16) 1_554 _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 72.78 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.228 _refine_diff_density_min -0.206 _refine_diff_density_rms 0.044 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P n m a' _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.6821 _exptl_absorpt_correction_T_max 0.8639 loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0.00 1.00 0.00 0.0600 0.00 -1.00 0.00 0.0600 0.00 0.00 1.00 0.0900 0.00 0.00 -1.00 0.0900 1.00 0.00 0.00 0.2100 -1.00 0.00 0.00 0.2100 _exptl_crystal_description block _exptl_crystal_colour colourless _chemical_name_systematic ; 3-Oxauracil monohydrate ; _computing_data_merging 'SHELXTL V6.10 UNIX (Bruker, 2001)' _computing_structure_solution 'SHELXTL V6.10 UNIX (Bruker, 2001)' _computing_structure_refinement 'SHELXTL V6.10 UNIX (Bruker, 2001)' _computing_molecular_graphics 'SHELXTL V5.10 UNIX (Bruker, 1997)' _computing_publication_material 'SHELXTL V6.10 UNIX (Bruker, 2001)' _atom_sites_solution_primary direct _atom_sites_solution_secondary ? _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _computing_data_collection 'SMART V5.604 [NT] (Bruker, 2000)' _computing_cell_refinement 'SMART V5.604 [NT] (Bruker, 2000)' _computing_data_reduction 'SAINT+ V6.02A [NT] (Bruker, 1999)' _diffrn_measurement_device_type 'Bruker AXS SMART 6000' _diffrn_measurement_method \w _diffrn_radiation_collimation '0.8 mm double-pinhole' _diffrn_radiation_monochromator 'graphite - parallel geometry' _diffrn_radiation_source 'normal focus sealed tube' #===END data_5hydroxyuracil _database_code_depnum_ccdc_archive 'CCDC 267950' _audit_creation_method SHELXL-97 _chemical_name_common 5-hydroxy-2,4(1H,3H)pyrimidinedione _chemical_melting_point ? _chemical_formula_moiety 'C4 H4 N2 O3' _chemical_formula_sum 'C4 H4 N2 O3' _chemical_formula_weight 128.09 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 4.61950(10) _cell_length_b 7.04930(10) _cell_length_c 7.3452(2) _cell_angle_alpha 88.1690(10) _cell_angle_beta 81.5040(10) _cell_angle_gamma 86.2450(10) _cell_volume 235.998(9) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _exptl_crystal_size_max 0.11 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.803 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 132 _exptl_absorpt_coefficient_mu 1.373 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3677 _diffrn_reflns_av_R_equivalents 0.0157 _diffrn_reflns_av_sigmaI/netI 0.0126 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 6.09 _diffrn_reflns_theta_max 72.56 _reflns_number_total 902 _reflns_number_gt 788 _reflns_threshold_expression >2sigma(I) _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0920P)^2^+0.0243P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 902 _refine_ls_number_parameters 94 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0463 _refine_ls_R_factor_gt 0.0409 _refine_ls_wR_factor_ref 0.1236 _refine_ls_wR_factor_gt 0.1193 _refine_ls_goodness_of_fit_ref 1.069 _refine_ls_restrained_S_all 1.069 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.3091(3) 0.07643(19) 0.33662(18) 0.0210(4) Uani 1 1 d D . . H1 H 0.225(4) -0.030(2) 0.373(3) 0.027(5) Uiso 1 1 d D . . C2 C 0.1840(3) 0.2428(2) 0.4025(2) 0.0199(4) Uani 1 1 d . . . N3 N 0.3209(3) 0.40227(17) 0.33474(17) 0.0201(4) Uani 1 1 d D . . H3 H 0.234(4) 0.505(2) 0.382(3) 0.030(5) Uiso 1 1 d D . . C4 C 0.5706(3) 0.4055(2) 0.2063(2) 0.0203(4) Uani 1 1 d . . . C5 C 0.6837(3) 0.2213(2) 0.1356(2) 0.0225(4) Uani 1 1 d . . . C6 C 0.5548(3) 0.0636(2) 0.2043(2) 0.0212(4) Uani 1 1 d . . . H6 H 0.6332 -0.0576 0.1615 0.025 Uiso 1 1 calc R . . O7 O -0.0434(2) 0.25430(15) 0.51771(15) 0.0239(3) Uani 1 1 d . . . O8 O 0.6848(3) 0.55421(17) 0.15938(17) 0.0283(4) Uani 1 1 d . . . O9 O 0.9196(3) 0.21100(17) 0.00291(19) 0.0325(4) Uani 1 1 d D . . H9 H 0.965(4) 0.3233(16) -0.011(3) 0.024(5) Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0208(7) 