Electronic Supplementary Material for CrystEngComm This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_coden_Cambridge 1350 _publ_contact_author_name 'Pierre Thuery' _publ_contact_author_address ; CEA/Saclay, SCM (CNRS URA 331) Bat. 125 91191 Gif-sur-Yvette France ; _publ_contact_author_phone '33 1 69 08 63 29' _publ_contact_author_fax '33 1 69 08 66 40' _publ_contact_author_email pierre.thuery@cea.fr _publ_requested_journal CrystEngComm loop_ _publ_author_name 'Pierre Thuery' _publ_section_title ; Novel two-dimensional uranyl-organic assemblages in the citrate and D(-)-citramalate families ; data_1 _database_code_depnum_ccdc_archive 'CCDC 655324' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C5 H6 O7 U' _chemical_formula_weight 416.13 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' 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 'P 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 8.3067(9) _cell_length_b 9.7312(12) _cell_length_c 10.7272(13) _cell_angle_alpha 90.00 _cell_angle_beta 106.181(8) _cell_angle_gamma 90.00 _cell_volume 832.77(17) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 24997 _cell_measurement_theta_min 2.55 _cell_measurement_theta_max 25.68 _exptl_crystal_description irregular _exptl_crystal_colour 'translucent light yellow' _exptl_crystal_size_max 0.06 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 3.319 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 736 _exptl_absorpt_coefficient_mu 19.496 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.350 _exptl_absorpt_correction_T_max 0.557 _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' _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 24997 _diffrn_reflns_av_R_equivalents 0.0785 _diffrn_reflns_av_sigmaI/netI 0.0332 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.55 _diffrn_reflns_theta_max 25.68 _reflns_number_total 3159 _reflns_number_gt 2971 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, 1998)' _computing_cell_refinement 'HKL2000 (Otwinowski & Minor, 1997)' _computing_data_reduction 'HKL2000 (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 1999)' _computing_publication_material 'SHELXTL (Sheldrick, 1999); 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 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 (OH, CH~2~) or 1.5 (CH~3~) 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^)+(0.0524P)^2^+2.7900P] 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 ? _chemical_absolute_configuration ad _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.002(19) _refine_ls_number_reflns 3159 _refine_ls_number_parameters 238 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0384 _refine_ls_R_factor_gt 0.0342 _refine_ls_wR_factor_ref 0.0837 _refine_ls_wR_factor_gt 0.0815 _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_restrained_S_all 1.025 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.68 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.645 _refine_diff_density_min -1.846 _refine_diff_density_rms 0.180 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 0.23161(6) 0.50884(5) 0.58806(6) 0.03918(14) Uani 1 1 d . . . U2 U 0.78779(6) 0.24982(5) 0.88299(6) 0.03958(14) Uani 1 1 d . . . O1 O 0.2655(9) 0.5211(16) 0.4337(8) 0.046(2) Uani 1 1 d . . . O2 O 0.1998(12) 0.4925(15) 0.7424(9) 0.052(3) Uani 1 1 d . . . O3 O 0.8504(11) 0.2715(13) 0.7409(8) 0.049(3) Uani 1 1 d . . . O4 O 0.7281(11) 0.2288(15) 1.0263(9) 0.053(3) Uani 1 1 d . . . O5 O 0.0641(9) 0.0850(9) 0.5087(9) 0.0373(19) Uani 1 1 d . . . H5 H 0.0342 0.1815 0.5195 0.045 Uiso 1 1 d R . . O6 O -0.0140(12) -0.1587(9) 0.4903(11) 0.048(2) Uani 1 1 d . . . O7 O 0.2313(9) -0.2429(13) 0.6092(8) 0.043(2) Uani 1 1 d . . . O8 O 0.3377(11) 0.2825(10) 0.5904(11) 0.054(3) Uani 1 1 d . . . O9 O 0.5214(10) 0.1961(9) 0.7619(9) 0.045(2) Uani 1 1 d . . . O10 O 0.9201(11) 0.6729(11) 1.0010(10) 0.050(2) Uani 1 1 d . . . H10 H 0.9579 0.5843 0.9883 0.060 Uiso 1 1 d R . . O11 O 1.0133(14) 0.9159(10) 1.0003(11) 0.057(3) Uani 1 1 d . . . O12 O 0.7852(9) 1.0012(13) 0.8683(7) 0.042(2) Uani 1 1 d . . . O13 O 0.5130(11) 0.5657(10) 0.6721(10) 0.053(2) Uani 1 1 d . . . O14 O 0.6795(12) 0.4790(11) 0.8579(10) 0.057(3) Uani 1 1 d . . . C1 C 0.1800(16) 0.004(2) 0.6057(14) 0.043(4) Uani 1 1 d . . . C2 C 0.1302(15) -0.1433(12) 0.5633(13) 0.038(3) Uani 1 1 d . . . C3 C 0.3628(14) 0.0372(12) 0.6046(13) 0.041(3) Uani 1 1 d . . . H3A H 0.4389 -0.0289 0.6581 0.049 Uiso 1 1 calc R . . H3B H 0.3720 0.0297 0.5166 0.049 Uiso 1 1 calc R . . C4 C 0.4126(16) 0.1831(14) 0.6562(15) 0.046(3) Uani 1 1 d . . . C5 C 0.1562(16) 0.0271(15) 0.7385(12) 0.043(3) Uani 1 1 d . . . H5A H 0.1759 0.1221 0.7620 0.064 Uiso 1 1 calc R . . H5B H 0.2339 -0.0290 0.8008 0.064 Uiso 1 1 calc R . . H5C H 0.0437 0.0030 0.7372 0.064 Uiso 1 1 calc R . . C6 C 0.7883(16) 0.753(2) 0.9223(10) 0.039(4) Uani 1 1 d . . . C7 C 0.8660(16) 0.9027(14) 0.9288(12) 0.043(3) Uani 1 1 d . . . C8 C 0.7383(18) 0.7077(13) 0.7830(12) 0.047(3) Uani 