# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Pierre Thuery' _publ_contact_author_email PIERRE.THUERY@CEA.FR _publ_section_title ; Uranyl-organic assemblies with the macrocyclic ligand 1,4,8,11-tetraazacyclotetradecane-1,4,8,11-tetraacetate (TETA) ; _publ_author_name 'Pierre Thuery' # Attachment 'CIF.txt' data_1 _database_code_depnum_ccdc_archive 'CCDC 756415' #TrackingRef 'CIF.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H34 N4 O18 U2' _chemical_formula_weight 1094.57 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 8.5290(9) _cell_length_b 8.6076(5) _cell_length_c 10.7849(11) _cell_angle_alpha 72.602(6) _cell_angle_beta 75.267(5) _cell_angle_gamma 79.158(6) _cell_volume 725.30(12) _cell_formula_units_Z 1 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 23982 _cell_measurement_theta_min 2.49 _cell_measurement_theta_max 25.68 _exptl_crystal_description lath _exptl_crystal_colour 'translucent light yellow' _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.506 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 510 _exptl_absorpt_coefficient_mu 11.239 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.481 _exptl_absorpt_correction_T_max 0.714 _exptl_absorpt_process_details 'SCALEPACK (Otwinowski & Minor, 1997)' _exptl_special_details 'crystal-to-detector distance 30 mm' _diffrn_ambient_temperature 100(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 'Nonius Kappa-CCD area-detector diffractometer' _diffrn_measurement_method 'two \f and four \w scans with 2\% steps (442 frames)' _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 23982 _diffrn_reflns_av_R_equivalents 0.0362 _diffrn_reflns_av_sigmaI/netI 0.0478 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.49 _diffrn_reflns_theta_max 25.68 _reflns_number_total 2748 _reflns_number_gt 2440 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Nonius, 1998)' _computing_cell_refinement 'HKL2000 (Otwinowski & Minor, 1997)' _computing_data_reduction 'HKL2000 (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXTL (Sheldrick, 2008); PLATON (Spek, 2003)' _refine_special_details ; Structure solved by Patterson map interpretation and subsequent Fourier-difference synthesis. All non-hydrogen atoms were refined with anisotropic displacement parameters. The H atoms bound to O and N atoms were found on a Fourier-difference map and all the others were introduced at calculated positions. All were treated as riding atoms with an isotropic displacement parameter equal to 1.2 times that of the parent atom. 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^)+(0.0429P)^2^] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary heavy _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 2748 _refine_ls_number_parameters 199 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0363 _refine_ls_R_factor_gt 0.0294 _refine_ls_wR_factor_ref 0.0725 _refine_ls_wR_factor_gt 0.0703 _refine_ls_goodness_of_fit_ref 1.028 _refine_ls_restrained_S_all 1.028 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.68 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.825 _refine_diff_density_min -1.645 _refine_diff_density_rms 0.191 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 U U 0.81631(3) 0.55619(3) 0.78103(2) 0.02276(10) Uani 1 1 d . . . O1 O 1.0082(5) 0.5875(6) 0.7977(5) 0.0286(10) Uani 1 1 d . . . O2 O 0.6265(6) 0.5255(5) 0.7598(5) 0.0300(10) Uani 1 1 d . . . O3 O 0.7276(6) 0.8394(5) 0.7440(5) 0.0301(10) Uani 1 1 d . . . O4 O 0.7730(6) 0.9015(6) 0.9184(5) 0.0317(11) Uani 1 1 d . . . O5 O 0.8462(6) 1.2969(5) -0.0711(4) 0.0282(10) Uani 1 1 d . . . O6 O 0.5970(6) 1.2329(6) 0.0511(5) 0.0315(11) Uani 1 1 d . . . O7 O 0.8996(6) 0.6782(5) 0.5416(5) 0.0298(10) Uani 1 1 d . . . O8 O 1.0444(6) 0.6407(5) 0.3459(4) 0.0258(10) Uani 1 1 d . . . O9 O 0.6934(6) 0.5990(6) 1.0010(4) 0.0288(10) Uani 1 1 d . . . H9A H 0.7373 0.7008 0.9870 0.035 Uiso 1 1 d R . . H9B H 0.5880 0.6402 1.0027 0.035 Uiso 1 1 d R . . N1 N 0.5667(7) 1.1432(6) 0.6514(6) 0.0271(12) Uani 1 1 d . . . N2 N 0.7123(7) 1.0249(7) 0.2545(5) 0.0268(12) Uani 1 1 d . . . H2 H 0.6118 1.0816 0.2403 0.032 Uiso 1 1 d R . . C1 C 0.6874(8) 1.2212(8) 0.5364(7) 0.0295(15) Uani 1 1 d . . . H1A H 0.7960 1.1719 0.5497 0.035 Uiso 1 1 calc R . . H1B H 0.6783 1.3365 0.5327 0.035 Uiso 1 1 calc R . . C2 C 0.6690(9) 1.2068(8) 0.4034(7) 0.0297(15) Uani 1 1 d . . . H2A H 0.5551 1.2348 0.3973 0.036 Uiso 1 1 calc R . . H2B H 0.7314 1.2842 0.3318 0.036 Uiso 1 1 calc R . . C3 C 0.7275(9) 1.0352(8) 0.3873(6) 0.0285(15) Uani 1 1 d . . . H3A H 0.8406 1.0059 0.3954 0.034 Uiso 1 1 calc R . . H3B H 0.6631 0.9578 0.4573 0.034 Uiso 1 1 calc R . . C4 C 0.7265(9) 0.8529(9) 0.2426(7) 0.0326(16) Uani 1 1 d . . . H4A H 0.8318 0.7955 0.2585 0.039 Uiso 1 1 calc R . . H4B H 0.7220 0.8573 0.1526 0.039 Uiso 1 1 calc R . . C5 C 0.5923(9) 0.7569(8) 0.3396(7) 0.0311(16) Uani 1 1 d . . . H5A H 0.5868 0.6618 0.3109 0.037 Uiso 1 1 calc R . . H5B H 0.6188 0.7181 0.4269 0.037 Uiso 1 1 calc R . . C6 C 0.6274(9) 1.1078(8) 0.7749(7) 0.0288(15) Uani 1 1 d . . . H6A H 0.5352 1.1208 0.8468 0.035 Uiso 1 1 calc R . . H6B H 0.6990 1.1883 0.7639 0.035 Uiso 1 1 calc R . . C7 C 0.7194(8) 0.9369(8) 0.8146(7) 0.0276(14) Uani 1 1 d . . . C8 C 0.8320(9) 1.1174(9) 0.1413(7) 0.0329(16) Uani 1 1 d . . . H8A H 0.9178 1.0404 0.1067 0.039 Uiso 1 1 calc R . . H8B H 0.8818 1.1862 0.1732 0.039 Uiso 1 1 calc R . . C9 C 0.7467(8) 1.2235(8) 0.0309(7) 0.0266(14) Uani 1 1 d . . . C10 C 0.9841(8) 0.5933(7) 0.4670(6) 0.0252(14) 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 U 0.02536(15) 0.01986(14) 0.02433(15) -0.00613(9) -0.00643(9) -0.00375(9) O1 0.024(2) 0.030(2) 0.034(3) -0.009(2) -0.007(2) -0.0077(19) O2 0.028(2) 0.027(2) 0.038(3) -0.009(2) -0.012(2) -0.0013(19) O3 0.041(3) 0.021(2) 0.028(3) -0.0082(19) -0.010(2) 0.002(2) O4 0.038(3) 0.030(2) 0.027(3) -0.006(2) -0.011(2) -0.001(2) O5 0.033(3) 0.021(2) 0.027(2) -0.0029(18) -0.002(2) -0.0038(19) O6 0.027(3) 0.031(3) 0.034(3) -0.004(2) -0.008(2) -0.004(2) O7 0.038(3) 0.022(2) 0.030(3) -0.0097(19) -0.007(2) 0.001(2) O8 0.033(3) 0.022(2) 0.022(2) -0.0052(18) -0.0086(19) -0.0020(19) O9 0.029(2) 0.029(2) 0.027(2) -0.0065(19) -0.0036(19) -0.0042(19) N1 0.034(3) 0.023(3) 0.027(3) -0.009(2) -0.012(2) -0.002(2) N2 0.025(3) 0.031(3) 0.026(3) -0.007(2) -0.006(2) -0.009(2) C1 0.024(3) 0.031(4) 0.039(4) -0.015(3) -0.010(3) -0.004(3) C2 0.032(4) 0.025(3) 0.031(4) -0.002(3) -0.007(3) -0.008(3) C3 0.034(4) 0.034(4) 0.017(3) -0.003(3) -0.008(3) -0.005(3) C4 0.037(4) 0.035(4) 0.027(4) -0.013(3) -0.010(3) 0.004(3) C5 0.039(4) 0.026(3) 0.031(4) -0.009(3) -0.020(3) 0.008(3) C6 0.039(4) 0.018(3) 0.034(4) -0.008(3) -0.020(3) 0.005(3) C7 0.031(4) 0.022(3) 0.027(4) -0.004(3) -0.003(3) -0.008(3) C8 0.033(4) 0.041(4) 0.022(3) -0.002(3) -0.005(3) -0.012(3) C9 0.032(4) 0.021(3) 0.027(4) -0.008(3) -0.004(3) -0.005(3) C10 0.031(4) 0.018(3) 0.027(4) -0.001(3) -0.012(3) -0.003(3) _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 U O1 1.768(5) . ? U O2 1.768(5) . ? U O5 2.335(4) 1_546 ? U O3 2.357(4) . ? U O8 2.441(4) 2_766 ? U O9 2.445(4) . ? U O7 2.450(5) . ? O3 C7 1.274(8) . ? O4 C7 1.249(8) . ? O5 C9 1.281(8) . ? O5 U 2.335(4) 1_564 ? O6 C9 1.231(8) . ? O7 C10 1.248(8) . ? O8 C10 1.248(8) . ? O8 U 2.441(4) 2_766 ? O9 H9A 0.9732 . ? O9 H9B 0.8995 . ? N1 C5 1.460(8) 2_676 ? N1 C1 1.470(9) . ? N1 C6 1.478(8) . ? N2 C3 1.501(8) . ? N2 C8 1.502(8) . ? N2 C4 1.504(9) . ? N2 H2 0.9279 . ? C1 C2 1.526(10) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 C3 1.514(9) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.522(10) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 N1 1.460(8) 2_676 ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 C7 1.525(9) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C8 C9 1.524(9) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C10 C10 1.552(12) 2_766 ? 