0.0210(6) 0.0201(7) -0.0003(5) 0.0020(5) -0.0038(5) C2 0.0188(7) 0.0242(8) 0.0164(8) -0.0011(6) -0.0015(6) -0.0026(6) N3 0.0186(7) 0.0201(7) 0.0203(7) -0.0031(5) 0.0024(5) -0.0022(5) C4 0.0176(8) 0.0248(8) 0.0184(8) 0.0005(6) -0.0014(6) -0.0033(6) C5 0.0176(7) 0.0285(8) 0.0199(8) -0.0007(6) 0.0015(6) -0.0002(6) C6 0.0200(8) 0.0220(8) 0.0204(8) -0.0023(6) 0.0000(6) 0.0010(6) O7 0.0227(6) 0.0235(6) 0.0228(6) -0.0026(4) 0.0075(4) -0.0045(4) O8 0.0255(6) 0.0256(6) 0.0320(7) 0.0004(5) 0.0036(5) -0.0059(4) O9 0.0274(7) 0.0251(7) 0.0390(8) -0.0004(5) 0.0158(5) -0.0024(5) _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_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C2 1.345(2) . yes N1 C6 1.381(2) . yes N1 H1 0.884(10) . ? C2 O7 1.2477(19) . yes C2 N3 1.3696(19) . yes N3 C4 1.3788(19) . yes N3 H3 0.863(10) . ? C4 O8 1.221(2) . yes C4 C5 1.450(2) . yes C5 C6 1.345(2) . yes C5 O9 1.3501(19) . yes C6 H6 0.9500 . ? O9 H9 0.832(10) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 N1 C6 123.15(13) . . yes C2 N1 H1 119.1(14) . . ? C6 N1 H1 117.6(13) . . ? O7 C2 N1 122.99(14) . . yes O7 C2 N3 121.13(13) . . yes N1 C2 N3 115.88(13) . . yes C2 N3 C4 125.75(13) . . yes C2 N3 H3 112.5(15) . . ? C4 N3 H3 121.8(15) . . ? O8 C4 N3 121.22(14) . . yes O8 C4 C5 123.82(15) . . yes N3 C4 C5 114.96(14) . . yes C6 C5 O9 121.04(14) . . yes C6 C5 C4 119.66(15) . . yes O9 C5 C4 119.29(15) . . yes C5 C6 N1 120.48(14) . . yes C5 C6 H6 119.8 . . ? N1 C6 H6 119.8 . . ? C5 O9 H9 103.1(14) . . ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 N1 C2 O7 177.62(13) . . . . yes C6 N1 C2 N3 -2.1(2) . . . . yes O7 C2 N3 C4 -179.36(13) . . . . yes N1 C2 N3 C4 0.4(2) . . . . yes C2 N3 C4 O8 -176.93(14) . . . . yes C2 N3 C4 C5 2.5(2) . . . . yes O8 C4 C5 C6 175.57(15) . . . . yes N3 C4 C5 C6 -3.8(2) . . . . yes O8 C4 C5 O9 -3.7(2) . . . . yes N3 C4 C5 O9 176.92(12) . . . . yes O9 C5 C6 N1 -178.34(13) . . . . yes C4 C5 C6 N1 2.4(2) . . . . yes C2 N1 C6 C5 0.7(2) . . . . yes 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_site_symmetry_A N1 H1 O7 0.884(10) 1.934(10) 2.8132(18) 173.3(18) 2_556 N3 H3 O7 0.863(10) 1.971(10) 2.8336(17) 178(2) 2_566 O9 H9 O8 0.832(10) 2.037(16) 2.6696(17) 132.3(17) 2_765 O9 H9 O8 0.832(10) 2.294(18) 2.7959(16) 119.2(16) . C6 H6 O9 0.95 2.44 3.231(2) 140.7 2_755 _diffrn_measured_fraction_theta_max 0.966 _diffrn_reflns_theta_full 72.56 _diffrn_measured_fraction_theta_full 0.966 _refine_diff_density_max 0.597 _refine_diff_density_min -0.228 _refine_diff_density_rms 0.062 _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.8538 _exptl_absorpt_correction_T_max 0.9556 loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0.00 -1.00 -1.00 0.0200 0.00 1.00 1.00 0.0200 0.00 0.00 -1.00 0.0350 0.00 0.00 1.00 0.0350 1.00 0.00 2.00 0.0400 -1.00 0.00 0.00 0.0700 _exptl_crystal_description blade _exptl_crystal_colour colourless _chemical_name_systematic ; 5-hydroxy-2,4(1H,3H)pyrimidinedione ; _computing_data_merging 'SHELXTL V6.10 UNIX (Bruker, 2001)' _computing_structure_solution 'SHELXTL V6.10 UNIX (Bruker, 2001)' _computing_structure_refinement 'SHELXTL V6.10 UNIX (Bruker, 2001)' _computing_molecular_graphics 'SHELXTL V5.10 UNIX (Bruker, 1997)' _computing_publication_material 'SHELXTL V6.10 UNIX (Bruker, 2001)' _atom_sites_solution_primary direct _atom_sites_solution_secondary ? _atom_sites_solution_hydrogens mixed _refine_ls_hydrogen_treatment mixed _computing_data_collection 'SMART V5.604 [NT] (Bruker, 2000)' _computing_cell_refinement 'SMART V5.604 [NT] (Bruker, 2000)' _computing_data_reduction 'SAINT+ V6.02A [NT] (Bruker, 1999)' _diffrn_measurement_device_type 'Bruker AXS SMART 6000' _diffrn_measurement_method \w _diffrn_radiation_collimation '0.8 mm double-pinhole' _diffrn_radiation_monochromator 'graphite - parallel geometry' _diffrn_radiation_source 'normal focus sealed tube' #===END