# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Dr Michael Andrews' _publ_contact_author_email andrewsm@gwu.edu _publ_section_title ; In situ oxalate formation during hydrothermal synthesis of uranyl hybrid materials ; loop_ _publ_author_name M.Andrews C.Cahill # Attachment '- Combined.cif' data_compound1 _database_code_depnum_ccdc_archive 'CCDC 835692' #TrackingRef '- Combined.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C6 H4 N O6 U' _chemical_formula_weight 424.13 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' 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' U U -9.6767 9.6646 '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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/c 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 10.4417(3) _cell_length_b 7.8434(3) _cell_length_c 12.2703(4) _cell_angle_alpha 90.00 _cell_angle_beta 111.1640(10) _cell_angle_gamma 90.00 _cell_volume 937.14(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description yellow _exptl_crystal_colour block _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 3.006 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 748 _exptl_absorpt_coefficient_mu 17.323 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.351 _exptl_absorpt_correction_T_max 0.746 _exptl_absorpt_process_details 'SADABS, Sheldrick (2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX II CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17373 _diffrn_reflns_av_R_equivalents 0.0400 _diffrn_reflns_av_sigmaI/netI 0.0268 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.09 _diffrn_reflns_theta_max 31.32 _reflns_number_total 2688 _reflns_number_gt 2324 _reflns_threshold_expression >2\s(I) _computing_data_collection 'APEX II (Bruker AXS, 2005)' _computing_cell_refinement 'SAINTPLUS (Bruker AXS, 2005)' _computing_data_reduction 'SAINTPLUS (Bruker AXS, 2005)' _computing_structure_solution 'SIR92 (Gualardi, 1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Crystal Maker (Palmer 2009)' _computing_publication_material 'WINGX (Farrugia, 1998)' _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^ > 2\s(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^)+(0.0303P)^2^+0.3017P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2688 _refine_ls_number_parameters 136 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0278 _refine_ls_R_factor_gt 0.0213 _refine_ls_wR_factor_ref 0.0540 _refine_ls_wR_factor_gt 0.0512 _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_restrained_S_all 1.044 _refine_ls_shift/su_max 0.002 _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 O3 O 0.5469(3) 0.7003(3) 0.9659(3) 0.0349(7) Uani 1 1 d . . . O6 O 0.6723(3) 0.8301(4) 1.2118(3) 0.0388(7) Uani 1 1 d . . . O4 O 0.3641(2) 0.5386(4) 0.8713(2) 0.0383(7) Uani 1 1 d . . . O5 O 0.8472(3) 0.6219(4) 1.0538(3) 0.0393(7) Uani 1 1 d . . . C7 C 0.4743(3) 0.5686(5) 0.9530(3) 0.0281(8) Uani 1 1 d . . . O2 O 0.9029(2) 0.6018(3) 1.3084(2) 0.0313(6) Uani 1 1 d . . . U1 U 0.760241(12) 0.723719(18) 1.133716(11) 0.02429(6) Uani 1 1 d . . . N1 N 0.7544(3) 0.9974(4) 1.0157(3) 0.0277(6) Uani 1 1 d . . . O1 O 0.9543(3) 0.9039(4) 1.2105(2) 0.0396(7) Uani 1 1 d . . . C6 C 0.9815(3) 1.0288(5) 1.1586(3) 0.0273(7) Uani 1 1 d . . . C5 C 0.8706(3) 1.0933(5) 1.0518(3) 0.0264(7) Uani 1 1 d . . . C4 C 0.8849(4) 1.2404(5) 0.9967(4) 0.0318(8) Uani 1 1 d . . . H4 H 0.9663 1.3024 1.0241 0.038 Uiso 1 1 calc R . . C3 C 0.7760(5) 1.2949(5) 0.8993(4) 0.0366(9) Uani 1 1 d . . . H3 H 0.7823 1.3946 0.8605 0.044 Uiso 1 1 calc R . . C2 C 0.6574(4) 1.1970(5) 0.8612(4) 0.0343(9) Uani 1 1 d . . . H2 H 0.5830 1.2298 0.7957 0.041 Uiso 1 1 calc R . . C1 C 0.6505(4) 1.0510(5) 0.9209(3) 0.0329(8) Uani 1 1 d . . . H1 H 0.5702 0.9868 0.8944 0.039 Uiso 1 1 calc R . . 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 O3 0.0320(15) 0.0294(16) 0.0337(15) 0.0079(11) 0.0002(12) -0.0131(11) O6 0.0297(14) 0.0433(18) 0.0402(17) -0.0047(13) 0.0086(12) 0.0084(13) O4 0.0306(13) 0.0398(17) 0.0310(15) 0.0092(12) -0.0052(11) -0.0151(12) O5 0.0396(15) 0.0331(16) 0.0484(17) -0.0041(13) 0.0198(13) -0.0007(12) C7 0.0248(16) 0.030(2) 0.0265(18) 0.0037(15) 0.0056(14) -0.0050(14) O2 0.0220(11) 0.0297(15) 0.0392(15) 0.0062(11) 0.0074(10) 0.0055(10) U1 0.01749(8) 0.02212(9) 0.02968(9) -0.00064(5) 0.00421(5) -0.00262(4) N1 0.0232(14) 0.0254(16) 0.0290(16) 0.0009(12) 0.0028(12) -0.0012(12) O1 0.0308(13) 0.0318(16) 0.0433(16) 0.0093(12) -0.0023(12) -0.0115(11) C6 0.0212(15) 0.0256(18) 0.0316(19) -0.0060(14) 0.0054(14) -0.0009(13) C5 0.0245(16) 0.0244(19) 0.0289(18) -0.0021(14) 0.0080(14) -0.0002(13) C4 0.0295(19) 0.0291(19) 0.037(2) -0.0012(16) 0.0129(17) -0.0041(15) C3 0.044(2) 0.031(2) 0.038(2) 0.0041(16) 0.0173(19) 0.0019(17) C2 0.036(2) 0.035(2) 0.029(2) 0.0044(15) 0.0080(17) 0.0063(16) C1 0.0243(17) 0.034(2) 0.033(2) 0.0009(16) 0.0020(15) -0.0027(15) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 O3 C7 1.258(4) . ? O3 U1 2.434(3) . ? O6 U1 1.759(3) . ? O4 C7 1.245(4) . ? O4 U1 2.422(3) 3_667 ? O5 U1 1.751(3) . ? C7 C7 1.526(7) 3_667 ? O2 C6 1.263(4) 2_747 ? O2 U1 2.329(2) . ? U1 O1 2.369(3) . ? U1 O4 2.422(3) 3_667 ? U1 N1 2.578(3) . ? N1 C1 1.340(4) . ? N1 C5 1.359(4) . ? O1 C6 1.256(4) . ? C6 O2 1.263(4) 2_757 ? C6 C5 1.490(5) . ? C5 C4 1.373(5) . ? C4 C3 1.386(6) . ? C3 C2 1.388(6) . ? C2 C1 1.375(5) . ? 