1 1 d . . . H8A H 0.8374 0.6924 0.7539 0.056 Uiso 1 1 calc R . . H8B H 0.6710 0.7782 0.7287 0.056 Uiso 1 1 calc R . . C9 C 0.6371(16) 0.5744(15) 0.7716(17) 0.051(4) Uani 1 1 d . . . C10 C 0.6457(17) 0.7698(16) 0.9820(14) 0.055(3) Uani 1 1 d . . . H10A H 0.6096 0.6810 1.0023 0.083 Uiso 1 1 calc R . . H10B H 0.5542 0.8158 0.9218 0.083 Uiso 1 1 calc R . . H10C H 0.6823 0.8233 1.0600 0.083 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 0.0342(2) 0.0285(2) 0.0504(3) 0.0027(2) 0.0042(2) -0.0022(2) U2 0.0394(3) 0.0353(3) 0.0411(2) -0.0047(3) 0.0062(2) -0.0022(2) O1 0.040(4) 0.049(6) 0.053(5) 0.002(5) 0.019(4) -0.002(5) O2 0.064(6) 0.045(7) 0.048(5) 0.000(5) 0.015(4) -0.007(6) O3 0.055(5) 0.048(7) 0.044(5) 0.006(5) 0.013(4) -0.012(5) O4 0.053(5) 0.065(9) 0.041(5) 0.005(5) 0.010(4) -0.001(5) O5 0.028(4) 0.034(5) 0.047(5) 0.000(4) 0.004(4) -0.003(3) O6 0.033(5) 0.022(5) 0.078(7) 0.007(4) -0.003(5) 0.005(4) O7 0.041(5) 0.030(5) 0.057(5) -0.007(5) 0.012(4) 0.001(4) O8 0.048(5) 0.035(6) 0.073(7) 0.013(5) 0.004(5) 0.011(4) O9 0.034(5) 0.041(5) 0.051(5) -0.002(4) -0.002(4) 0.000(4) O10 0.032(5) 0.054(6) 0.055(6) 0.013(5) -0.001(4) 0.007(4) O11 0.051(6) 0.037(6) 0.068(7) 0.010(5) -0.009(5) 0.004(5) O12 0.034(4) 0.045(5) 0.041(4) -0.003(5) 0.000(4) 0.000(5) O13 0.042(5) 0.043(5) 0.066(6) -0.004(4) 0.003(5) -0.004(4) O14 0.049(5) 0.047(7) 0.059(6) -0.017(5) -0.011(5) 0.005(5) C1 0.027(5) 0.022(6) 0.077(10) -0.012(8) 0.007(5) 0.006(6) C2 0.036(6) 0.020(6) 0.057(8) -0.013(5) 0.013(6) -0.007(5) C3 0.031(6) 0.035(7) 0.055(7) -0.004(5) 0.009(5) -0.003(5) C4 0.036(7) 0.029(6) 0.069(10) -0.004(6) 0.008(7) 0.000(5) C5 0.048(7) 0.046(8) 0.037(6) -0.003(6) 0.014(5) 0.005(6) C6 0.051(7) 0.043(9) 0.021(5) 0.011(7) 0.007(5) 0.000(8) C7 0.040(7) 0.043(7) 0.035(6) 0.011(6) -0.007(5) 0.000(6) C8 0.058(8) 0.042(7) 0.034(7) -0.011(5) 0.005(6) -0.003(6) C9 0.035(7) 0.038(7) 0.082(11) -0.010(7) 0.020(7) 0.005(6) C10 0.059(8) 0.047(8) 0.062(8) -0.017(7) 0.020(7) -0.014(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 U1 O2 1.755(10) . ? U1 O1 1.760(9) . ? U1 O13 2.326(9) . ? U1 O8 2.370(9) . ? U1 O6 2.405(9) 2_556 ? U1 O7 2.427(13) 1_565 ? U1 O5 2.498(7) 2_556 ? U2 O4 1.754(10) . ? U2 O3 1.755(9) . ? U2 O9 2.292(8) . ? U2 O14 2.392(10) . ? U2 O11 2.400(10) 2_747 ? U2 O12 2.424(12) 1_545 ? U2 O10 2.513(9) 2_747 ? O5 C1 1.439(18) . ? O5 U1 2.498(7) 2_546 ? O5 H5 0.9864 . ? O6 C2 1.244(16) . ? O6 U1 2.405(9) 2_546 ? O7 C2 1.287(17) . ? O7 U1 2.427(13) 1_545 ? O8 C4 1.255(16) . ? O9 C4 1.244(17) . ? O10 C6 1.417(18) . ? O10 U2 2.513(9) 2_757 ? O10 H10 0.9401 . ? O11 C7 1.256(17) . ? O11 U2 2.400(10) 2_757 ? O12 C7 1.244(17) . ? O12 U2 2.424(12) 1_565 ? O13 C9 1.264(17) . ? O14 C9 1.288(19) . ? C1 C5 1.508(18) . ? C1 C2 1.53(2) . ? C1 C3 1.556(16) . ? C3 C4 1.538(17) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C5 H5A 0.9600 . ? C5 H5B 0.9600 . ? C5 H5C 0.9600 . ? C6 C8 1.502(17) . ? C6 C10 1.504(17) . ? C6 C7 1.58(3) . ? C8 C9 1.532(19) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? 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 O2 U1 O1 178.6(8) . . ? O2 U1 O13 93.2(4) . . ? O1 U1 O13 86.6(4) . . ? O2 U1 O8 93.4(5) . . ? O1 U1 O8 85.2(5) . . ? O13 U1 O8 83.5(3) . . ? O2 U1 O6 88.4(5) . 2_556 ? O1 U1 O6 91.1(5) . 2_556 ? O13 U1 O6 150.8(3) . 2_556 ? O8 U1 O6 67.3(3) . 2_556 ? O2 U1 O7 89.8(5) . 1_565 ? O1 U1 O7 91.4(5) . 1_565 ? O13 U1 O7 75.8(3) . 1_565 ? O8 U1 O7 159.1(3) . 1_565 ? O6 U1 O7 133.4(3) 2_556 1_565 ? O2 U1 O5 91.7(4) . 2_556 ? O1 U1 O5 89.2(3) . 2_556 ? O13 U1 O5 148.9(3) . 2_556 ? O8 U1 O5 126.9(3) . 2_556 ? O6 U1 O5 60.0(3) 2_556 2_556 ? O7 U1 O5 73.6(3) 1_565 2_556 ? O4 U2 O3 179.2(4) . . ? O4 U2 O9 90.4(4) . . ? O3 U2 O9 90.5(4) . . ? O4 U2 O14 91.1(5) . . ? O3 U2 O14 89.0(5) . . ? O9 U2 O14 82.8(3) . . ? O4 U2 O11 86.7(5) . 2_747 ? O3 U2 O11 92.6(5) . 2_747 ? O9 U2 O11 149.9(4) . 2_747 ? O14 U2 O11 67.3(3) . 2_747 ? O4 U2 O12 86.6(5) . 1_545 ? O3 U2 O12 93.6(5) . 1_545 ? O9 U2 O12 75.3(3) . 1_545 ? O14 U2 O12 158.0(3) . 1_545 ? O11 U2 O12 134.3(3) 2_747 1_545 ? O4 U2 O10 90.0(4) . 2_747 ? O3 U2 O10 89.3(4) . 2_747 ? O9 U2 O10 149.2(3) . 2_747 ? O14 U2 O10 127.9(3) . 2_747 ? O11 U2 O10 60.8(3) 2_747 2_747 ? O12 U2 O10 74.0(3) 1_545 2_747 ? C1 O5 U1 121.3(8) . 2_546 ? C1 O5 H5 125.2 . . ? U1 O5 H5 94.6 2_546 . ? C2 O6 U1 129.5(8) . 2_546 ? C2 O7 U1 137.0(7) . 1_545 ? C4 O8 U1 147.9(11) . . ? C4 O9 U2 151.8(10) . . ? C6 O10 U2 127.5(10) . 2_757 ? C6 O10 H10 130.9 . . ? U2 O10 H10 91.7 2_757 . ? C7 O11 U2 131.4(9) . 2_757 ? C7 O12 U2 137.8(8) . 