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 O1 U O2 178.5(2) . . ? O1 U O5 88.42(19) . 1_546 ? O2 U O5 92.31(19) . 1_546 ? O1 U O3 90.61(19) . . ? O2 U O3 89.43(19) . . ? O5 U O3 149.48(16) 1_546 . ? O1 U O8 89.16(18) . 2_766 ? O2 U O8 89.84(19) . 2_766 ? O5 U O8 71.37(15) 1_546 2_766 ? O3 U O8 139.13(15) . 2_766 ? O1 U O9 89.72(19) . . ? O2 U O9 91.73(19) . . ? O5 U O9 75.04(15) 1_546 . ? O3 U O9 74.44(15) . . ? O8 U O9 146.42(15) 2_766 . ? O1 U O7 88.07(19) . . ? O2 U O7 90.50(19) . . ? O5 U O7 136.99(15) 1_546 . ? O3 U O7 73.42(15) . . ? O8 U O7 65.72(14) 2_766 . ? O9 U O7 147.76(15) . . ? C7 O3 U 130.7(4) . . ? C9 O5 U 131.1(4) . 1_564 ? C10 O7 U 120.7(4) . . ? C10 O8 U 120.7(4) . 2_766 ? U O9 H9A 97.2 . . ? U O9 H9B 108.3 . . ? H9A O9 H9B 98.3 . . ? C5 N1 C1 111.6(5) 2_676 . ? C5 N1 C6 111.3(5) 2_676 . ? C1 N1 C6 110.2(5) . . ? C3 N2 C8 112.7(5) . . ? C3 N2 C4 114.4(5) . . ? C8 N2 C4 108.7(5) . . ? C3 N2 H2 106.8 . . ? C8 N2 H2 103.4 . . ? C4 N2 H2 110.3 . . ? N1 C1 C2 114.3(6) . . ? N1 C1 H1A 108.7 . . ? C2 C1 H1A 108.7 . . ? N1 C1 H1B 108.7 . . ? C2 C1 H1B 108.7 . . ? H1A C1 H1B 107.6 . . ? C3 C2 C1 111.6(5) . . ? C3 C2 H2A 109.3 . . ? C1 C2 H2A 109.3 . . ? C3 C2 H2B 109.3 . . ? C1 C2 H2B 109.3 . . ? H2A C2 H2B 108.0 . . ? N2 C3 C2 110.7(5) . . ? N2 C3 H3A 109.5 . . ? C2 C3 H3A 109.5 . . ? N2 C3 H3B 109.5 . . ? C2 C3 H3B 109.5 . . ? H3A C3 H3B 108.1 . . ? N2 C4 C5 112.8(6) . . ? N2 C4 H4A 109.0 . . ? C5 C4 H4A 109.0 . . ? N2 C4 H4B 109.0 . . ? C5 C4 H4B 109.0 . . ? H4A C4 H4B 107.8 . . ? N1 C5 C4 111.8(5) 2_676 . ? N1 C5 H5A 109.3 2_676 . ? C4 C5 H5A 109.3 . . ? N1 C5 H5B 109.3 2_676 . ? C4 C5 H5B 109.3 . . ? H5A C5 H5B 107.9 . . ? N1 C6 C7 114.5(5) . . ? N1 C6 H6A 108.6 . . ? C7 C6 H6A 108.6 . . ? N1 C6 H6B 108.6 . . ? C7 C6 H6B 108.6 . . ? H6A C6 H6B 107.6 . . ? O4 C7 O3 125.4(6) . . ? O4 C7 C6 116.8(6) . . ? O3 C7 C6 117.7(6) . . ? N2 C8 C9 110.6(6) . . ? N2 C8 H8A 109.5 . . ? C9 C8 H8A 109.5 . . ? N2 C8 H8B 109.5 . . ? C9 C8 H8B 109.5 . . ? H8A C8 H8B 108.1 . . ? O6 C9 O5 129.0(6) . . ? O6 C9 C8 118.4(6) . . ? O5 C9 C8 112.6(6) . . ? O8 C10 O7 127.6(6) . . ? O8 C10 C10 116.5(7) . 2_766 ? O7 C10 C10 115.9(7) . 2_766 ? 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 N2 H2 O6 0.93 2.09 2.659(7) 118.6 . O9 H9A O4 0.97 1.72 2.647(7) 158.9 . O9 H9B O6 0.90 1.86 2.723(6) 160.3 2_676 #===END data_2 _database_code_depnum_ccdc_archive 'CCDC 756416' #TrackingRef 'CIF.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H34 Cl N5 O14 U' _chemical_formula_weight 817.98 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' Cl Cl 0.1484 0.1585 '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 monoclinic _symmetry_space_group_name_H-M 'C 2/m' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x, -y, z' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z' _cell_length_a 20.3512(13) _cell_length_b 12.8168(6) _cell_length_c 10.9421(6) _cell_angle_alpha 90.00 _cell_angle_beta 103.303(4) _cell_angle_gamma 90.00 _cell_volume 2777.5(3) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 42985 _cell_measurement_theta_min 2.47 _cell_measurement_theta_max 25.67 _exptl_crystal_description platelet _exptl_crystal_colour 'translucent light yellow' _exptl_crystal_size_max 0.11 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.956 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1592 _exptl_absorpt_coefficient_mu 6.014 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.615 _exptl_absorpt_correction_T_max 0.835 _exptl_absorpt_process_details 'SCALEPACK (Otwinowski & Minor, 1997)' _exptl_special_details 'crystal-to-detector distance 30 mm' _diffrn_ambient_temperature 150(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 'Nonius Kappa-CCD area-detector diffractometer' _diffrn_measurement_method 'two \f and four \w scans with 2\% steps (412 frames)' _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 42985 _diffrn_reflns_av_R_equivalents 0.0340 _diffrn_reflns_av_sigmaI/netI 0.0472 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.47 _diffrn_reflns_theta_max 25.67 _reflns_number_total 2763 _reflns_number_gt 2456 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Nonius, 1998)' _computing_cell_refinement 'HKL2000 (Otwinowski & Minor, 1997)' _computing_data_reduction 'HKL2000 (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXTL (Sheldrick, 2008); PLATON (Spek, 2003)' _refine_special_details ; Structure solved by direct methods and subsequent Fourier-difference synthesis. All non-hydrogen atoms were refined with anisotropic displacement parameters. The H atoms bound to N and O atoms were found on a Fourier-difference map and all the others were introduced at calculated positions. All were treated as riding atoms with an isotropic displacement parameter equal to 1.2 times that of the parent atom. 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^)+(0.0360P)^2^+10.8841P] 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 2763 _refine_ls_number_parameters 187 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0412 _refine_ls_R_factor_gt 0.0326 _refine_ls_wR_factor_ref 0.0738 _refine_ls_wR_factor_gt 0.0717 _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_restrained_S_all 1.048 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.67 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.804 _refine_diff_density_min -1.098 _refine_diff_density_rms 0.150 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 U U 0.119529(13) 0.0000 0.42113(3) 0.01820(10) Uani 1 2 d S . . Cl Cl 0.26483(12) 0.5000 0.0576(2) 0.0414(5) Uani 1 2 d S . . O1 O 0.1166(3) 0.0000 0.5815(5) 0.0223(11) Uani 1 2 d S . . O2 O 0.1244(3) 0.0000 0.2608(5) 0.0261(12) Uani 1 2 d S . . O3 O 0.16124(19) 0.1733(3) 0.4369(4) 0.0264(8) Uani 1 1 d . . . O4 O 0.1777(2) 0.3319(3) 0.5176(4) 0.0351(10) Uani 1 1 d . . . O5 O 0.52519(18) 0.3907(3) 0.3697(4) 0.0338(10) Uani 1 1 d . . . O6 O 0.52795(18) 0.3098(3) 0.1884(4) 0.0315(9) Uani 1 1 d . . . O7 O 0.2442(3) 0.0000 0.4833(5) 0.0291(13) Uani 1 2 d S . . H7 H 0.2680 0.0523 0.4697 0.035 Uiso 1 1 d R . . O8 O 0.5066(2) 0.0848(4) 0.2018(7) 0.0704(18) Uani 1 1 d . . . O9 O 0.4248(4) 0.0000 0.0853(7) 0.0511(18) Uani 1 2 d S . . N1 N 0.1574(2) 0.2400(3) 0.1954(4) 0.0194(9) Uani 1 1 d . . . H1 H 0.1191 0.1896 0.2045 0.023 Uiso 1 1 d R . . N2 N 0.4001(2) 0.2318(3) 0.1615(4) 0.0209(9) Uani 1 1 d . . . H2 H 0.4404 0.1923 0.1706 0.025 Uiso 1 1 d R . . N3 N 0.4791(4) 0.0000 0.1624(9) 0.042(2) Uani 1 2 d S . . C1 C 0.2211(2) 0.1773(4) 0.2047(5) 0.0216(11) Uani 1 1 d . . . H1A H 0.2128 0.1233 0.1408 0.026 Uiso 1 1 calc R . . H1B H 0.2327 0.1433 0.2860 0.026 Uiso 1 1 calc R . . C2 C 0.2804(3) 0.2438(5) 0.1883(6) 0.0323(13) Uani 1 1 d . . . H2A H 0.2922 0.2935 0.2567 0.039 Uiso 1 1 calc R . . H2B H 0.2682 0.2822 0.1100 0.039 Uiso 1 1 calc R . . C3 C 0.3402(2) 0.1725(4) 0.1875(5) 0.0206(11) Uani 1 1 d . . . H3A H 0.3537 0.1379 0.2682 0.025 Uiso 1 1 calc R . . H3B H 0.3265 0.1193 0.1237 0.025 Uiso 1 1 calc R . . C4 C 0.3849(3) 0.2845(4) 0.0354(5) 0.0226(11) Uani 1 1 d . . . H4A H 0.4240 0.3247 0.0265 0.027 Uiso 1 1 calc R . . H4B H 0.3475 0.3325 0.0302 0.027 Uiso 1 1 calc R . . C5 C 0.3670(3) 0.2050(4) -0.0719(5) 0.0220(11) Uani 1 1 d . . . H5A H 0.4065 0.1634 -0.0746 0.026 Uiso 1 1 calc R . . H5B H 0.3321 