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 C7 O3 U1 119.7(2) . . ? C7 O4 U1 120.8(2) . 3_667 ? O4 C7 O3 126.6(3) . . ? O4 C7 C7 116.5(4) . 3_667 ? O3 C7 C7 116.9(4) . 3_667 ? C6 O2 U1 134.5(2) 2_747 . ? O5 U1 O6 178.64(14) . . ? O5 U1 O2 92.26(11) . . ? O6 U1 O2 88.86(11) . . ? O5 U1 O1 87.27(12) . . ? O6 U1 O1 92.32(12) . . ? O2 U1 O1 73.00(9) . . ? O5 U1 O4 88.88(12) . 3_667 ? O6 U1 O4 92.07(12) . 3_667 ? O2 U1 O4 80.42(9) . 3_667 ? O1 U1 O4 152.95(9) . 3_667 ? O5 U1 O3 89.61(12) . . ? O6 U1 O3 89.88(12) . . ? O2 U1 O3 146.50(8) . . ? O1 U1 O3 140.50(9) . . ? O4 U1 O3 66.17(8) 3_667 . ? O5 U1 N1 88.68(12) . . ? O6 U1 N1 89.97(12) . . ? O2 U1 N1 137.44(9) . . ? O1 U1 N1 64.54(9) . . ? O4 U1 N1 142.14(9) 3_667 . ? O3 U1 N1 76.03(8) . . ? C1 N1 C5 117.2(3) . . ? C1 N1 U1 126.6(2) . . ? C5 N1 U1 116.1(2) . . ? C6 O1 U1 125.6(2) . . ? O1 C6 O2 123.8(3) . 2_757 ? O1 C6 C5 117.7(3) . . ? O2 C6 C5 118.5(3) 2_757 . ? N1 C5 C4 123.2(3) . . ? N1 C5 C6 114.7(3) . . ? C4 C5 C6 122.0(3) . . ? C5 C4 C3 118.8(4) . . ? C2 C3 C4 118.3(4) . . ? C1 C2 C3 119.6(4) . . ? N1 C1 C2 122.8(4) . . ? _diffrn_measured_fraction_theta_max 0.874 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 2.484 _refine_diff_density_min -1.490 _refine_diff_density_rms 0.163 data_cc _database_code_depnum_ccdc_archive 'CCDC 835693' #TrackingRef 'web_deposit_cif_file_1_MichaelAndrews_1311108432.Compound 2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H8 N2 O6 U' _chemical_formula_weight 514.23 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' 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' U U -9.6767 9.6646 '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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M Cc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' 'x+1/2, y+1/2, z' 'x+1/2, -y+1/2, z+1/2' _cell_length_a 8.4634(3) _cell_length_b 13.0284(5) _cell_length_c 11.8917(6) _cell_angle_alpha 90.00 _cell_angle_beta 96.8210(10) _cell_angle_gamma 90.00 _cell_volume 1301.95(9) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.623 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 936 _exptl_absorpt_coefficient_mu 12.497 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.515 _exptl_absorpt_correction_T_max 0.746 _exptl_absorpt_process_details 'SADABS, Sheldrick (2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'phi and omega scans' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12836 _diffrn_reflns_av_R_equivalents 0.0492 _diffrn_reflns_av_sigmaI/netI 0.0594 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.88 _diffrn_reflns_theta_max 30.69 _reflns_number_total 3634 _reflns_number_gt 3190 _reflns_threshold_expression >2\s(I) _computing_data_collection 'APEX II (Bruker AXS, 2008)' _computing_cell_refinement 'SAINTPLUS (Bruker AXS, 2008)' _computing_data_reduction 'SAINTPLUS (Bruker AXS, 2008)' _computing_structure_solution 'SIR92 (Gualardi, 1993)' _computing_structure_refinement 'SHELXL-97(Sheldrick, 2008)' _computing_molecular_graphics 'Crystal Maker (Palmer, 2009)' _computing_publication_material 'WINGX (Farrugia, 1998)' _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^ > 2\s(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^)+(0.0114P)^2^+11.0135P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.067(14) _refine_ls_number_reflns 3634 _refine_ls_number_parameters 190 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0433 _refine_ls_R_factor_gt 0.0341 _refine_ls_wR_factor_ref 0.0754 _refine_ls_wR_factor_gt 0.0721 _refine_ls_goodness_of_fit_ref 1.088 _refine_ls_restrained_S_all 1.088 _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 U1 U 0.27936(8) 0.07960(2) 0.21203(7) 0.02454(8) Uani 1 1 d . . . C6 C 0.4099(10) -0.0390(7) 0.4496(7) 0.0250(18) Uani 1 1 d . . . C5 C 0.5532(10) -0.0567(7) 0.3878(7) 0.0249(18) Uani 1 1 d . . . C1 C 0.6609(11) -0.0340(7) 0.2225(7) 0.0302(19) Uani 1 1 d . . . H8 H 0.6498 -0.0135 0.1471 0.036 Uiso 1 1 calc R . . C2 C 0.8042(12) -0.0773(8) 0.2701(8) 0.039(2) Uani 1 1 d . . . H7 H 0.8902 -0.0817 0.2283 0.047 Uiso 1 1 calc R . . C3 C 0.8171(12) -0.1140(8) 0.3808(8) 0.038(2) Uani 1 1 d . . . H6 H 0.9103 -0.1449 0.4137 0.045 Uiso 1 1 calc R . . C4 C 0.6879(12) -0.1032(8) 0.4401(9) 0.035(2) Uani 1 1 d . . . H5 H 0.6919 -0.1269 0.5141 0.042 Uiso 1 1 calc R . . C7 C 0.0135(13) 0.1382(9) 0.4120(8) 0.042(2) Uani 1 1 d . . . H4 H 0.0867 0.1016 0.4609 0.050 Uiso 1 1 calc R . . C8 C -0.1234(11) 0.1711(8) 0.4517(8) 0.034(2) Uani 1 1 d . . . H3 H -0.1402 0.1595 0.5266 0.041 Uiso 1 1 calc R . . C9 C -0.2366(12) 0.2222(8) 0.3776(9) 0.041(2) Uani 1 1 d . . . H2 H -0.3341 0.2413 0.3999 0.049 Uiso 1 1 calc R . . C10 C -0.2006(12) 0.2431(8) 0.2725(8) 0.038(2) Uani 1 1 d . . . H1 H -0.2746 0.2777 0.2222 0.046 Uiso 1 1 calc R . . C11 C -0.0573(11) 0.2146(8) 0.2373(8) 0.033(2) Uani 1 1 d . . . C12 C -0.0072(11) 0.2365(7) 0.1229(8) 0.033(2) Uani 1 1 d . . . N1 N 0.5389(8) -0.0216(6) 0.2835(6) 0.0228(14) Uani 1 1 d . . . N2 N 0.0476(8) 0.1560(6) 0.3069(6) 0.0245(15) Uani 1 1 d . . . O4 O 0.3988(8) 0.1845(5) 0.2632(6) 0.0338(15) Uani 1 1 d . . . O5 O 0.1590(8) -0.0252(5) 0.1646(5) 0.0352(15) Uani 1 1 d . . . O1 O 0.2931(8) 0.0034(5) 0.3958(5) 0.0345(15) Uani 1 1 d . . . O3 O 0.4161(8) 0.0734(5) 0.0500(5) 0.0348(15) Uani 1 1 d . . . O2 O 0.1128(8) 0.1865(6) 0.0984(6) 0.0414(18) Uani 1 1 d . . . O6 O -0.0821(10) 0.2993(6) 0.0614(6) 0.050(2) 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 U1 0.02179(12) 0.03386(14) 0.01887(11) -0.0003(4) 0.00618(8) 0.0014(4) C6 0.021(4) 0.040(5) 0.014(4) -0.002(3) 0.002(3) -0.007(4) C5 0.023(4) 0.033(5) 0.019(4) -0.001(3) 0.002(3) -0.003(3) C1 0.033(5) 0.039(5) 0.020(4) 0.005(4) 0.011(4) 0.004(4) C2 0.034(5) 0.047(6) 0.041(5) 0.008(5) 0.022(4) 0.021(5) C3 0.033(5) 0.049(6) 0.032(5) 0.005(4) 0.009(4) 0.014(5) C4 0.036(5) 0.037(6) 0.031(5) 0.002(4) 0.005(4) 0.007(4) C7 0.050(6) 0.050(6) 0.026(5) 0.004(4) 0.002(4) 0.002(5) C8 0.033(5) 0.052(6) 0.020(4) -0.002(4) 0.013(4) 0.008(5) C9 0.037(5) 0.044(6) 0.046(6) 0.003(5) 0.021(5) 0.009(5) C10 0.036(5) 0.047(6) 0.031(5) 0.008(4) 0.002(4) 0.014(5) C11 0.029(5) 0.043(6) 0.028(5) -0.013(4) 0.006(4) -0.002(4) C12 0.033(5) 0.032(5) 0.032(5) -0.003(4) -0.005(4) 0.002(4) N1 0.016(3) 0.029(4) 0.024(3) -0.001(3) 0.007(3) 0.000(3) N2 0.018(3) 0.035(4) 0.021(3) -0.004(3) 0.001(3) 0.005(3) O4 0.024(3) 0.036(4) 0.041(4) -0.004(3) 0.004(3) 0.003(3) O5 0.033(4) 0.044(4) 0.031(4) -0.005(3) 0.014(3) -0.006(3) O1 0.032(3) 0.053(4) 0.022(3) 0.004(3) 0.016(3) 0.005(3) O3 0.032(3) 0.049(4) 0.024(3) 0.003(3) 0.010(3) -0.002(3) O2 0.035(4) 0.068(5) 0.022(3) 0.009(4) 0.005(3) 0.019(4) O6 0.063(5) 0.061(5) 0.027(4) 0.010(3) 0.003(3) 0.033(4) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 U1 O5 1.756(7) . ? U1 O4 1.765(7) . ? U1 O2 2.302(7) . ? U1 O3 2.364(6) . ? U1 O1 2.390(6) . ? U1 N2 2.576(7) . ? U1 N1 2.615(7) . ? C6 O1 1.241(10) . ? C6 O3 1.271(10) 2 ? C6 C5 1.509(12) . ? C5 N1 1.314(10) . ? C5 C4 1.373(13) . ? C1 N1 1.340(10) . ? C1 C2 1.395(13) . ? C2 C3 1.392(13) . ? C3 C4 1.376(13) . ? C7 N2 1.336(11) . ? C7 C8 1.370(14) . ? C8 C9 1.392(14) . ? C9 C10 1.350(13) . ? C10 C11 1.380(13) . ? C11 N2 1.372(12) . ? C11 C12 1.499(13) . ? C12 O6 1.223(11) . ? C12 O2 1.269(11) . ? O3 C6 1.271(10) 2_554 ? 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 O5 U1 O4 178.5(3) . . ? O5 U1 O2 89.5(3) . . ? O4 U1 O2 91.1(3) . . ? O5 U1 O3 91.9(3) . . ? O4 U1 O3 89.5(3) . . ? O2 U1 O3 82.4(2) . . ? O5 U1 O1 86.2(3) . . ? O4 U1 O1 92.5(3) . . ? O2 U1 O1 138.4(2) . . ? O3 U1 O1 139.1(2) . . ? O5 U1 N2 89.9(3) . . ? O4 U1 N2 89.1(3) . . ? O2 U1 N2 65.0(2) . . ? O3 U1 N2 147.4(2) . . ? O1 U1 N2 73.6(2) . . ? O5 U1 N1 98.3(3) . . ? O4 U1 N1 81.6(3) . . ? O2 U1 N1 158.1(2) . . ? O3 U1 N1 76.9(2) . . ? O1 U1 N1 63.0(2) . . ? N2 U1 N1 134.9(2) . . ? O1 C6 O3 125.7(8) . 2 ? O1 C6 C5 117.0(7) . . ? O3 C6 C5 117.2(8) 2 . ? N1 C5 C4 124.1(8) . . ? N1 C5 C6 114.6(7) . . ? C4 C5 C6 121.3(8) . . ? N1 C1 C2 121.2(8) . . ? C3 C2 C1 119.2(8) . . ? C4 C3 C2 118.1(9) . . ? C5 C4 C3 118.7(9) . . ? N2 C7 C8 123.7(10) . . ? C7 C8 C9 118.5(9) . . ? C10 C9 C8 117.9(9) . . ? C9 C10 C11 122.0(9) . . ? N2 C11 C10 119.7(8) . . ? N2 C11 C12 114.9(7) . . ? C10 C11 C12 125.3(9) . . ? O6 C12 O2 125.3(9) . . ? O6 C12 C11 119.2(9) . . ? O2 C12 C11 115.5(8) . . ? C5 N1 C1 118.5(7) . . ? C5 N1 U1 117.5(5) . . ? C1 N1 U1 123.8(6) . . ? C7 N2 C11 117.7(8) . . ? C7 N2 U1 127.1(6) . . ? C11 N2 U1 115.0(5) . . ? C6 O1 U1 127.2(5) . . ? C6 O3 U1 143.9(6) 2_554 . ? C12 O2 U1 128.8(6) . . ? _diffrn_measured_fraction_theta_max 0.936 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 1.623 _refine_diff_density_min -1.149 _refine_diff_density_rms 0.190 #===END data_compound2 _database_code_depnum_ccdc_archive 'CCDC 835694' #TrackingRef '- Combined.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C6 H4 N O5 U' _chemical_formula_weight 408.13 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' U U -9.6767 9.6646 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.2890(17) _cell_length_b 7.949(2) _cell_length_c 8.347(2) _cell_angle_alpha 79.554(4) _cell_angle_beta 87.819(4) _cell_angle_gamma 79.199(4) _cell_volume 403.09(18) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.04 _exptl_crystal_size_mid 0.03 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 3.363 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 358 _exptl_absorpt_coefficient_mu 20.121 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.480 _exptl_absorpt_correction_T_max 0.746 _exptl_absorpt_process_details 'SADABS, Sheldrick (2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX II CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7525 _diffrn_reflns_av_R_equivalents 0.0442 _diffrn_reflns_av_sigmaI/netI 0.0442 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.48 _diffrn_reflns_theta_max 30.41 _reflns_number_total 2212 _reflns_number_gt 2057 _reflns_threshold_expression >2\s(I) _computing_data_collection 'APEX II (Bruker AXS, 2005)' _computing_cell_refinement 'SAINTPLUS (Bruker AXS, 2005)' _computing_data_reduction 'SAINTPLUS (Bruker AXS, 2005)' _computing_structure_solution 'SIR92 (Gualardi, 1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Crystal Maker (Palmer 2009)' _computing_publication_material 'WINGX (Farrugia, 1998)' _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^ > 2\s(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^)+(0.0000P)^2^+3.1164P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2212 _refine_ls_number_parameters 118 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0307 _refine_ls_R_factor_gt 0.0276 _refine_ls_wR_factor_ref 0.0603 _refine_ls_wR_factor_gt 0.0596 _refine_ls_goodness_of_fit_ref 1.152 _refine_ls_restrained_S_all 1.152 _refine_ls_shift/su_max 0.001 _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 C5 C 0.9700(10) 0.7344(8) 0.0084(7) 0.0109(11) Uani 1 1 d . . . C1 C 0.6664(10) 0.6307(8) 0.1119(8) 0.0142(12) Uani 1 1 d . . . H1 H 0.5328 0.6025 0.0954 0.017 Uiso 1 1 calc R . . C4 C 1.0569(10) 0.7128(8) 0.1612(7) 0.0117(11) Uani 1 1 d . . . H2 H 1.1911 0.7417 0.1742 0.014 Uiso 1 1 calc R . . C6 C 1.0920(10) 0.7923(8) -0.1436(7) 0.0106(11) Uani 1 1 d . . . C2 C 0.7472(10) 0.5999(8) 0.2709(7) 0.0124(12) Uani 1 1 d . . . H3 H 0.6713 0.5485 0.3582 0.015 Uiso 1 1 calc R . . C3 C 0.9425(10) 0.6478(8) 0.2947(7) 0.0136(12) Uani 1 1 d . . . H4 H 0.9957 0.6362 0.3993 0.016 Uiso 1 1 calc R . . N1 N 0.7738(8) 0.6986(7) -0.0159(6) 0.0120(10) Uani 1 1 d . . . O4 O 1.2887(7) 0.7985(6) -0.1304(5) 0.0134(9) Uani 1 1 d . . . O2 O 0.5835(7) 1.0520(6) -0.2057(5) 0.0142(9) Uani 1 1 d . . . O1 O 0.6157(7) 0.6628(6) -0.3621(5) 0.0146(9) Uani 1 1 d . . . O5 O 0.7004(7) 1.0041(6) -0.5407(5) 0.0138(9) Uani 1 1 d . . . O3 O 0.9879(7) 0.8297(6) -0.2758(5) 0.0141(9) Uani 1 1 d . . . U1 U 0.59573(3) 0.86301(3) -0.29239(3) 0.00871(7) 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 C5 0.008(3) 0.015(3) 0.010(3) 0.000(2) -0.002(2) -0.005(2) C1 0.009(3) 0.015(3) 0.017(3) 0.000(2) 0.000(2) -0.002(2) C4 0.009(3) 0.016(3) 0.011(3) -0.001(2) -0.001(2) -0.005(2) C6 0.008(3) 0.010(3) 0.014(3) -0.003(2) -0.001(2) -0.001(2) C2 0.013(3) 0.014(3) 0.009(3) 0.001(2) 0.003(2) -0.003(2) C3 0.014(3) 0.017(3) 0.009(3) 0.001(2) 0.000(2) -0.005(2) N1 0.009(2) 0.012(3) 0.015(2) 0.000(2) -0.0015(19) -0.0047(19) O4 0.009(2) 0.020(2) 0.010(2) 0.0047(17) -0.0011(15) -0.0058(17) O2 0.016(2) 0.011(2) 0.017(2) -0.0021(17) -0.0030(17) -0.0041(17) O1 0.018(2) 0.018(2) 0.011(2) -0.0054(18) 0.0025(17) -0.0078(18) O5 0.011(2) 0.023(2) 0.0077(19) 0.0014(17) -0.0017(15) -0.0060(18) O3 0.009(2) 0.018(2) 0.015(2) 0.0020(18) -0.0030(16) -0.0076(17) U1 0.00694(11) 0.01129(12) 0.00778(10) 0.00061(7) -0.00093(7) -0.00341(8) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 C5 N1 1.348(7) . ? C5 C4 1.376(8) . ? C5 C6 1.503(8) . ? C1 N1 1.326(8) . ? C1 C2 1.402(8) . ? C1 H1 0.9300 . ? C4 C3 1.377(8) . ? C4 H2 0.9300 . ? C6 O4 1.256(7) . ? C6 O3 1.264(7) . ? C2 C3 1.383(8) . ? C2 H3 0.9300 . ? C3 H4 0.9300 . ? N1 U1 2.616(5) . ? O4 U1 2.396(4) 1_655 ? O2 U1 1.770(4) . ? O1 U1 1.773(4) . ? O5 U1 2.306(4) . ? O5 U1 2.335(4) 2_674 ? O3 U1 2.437(4) . ? U1 O5 2.335(4) 2_674 ? U1 O4 2.396(4) 1_455 ? U1 U1 3.8474(8) 2_674 ? 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 N1 C5 C4 122.6(5) . . ? N1 C5 C6 115.3(5) . . ? C4 C5 C6 122.1(5) . . ? N1 C1 C2 122.3(6) . . ? N1 C1 H1 118.9 . . ? C2 C1 H1 118.9 . . ? C5 C4 C3 119.1(6) . . ? C5 C4 H2 120.5 . . ? C3 C4 H2 120.5 . . ? O4 C6 O3 125.0(6) . . ? O4 C6 C5 118.0(5) . . ? O3 C6 C5 116.9(5) . . ? C3 C2 C1 118.4(5) . . ? C3 C2 H3 120.8 . . ? C1 C2 H3 120.8 . . ? C4 C3 C2 119.1(6) . . ? C4 C3 H4 120.5 . . ? C2 C3 H4 120.5 . . ? C1 N1 C5 118.5(5) . . ? C1 N1 U1 124.6(4) . . ? C5 N1 U1 113.8(4) . . ? C6 O4 U1 141.1(4) . 1_655 ? U1 O5 U1 111.99(18) . 2_674 ? C6 O3 U1 124.0(4) . . ? O2 U1 O1 174.9(2) . . ? O2 U1 O5 91.26(18) . . ? O1 U1 O5 92.96(18) . . ? O2 U1 O5 91.46(18) . 2_674 ? O1 U1 O5 92.75(18) . 2_674 ? O5 U1 O5 68.01(18) . 2_674 ? O2 U1 O4 89.13(18) . 1_455 ? O1 U1 O4 89.13(18) . 1_455 ? O5 U1 O4 143.90(15) . 1_455 ? O5 U1 O4 75.89(14) 2_674 1_455 ? O2 U1 O3 86.27(18) . . ? O1 U1 O3 92.09(18) . . ? O5 U1 O3 74.92(14) . . ? O5 U1 O3 142.80(14) 2_674 . ? O4 U1 O3 141.06(14) 1_455 . ? O2 U1 N1 84.60(18) . . ? O1 U1 N1 90.36(18) . . ? O5 U1 N1 138.36(15) . . ? O5 U1 N1 153.25(15) 2_674 . ? O4 U1 N1 77.60(15) 1_455 . ? O3 U1 N1 63.48(15) . . ? O2 U1 U1 91.65(14) . 2_674 ? O1 U1 U1 93.44(14) . 2_674 ? O5 U1 U1 34.25(11) . 2_674 ? O5 U1 U1 33.76(10) 2_674 2_674 ? O4 U1 U1 109.65(10) 1_455 2_674 ? O3 U1 U1 109.11(10) . 2_674 ? N1 U1 U1 171.84(11) . 2_674 ? 