1_565 ? C9 O13 U1 147.0(10) . . ? C9 O14 U2 140.5(9) . . ? O5 C1 C5 111.3(11) . . ? O5 C1 C2 103.2(11) . . ? C5 C1 C2 109.0(14) . . ? O5 C1 C3 109.8(13) . . ? C5 C1 C3 111.2(12) . . ? C2 C1 C3 112.1(11) . . ? O6 C2 O7 124.2(11) . . ? O6 C2 C1 115.7(11) . . ? O7 C2 C1 120.0(11) . . ? C4 C3 C1 110.7(11) . . ? C4 C3 H3A 109.5 . . ? C1 C3 H3A 109.5 . . ? C4 C3 H3B 109.5 . . ? C1 C3 H3B 109.5 . . ? H3A C3 H3B 108.1 . . ? O9 C4 O8 123.6(13) . . ? O9 C4 C3 118.5(12) . . ? O8 C4 C3 117.9(12) . . ? C1 C5 H5A 109.5 . . ? C1 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C1 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? O10 C6 C8 112.5(15) . . ? O10 C6 C10 112.0(11) . . ? C8 C6 C10 115.0(12) . . ? O10 C6 C7 104.1(11) . . ? C8 C6 C7 108.2(11) . . ? C10 C6 C7 104.0(15) . . ? O12 C7 O11 122.1(13) . . ? O12 C7 C6 122.0(11) . . ? O11 C7 C6 115.9(11) . . ? C6 C8 C9 108.9(13) . . ? C6 C8 H8A 109.9 . . ? C9 C8 H8A 109.9 . . ? C6 C8 H8B 109.9 . . ? C9 C8 H8B 109.9 . . ? H8A C8 H8B 108.3 . . ? O13 C9 O14 123.7(14) . . ? O13 C9 C8 115.1(14) . . ? O14 C9 C8 121.3(13) . . ? C6 C10 H10A 109.5 . . ? C6 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C6 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? 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 O5 H5 O6 0.99 1.56 2.529(12) 164.6 2_556 O10 H10 O11 0.94 1.66 2.562(14) 160.7 2_747 #===END data_2 _database_code_depnum_ccdc_archive 'CCDC 655325' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H56 N2 O24 U3' _chemical_formula_weight 1518.84 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 8.4980(3) _cell_length_b 9.2992(4) _cell_length_c 13.2045(6) _cell_angle_alpha 86.048(2) _cell_angle_beta 87.745(3) _cell_angle_gamma 88.381(3) _cell_volume 1039.85(7) _cell_formula_units_Z 1 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 51509 _cell_measurement_theta_min 2.40 _cell_measurement_theta_max 25.68 _exptl_crystal_description parallelepiped _exptl_crystal_colour 'translucent light yellow' _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.425 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 706 _exptl_absorpt_coefficient_mu 11.740 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.240 _exptl_absorpt_correction_T_max 0.391 _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 eight \w scans with 2\% steps' _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 51509 _diffrn_reflns_av_R_equivalents 0.0475 _diffrn_reflns_av_sigmaI/netI 0.0495 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.40 _diffrn_reflns_theta_max 25.68 _reflns_number_total 3951 _reflns_number_gt 3748 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, 1998)' _computing_cell_refinement 'HKL2000 (Otwinowski & Minor, 1997)' _computing_data_reduction 'HKL2000 (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 1999)' _computing_publication_material 'SHELXTL (Sheldrick, 1999); 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 O11 and O12 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 (OH, CH~2~) or 1.5 (CH~3~) 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^)+(0.0192P)^2^+0.3830P] 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 3951 _refine_ls_number_parameters 263 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0232 _refine_ls_R_factor_gt 0.0204 _refine_ls_wR_factor_ref 0.0489 _refine_ls_wR_factor_gt 0.0482 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.056 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.68 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.686 _refine_diff_density_min -1.662 _refine_diff_density_rms 0.167 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 0.701452(14) 0.067762(11) 0.548765(9) 0.01430(5) Uani 1 1 d . . . U2 U 0.0000 0.0000 1.0000 0.01690(6) Uani 1 2 d S . . O1 O 0.4277(3) 0.0376(2) 0.58492(16) 0.0174(5) Uani 1 1 d . . . O2 O 0.6156(3) 0.1441(2) 0.71008(18) 0.0196(5) Uani 1 1 d . . . O3 O 0.4230(3) 0.1962(2) 0.82296(17) 0.0195(5) Uani 1 1 d . . . O4 O 0.2566(3) -0.0843(2) 0.92275(17) 0.0212(5) Uani 1 1 d . . . O5 O 0.0663(3) -0.0314(2) 0.81877(18) 0.0220(5) Uani 1 1 d . . . O6 O -0.0621(3) 0.1489(2) 0.62169(18) 0.0197(5) Uani 1 1 d . . . O7 O 0.1038(3) -0.0279(2) 0.57773(17) 0.0169(5) Uani 1 1 d . . . O8 O 0.6695(3) 0.2454(2) 0.49229(18) 0.0195(5) Uani 1 1 d . . . O9 O 0.7399(3) -0.1077(2) 0.60598(18) 0.0195(5) Uani 1 1 d . . . O10 O 0.0444(3) 0.1838(2) 0.97267(18) 0.0232(6) Uani 1 1 d . . . O11 O 0.2250(3) -0.0120(3) 1.11092(18) 0.0287(6) Uani 1 1 d . . . H11A H 0.3176 0.0353 1.0983 0.034 Uiso 1 1 d R . . H11B H 0.2301 -0.0455 1.1729 0.034 Uiso 1 1 d R . . O12 O 0.4403(3) 0.1698(2) 1.03542(18) 0.0235(5) Uani 1 1 d . . . H12A H 0.4434 0.1693 0.9622 0.028 Uiso 1 1 d R . . H12B H 0.5318 0.1403 1.0494 0.028 Uiso 1 1 d R . . N1 N 0.7708(4) 0.5342(3) 0.7656(2) 0.0226(7) Uani 1 1 d . . . C1 C 0.3553(4) 0.0679(3) 0.6801(2) 0.0165(7) Uani 1 1 d . . . C2 C 0.4719(4) 0.1446(3) 0.7437(3) 0.0168(7) Uani 1 1 d . . . C3 C 0.3224(4) -0.0774(3) 0.7426(2) 0.0174(7) Uani 1 1 d . . . H3A H 0.2798 -0.1440 0.6980 0.021 Uiso 1 1 calc R . . H3B H 0.4215 -0.1187 0.7663 0.021 Uiso 1 1 calc R . . C4 C 0.2105(5) -0.0638(3) 0.8322(3) 0.0192(8) Uani 1 1 d . . . C5 C 0.2075(4) 0.1645(3) 0.6639(2) 0.0162(7) Uani 1 1 d . . . H5A H 0.1716 0.1992 0.7287 0.019 Uiso 1 1 calc R . . H5B H 0.2357 0.2477 0.6192 0.019 Uiso 1 1 calc R . . C6 C 0.0728(4) 0.0902(3) 0.6189(2) 0.0160(7) Uani 1 1 d . . . C7 C 0.6166(5) 0.6195(3) 0.7580(3) 0.0277(9) Uani 1 1 d . . . H7A H 0.6306 0.6996 0.7077 0.033 Uiso 1 1 calc R . . H7B H 0.5918 0.6596 0.8228 0.033 Uiso 1 1 calc R . . C8 C 0.4774(5) 0.5338(4) 0.7298(4) 0.0479(13) Uani 1 1 d . . . H8A H 0.4994 0.4950 0.6651 0.072 Uiso 1 1 calc R . . H8B H 0.3852 0.5958 0.7260 0.072 Uiso 1 1 calc R . . H8C H 0.4594 0.4564 0.7805 0.072 Uiso 1 1 calc R . . C9 C 0.8091(5) 0.4611(4) 0.6687(3) 0.0334(10) Uani 1 1 d . . . H9A H 0.7319 0.3877 0.6622 0.040 Uiso 1 1 calc R . . H9B H 0.9112 0.4125 0.6746 0.040 Uiso 1 1 calc R . . C10 C 0.8125(7) 0.5603(4) 0.5712(3) 0.0493(14) Uani 1 1 d . . . H10A H 0.7109 0.6063 0.5628 0.074 Uiso 1 1 calc R . . H10B H 0.8387 0.5046 0.5141 0.074 Uiso 1 1 calc R . . H10C H 0.8902 0.6324 0.5758 0.074 Uiso 1 1 calc R . . C11 C 0.8942(5) 0.6423(4) 0.7846(3) 0.0331(10) Uani 1 1 d . . . H11C H 0.8663 0.6860 0.8477 0.040 Uiso 1 1 calc R . . H11D H 0.8929 0.7181 0.7303 0.040 Uiso 1 1 calc R . . C12 C 1.0595(6) 0.5783(5) 0.7909(4) 0.0521(14) Uani 1 1 d . . . H12C H 1.0594 0.4952 0.8382 0.078 Uiso 1 1 calc R . . H12D H 1.1284 0.6487 0.8133 0.078 Uiso 1 1 calc R . . H12E H 1.0956 0.5505 0.7251 0.078 Uiso 1 1 calc R . . C13 C 0.7597(5) 0.4151(4) 0.8493(3) 0.0313(9) Uani 1 1 d . . . H13A H 0.6725 0.3547 0.8362 0.038 Uiso 1 1 calc R . . H13B H 0.8553 0.3558 0.8465 0.038 Uiso 1 1 calc R . . C14 C 0.7367(7) 0.4653(4) 0.9551(3) 0.0515(14) Uani 1 1 d . . . H14A H 0.8243 0.5221 0.9701 0.077 Uiso 1 1 calc R . . H14B H 0.7300 0.3831 1.0031 0.077 Uiso 1 1 calc R . . H14C H 0.6412 0.5226 0.9595 0.077 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 0.01440(8) 0.01574(7) 0.01285(8) -0.00195(5) 0.00014(6) -0.00055(5) U2 0.01608(11) 0.02034(9) 0.01386(11) 0.00058(7) 0.00138(8) 0.00016(8) O1 0.0156(13) 0.0225(11) 0.0141(12) -0.0046(9) 0.0032(10) -0.0011(9) O2 0.0153(13) 0.0263(12) 0.0177(12) -0.0054(9) 0.0021(11) -0.0036(10) O3 0.0201(14) 0.0231(11) 0.0156(12) -0.0045(9) -0.0001(10) -0.0004(10) O4 0.0208(14) 0.0284(12) 0.0141(12) -0.0007(9) -0.0001(11) 0.0004(10) O5 0.0183(14) 0.0315(12) 0.0159(12) -0.0015(10) 0.0011(11) 0.0000(11) O6 0.0160(13) 0.0216(11) 0.0220(13) -0.0049(9) -0.0016(10) 0.0004(10) O7 0.0172(13) 0.0198(11) 0.0138(12) -0.0039(9) 0.0018(10) 0.0006(10) O8 0.0187(14) 0.0209(11) 0.0187(12) -0.0014(9) 0.0008(11) -0.0015(10) O9 0.0197(14) 0.0192(11) 0.0198(13) -0.0012(9) -0.0018(11) -0.0016(10) O10 0.0204(14) 0.0261(12) 0.0224(14) 0.0010(10) 0.0039(11) 0.0009(11) O11 0.0173(14) 0.0513(15) 0.0164(13) 0.0048(11) -0.0009(11) -0.0010(12) O12 0.0198(14) 0.0329(12) 0.0173(13) -0.0023(10) 0.0008(11) 0.0048(11) N1 0.0214(18) 0.0166(13) 0.0295(17) -0.0014(12) 0.0013(14) -0.0006(12) C1 0.0167(18) 0.0199(15) 0.0129(16) -0.0018(12) 0.0025(14) -0.0014(13) C2 0.020(2) 0.0151(14) 0.0153(17) 0.0014(12) -0.0003(15) 0.0003(13) C3 0.0202(19) 0.0161(15) 0.0157(17) -0.0022(12) 0.0012(15) 0.0000(13) C4 0.0186(19) 0.0168(15) 0.022(2) 0.0009(13) 0.0021(16) -0.0030(14) C5 0.0158(19) 0.0168(14) 0.0162(16) -0.0027(12) -0.0024(14) 0.0001(13) C6 0.0198(19) 0.0169(14) 0.0112(16) -0.0010(12) 0.0005(14) -0.0004(14) C7 0.027(2) 0.0198(16) 0.035(2) 0.0017(14) 0.0038(18) 0.0033(15) C8 0.021(2) 0.031(2) 0.089(4) 0.015(2) -0.005(3) 0.0002(18) C9 0.043(3) 0.0206(17) 0.037(2) -0.0098(15) 0.011(2) 0.0007(17) C10 0.082(4) 0.030(2) 0.037(3) -0.0152(18) 0.021(3) -0.013(2) C11 0.035(3) 0.0204(17) 0.044(3) -0.0006(16) -0.003(2) -0.0068(17) C12 0.030(3) 0.037(2) 0.090(4) 0.003(2) -0.017(3) -0.011(2) C13 0.035(2) 0.0169(16) 0.042(2) 0.0052(15) -0.008(2) -0.0010(16) C14 0.086(4) 0.033(2) 0.034(2) 0.0087(18) -0.006(3) -0.012(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 U1 O9 1.777(2) . ? U1 O8 1.783(2) . ? U1 O7 2.345(2) 2_656 ? U1 O2 2.373(2) . ? U1 O1 2.377(2) . ? U1 O1 2.394(2) 2_656 ? U1 O6 2.423(2) 1_655 ? U1 U1 3.9728(3) 2_656 ? U2 O10 1.770(2) 2_557 ? U2 O10 1.770(2) . ? U2 O11 2.449(3) 2_557 ? U2 O11 2.449(3) . ? U2 O5 2.472(2) . ? U2 O5 2.472(2) 2_557 ? U2 O4 2.500(2) . ? U2 O4 2.500(2) 2_557 ? O1 C1 1.419(4) . ? O1 U1 2.394(2) 2_656 ? O2 C2 1.283(4) . ? O3 C2 1.234(4) . ? O4 C4 1.273(4) . ? O5 C4 1.270(5) . ? O6 C6 1.256(4) . ? O6 U1 2.423(2) 1_455 ? O7 C6 1.275(4) . ? O7 U1 2.345(2) 2_656 ? O11 H11A 0.9162 . ? O11 H11B 0.8580 . ? O12 H12A 0.9668 . ? O12 H12B 0.8409 . ? N1 C9 1.510(4) . ? N1 C13 1.512(4) . ? N1 C11 1.512(5) . ? N1 C7 1.516(5) . ? C1 C5 1.537(4) . ? C1 C2 1.544(5) . ? C1 C3 1.560(4) . ? C3 C4 1.499(5) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C5 C6 1.515(5) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C7 C8 1.517(6) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 C10 1.530(6) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 C12 1.513(6) . ? C11 H11C 0.9700 . ? C11 H11D 0.9700 . ? C12 H12C 0.9600 . ? C12 H12D 0.9600 . ? C12 H12E 0.9600 . ? C13 C14 1.507(6) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? 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 O9 U1 O8 178.06(11) . . ? O9 U1 O7 90.01(9) . 