0.1584 -0.0571 0.026 Uiso 1 1 calc R . . C6 C 0.1628(3) 0.3189(4) 0.3001(5) 0.0231(11) Uani 1 1 d . . . H6A H 0.1234 0.3639 0.2812 0.028 Uiso 1 1 calc R . . H6B H 0.2023 0.3621 0.3032 0.028 Uiso 1 1 calc R . . C7 C 0.1680(2) 0.2698(4) 0.4283(5) 0.0238(12) Uani 1 1 d . . . C8 C 0.4265(3) 0.3085(5) 0.2645(5) 0.0273(12) Uani 1 1 d . . . H8A H 0.4230 0.2785 0.3442 0.033 Uiso 1 1 calc R . . H8B H 0.3988 0.3708 0.2507 0.033 Uiso 1 1 calc R . . C9 C 0.4995(3) 0.3383(4) 0.2717(5) 0.0254(12) 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 U 0.01685(14) 0.01824(15) 0.01956(15) 0.000 0.00430(10) 0.000 Cl 0.0439(13) 0.0260(10) 0.0565(14) 0.000 0.0161(11) 0.000 O1 0.030(3) 0.019(3) 0.020(3) 0.000 0.010(2) 0.000 O2 0.024(3) 0.030(3) 0.023(3) 0.000 0.003(2) 0.000 O3 0.031(2) 0.0173(19) 0.034(2) 0.0042(16) 0.0133(17) -0.0007(15) O4 0.046(2) 0.033(2) 0.027(2) -0.0054(19) 0.0095(18) -0.0120(19) O5 0.024(2) 0.047(3) 0.032(2) -0.015(2) 0.0084(17) -0.0161(18) O6 0.022(2) 0.040(2) 0.035(2) -0.0107(19) 0.0121(17) -0.0039(17) O7 0.018(3) 0.020(3) 0.047(4) 0.000 0.004(2) 0.000 O8 0.037(3) 0.028(3) 0.139(6) -0.011(3) 0.006(3) -0.006(2) O9 0.052(5) 0.040(4) 0.062(5) 0.000 0.013(4) 0.000 N1 0.020(2) 0.019(2) 0.021(2) 0.0023(18) 0.0074(17) 0.0008(17) N2 0.017(2) 0.025(2) 0.021(2) -0.0018(19) 0.0055(17) -0.0002(18) N3 0.029(4) 0.025(4) 0.074(6) 0.000 0.013(4) 0.000 C1 0.019(3) 0.022(3) 0.023(3) 0.002(2) 0.004(2) 0.001(2) C2 0.024(3) 0.026(3) 0.047(4) 0.007(3) 0.009(3) 0.003(2) C3 0.018(2) 0.021(3) 0.022(3) 0.004(2) 0.005(2) -0.001(2) C4 0.023(3) 0.022(3) 0.024(3) 0.002(2) 0.007(2) -0.002(2) C5 0.021(3) 0.023(3) 0.022(3) 0.002(2) 0.004(2) 0.000(2) C6 0.023(3) 0.023(3) 0.024(3) -0.002(2) 0.008(2) 0.000(2) C7 0.016(2) 0.026(3) 0.030(3) -0.001(2) 0.006(2) -0.001(2) C8 0.021(3) 0.037(3) 0.027(3) -0.010(3) 0.010(2) -0.006(2) C9 0.018(3) 0.029(3) 0.027(3) -0.001(2) 0.003(2) 0.000(2) _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 U O1 1.770(5) . ? U O2 1.780(5) . ? U O5 2.339(4) 3_445 ? U O5 2.339(4) 8_455 ? U O3 2.369(4) . ? U O3 2.369(4) 6 ? U O7 2.471(5) . ? O3 C7 1.251(6) . ? O4 C7 1.241(7) . ? O5 C9 1.271(6) . ? O5 U 2.339(4) 3 ? O6 C9 1.242(7) . ? O7 H7 0.8592 . ? O8 N3 1.253(6) . ? O9 N3 1.226(10) . ? N1 C5 1.503(6) 7 ? N1 C1 1.509(6) . ? N1 C6 1.513(6) . ? N1 H1 1.0341 . ? N2 C8 1.499(7) . ? N2 C4 1.504(7) . ? N2 C3 1.516(6) . ? N2 H2 0.9487 . ? N3 O8 1.253(6) 6 ? C1 C2 1.521(7) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 C3 1.524(7) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.535(7) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 N1 1.503(6) 7 ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 C7 1.518(7) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C8 C9 1.519(7) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? 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 O1 U O2 178.8(2) . . ? O1 U O5 91.46(16) . 3_445 ? O2 U O5 89.53(16) . 3_445 ? O1 U O5 91.46(16) . 8_455 ? O2 U O5 89.53(16) . 8_455 ? O5 U O5 73.6(2) 3_445 8_455 ? O1 U O3 91.20(11) . . ? O2 U O3 88.37(11) . . ? O5 U O3 147.10(14) 3_445 . ? O5 U O3 73.53(14) 8_455 . ? O1 U O3 91.20(11) . 6 ? O2 U O3 88.37(11) . 6 ? O5 U O3 73.53(14) 3_445 6 ? O5 U O3 147.10(14) 8_455 6 ? O3 U O3 139.17(18) . 6 ? O1 U O7 89.7(2) . . ? O2 U O7 89.1(2) . . ? O5 U O7 143.16(11) 3_445 . ? O5 U O7 143.16(11) 8_455 . ? O3 U O7 69.63(9) . . ? O3 U O7 69.63(9) 6 . ? C7 O3 U 164.9(4) . . ? C9 O5 U 132.4(4) . 3 ? U O7 H7 122.4 . . ? C5 N1 C1 114.3(4) 7 . ? C5 N1 C6 108.6(4) 7 . ? C1 N1 C6 113.2(4) . . ? C5 N1 H1 106.2 7 . ? C1 N1 H1 108.3 . . ? C6 N1 H1 105.6 . . ? C8 N2 C4 110.9(4) . . ? C8 N2 C3 110.6(4) . . ? C4 N2 C3 113.2(4) . . ? C8 N2 H2 96.8 . . ? C4 N2 H2 109.0 . . ? C3 N2 H2 115.2 . . ? O9 N3 O8 119.8(4) . 