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 N1 C5 C4 C3 1.8(10) . . . . ? C6 C5 C4 C3 -175.5(6) . . . . ? N1 C5 C6 O4 -168.0(6) . . . . ? C4 C5 C6 O4 9.6(9) . . . . ? N1 C5 C6 O3 11.4(8) . . . . ? C4 C5 C6 O3 -171.1(6) . . . . ? N1 C1 C2 C3 2.2(10) . . . . ? C5 C4 C3 C2 2.4(10) . . . . ? C1 C2 C3 C4 -4.3(9) . . . . ? C2 C1 N1 C5 1.9(9) . . . . ? C2 C1 N1 U1 -156.9(5) . . . . ? C4 C5 N1 C1 -4.0(9) . . . . ? C6 C5 N1 C1 173.5(5) . . . . ? C4 C5 N1 U1 157.0(5) . . . . ? C6 C5 N1 U1 -25.5(7) . . . . ? O3 C6 O4 U1 -1.2(11) . . . 1_655 ? C5 C6 O4 U1 178.0(4) . . . 1_655 ? O4 C6 O3 U1 -169.4(4) . . . . ? C5 C6 O3 U1 11.3(7) . . . . ? U1 O5 U1 O2 -91.1(2) 2_674 . . . ? U1 O5 U1 O1 91.8(2) 2_674 . . . ? U1 O5 U1 O5 0.0 2_674 . . 2_674 ? U1 O5 U1 O4 -0.8(4) 2_674 . . 1_455 ? U1 O5 U1 O3 -176.9(2) 2_674 . . . ? U1 O5 U1 N1 -174.35(18) 2_674 . . . ? C6 O3 U1 O2 68.3(5) . . . . ? C6 O3 U1 O1 -106.9(5) . . . . ? C6 O3 U1 O5 160.6(5) . . . . ? C6 O3 U1 O5 155.8(4) . . . 2_674 ? C6 O3 U1 O4 -15.7(6) . . . 1_455 ? C6 O3 U1 N1 -17.6(4) . . . . ? C6 O3 U1 U1 158.7(4) . . . 2_674 ? C1 N1 U1 O2 92.9(5) . . . . ? C5 N1 U1 O2 -66.8(4) . . . . ? C1 N1 U1 O1 -86.4(5) . . . . ? C5 N1 U1 O1 113.9(4) . . . . ? C1 N1 U1 O5 178.7(4) . . . . ? C5 N1 U1 O5 19.0(5) . . . . ? C1 N1 U1 O5 10.4(7) . . . 2_674 ? C5 N1 U1 O5 -149.3(4) . . . 2_674 ? C1 N1 U1 O4 2.6(5) . . . 1_455 ? C5 N1 U1 O4 -157.1(5) . . . 1_455 ? C1 N1 U1 O3 -178.6(5) . . . . ? C5 N1 U1 O3 21.8(4) . . . . ? C1 N1 U1 U1 155.8(6) . . . 2_674 ? C5 N1 U1 U1 -3.9(12) . . . 2_674 ? _diffrn_measured_fraction_theta_max 0.910 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 2.140 _refine_diff_density_min -1.949 _refine_diff_density_rms 0.332 #===END data_compound3 _database_code_depnum_ccdc_archive 'CCDC 835695' #TrackingRef '- Combined.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C6 H5 N2 O7 U' _chemical_formula_weight 455.15 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' 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' U U -9.6767 9.6646 '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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/c 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 9.1584(9) _cell_length_b 9.6660(9) _cell_length_c 11.1105(11) _cell_angle_alpha 90.00 _cell_angle_beta 103.353(2) _cell_angle_gamma 90.00 _cell_volume 956.97(16) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.07 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 3.159 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 812 _exptl_absorpt_coefficient_mu 16.986 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.480 _exptl_absorpt_correction_T_max 0.746 _exptl_absorpt_process_details 'SADABS, Sheldrick (2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Apex II CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18266 _diffrn_reflns_av_R_equivalents 0.0549 _diffrn_reflns_av_sigmaI/netI 0.0352 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.29 _diffrn_reflns_theta_max 31.17 _reflns_number_total 2747 _reflns_number_gt 2567 _reflns_threshold_expression >2\s(I) _computing_cell_refinement 'SAINTPLUS (Bruker AXS, 2005)' _computing_data_reduction 'SAINTPLUS (Bruker AXS, 2005)' _computing_structure_solution 'SIR92 (Gualardi, 1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Crystal Maker (Palmer 2009)' _computing_publication_material 'WINGX (Farrugia, 1998)' _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^ > 2\s(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^)+(0.0143P)^2^+1.2594P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2747 _refine_ls_number_parameters 153 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0229 _refine_ls_R_factor_gt 0.0207 _refine_ls_wR_factor_ref 0.0490 _refine_ls_wR_factor_gt 0.0482 _refine_ls_goodness_of_fit_ref 1.076 _refine_ls_restrained_S_all 1.076 _refine_ls_shift/su_max 0.002 _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 U1 U 0.720939(12) 0.320688(11) 0.876889(10) 0.00819(5) Uani 1 1 d . . . O1 O 0.9561(3) 0.3294(2) 1.0270(2) 0.0126(5) Uani 1 1 d . . . O6 O 0.6207(3) 0.3681(3) 0.9887(2) 0.0148(5) Uani 1 1 d . . . O5 O 0.8221(3) 0.2673(2) 0.7680(2) 0.0122(5) Uani 1 1 d . . . C1 C 0.8733(3) 0.0392(3) 1.0762(3) 0.0111(6) Uani 1 1 d . . . H1 H 0.9479 0.1022 1.1110 0.013 Uiso 1 1 calc R . . O2 O 0.8385(3) 0.5456(2) 0.8914(2) 0.0127(5) Uani 1 1 d . . . C4 C 0.6608(3) -0.0205(3) 0.9323(3) 0.0099(6) Uani 1 1 d . . . O3 O 0.5387(3) 0.1495(2) 0.7934(2) 0.0141(5) Uani 1 1 d . . . O4 O 0.5617(3) 0.4391(2) 0.7196(2) 0.0152(5) Uani 1 1 d . . . N1 N 0.7626(3) 0.0772(3) 0.9802(3) 0.0095(5) Uani 1 1 d . . . N2 N 0.7763(4) -0.1914(3) 1.0771(3) 0.0149(6) Uani 1 1 d . . . C3 C 0.6684(4) -0.1537(3) 0.9789(3) 0.0132(6) Uani 1 1 d . . . H013 H 0.5973 -0.2185 0.9414 0.016 Uiso 1 1 calc R . . C5 C 0.5374(3) 0.0260(3) 0.8267(3) 0.0104(6) Uani 1 1 d . . . C2 C 0.8768(4) -0.0948(4) 1.1240(3) 0.0140(6) Uani 1 1 d . . . H3 H 0.9532 -0.1175 1.1920 0.017 Uiso 1 1 calc R . . C6 C 1.0342(4) 0.4383(3) 1.0396(3) 0.0105(6) Uani 1 1 d . . . OH1 O 0.8173(4) 0.5458(3) 1.2050(3) 0.0276(7) Uani 1 1 d . . . H4 H 0.789(6) 0.616(7) 1.173(6) 0.049(17) Uiso 1 1 d . . . H5 H 0.760(6) 0.489(6) 1.162(5) 0.038(15) Uiso 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 U1 0.00673(7) 