2_656 ? O8 U1 O7 89.14(9) . 2_656 ? O9 U1 O2 89.23(9) . . ? O8 U1 O2 90.72(9) . . ? O7 U1 O2 152.53(9) 2_656 . ? O9 U1 O1 89.56(9) . . ? O8 U1 O1 92.20(9) . . ? O7 U1 O1 140.94(8) 2_656 . ? O2 U1 O1 66.51(8) . . ? O9 U1 O1 89.45(9) . 2_656 ? O8 U1 O1 91.98(9) . 2_656 ? O7 U1 O1 73.70(8) 2_656 2_656 ? O2 U1 O1 133.74(8) . 2_656 ? O1 U1 O1 67.24(8) . 2_656 ? O9 U1 O6 89.08(9) . 1_655 ? O8 U1 O6 89.04(10) . 1_655 ? O7 U1 O6 77.07(8) 2_656 1_655 ? O2 U1 O6 75.46(8) . 1_655 ? O1 U1 O6 141.96(7) . 1_655 ? O1 U1 O6 150.74(8) 2_656 1_655 ? O10 U2 O10 180.0 2_557 . ? O10 U2 O11 86.52(11) 2_557 2_557 ? O10 U2 O11 93.48(11) . 2_557 ? O10 U2 O11 93.48(11) 2_557 . ? O10 U2 O11 86.52(11) . . ? O11 U2 O11 180.0 2_557 . ? O10 U2 O5 93.72(9) 2_557 . ? O10 U2 O5 86.28(9) . . ? O11 U2 O5 64.88(8) 2_557 . ? O11 U2 O5 115.12(8) . . ? O10 U2 O5 86.28(9) 2_557 2_557 ? O10 U2 O5 93.72(9) . 2_557 ? O11 U2 O5 115.12(8) 2_557 2_557 ? O11 U2 O5 64.88(8) . 2_557 ? O5 U2 O5 180.0 . 2_557 ? O10 U2 O4 87.43(10) 2_557 . ? O10 U2 O4 92.57(10) . . ? O11 U2 O4 116.08(8) 2_557 . ? O11 U2 O4 63.92(8) . . ? O5 U2 O4 52.16(8) . . ? O5 U2 O4 127.84(8) 2_557 . ? O10 U2 O4 92.57(10) 2_557 2_557 ? O10 U2 O4 87.43(10) . 2_557 ? O11 U2 O4 63.92(8) 2_557 2_557 ? O11 U2 O4 116.08(8) . 2_557 ? O5 U2 O4 127.84(8) . 2_557 ? O5 U2 O4 52.16(8) 2_557 2_557 ? O4 U2 O4 180.0 . 2_557 ? C1 O1 U1 122.16(19) . . ? C1 O1 U1 124.85(19) . 2_656 ? U1 O1 U1 112.76(8) . 2_656 ? C2 O2 U1 124.5(2) . . ? C4 O4 U2 93.6(2) . . ? C4 O5 U2 95.0(2) . . ? C6 O6 U1 127.5(2) . 1_455 ? C6 O7 U1 126.6(2) . 2_656 ? U2 O11 H11A 125.8 . . ? U2 O11 H11B 129.1 . . ? H11A O11 H11B 104.1 . . ? H12A O12 H12B 101.9 . . ? C9 N1 C13 106.2(3) . . ? C9 N1 C11 111.2(3) . . ? C13 N1 C11 112.3(3) . . ? C9 N1 C7 110.6(3) . . ? C13 N1 C7 110.8(3) . . ? C11 N1 C7 105.8(3) . . ? O1 C1 C5 110.0(3) . . ? O1 C1 C2 110.0(3) . . ? C5 C1 C2 109.5(2) . . ? O1 C1 C3 108.8(2) . . ? C5 C1 C3 113.7(3) . . ? C2 C1 C3 104.6(3) . . ? O3 C2 O2 125.3(3) . . ? O3 C2 C1 118.9(3) . . ? O2 C2 C1 115.7(3) . . ? C4 C3 C1 114.2(3) . . ? C4 C3 H3A 108.7 . . ? C1 C3 H3A 108.7 . . ? C4 C3 H3B 108.7 . . ? C1 C3 H3B 108.7 . . ? H3A C3 H3B 107.6 . . ? O5 C4 O4 118.6(3) . . ? O5 C4 C3 120.1(3) . . ? O4 C4 C3 121.4(3) . . ? C6 C5 C1 114.2(3) . . ? C6 C5 H5A 108.7 . . ? C1 C5 H5A 108.7 . . ? C6 C5 H5B 108.7 . . ? C1 C5 H5B 108.7 . . ? H5A C5 H5B 107.6 . . ? O6 C6 O7 123.3(3) . . ? O6 C6 C5 118.9(3) . . ? O7 C6 C5 117.8(3) . . ? N1 C7 C8 114.9(3) . . ? N1 C7 H7A 108.5 . . ? C8 C7 H7A 108.5 . . ? N1 C7 H7B 108.5 . . ? C8 C7 H7B 108.5 . . ? H7A C7 H7B 107.5 . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? N1 C9 C10 115.5(3) . . ? N1 C9 H9A 108.4 . . ? C10 C9 H9A 108.4 . . ? N1 C9 H9B 108.4 . . ? C10 C9 H9B 108.4 . . ? H9A C9 H9B 107.5 . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? N1 C11 C12 114.0(3) . . ? N1 C11 H11C 108.8 . . ? C12 C11 H11C 108.8 . . ? N1 C11 H11D 108.8 . . ? C12 C11 H11D 108.8 . . ? H11C C11 H11D 107.6 . . ? C11 C12 H12C 109.5 . . ? C11 C12 H12D 109.5 . . ? H12C C12 H12D 109.5 . . ? C11 C12 H12E 109.5 . . ? H12C C12 H12E 109.5 . . ? H12D C12 H12E 109.5 . . ? C14 C13 N1 115.1(3) . . ? C14 C13 H13A 108.5 . . ? N1 C13 H13A 108.5 . . ? C14 C13 H13B 108.5 . . ? N1 C13 H13B 108.5 . . ? H13A C13 H13B 107.5 . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? 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 O11 H11A O12 0.92 1.79 2.645(4) 154.3 . O11 H11B O2 0.86 2.20 2.947(3) 145.4 2_657 O12 H12A O3 0.97 1.85 2.808(3) 169.5 . O12 H12B O4 0.84 1.90 2.740(4) 176.5 2_657 #===END data_3 _database_code_depnum_ccdc_archive 'CCDC 655326' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H22 N2 O21 U3' _chemical_formula_weight 1364.51 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 'P 21/n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 10.0669(5) _cell_length_b 29.4919(13) _cell_length_c 11.1076(6) _cell_angle_alpha 90.00 _cell_angle_beta 107.873(3) _cell_angle_gamma 90.00 _cell_volume 3138.6(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 77666 _cell_measurement_theta_min 2.97 _cell_measurement_theta_max 25.68 _exptl_crystal_description platelet _exptl_crystal_colour 'translucent light yellow' _exptl_crystal_size_max 0.09 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.888 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2448 _exptl_absorpt_coefficient_mu 15.534 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.477 _exptl_absorpt_correction_T_max 0.627 _exptl_absorpt_process_details 'SCALEPACK (Otwinowski & Minor, 1997)' _exptl_special_details 'crystal-to-detector distance 50 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 'one \f and eight \w scans with 2\% steps' _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 77666 _diffrn_reflns_av_R_equivalents 0.0376 _diffrn_reflns_av_sigmaI/netI 0.0481 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -35 _diffrn_reflns_limit_k_max 35 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.97 _diffrn_reflns_theta_max 25.68 _reflns_number_total 5939 _reflns_number_gt 4923 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, 1998)' _computing_cell_refinement 'HKL2000 (Otwinowski & Minor, 1997)' _computing_data_reduction 'HKL2000 (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 1999)' _computing_publication_material 'SHELXTL (Sheldrick, 1999); 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, with restraints for some badly behaving atoms. 