6 ? O9 N3 O8 119.8(4) . . ? O8 N3 O8 120.4(8) 6 . ? N1 C1 C2 112.7(4) . . ? N1 C1 H1A 109.1 . . ? C2 C1 H1A 109.1 . . ? N1 C1 H1B 109.1 . . ? C2 C1 H1B 109.1 . . ? H1A C1 H1B 107.8 . . ? C1 C2 C3 108.8(4) . . ? C1 C2 H2A 109.9 . . ? C3 C2 H2A 109.9 . . ? C1 C2 H2B 109.9 . . ? C3 C2 H2B 109.9 . . ? H2A C2 H2B 108.3 . . ? N2 C3 C2 112.3(4) . . ? N2 C3 H3A 109.1 . . ? C2 C3 H3A 109.1 . . ? N2 C3 H3B 109.1 . . ? C2 C3 H3B 109.1 . . ? H3A C3 H3B 107.9 . . ? N2 C4 C5 111.4(4) . . ? N2 C4 H4A 109.3 . . ? C5 C4 H4A 109.3 . . ? N2 C4 H4B 109.3 . . ? C5 C4 H4B 109.3 . . ? H4A C4 H4B 108.0 . . ? N1 C5 C4 110.3(4) 7 . ? N1 C5 H5A 109.6 7 . ? C4 C5 H5A 109.6 . . ? N1 C5 H5B 109.6 7 . ? C4 C5 H5B 109.6 . . ? H5A C5 H5B 108.1 . . ? N1 C6 C7 113.6(4) . . ? N1 C6 H6A 108.8 . . ? C7 C6 H6A 108.8 . . ? N1 C6 H6B 108.8 . . ? C7 C6 H6B 108.8 . . ? H6A C6 H6B 107.7 . . ? O4 C7 O3 125.1(5) . . ? O4 C7 C6 115.3(5) . . ? O3 C7 C6 119.6(5) . . ? N2 C8 C9 112.5(4) . . ? N2 C8 H8A 109.1 . . ? C9 C8 H8A 109.1 . . ? N2 C8 H8B 109.1 . . ? C9 C8 H8B 109.1 . . ? H8A C8 H8B 107.8 . . ? O6 C9 O5 127.2(5) . . ? O6 C9 C8 120.2(5) . . ? O5 C9 C8 112.6(5) . . ? 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 O6 1.03 1.82 2.694(5) 139.4 8_455 N2 H2 O8 0.95 1.90 2.829(7) 164.6 . O7 H7 O4 0.86 1.84 2.678(5) 165.9 7_556 #===END data_3 _database_code_depnum_ccdc_archive 'CCDC 756417' #TrackingRef 'CIF.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H44 N4 O17 U' _chemical_formula_weight 826.60 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 monoclinic _symmetry_space_group_name_H-M 'C 2/c' 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' '-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 21.3207(11) _cell_length_b 16.6570(9) _cell_length_c 10.1919(4) _cell_angle_alpha 90.00 _cell_angle_beta 97.853(3) _cell_angle_gamma 90.00 _cell_volume 3585.6(3) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 45059 _cell_measurement_theta_min 3.17 _cell_measurement_theta_max 25.68 _exptl_crystal_description platelet _exptl_crystal_colour 'translucent light yellow' _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.531 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1632 _exptl_absorpt_coefficient_mu 4.592 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.479 _exptl_absorpt_correction_T_max 0.759 _exptl_absorpt_process_details 'SCALEPACK (Otwinowski & Minor, 1997)' _exptl_special_details 'crystal-to-detector distance 40 mm' _diffrn_ambient_temperature 150(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 'Nonius Kappa-CCD area-detector diffractometer' _diffrn_measurement_method 'two \f and five \w scans with 2\% steps (487 frames)' _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 45059 _diffrn_reflns_av_R_equivalents 0.0505 _diffrn_reflns_av_sigmaI/netI 0.0562 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.17 _diffrn_reflns_theta_max 25.68 _reflns_number_total 3400 _reflns_number_gt 3069 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Nonius, 1998)' _computing_cell_refinement 'HKL2000 (Otwinowski & Minor, 1997)' _computing_data_reduction 'HKL2000 (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXTL (Sheldrick, 2008); PLATON (Spek, 2003)' _refine_special_details ; Structure solved by direct methods and subsequent Fourier-difference synthesis. All non-hydrogen atoms were refined with anisotropic displacement parameters. The water solvent molecules containing O8 and O9 are too close to one another and they were refined with occupancy parameters constrained to sum to unity and restraints on displacement parameters. The H atoms bound to O6, N1 and N2 were found on a Fourier-difference map and all the others were introduced at calculated positions. The hydrogen atoms bound to N1 and N2 were given occupancy parameters of 0.5 for charge equilibrium. All H atoms were treated as riding atoms with an isotropic displacement parameter equal to 1.2 times that of the parent atom. Some voids in the lattice likely indicate the presence of other, unresolved water solvent molecules. 