data_6-umpa _database_code_CSD 167669 _publ_contact_author_name 'Prof. Helmut Sigel' _publ_contact_author_address ; Institute of Inorganic Chemistry University of Basel Spitalstrasse 51 CH-4056 Basel Switzerland ; _publ_contact_author_email 'Helmut.Sigel@unibas.ch' _publ_contact_author_fax '(++41)-61-267 1017' _publ_contact_author_phone '(++41)-61-267 1007' _publ_contact_letter ? _journal_coden_Cambridge 188 _publ_requested_journal 'J. Chem. Soc., Perkin Trans.' _publ_title ; Comparison of the acid-base properties of 5- and 6-uracilmethylphosphonate (5Umpa(2-) and 6Umpa(2-)) and some related compounds. Evidence for intramolecular hydrogen-bond formation in aqueous solution between (N1)H and the phosphonate group of 6Umpa(2-) ; loop_ _publ_author_name 'Freisinger, Eva' 'Griesser, Rolf' 'Lippert, B.' 'Moreno-Luque, Cristobal F.' 'Ochocki, Justyn' 'Sigel, H.' _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural '6-Uracilmethylphosphonsaure' _chemical_formula_analytical ? _chemical_formula_sum 'C5 H7 N2 O5 P' _chemical_formula_weight 206.10 _chemical_melting_point ? _chemical_compound_source ? 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' 'P' 'P' 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/n 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' _cell_length_a 5.3870(10) _cell_length_b 7.948(2) _cell_length_c 18.060(4) _cell_angle_alpha 90.00 _cell_angle_beta 93.36(3) _cell_angle_gamma 90.00 _cell_volume 771.9(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2598 _cell_measurement_theta_min 4.58 _cell_measurement_theta_max 25.69 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.38 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.773 _exptl_crystal_density_method ? _exptl_crystal_F_000 424 _exptl_absorpt_coefficient_mu 0.349 _exptl_absorpt_correction_type SCALEPACK _exptl_absorpt_correction_T_min 0.8616 _exptl_absorpt_correction_T_max 0.8788 _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Enraf-Nonius-KappaCCD' _diffrn_measurement_method ; 360 frames via \w-rotation (\D\w\=1\%) and two times 45s per frame ; _diffrn_detector_area_resol_mean '19 vertical, 18 horizontal' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2598 _diffrn_reflns_av_R_equivalents 0.034 _diffrn_reflns_av_sigmaI/netI 0.0552 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 4.58 _diffrn_reflns_theta_max 25.69 _reflns_number_total 1467 _reflns_number_observed 974 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'KappaCCD (Nonius BV, Netherlands)' _computing_cell_refinement 'DENZO, SCALEPACK (Otwinowski, Minor, 1997)' _computing_data_reduction 'DENZO, SCALEPACK (Otwinowski, Minor, 1997)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'Siemens SHELXTL-PLUS(VMS)' _computing_publication_material 'SHELXL-93' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 4 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0487P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment 'refall, final cycles noref to save parameter' _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1463 _refine_ls_number_parameters 119 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0660 _refine_ls_R_factor_obs 0.0360 _refine_ls_wR_factor_all 0.0951 _refine_ls_wR_factor_obs 0.0801 _refine_ls_goodness_of_fit_all 0.925 _refine_ls_goodness_of_fit_obs 1.057 _refine_ls_restrained_S_all 1.003 _refine_ls_restrained_S_obs 1.057 _refine_ls_shift/esd_max -0.001 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group P1 P 0.06620(11) 0.55311(7) 0.75674(3) 0.0394(2) Uani 1 d . . C11 C -0.0377(4) 0.5415(3) 0.84969(13) 0.0445(6) Uani 1 d . . H11A H 0.0308 0.6367 0.8750 0.057 Uiso 1 d . . H11B H -0.2152 0.5464 0.8446 0.057 Uiso 1 d . . O12 O 0.3491(3) 0.5215(2) 0.76269(9) 0.0486(4) Uani 1 d . . H12 H 0.3811 