0.00502(7) 0.01158(8) -0.00002(4) -0.00044(5) -0.00040(4) O1 0.0136(12) 0.0086(11) 0.0138(12) 0.0020(8) -0.0001(9) -0.0025(8) O6 0.0147(12) 0.0113(11) 0.0188(12) -0.0019(10) 0.0048(9) -0.0020(9) O5 0.0133(11) 0.0085(11) 0.0145(12) 0.0004(9) 0.0027(9) 0.0030(9) C1 0.0092(14) 0.0104(14) 0.0120(15) -0.0006(12) -0.0008(11) 0.0003(12) O2 0.0099(10) 0.0111(11) 0.0146(12) 0.0024(9) -0.0023(9) -0.0027(9) C4 0.0068(13) 0.0086(14) 0.0145(15) -0.0012(12) 0.0028(11) -0.0012(11) O3 0.0130(12) 0.0078(10) 0.0186(13) 0.0022(9) -0.0023(9) -0.0020(9) O4 0.0132(11) 0.0070(11) 0.0221(13) 0.0012(9) -0.0029(9) 0.0017(9) N1 0.0081(12) 0.0085(13) 0.0109(13) -0.0012(10) 0.0002(10) -0.0018(9) N2 0.0161(15) 0.0107(14) 0.0178(16) 0.0047(11) 0.0037(12) 0.0036(10) C3 0.0128(16) 0.0090(14) 0.0173(17) -0.0005(12) 0.0025(13) -0.0006(12) C5 0.0113(14) 0.0071(14) 0.0119(15) -0.0020(11) 0.0007(11) -0.0008(11) C2 0.0144(15) 0.0136(15) 0.0133(16) 0.0013(12) 0.0018(12) 0.0063(13) C6 0.0107(14) 0.0104(15) 0.0100(14) -0.0002(11) 0.0015(11) 0.0001(11) OH1 0.0401(18) 0.0112(13) 0.0260(16) 0.0038(12) -0.0039(13) -0.0010(13) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 U1 O5 1.763(2) . ? U1 O6 1.767(3) . ? U1 O4 2.306(2) . ? U1 O3 2.381(2) . ? U1 O1 2.402(2) . ? U1 O2 2.415(2) . ? U1 N1 2.608(3) . ? O1 C6 1.262(4) . ? C1 N1 1.342(4) . ? C1 C2 1.397(5) . ? O2 C6 1.248(4) 3_767 ? C4 N1 1.348(4) . ? C4 C3 1.383(4) . ? C4 C5 1.497(4) . ? O3 C5 1.251(4) . ? O4 C5 1.256(4) 2_656 ? N2 C2 1.330(5) . ? N2 C3 1.342(5) . ? C5 O4 1.256(4) 2_646 ? C6 O2 1.248(4) 3_767 ? C6 C6 1.528(6) 3_767 ? 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 O5 U1 O6 177.87(10) . . ? O5 U1 O4 88.03(10) . . ? O6 U1 O4 93.66(10) . . ? O5 U1 O3 87.80(10) . . ? O6 U1 O3 91.31(10) . . ? O4 U1 O3 77.64(8) . . ? O5 U1 O1 87.57(10) . . ? O6 U1 O1 91.77(10) . . ? O4 U1 O1 144.86(8) . . ? O3 U1 O1 136.93(8) . . ? O5 U1 O2 90.73(10) . . ? O6 U1 O2 90.87(10) . . ? O4 U1 O2 78.33(8) . . ? O3 U1 O2 155.96(8) . . ? O1 U1 O2 66.89(7) . . ? O5 U1 N1 89.49(10) . . ? O6 U1 N1 88.38(10) . . ? O4 U1 N1 141.68(8) . . ? O3 U1 N1 64.05(8) . . ? O1 U1 N1 73.11(8) . . ? O2 U1 N1 139.95(8) . . ? C6 O1 U1 120.0(2) . . ? N1 C1 C2 120.2(3) . . ? C6 O2 U1 119.5(2) 3_767 . ? N1 C4 C3 122.3(3) . . ? N1 C4 C5 115.3(3) . . ? C3 C4 C5 122.5(3) . . ? C5 O3 U1 127.0(2) . . ? C5 O4 U1 155.9(2) 2_656 . ? C1 N1 C4 116.7(3) . . ? C1 N1 U1 127.1(2) . . ? C4 N1 U1 116.2(2) . . ? C2 N2 C3 116.1(3) . . ? N2 C3 C4 121.4(3) . . ? O3 C5 O4 124.9(3) . 2_646 ? O3 C5 C4 117.5(3) . . ? O4 C5 C4 117.6(3) 2_646 . ? N2 C2 C1 123.3(3) . . ? O2 C6 O1 126.6(3) 3_767 . ? O2 C6 C6 117.2(3) 3_767 3_767 ? O1 C6 C6 116.1(3) . 3_767 ? _diffrn_measured_fraction_theta_max 0.888 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.736 _refine_diff_density_min -1.241 _refine_diff_density_rms 0.192 # Attachment 'web_deposit_cif_file_4_MichaelAndrews_1311108432. #Compound 5.cif' data_pca2on1 _database_code_depnum_ccdc_archive 'CCDC 835696' #TrackingRef 'web_deposit_cif_file_4_MichaelAndrews_1311108432. #Compound 5.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C5 H3 N2 O5 U' _chemical_formula_weight 409.12 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' 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' U U -9.6767 9.6646 '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' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pca21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x+1/2, y, z+1/2' 'x+1/2, -y, z' _cell_length_a 13.5463(15) _cell_length_b 6.6022(7) _cell_length_c 8.3418(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 746.05(14) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description rod _exptl_crystal_colour yellow _exptl_crystal_size_max 0.08 _exptl_crystal_size_mid 0.03 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 3.642 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 716 _exptl_absorpt_coefficient_mu 21.747 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.430 _exptl_absorpt_correction_T_max 0.746 _exptl_absorpt_process_details 'SADABS, Sheldrick (2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX II CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13285 _diffrn_reflns_av_R_equivalents 0.0319 _diffrn_reflns_av_sigmaI/netI 0.0275 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 3.01 _diffrn_reflns_theta_max 30.40 _reflns_number_total 2109 _reflns_number_gt 1908 _reflns_threshold_expression >2\s(I) _computing_data_collection 'APEX II (Bruker AXS, 2008)' _computing_cell_refinement 'SAINTPLUS (Bruker AXS, 2008)' _computing_data_reduction 'SAINTPLUS (Bruker AXS, 2008)' _computing_structure_solution 'SIR92 (Gualardi, 1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Crystal Maker (Palmer, 2009)' _computing_publication_material 'WINGX (Farrugia, 1998)' _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^ > 2\s(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^)+(0.0059P)^2^+0.0224P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.015(7) _refine_ls_number_reflns 2109 _refine_ls_number_parameters 118 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0176 _refine_ls_R_factor_gt 0.0142 _refine_ls_wR_factor_ref 0.0289 _refine_ls_wR_factor_gt 0.0280 _refine_ls_goodness_of_fit_ref 1.042 _refine_ls_restrained_S_all 1.042 _refine_ls_shift/su_max 0.002 _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 U1 U 0.963160(7) 0.042509(16) 0.53590(4) 0.00556(3) Uani 1 1 d . . . O1 O 1.13056(18) -0.0410(4) 0.5849(3) 0.0089(5) Uani 1 1 d . . . O2 O 0.79269(18) 0.0186(4) 0.6201(4) 0.0098(6) Uani 1 1 d . . . O5 O 0.98956(17) 0.2848(4) 0.6172(3) 0.0087(5) Uani 1 1 d . . . O4 O 0.93577(18) -0.1972(4) 0.4498(3) 0.0087(5) Uani 1 1 d . . . O3 O 1.03652(18) 0.1162(5) 0.2906(3) 0.0094(5) Uani 1 1 d . . . N1 N 0.8308(2) 0.2841(5) 0.3939(3) 0.0064(6) Uani 1 1 d . . . N2 N 0.6845(3) 0.5651(7) 0.3064(6) 0.0111(10) Uani 1 1 d . . . C5 C 1.2175(2) -0.0938(5) 0.5554(6) 0.0063(9) Uani 1 1 d . . . C1 C 0.8510(3) 0.4441(6) 0.3026(5) 0.0093(8) Uani 1 1 d . . . H1 H 0.9150 0.4615 0.2650 0.011 Uiso 1 1 calc R . . C3 C 0.6637(3) 0.4018(6) 0.3961(5) 0.0090(8) Uani 1 1 d . . . H3 H 0.5990 0.3814 0.4297 0.011 Uiso 1 1 calc R . . C4 C 0.7353(2) 0.2624(6) 0.4403(4) 0.0066(7) Uani 1 1 d . . . C2 C 0.7794(3) 0.5865(8) 0.2614(6) 0.0074(10) Uani 1 1 d . . . H21 H 0.7976 0.6990 0.2012 0.009 Uiso 1 1 calc R . . 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 U1 0.00346(5) 0.00687(6) 0.00635(6) 0.00002(17) 0.00001(13) -0.00007(4) O1 0.0067(12) 0.0100(13) 0.0101(13) 0.0022(10) -0.0024(9) 0.0034(10) O2 0.0048(13) 0.0115(14) 0.0131(15) 0.0012(11) -0.0027(10) 0.0024(10) O5 0.0063(12) 0.0098(14) 0.0101(13) 0.0008(11) 0.0012(10) 0.0017(10) O4 0.0069(11) 0.0091(14) 0.0102(13) -0.0013(10) -0.0023(10) -0.0021(10) O3 0.0100(13) 0.0120(14) 0.0063(12) -0.0018(11) -0.0006(10) 0.0011(11) N1 0.0064(14) 0.0067(16) 0.0062(14) -0.0028(12) -0.0004(12) -0.0012(12) N2 0.007(2) 0.012(2) 0.0137(19) -0.0020(15) -0.0048(17) -0.0022(16) C5 0.0069(14) 0.0074(15) 0.005(3) 0.0001(15) 0.0024(14) -0.0016(11) C1 0.0064(18) 0.011(2) 0.0102(18) -0.0013(15) 0.0029(15) -0.0019(15) C3 0.0075(17) 0.010(2) 0.0100(18) -0.0007(15) -0.0007(15) -0.0001(14) C4 0.0043(15) 0.0084(19) 0.0071(17) 0.0009(14) -0.0014(14) -0.0010(13) C2 0.012(3) 0.004(2) 0.006(2) -0.0030(15) -0.005(2) -0.0017(16) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 U1 O5 1.774(3) . ? U1 O4 1.777(3) . ? U1 O3 2.326(3) . ? U1 O3 2.369(3) 2_755 ? U1 O1 2.369(3) . ? U1 O2 2.419(3) . ? U1 N1 2.676(3) . ? O1 C5 1.252(4) . ? O2 C5 1.256(4) 4_455 ? O3 U1 2.369(3) 2_754 ? N1 C1 1.330(5) . ? N1 C4 1.359(4) . ? N2 C3 1.342(6) . ? N2 C2 1.347(5) . ? C5 O2 1.256(4) 4 ? C5 C4 1.489(5) 4 ? C1 C2 1.394(6) . ? C3 C4 1.387(5) . ? C4 C5 1.489(5) 4_455 ? 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 O5 U1 O4 178.54(12) . . ? O5 U1 O3 93.54(11) . . ? O4 U1 O3 85.41(11) . . ? O5 U1 O3 93.17(12) . 2_755 ? O4 U1 O3 88.22(11) . 2_755 ? O3 U1 O3 151.719(16) . 2_755 ? O5 U1 O1 87.19(10) . . ? O4 U1 O1 93.57(10) . . ? O3 U1 O1 77.96(9) . . ? O3 U1 O1 74.97(8) 2_755 . ? O5 U1 O2 98.06(10) . . ? O4 U1 O2 81.95(10) . . ? O3 U1 O2 132.61(9) . . ? O3 U1 O2 73.29(9) 2_755 . ? O1 U1 O2 148.05(10) . . ? O5 U1 N1 76.52(10) . . ? O4 U1 N1 102.25(10) . . ? O3 U1 N1 76.83(9) . . ? O3 U1 N1 131.44(9) 2_755 . ? O1 U1 N1 148.90(9) . . ? O2 U1 N1 61.83(9) . . ? C5 O1 U1 158.6(3) . . ? C5 O2 U1 128.6(3) 4_455 . ? U1 O3 U1 134.21(13) . 2_754 ? C1 N1 C4 116.2(3) . . ? C1 N1 U1 126.1(2) . . ? C4 N1 U1 116.7(2) . . ? C3 N2 C2 116.1(5) . . ? O1 C5 O2 124.6(4) . 4 ? O1 C5 C4 119.1(3) . 4 ? O2 C5 C4 116.2(3) 4 4 ? N1 C1 C2 122.3(4) . . ? N2 C3 C4 122.3(3) . . ? N1 C4 C3 121.4(3) . . ? N1 C4 C5 114.6(3) . 4_455 ? C3 C4 C5 123.7(3) . 4_455 ? N2 C2 C1 121.6(5) . . ? _diffrn_measured_fraction_theta_max 0.968 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.626 _refine_diff_density_min -1.041 _refine_diff_density_rms 0.165 #===END data_compound4 _database_code_depnum_ccdc_archive 'CCDC 835697' #TrackingRef '- Combined.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C5 H10 N2 O6 U' _chemical_formula_weight 432.18 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' 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' U U -9.6767 9.6646 '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' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.2323(12) _cell_length_b 6.7790(13) _cell_length_c 10.594(2) _cell_angle_alpha 104.120(3) _cell_angle_beta 93.875(3) _cell_angle_gamma 91.976(3) _cell_volume 432.49(14) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description rod _exptl_crystal_colour yellow _exptl_crystal_size_max 0.13 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 3.319 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 388 _exptl_absorpt_coefficient_mu 18.774 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.453 _exptl_absorpt_correction_T_max 0.746 _exptl_absorpt_process_details 'SADABS, Sheldrick (2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX II CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4503 