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^)+(0.0590P)^2^+18.5474P] 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 3400 _refine_ls_number_parameters 193 _refine_ls_number_restraints 13 _refine_ls_R_factor_all 0.0481 _refine_ls_R_factor_gt 0.0391 _refine_ls_wR_factor_ref 0.1062 _refine_ls_wR_factor_gt 0.1032 _refine_ls_goodness_of_fit_ref 1.081 _refine_ls_restrained_S_all 1.083 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.68 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 2.301 _refine_diff_density_min -3.536 _refine_diff_density_rms 0.222 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 U U 0.5000 0.148902(17) 0.2500 0.01996(13) Uani 1 2 d S . . O1 O 0.5480(2) 0.1517(2) 0.1221(4) 0.0272(9) Uani 1 1 d . . . O2 O 0.4174(2) 0.1917(3) 0.0849(4) 0.0327(10) Uani 1 1 d . . . O3 O 0.3189(2) 0.2052(3) -0.0142(4) 0.0421(12) Uani 1 1 d . . . O4 O 0.44608(19) -0.0328(3) 0.6562(4) 0.0295(10) Uani 1 1 d . . . O5 O 0.3495(2) -0.0454(3) 0.7194(4) 0.0332(10) Uani 1 1 d . . . O6 O 0.5000 0.2943(4) 0.2500 0.062(2) Uani 1 2 d S . . H6 H 0.4908 0.3258 0.3122 0.074 Uiso 1 1 d R . . N1 N 0.2821(2) 0.2818(3) 0.2057(5) 0.0316(12) Uani 1 1 d . . . H1 H 0.2620 0.2941 0.1267 0.038 Uiso 0.50 1 d PR . . N2 N 0.2981(2) 0.0760(3) 0.5711(5) 0.0285(12) Uani 1 1 d . . . H2 H 0.2807 0.0302 0.6009 0.034 Uiso 0.50 1 d PR . . C1 C 0.2598(3) 0.2023(4) 0.2551(6) 0.0288(14) Uani 1 1 d . . . H1A H 0.2666 0.1604 0.1925 0.035 Uiso 1 1 calc R . . H1B H 0.2146 0.2054 0.2593 0.035 Uiso 1 1 calc R . . C2 C 0.2941(3) 0.1799(4) 0.3919(6) 0.0311(14) Uani 1 1 d . . . H2A H 0.3388 0.1716 0.3872 0.037 Uiso 1 1 calc R . . H2B H 0.2901 0.2231 0.4541 0.037 Uiso 1 1 calc R . . C3 C 0.2652(3) 0.1037(4) 0.4382(6) 0.0307(14) Uani 1 1 d . . . H3A H 0.2678 0.0617 0.3733 0.037 Uiso 1 1 calc R . . H3B H 0.2208 0.1131 0.4444 0.037 Uiso 1 1 calc R . . C4 C 0.2951(3) 0.1351(4) 0.6840(6) 0.0293(14) Uani 1 1 d . . . H4A H 0.3132 0.1860 0.6625 0.035 Uiso 1 1 calc R . . H4B H 0.3198 0.1147 0.7641 0.035 Uiso 1 1 calc R . . C5 C 0.2267(4) 0.1476(4) 0.7078(7) 0.0351(16) Uani 1 1 d . . . H5A H 0.2005 0.1550 0.6230 0.042 Uiso 1 1 calc R . . H5B H 0.2121 0.0997 0.7483 0.042 Uiso 1 1 calc R . . C6 C 0.3503(3) 0.2776(4) 0.1860(6) 0.0326(15) Uani 1 1 d . . . H6A H 0.3753 0.2610 0.2683 0.039 Uiso 1 1 calc R . . H6B H 0.3645 0.3306 0.1640 0.039 Uiso 1 1 calc R . . C7 C 0.3615(3) 0.2190(4) 0.0766(6) 0.0317(14) Uani 1 1 d . . . C8 C 0.3667(3) 0.0545(4) 0.5633(6) 0.0278(13) Uani 1 1 d . . . H8A H 0.3713 0.0389 0.4734 0.033 Uiso 1 1 calc R . . H8B H 0.3934 0.1010 0.5864 0.033 Uiso 1 1 calc R . . C9 C 0.3878(3) -0.0139(4) 0.6568(5) 0.0242(12) Uani 1 1 d . . . O7 O 0.4445(3) 0.0974(5) -0.1381(7) 0.083(2) Uani 1 1 d U . . O8 O 0.1874(3) -0.0580(3) 0.5413(7) 0.053(2) Uani 0.576(17) 1 d PU . . O9 O 0.2206(6) -0.0737(6) 0.4790(10) 0.047(3) Uani 0.424(17) 1 d PU . . O10 O 0.1134(5) 0.1872(7) 0.4002(12) 0.127(4) 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 U 0.01673(18) 0.01844(18) 0.02464(19) 0.000 0.00252(11) 0.000 O1 0.022(2) 0.031(2) 0.029(2) 0.0027(17) 0.0041(17) 0.0013(18) O2 0.025(2) 0.045(3) 0.028(2) 0.0024(19) 0.0027(18) 0.014(2) O3 0.028(3) 0.068(4) 0.031(2) 0.003(2) 0.003(2) 0.019(2) O4 0.022(2) 0.030(2) 0.037(2) 0.0056(18) 0.0044(18) 0.0054(18) O5 0.026(2) 0.038(3) 0.035(2) 0.015(2) 0.0064(18) 0.002(2) O6 0.066(6) 0.014(3) 0.108(7) 0.000 0.018(5) 0.000 N1 0.025(3) 0.042(3) 0.028(3) 0.006(2) 0.006(2) 0.017(2) N2 0.027(3) 0.038(3) 0.021(2) 0.008(2) 0.006(2) 0.013(2) C1 0.025(3) 0.038(3) 0.023(3) 0.007(2) 