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. Some voids in the lattice likely indicate the presence of other, unresolved 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^)+(0.0369P)^2^+12.7920P] 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 5939 _refine_ls_number_parameters 433 _refine_ls_number_restraints 12 _refine_ls_R_factor_all 0.0445 _refine_ls_R_factor_gt 0.0324 _refine_ls_wR_factor_ref 0.0806 _refine_ls_wR_factor_gt 0.0775 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 1.045 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.68 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 2.778 _refine_diff_density_min -1.432 _refine_diff_density_rms 0.216 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 0.59415(3) -0.039316(11) 0.14165(3) 0.03147(10) Uani 1 1 d . . . U2 U 0.83755(3) 0.138250(10) 0.52382(3) 0.02401(9) Uani 1 1 d . . . U3 U 0.87278(3) 0.258160(10) 0.67684(3) 0.02001(9) Uani 1 1 d . . . O1 O 0.4597(7) -0.0319(3) 0.2142(7) 0.054(2) Uani 1 1 d . . . O2 O 0.7331(6) -0.04776(19) 0.0747(5) 0.0303(14) Uani 1 1 d . . . O3 O 0.7454(6) 0.10701(18) 0.6111(5) 0.0330(14) Uani 1 1 d . . . O4 O 0.9326(6) 0.16501(19) 0.4327(5) 0.0333(14) Uani 1 1 d . . . O5 O 0.7541(6) 0.25787(18) 0.7670(5) 0.0262(13) Uani 1 1 d . . . O6 O 0.9941(6) 0.26207(19) 0.5897(5) 0.0311(14) Uani 1 1 d . . . O7 O 0.7367(5) 0.20550(18) 0.5445(5) 0.0259(13) Uani 1 1 d . . . H7 H 0.6829 0.2110 0.4747 0.031 Uiso 1 1 d R . . O1A O 0.5650(6) 0.03638(18) 0.0688(6) 0.0338(14) Uani 1 1 d . . . O2A O 0.4956(6) 0.1120(2) -0.0724(6) 0.0399(16) Uani 1 1 d . . . O3A O 0.6509(8) 0.1578(3) 0.0304(7) 0.063(2) Uani 1 1 d U . . O4A O 0.7398(7) 0.0069(2) 0.3028(5) 0.0373(15) Uani 1 1 d . . . O5A O 0.8283(9) 0.0674(2) 0.4137(8) 0.060(2) Uani 1 1 d . . . O6A O 0.6366(7) 0.1433(2) 0.3501(6) 0.0450(17) Uani 1 1 d . . . O7A O 0.4271(6) 0.16500(19) 0.2389(5) 0.0300(13) Uani 1 1 d . . . C1A C 0.6025(9) 0.0821(3) 0.1246(9) 0.069(3) Uani 1 1 d . . . C2A C 0.5925(11) 0.1187(3) 0.0243(8) 0.050(3) Uani 1 1 d . . . C3A C 0.7574(10) 0.0818(5) 0.1965(12) 0.086(4) Uani 1 1 d . . . H3A1 H 0.7907 0.1119 0.2260 0.104 Uiso 1 1 calc R . . H3A2 H 0.8116 0.0700 0.1449 0.104 Uiso 1 1 calc R . . C4A C 0.7637(14) 0.0487(4) 0.3121(10) 0.057(3) Uani 1 1 d . . . C5A C 0.5028(8) 0.0906(3) 0.2017(8) 0.034(2) Uani 1 1 d . . . H5A1 H 0.4077 0.0887 0.1459 0.041 Uiso 1 1 calc R . . H5A2 H 0.5154 0.0668 0.2645 0.041 Uiso 1 1 calc R . . C6A C 0.5229(9) 0.1360(3) 0.2683(7) 0.0234(18) Uani 1 1 d . . . O1B O 0.9478(5) 0.17873(18) 0.7129(5) 0.0245(12) Uani 1 1 d . . . O2B O 1.0563(6) 0.24398(17) 0.8683(5) 0.0273(13) Uani 1 1 d . . . O3B O 1.2100(6) 0.19964(19) 1.0067(5) 0.0339(15) Uani 1 1 d . . . O4B O 1.0533(6) 0.09993(19) 0.6185(5) 0.0297(13) Uani 1 1 d . . . O5B O 1.2827(6) 0.08951(19) 0.6939(5) 0.0322(14) Uani 1 1 d . . . O6B O 0.8334(7) 0.0945(2) 0.9212(7) 0.0492(18) Uani 1 1 d . . . O7B O 0.8965(7) 0.1656(2) 0.9788(6) 0.0412(16) Uani 1 1 d . . . H7B H 0.8047 0.1667 0.9881 0.049 Uiso 1 1 d R . . C1B C 1.0683(9) 0.1657(3) 0.8109(7) 0.0247(18) Uani 1 1 d . . . C2B C 1.1120(8) 0.2056(3) 0.9058(7) 0.0280(19) Uani 1 1 d . . . C3B C 1.1887(9) 0.1551(3) 0.7635(8) 0.0296(19) Uani 1 1 d . . . H3B1 H 1.2725 0.1528 0.8354 0.036 Uiso 1 1 calc R . . H3B2 H 1.2014 0.1802 0.7117 0.036 Uiso 1 1 calc R . . C4B C 1.1737(9) 0.1124(3) 0.6875(8) 0.030(2) Uani 1 1 d . . . C5B C 1.0384(9) 0.1239(3) 0.8848(7) 0.029(2) Uani 1 1 d . . . H5B1 H 1.0318 0.0973 0.8319 0.035 Uiso 1 1 calc R . . H5B2 H 1.1183 0.1196 0.9594 0.035 Uiso 1 1 calc R . . C6B C 0.9103(9) 0.1256(3) 0.9263(7) 0.030(2) Uani 1 1 d . . . N1 N 0.5092(7) 0.2030(2) -0.1989(7) 0.0348(18) Uani 1 1 d . . . H1 H 0.5558 0.1933 -0.1224 0.042 Uiso 1 1 d R . . N2 N 0.8328(9) 0.0003(3) 0.6203(8) 0.052(2) Uani 1 1 d . . . H2 H 0.8150 0.0252 0.5629 0.062 Uiso 1 1 d R . . C1 C 0.5071(11) 0.1800(4) -0.2998(12) 0.051(3) Uani 1 1 d . . . H1A H 0.5583 0.1532 -0.2912 0.061 Uiso 1 1 calc R . . C2 C 0.4317(13) 0.1943(4) -0.4172(11) 0.059(3) Uani 1 1 d . . . H2A H 0.4296 0.1778 -0.4891 0.071 Uiso 1 1 calc R . . C3 C 0.3581(13) 0.2343(4) -0.4253(10) 0.055(3) Uani 1 1 d . . . H3 H 0.3074 0.2453 -0.5045 0.066 Uiso 1 1 calc R . . C4 C 0.3579(10) 0.2585(3) -0.3182(8) 0.037(2) Uani 1 1 d . . . H4 H 0.3055 0.2848 -0.3235 0.045 Uiso 1 1 calc R . . C5 C 0.4384(9) 0.2417(3) -0.2048(9) 0.033(2) Uani 1 1 d . . . H5 H 0.4441 0.2574 -0.1307 0.040 Uiso 1 1 calc R . . C6 C 0.8503(11) -0.0416(3) 0.5777(9) 0.048(3) Uani 1 1 d . . . H6 H 0.8546 -0.0446 0.4956 0.057 Uiso 1 1 calc R . . C7 C 0.8616(13) -0.0784(4) 0.6481(13) 0.069(4) Uani 1 1 d . . . H7A H 0.8739 -0.1068 0.6167 0.083 Uiso 1 1 calc R . . C8 C 0.8547(12) -0.0733(5) 0.7707(12) 0.065(3) Uani 1 1 d U . . H8 H 0.8628 -0.0986 0.8225 0.078 Uiso 1 1 calc R . . C9 C 0.8360(12) -0.0315(5) 0.8149(10) 0.068(4) Uani 1 1 d . . . H9 H 0.8321 -0.0284 0.8971 0.082 Uiso 1 1 calc R . . C10 C 0.8225(10) 0.0067(4) 0.7385(9) 0.045(3) Uani 1 1 d . . . H10 H 0.8071 0.0353 0.7669 0.054 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 0.02573(18) 0.0312(2) 0.03685(19) 0.00406(15) 0.00870(15) 0.00906(15) U2 0.02507(18) 0.02123(17) 0.02333(16) -0.00036(12) 0.00389(13) 0.00193(13) U3 0.01954(16) 0.01949(17) 0.01776(15) 0.00021(12) 0.00092(12) -0.00136(12) O1 0.045(4) 0.065(5) 0.063(5) 0.020(4) 0.033(4) 0.025(4) O2 0.024(3) 0.032(3) 0.031(3) 0.002(3) 0.004(3) 0.007(3) O3 0.043(4) 0.024(3) 0.037(3) -0.003(3) 0.020(3) -0.004(3) O4 0.046(4) 0.026(3) 0.029(3) 0.006(3) 0.013(3) 0.003(3) O5 0.026(3) 0.024(3) 0.027(3) -0.001(2) 0.007(3) 0.002(3) O6 0.027(3) 0.036(3) 0.031(3) -0.005(3) 0.009(3) -0.010(3) O7 0.024(3) 0.025(3) 0.020(3) -0.002(2) -0.006(2) -0.004(2) O1A 0.026(3) 0.022(3) 0.047(4) -0.010(3) 0.002(3) 0.005(3) O2A 0.030(3) 0.030(4) 0.052(4) 0.017(3) 0.002(3) 0.003(3) O3A 0.052(3) 0.061(3) 0.069(3) -0.018(3) 0.010(2) 0.011(3) O4A 0.052(4) 0.024(3) 0.026(3) 0.002(3) -0.001(3) 0.005(3) O5A 0.090(6) 0.036(4) 0.073(5) -0.023(4) 0.054(5) -0.020(4) O6A 0.041(4) 0.043(4) 0.041(4) -0.014(3) -0.003(3) 0.003(3) O7A 0.035(3) 0.024(3) 0.029(3) -0.001(3) 0.007(3) 0.002(3) C1A 0.056(6) 0.065(6) 0.086(7) -0.035(5) 0.020(5) 0.004(5) C2A 0.065(8) 0.059(7) 0.030(5) 0.001(5) 0.020(5) 0.033(6) C3A 0.084(7) 0.090(7) 0.092(7) -0.033(6) 0.039(6) -0.018(6) C4A 0.095(7) 0.039(5) 0.044(5) 0.008(4) 0.031(5) 0.017(5) C5A 0.034(5) 0.028(5) 0.033(5) 0.004(4) -0.002(4) -0.001(4) C6A 0.025(5) 0.019(4) 0.023(4) -0.001(3) 0.003(4) 0.001(4) O1B 0.023(3) 0.023(3) 0.023(3) 0.005(2) 0.001(2) 0.002(2) O2B 0.035(3) 0.015(3) 0.024(3) 0.001(2) -0.002(3) 0.005(3) O3B 0.034(3) 0.024(3) 0.027(3) -0.004(3) -0.016(3) 0.001(3) O4B 0.028(3) 0.025(3) 0.034(3) -0.001(3) 0.007(3) 0.007(3) O5B 0.029(3) 0.028(3) 0.037(3) 0.003(3) 0.006(3) 0.007(3) O6B 0.056(5) 0.036(4) 0.064(5) -0.017(3) 0.030(4) -0.007(4) O7B 0.055(4) 0.033(4) 0.038(4) -0.008(3) 0.019(3) 0.003(3) C1B 0.028(4) 0.018(4) 0.024(4) -0.001(3) 0.001(4) 0.001(4) C2B 0.024(4) 0.030(5) 0.026(4) -0.003(4) 0.002(4) -0.005(4) C3B 0.028(5) 0.020(4) 0.037(5) 0.000(4) 0.005(4) 0.002(4) C4B 0.037(5) 0.026(5) 0.027(4) 0.008(4) 0.012(4) 0.001(4) C5B 0.042(5) 0.022(4) 0.021(4) -0.001(3) 0.005(4) 0.003(4) C6B 0.038(5) 0.027(5) 0.021(4) -0.002(4) 0.004(4) 0.007(4) N1 0.026(4) 0.028(4) 0.050(5) 0.004(4) 0.010(4) -0.002(3) N2 0.059(6) 0.055(6) 0.043(5) 0.011(4) 0.015(4) 0.010(5) C1 0.047(6) 0.037(6) 0.086(9) -0.019(6) 0.045(6) -0.011(5) C2 0.095(9) 0.046(7) 0.057(7) -0.018(6) 0.056(7) -0.032(7) C3 0.084(9) 0.048(7) 0.037(6) -0.001(5) 0.026(6) -0.029(6) C4 0.053(6) 0.028(5) 0.031(5) 0.006(4) 0.012(5) -0.003(4) C5 0.034(5) 0.027(5) 0.038(5) 0.000(4) 0.010(4) -0.004(4) C6 0.073(8) 0.039(6) 0.039(5) 0.011(5) 0.028(5) 0.022(5) C7 0.078(9) 0.062(8) 0.083(9) 0.020(7) 0.047(7) 0.028(7) C8 0.058(6) 0.074(6) 0.068(6) 0.024(5) 0.029(5) 0.017(5) C9 0.048(7) 0.126(12) 0.037(6) 0.005(7) 0.021(5) -0.016(8) C10 0.037(6) 0.062(7) 0.036(5) -0.005(5) 0.010(5) 0.003(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag U1 O1 1.789(6) . ? U1 O2 1.792(6) . ? U1 O2A 2.360(6) 3_655 ? U1 O1A 2.362(6) . ? U1 O4A 2.367(6) . ? U1 O5B 2.382(6) 3_756 ? U1 O1A 2.396(6) 3_655 ? U1 U1 3.9001(7) 3_655 ? U2 O4 1.777(6) . ? U2 O3 1.789(6) . ? U2 O7 2.272(5) . ? U2 O6A 2.333(6) . ? U2 O1B 2.374(5) . ? U2 O4B 2.387(5) . ? U2 O5A 2.408(7) . ? U2 U3 3.8924(4) . ? U3 O5 1.779(5) . ? U3 O6 1.780(6) . ? U3 O7 2.283(5) . ? U3 O7A 2.383(6) 4_666 ? U3 O2B 2.387(5) . ? U3 O3B 2.430(5) 4_565 ? U3 O1B 2.456(5) . ? O7 H7 0.8145 . ? O1A C1A 1.485(11) . ? O1A U1 2.396(6) 3_655 ? O2A C2A 1.224(11) . ? O2A U1 2.360(6) 3_655 ? O3A C2A 1.289(8) . ? O4A C4A 1.253(12) . ? O5A C4A 1.245(13) . ? O6A C6A 1.243(10) . ? O7A C6A 1.254(9) . ? O7A U3 2.383(6) 4_565 ? C1A C3A 1.518(15) . ? C1A C5A 1.527(13) . ? C1A C2A 1.532(13) . ? C3A C4A 1.599(17) . ? C3A H3A1 0.9700 . ? C3A H3A2 0.9700 . ? C5A C6A 1.513(11) . ? C5A H5A1 0.9700 . ? C5A H5A2 0.9700 . ? O1B C1B 1.412(9) . ? O2B C2B 1.276(9) . ? O3B C2B 1.258(9) . ? O3B U3 2.430(5) 4_666 ? O4B C4B 1.272(10) . ? O5B C4B 1.272(10) . ? O5B U1 2.382(6) 3_756 ? O6B C6B 1.191(10) . ? O7B C6B 1.341(10) . ? O7B H7B 0.9611 . ? C1B C3B 1.495(12) . ? C1B C2B 1.551(11) . ? C1B C5B 1.559(11) . ? C3B C4B 1.499(11) . ? C3B H3B1 0.9700 . ? C3B H3B2 0.9700 . ? C5B C6B 1.498(12) . ? C5B H5B1 0.9700 . ? C5B H5B2 0.9700 . ? N1 C1 1.306(12) . ? N1 C5 1.337(11) . ? N1 H1 0.8836 . ? N2 C6 1.353(12) . ? N2 C10 1.361(12) . ? N2 H2 0.9542 . ? C1 C2 1.359(15) . ? C1 H1A 0.9300 . ? C2 C3 1.383(16) . ? C2 H2A 0.9300 . ? C3 C4 1.387(13) . ? C3 H3 0.9300 . ? C4 C5 1.365(12) . ? C4 H4 0.9300 . ? C5 H5 0.9300 . ? C6 C7 1.323(14) . ? C6 H6 0.9300 . ? C7 C8 1.393(16) . ? C7 H7A 0.9300 . ? C8 C9 1.362(17) . ? C8 H8 0.9300 . ? C9 C10 1.392(16) . ? C9 H9 0.9300 . ? C10 H10 0.9300 . ? 