0.4234 0.7663 0.057 Uiso 1 d . . O13 O -0.0516(3) 0.4039(2) 0.71327(9) 0.0509(5) Uani 1 d . . H13 H -0.1726 0.4294 0.6858 0.057 Uiso 1 d . . O14 O 0.0028(3) 0.7187(2) 0.72237(9) 0.0451(4) Uani 1 d . . N1 N -0.0624(3) 0.2388(2) 0.87204(10) 0.0418(5) Uani 1 d . . H1 H -0.2005 0.2402 0.8426 0.057 Uiso 1 d . . C2 C 0.0156(4) 0.0875(3) 0.89970(12) 0.0404(6) Uani 1 d . . O2 O -0.0938(3) -0.0461(2) 0.88565(9) 0.0496(4) Uani 1 d . . N3 N 0.2282(4) 0.0905(2) 0.94453(10) 0.0452(5) Uani 1 d . . H3 H 0.2879 -0.0079 0.9584 0.057 Uiso 1 d . . C4 C 0.3588(5) 0.2335(3) 0.96621(13) 0.0463(6) Uani 1 d . . O4 O 0.5518(3) 0.2202(2) 1.00705(9) 0.0607(5) Uani 1 d . . C5 C 0.2588(4) 0.3874(3) 0.93700(12) 0.0440(6) Uani 1 d . . H5 H 0.3390 0.4916 0.9465 0.057 Uiso 1 d . . C6 C 0.0572(4) 0.3874(3) 0.88988(12) 0.0383(5) Uani 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 P1 0.0383(4) 0.0285(3) 0.0502(4) 0.0039(3) -0.0085(3) 0.0003(3) C11 0.0437(14) 0.0334(12) 0.0550(15) -0.0028(11) -0.0090(11) 0.0027(10) O12 0.0410(9) 0.0337(9) 0.0703(11) 0.0028(8) -0.0036(8) 0.0012(7) O13 0.0579(11) 0.0336(9) 0.0583(10) 0.0009(7) -0.0210(8) -0.0016(7) O14 0.0450(9) 0.0286(9) 0.0599(10) 0.0060(7) -0.0112(7) -0.0008(7) N1 0.0420(11) 0.0357(11) 0.0460(11) 0.0032(9) -0.0123(9) -0.0013(8) C2 0.0457(15) 0.0380(14) 0.0366(12) 0.0031(10) -0.0064(11) -0.0031(10) O2 0.0565(10) 0.0353(9) 0.0546(10) 0.0051(8) -0.0161(8) -0.0097(8) N3 0.0509(12) 0.0352(11) 0.0474(11) 0.0052(9) -0.0151(10) -0.0042(9) C4 0.051(2) 0.0405(14) 0.0457(14) 0.0051(11) -0.0083(12) -0.0071(11) O4 0.0625(12) 0.0455(10) 0.0697(12) 0.0102(9) -0.0345(10) -0.0078(8) C5 0.051(2) 0.0344(12) 0.0451(13) 0.0006(11) -0.0134(12) -0.0064(11) C6 0.0432(14) 0.0312(12) 0.0400(13) -0.0002(10) -0.0027(11) -0.0024(10) _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 P1 O14 1.4864(15) . ? P1 O13 1.539(2) . ? P1 O12 1.542(2) . ? P1 C11 1.803(2) . ? C11 C6 1.498(3) . ? C11 H11A 0.948(2) . ? C11 H11B 0.956(2) . ? O12 H12 0.8006(15) . ? O13 H13 0.8218(15) . ? N1 C2 1.359(3) . ? N1 C6 1.375(3) . ? N1 H1 0.889(2) . ? C2 O2 1.234(2) . ? C2 N3 1.363(3) . ? N3 C4 1.381(3) . ? N3 H3 0.876(2) . ? C4 O4 1.243(3) . ? C4 C5 1.426(3) . ? C5 C6 1.340(3) . ? C5 H5 0.945(2) . ? 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 O14 P1 O13 113.06(9) . . ? O14 P1 O12 112.04(9) . . ? O13 P1 O12 106.64(9) . . ? O14 P1 C11 110.98(10) . . ? O13 P1 C11 107.12(10) . . ? O12 P1 C11 106.63(10) . . ? C6 C11 P1 112.2(2) . . ? C6 C11 H11A 107.8(2) . . ? P1 C11 H11A 106.0(2) . . ? C6 C11 H11B 113.0(2) . . ? P1 C11 H11B 105.8(2) . . ? H11A C11 H11B 111.9(2) . . ? P1 O12 H12 111.81(14) . . ? P1 O13 H13 114.02(14) . . ? C2 N1 C6 122.9(2) . . ? C2 N1 H1 117.5(2) . . ? C6 N1 H1 119.5(2) . . ? O2 C2 N1 123.5(2) . . ? O2 C2 N3 120.8(2) . . ? N1 C2 N3 115.7(2) . . ? C2 N3 C4 125.4(2) . . ? C2 N3 H3 115.8(2) . . ? C4 N3 H3 118.7(2) . . ? O4 C4 N3 119.5(2) . . ? O4 C4 C5 125.3(2) . . ? N3 C4 C5 115.2(2) . . ? C6 C5 C4 120.6(2) . . ? C6 C5 H5 117.4(2) . . ? C4 C5 H5 121.8(2) . . ? C5 C6 N1 120.0(2) . . ? C5 C6 C11 123.3(2) . . ? N1 C6 C11 116.6(2) . . ? 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 O14 P1 C11 C6 -171.25(14) . . . . ? O13 P1 C11 C6 64.9(2) . . . . ? O12 P1 C11 C6 -49.0(2) . . . . ? C6 N1 C2 O2 178.0(2) . . . . ? C6 N1 C2 N3 -2.6(3) . . . . ? O2 C2 N3 C4 -177.1(2) . . . . ? N1 C2 N3 C4 3.5(3) . . . . ? C2 N3 C4 O4 -179.6(2) . . . . ? C2 N3 C4 C5 -1.1(4) . . . . ? O4 C4 C5 C6 176.1(2) . . . . ? N3 C4 C5 C6 -2.3(3) . . . . ? C4 C5 C6 N1 3.1(4) . . . . ? C4 C5 C6 C11 -171.8(2) . . . . ? C2 N1 C6 C5 -0.6(4) . . . . ? C2 N1 C6 C11 174.7(2) . . . . ? P1 C11 C6 C5 97.4(2) . . . . ? P1 C11 C6 N1 -77.7(2) . . . . ? _refine_diff_density_max 0.180 _refine_diff_density_min -0.244 _refine_diff_density_rms 0.050