0.003(2) 0.013(3) C2 0.037(4) 0.035(3) 0.021(3) 0.007(3) 0.002(3) 0.015(3) C3 0.033(3) 0.038(4) 0.022(3) 0.003(3) 0.004(3) 0.010(3) C4 0.030(3) 0.038(4) 0.022(3) 0.005(2) 0.010(3) 0.017(3) C5 0.035(4) 0.035(4) 0.038(4) 0.009(3) 0.013(3) 0.010(3) C6 0.024(3) 0.041(4) 0.034(3) 0.008(3) 0.007(3) 0.013(3) C7 0.032(3) 0.038(3) 0.027(3) 0.008(3) 0.008(3) 0.012(3) C8 0.025(3) 0.034(3) 0.027(3) 0.006(3) 0.010(2) 0.013(3) C9 0.026(3) 0.025(3) 0.021(3) -0.001(2) 0.002(2) 0.005(3) O7 0.076(4) 0.111(6) 0.061(4) -0.022(4) 0.003(3) 0.010(4) O8 0.063(4) 0.033(3) 0.053(4) -0.013(3) -0.028(3) 0.007(3) O9 0.058(6) 0.042(5) 0.040(5) -0.009(4) 0.003(5) -0.006(5) O10 0.110(8) 0.105(8) 0.168(10) -0.014(7) 0.026(7) 0.007(7) _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 U O1 1.765(4) 2_655 ? U O1 1.765(4) . ? U O2 2.372(4) 2_655 ? U O2 2.372(4) . ? U O4 2.382(4) 6 ? U O4 2.382(4) 5_656 ? U O6 2.422(7) . ? O2 C7 1.269(7) . ? O3 C7 1.226(8) . ? O4 C9 1.283(7) . ? O4 U 2.382(4) 5_656 ? O5 C9 1.220(7) . ? O6 H6 0.8656 . ? N1 C6 1.496(8) . ? N1 C5 1.496(8) 7_556 ? N1 C1 1.516(8) . ? N1 H1 0.8830 . ? N2 C3 1.511(7) . ? N2 C8 1.518(7) . ? N2 C4 1.522(8) . ? N2 H2 0.9174 . ? C1 C2 1.530(8) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 C3 1.514(10) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.526(9) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 N1 1.496(8) 7_556 ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 C7 1.524(9) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C8 C9 1.513(8) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? 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 O1 U O1 177.0(3) 2_655 . ? O1 U O2 85.27(18) 2_655 2_655 ? O1 U O2 93.82(18) . 2_655 ? O1 U O2 93.82(18) 2_655 . ? O1 U O2 85.27(18) . . ? O2 U O2 145.0(2) 2_655 . ? O1 U O4 91.19(17) 2_655 6 ? O1 U O4 91.27(17) . 6 ? O2 U O4 143.06(16) 2_655 6 ? O2 U O4 71.89(16) . 6 ? O1 U O4 91.27(17) 2_655 5_656 ? O1 U O4 91.19(17) . 5_656 ? O2 U O4 71.89(16) 2_655 5_656 ? O2 U O4 143.06(16) . 5_656 ? O4 U O4 71.4(2) 6 5_656 ? O1 U O6 88.49(13) 2_655 . ? O1 U O6 88.49(13) . . ? O2 U O6 72.49(12) 2_655 . ? O2 U O6 72.49(12) . . ? O4 U O6 144.28(10) 6 . ? O4 U O6 144.28(11) 5_656 . ? C7 O2 U 139.0(4) . . ? C9 O4 U 127.7(4) . 5_656 ? U O6 H6 127.3 . . ? C6 N1 C5 108.5(5) . 7_556 ? C6 N1 C1 111.0(5) . . ? C5 N1 C1 114.8(5) 7_556 . ? C6 N1 H1 104.4 . . ? C5 N1 H1 105.7 7_556 . ? C1 N1 H1 111.7 . . ? C3 N2 C8 111.0(4) . . ? C3 N2 C4 114.7(5) . . ? C8 N2 C4 109.4(5) . . ? C3 N2 H2 113.0 . . ? C8 N2 H2 104.9 . . ? C4 N2 H2 103.1 . . ? N1 C1 C2 112.5(5) . . ? N1 C1 H1A 109.1 . . ? C2 C1 H1A 109.1 . . ? N1 C1 H1B 109.1 . . ? C2 C1 H1B 109.1 . . ? H1A C1 H1B 107.8 . . ? C3 C2 C1 108.9(6) . . ? C3 C2 H2A 109.9 . . ? C1 C2 H2A 109.9 . . ? C3 C2 H2B 109.9 . . ? C1 C2 H2B 109.9 . . ? H2A C2 H2B 108.3 . . ? C2 C3 N2 112.1(5) . . ? C2 C3 H3A 109.2 . . ? N2 C3 H3A 109.2 . . ? C2 C3 H3B 109.2 . . ? N2 C3 H3B 109.2 . . ? H3A C3 H3B 107.9 . . ? N2 C4 C5 110.4(6) . . ? N2 C4 H4A 109.6 . . ? C5 C4 H4A 109.6 . . ? N2 C4 H4B 109.6 . . ? C5 C4 H4B 109.6 . . ? H4A C4 H4B 108.1 . . ? N1 C5 C4 113.6(6) 7_556 . ? N1 C5 H5A 108.8 7_556 . ? C4 C5 H5A 108.8 . . ? N1 C5 H5B 108.8 7_556 . ? C4 C5 H5B 108.8 . . ? H5A C5 H5B 107.7 . . ? N1 C6 C7 112.3(6) . . ? N1 C6 H6A 109.1 . . ? C7 C6 H6A 109.1 . . ? N1 C6 H6B 109.1 . . ? C7 C6 H6B 109.1 . . ? H6A C6 H6B 107.9 . . ? O3 C7 O2 125.2(6) . . ? O3 C7 C6 119.9(6) . . ? O2 C7 C6 114.8(6) . . ? C9 C8 N2 110.5(5) . . ? C9 C8 H8A 109.6 . . ? N2 C8 H8A 109.6 . . ? C9 C8 H8B 109.6 . . ? N2 C8 H8B 109.6 . . ? H8A C8 H8B 108.1 . . ? O5 C9 O4 127.9(6) . . ? O5 C9 C8 119.4(5) . . ? O4 C9 C8 112.7(5) . . ? 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 O3 0.88 1.94 2.710(7) 145.4 7 N2 H2 O5 0.92 2.17 2.668(6) 113.1 .