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 U1 O2 177.7(3) . . ? O1 U1 O2A 89.5(3) . 3_655 ? O2 U1 O2A 90.5(2) . 3_655 ? O1 U1 O1A 90.4(3) . . ? O2 U1 O1A 91.1(2) . . ? O2A U1 O1A 138.7(2) 3_655 . ? O1 U1 O4A 88.1(3) . . ? O2 U1 O4A 90.7(2) . . ? O2A U1 O4A 148.8(2) 3_655 . ? O1A U1 O4A 72.40(19) . . ? O1 U1 O5B 91.0(3) . 3_756 ? O2 U1 O5B 86.8(2) . 3_756 ? O2A U1 O5B 75.1(2) 3_655 3_756 ? O1A U1 O5B 146.16(19) . 3_756 ? O4A U1 O5B 73.9(2) . 3_756 ? O1 U1 O1A 93.6(3) . 3_655 ? O2 U1 O1A 88.5(2) . 3_655 ? O2A U1 O1A 68.9(2) 3_655 3_655 ? O1A U1 O1A 69.9(2) . 3_655 ? O4A U1 O1A 142.26(19) . 3_655 ? O5B U1 O1A 143.66(19) 3_756 3_655 ? O4 U2 O3 175.4(3) . . ? O4 U2 O7 90.3(2) . . ? O3 U2 O7 94.2(2) . . ? O4 U2 O6A 89.0(3) . . ? O3 U2 O6A 91.1(3) . . ? O7 U2 O6A 74.1(2) . . ? O4 U2 O1B 95.4(2) . . ? O3 U2 O1B 87.6(2) . . ? O7 U2 O1B 64.76(17) . . ? O6A U2 O1B 138.7(2) . . ? O4 U2 O4B 83.4(2) . . ? O3 U2 O4B 94.0(2) . . ? O7 U2 O4B 138.01(18) . . ? O6A U2 O4B 146.7(2) . . ? O1B U2 O4B 74.53(18) . . ? O4 U2 O5A 92.3(2) . . ? O3 U2 O5A 83.3(2) . . ? O7 U2 O5A 149.3(2) . . ? O6A U2 O5A 75.3(3) . . ? O1B U2 O5A 145.1(2) . . ? O4B U2 O5A 72.6(2) . . ? O5 U3 O6 176.4(3) . . ? O5 U3 O7 89.2(2) . . ? O6 U3 O7 94.0(2) . . ? O5 U3 O7A 88.6(2) . 4_666 ? O6 U3 O7A 87.8(2) . 4_666 ? O7 U3 O7A 150.72(19) . 4_666 ? O5 U3 O2B 88.1(2) . . ? O6 U3 O2B 91.4(2) . . ? O7 U3 O2B 126.99(18) . . ? O7A U3 O2B 82.10(18) 4_666 . ? O5 U3 O3B 91.8(2) . 4_565 ? O6 U3 O3B 87.5(2) . 4_565 ? O7 U3 O3B 73.72(19) . 4_565 ? O7A U3 O3B 77.18(19) 4_666 4_565 ? O2B U3 O3B 159.27(18) . 4_565 ? O5 U3 O1B 97.5(2) . . ? O6 U3 O1B 85.5(2) . . ? O7 U3 O1B 63.25(17) . . ? O7A U3 O1B 145.89(18) 4_666 . ? O2B U3 O1B 64.70(17) . . ? O3B U3 O1B 135.69(18) 4_565 . ? U2 O7 U3 117.4(2) . . ? U2 O7 H7 105.4 . . ? U3 O7 H7 124.7 . . ? C1A O1A U1 136.7(5) . . ? C1A O1A U1 112.5(5) . 3_655 ? U1 O1A U1 110.1(2) . 3_655 ? C2A O2A U1 123.7(6) . 3_655 ? C4A O4A U1 133.4(7) . . ? C4A O5A U2 140.7(8) . . ? C6A O6A U2 164.6(6) . . ? C6A O7A U3 144.4(5) . 4_565 ? O1A C1A C3A 107.6(8) . . ? O1A C1A C5A 104.8(7) . . ? C3A C1A C5A 116.8(9) . . ? O1A C1A C2A 112.6(7) . . ? C3A C1A C2A 102.5(9) . . ? C5A C1A C2A 112.7(7) . . ? O2A C2A O3A 114.7(8) . . ? O2A C2A C1A 112.5(8) . . ? O3A C2A C1A 131.7(9) . . ? C1A C3A C4A 102.0(9) . . ? C1A C3A H3A1 111.4 . . ? C4A C3A H3A1 111.4 . . ? C1A C3A H3A2 111.4 . . ? C4A C3A H3A2 111.4 . . ? H3A1 C3A H3A2 109.2 . . ? O5A C4A O4A 123.0(10) . . ? O5A C4A C3A 109.7(10) . . ? O4A C4A C3A 125.1(10) . . ? C6A C5A C1A 114.0(7) . . ? C6A C5A H5A1 108.8 . . ? C1A C5A H5A1 108.8 . . ? C6A C5A H5A2 108.8 . . ? C1A C5A H5A2 108.8 . . ? H5A1 C5A H5A2 107.6 . . ? O6A C6A O7A 122.3(7) . . ? O6A C6A C5A 117.7(7) . . ? O7A C6A C5A 120.0(7) . . ? C1B O1B U2 127.0(4) . . ? C1B O1B U3 122.3(4) . . ? U2 O1B U3 107.36(19) . . ? C2B O2B U3 126.1(5) . . ? C2B O3B U3 141.2(5) . 4_666 ? C4B O4B U2 134.3(5) . . ? C4B O5B U1 127.5(5) . 3_756 ? C6B O7B H7B 107.9 . . ? O1B C1B C3B 112.5(6) . . ? O1B C1B C2B 108.3(6) . . ? C3B C1B C2B 107.8(7) . . ? O1B C1B C5B 111.2(6) . . ? C3B C1B C5B 109.3(7) . . ? C2B C1B C5B 107.6(6) . . ? O3B C2B O2B 124.1(7) . . ? O3B C2B C1B 118.8(7) . . ? O2B C2B C1B 116.6(7) . . ? C1B C3B C4B 114.8(7) . . ? C1B C3B H3B1 108.6 . . ? C4B C3B H3B1 108.6 . . ? C1B C3B H3B2 108.6 . . ? C4B C3B H3B2 108.6 . . ? H3B1 C3B H3B2 107.5 . . ? O5B C4B O4B 121.8(8) . . ? O5B C4B C3B 118.5(8) . . ? O4B C4B C3B 119.7(8) . . ? C6B C5B C1B 117.4(7) . . ? C6B C5B H5B1 108.0 . . ? C1B C5B H5B1 108.0 . . ? C6B C5B H5B2 108.0 . . ? C1B C5B H5B2 108.0 . . ? H5B1 C5B H5B2 107.2 . . ? O6B C6B O7B 123.1(8) . . ? O6B C6B C5B 124.6(8) . . ? O7B C6B C5B 112.1(8) . . ? C1 N1 C5 122.4(9) . . ? C1 N1 H1 121.4 . . ? C5 N1 H1 116.2 . . ? C6 N2 C10 121.4(9) . . ? C6 N2 H2 119.2 . . ? C10 N2 H2 118.9 . . ? N1 C1 C2 121.2(10) . . ? N1 C1 H1A 119.4 . . ? C2 C1 H1A 119.4 . . ? C1 C2 C3 117.3(10) . . ? C1 C2 H2A 121.4 . . ? C3 C2 H2A 121.4 . . ? C2 C3 C4 121.7(10) . . ? C2 C3 H3 119.1 . . ? C4 C3 H3 119.1 . . ? C5 C4 C3 116.6(10) . . ? C5 C4 H4 121.7 . . ? C3 C4 H4 121.7 . . ? N1 C5 C4 120.7(9) . . ? N1 C5 H5 119.6 . . ? C4 C5 H5 119.6 . . ? C7 C6 N2 122.7(10) . . ? C7 C6 H6 118.7 . . ? N2 C6 H6 118.7 . . ? C6 C7 C8 117.9(12) . . ? C6 C7 H7A 121.1 . . ? C8 C7 H7A 121.1 . . ? C9 C8 C7 120.3(12) . . ? C9 C8 H8 119.9 . . ? C7 C8 H8 119.9 . . ? C8 C9 C10 120.8(11) . . ? C8 C9 H9 119.6 . . ? C10 C9 H9 119.6 . . ? N2 C10 C9 117.0(10) . . ? N2 C10 H10 121.5 . . ? C9 C10 H10 121.5 . . ? 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 O3A 0.88 1.97 2.840(11) 166.9 . N2 H2 O5A 0.95 2.11 3.021(11) 159.4 . O7 H7 O2B 0.81 1.96 2.677(7) 145.8 4_565 O7B H7B O3A 0.96 1.77 2.713(10) 166.3 1_556