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0521 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.99 _diffrn_reflns_theta_max 30.37 _reflns_number_total 4503 _reflns_number_gt 3880 _reflns_threshold_expression >2\s(I) _computing_data_collection 'APEX II (Bruker AXS, 2005)' _computing_cell_refinement 'SAINTPLUS (Bruker AXS, 2005)' _computing_data_reduction 'SAINTPLUS (Bruker AXS, 2005)' _computing_structure_solution 'SIR92 (Gualardi, 1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Crystal Maker (Palmer 2009)' _computing_publication_material 'WINGX (Farrugia, 1998)' _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^ > 2\s(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^)+(0.0516P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4503 _refine_ls_number_parameters 138 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0457 _refine_ls_R_factor_gt 0.0367 _refine_ls_wR_factor_ref 0.0896 _refine_ls_wR_factor_gt 0.0861 _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_restrained_S_all 1.035 _refine_ls_shift/su_max 0.001 _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 U1 U 0.91032(3) 0.40786(3) 0.317962(17) 0.01649(7) Uani 1 1 d . . . O3 O 0.7973(7) 0.5265(9) 0.5256(4) 0.0307(11) Uani 1 1 d . . . C1 C 0.8330(9) 0.2285(11) -0.0326(5) 0.0233(12) Uani 1 1 d . . . H1 H 0.9827 0.2320 -0.0280 0.028 Uiso 1 1 calc R . . C2 C 0.7184(9) 0.1637(10) -0.1528(5) 0.0191(11) Uani 1 1 d . . . H2 H 0.7889 0.1209 -0.2286 0.023 Uiso 1 1 calc R . . N1 N 0.7319(7) 0.2871(8) 0.0787(4) 0.0155(9) Uani 1 1 d . . . O5 O 0.9235(8) 0.6600(7) 0.2993(4) 0.0285(10) Uani 1 1 d . . . C4 C 0.5137(8) 0.2784(9) 0.0608(5) 0.0151(10) Uani 1 1 d . . . N2 N 0.3940(8) 0.2228(8) -0.0484(4) 0.0184(9) Uani 1 1 d . . . O1 O 0.5237(7) 0.4029(9) 0.2903(4) 0.0311(11) Uani 1 1 d . . . C5 C 0.4025(9) 0.3438(9) 0.1867(5) 0.0176(10) Uani 1 1 d . . . O2 O 1.2021(6) 0.3375(7) 0.1808(3) 0.0185(8) Uani 1 1 d . . . O4 O 0.8914(8) 0.1510(7) 0.3278(4) 0.0272(10) Uani 1 1 d . . . C3 C 0.4976(10) 0.1641(10) -0.1575(5) 0.0202(11) Uani 1 1 d . . . H3 H 0.4182 0.1228 -0.2378 0.024 Uiso 1 1 calc R . . O10 O 0.6978(14) 0.9454(13) 0.5292(7) 0.048(3) Uani 0.694(15) 1 d P . . O11 O 0.503(4) 0.796(3) 0.458(2) 0.059(7) Uani 0.306(15) 1 d P . . 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 U1 0.00616(11) 0.02815(12) 0.01370(10) 0.00266(7) 0.00001(6) 0.00028(8) O3 0.006(2) 0.064(3) 0.0169(19) 0.000(2) -0.0001(14) 0.002(2) C1 0.007(3) 0.040(3) 0.022(3) 0.004(2) 0.005(2) 0.003(3) C2 0.014(3) 0.031(3) 0.012(2) 0.004(2) -0.0020(19) -0.001(2) N1 0.005(2) 0.023(2) 0.021(2) 0.0080(18) 0.0044(16) 0.0005(19) O5 0.024(3) 0.027(2) 0.035(2) 0.0058(18) 0.0071(19) 0.0044(19) C4 0.005(2) 0.019(3) 0.022(2) 0.006(2) 0.0008(18) 0.001(2) N2 0.011(2) 0.027(2) 0.017(2) 0.0044(18) 0.0004(16) 0.000(2) O1 0.007(2) 0.065(3) 0.0163(19) 0.003(2) -0.0023(15) -0.003(2) C5 0.013(3) 0.019(3) 0.022(3) 0.006(2) 0.0014(19) 0.001(2) O2 0.0070(19) 0.031(2) 0.0157(17) 0.0012(15) 0.0019(13) 0.0020(17) O4 0.025(3) 0.031(2) 0.029(2) 0.0122(18) 0.0012(18) -0.0017(19) C3 0.017(3) 0.026(3) 0.018(2) 0.006(2) 0.002(2) -0.001(2) O10 0.044(6) 0.060(6) 0.037(4) 0.008(4) 0.001(4) 0.018(4) O11 0.058(16) 0.070(15) 0.050(12) 0.014(10) 0.011(10) 0.016(12) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 U1 O5 1.768(5) . ? U1 O4 1.770(5) . ? U1 O3 2.317(4) . ? U1 O3 2.333(4) 2_766 ? U1 O2 2.393(4) . ? U1 O1 2.406(4) . ? U1 N1 2.622(4) . ? U1 U1 3.8286(8) 2_766 ? O3 U1 2.333(4) 2_766 ? C1 N1 1.354(7) . ? C1 C2 1.381(8) . ? C2 C3 1.374(8) . ? N1 C4 1.358(6) . ? C4 N2 1.299(7) . ? C4 C5 1.521(7) . ? N2 C3 1.343(7) . ? O1 C5 1.260(7) . ? C5 O2 1.245(6) 1_455 ? O2 C5 1.245(6) 1_655 ? O10 O11 1.57(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 O5 U1 O4 176.92(18) . . ? O5 U1 O3 89.7(2) . . ? O4 U1 O3 92.7(2) . . ? O5 U1 O3 92.5(2) . 2_766 ? O4 U1 O3 90.2(2) . 2_766 ? O3 U1 O3 69.12(17) . 2_766 ? O5 U1 O2 88.23(18) . . ? O4 U1 O2 90.78(18) . . ? O3 U1 O2 148.40(14) . . ? O3 U1 O2 79.47(13) 2_766 . ? O5 U1 O1 89.5(2) . . ? O4 U1 O1 89.2(2) . . ? O3 U1 O1 74.27(14) . . ? O3 U1 O1 143.32(14) 2_766 . ? O2 U1 O1 137.21(13) . . ? O5 U1 N1 88.83(19) . . ? O4 U1 N1 88.10(18) . . ? O3 U1 N1 137.23(14) . . ? O3 U1 N1 153.63(14) 2_766 . ? O2 U1 N1 74.25(13) . . ? O1 U1 N1 62.98(13) . . ? O5 U1 U1 91.35(15) . 2_766 ? O4 U1 U1 91.71(14) . 2_766 ? O3 U1 U1 34.70(10) . 2_766 ? O3 U1 U1 34.43(10) 2_766 2_766 ? O2 U1 U1 113.83(9) . 2_766 ? O1 U1 U1 108.94(10) . 2_766 ? N1 U1 U1 171.92(9) . 2_766 ? U1 O3 U1 110.88(17) . 2_766 ? N1 C1 C2 121.4(5) . . ? C3 C2 C1 118.3(5) . . ? C1 N1 C4 114.5(5) . . ? C1 N1 U1 127.4(4) . . ? C4 N1 U1 118.1(3) . . ? N2 C4 N1 128.0(5) . . ? N2 C4 C5 118.1(5) . . ? N1 C4 C5 113.9(5) . . ? C4 N2 C3 116.4(5) . . ? C5 O1 U1 128.6(4) . . ? O2 C5 O1 124.9(5) 1_455 . ? O2 C5 C4 118.8(5) 1_455 . ? O1 C5 C4 116.3(5) . . ? C5 O2 U1 141.0(3) 1_655 . ? N2 C3 C2 121.4(5) . . ? _diffrn_measured_fraction_theta_max 0.922 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 2.399 _refine_diff_density_min -2.002 _refine_diff_density_rms 0.280 #===END