# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_1 _database_code_depnum_ccdc_archive 'CCDC 914739' #TrackingRef 'web_deposit_cif_file_0_P.Thuery_1354890695.CIF.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H12 N2 O9 S U' _chemical_formula_weight 670.39 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' S S 0.1246 0.1234 '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 9.0811(6) _cell_length_b 9.5438(5) _cell_length_c 12.3439(9) _cell_angle_alpha 78.643(4) _cell_angle_beta 71.021(3) _cell_angle_gamma 67.775(4) _cell_volume 933.16(11) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 53249 _cell_measurement_theta_min 2.31 _cell_measurement_theta_max 30.51 _exptl_crystal_description platelet _exptl_crystal_colour 'translucent light yellow' _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.386 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 628 _exptl_absorpt_coefficient_mu 8.868 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.335 _exptl_absorpt_correction_T_max 0.642 _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 twelve \w scans with 2\% steps (728 frames)' _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 53249 _diffrn_reflns_av_R_equivalents 0.0692 _diffrn_reflns_av_sigmaI/netI 0.0758 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.31 _diffrn_reflns_theta_max 30.51 _reflns_number_total 5685 _reflns_number_gt 5006 _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 atom bound to N1 was 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^)+(0.0246P)^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 5685 _refine_ls_number_parameters 280 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0378 _refine_ls_R_factor_gt 0.0298 _refine_ls_wR_factor_ref 0.0692 _refine_ls_wR_factor_gt 0.0671 _refine_ls_goodness_of_fit_ref 1.022 _refine_ls_restrained_S_all 1.022 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 30.51 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 1.727 _refine_diff_density_min -1.911 _refine_diff_density_rms 0.204 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 0.740681(15) 0.579587(15) 0.547965(11) 0.01902(5) Uani 1 1 d . . . S1 S 0.66198(11) 0.89029(12) 0.71853(8) 0.0232(2) Uani 1 1 d . . . O1 O 0.7356(3) 0.4227(4) 0.6519(2) 0.0269(6) Uani 1 1 d . . . O2 O 0.7429(3) 0.7348(4) 0.4431(2) 0.0251(6) Uani 1 1 d . . . O3 O 0.9986(3) 0.5659(3) 0.5790(2) 0.0212(6) Uani 1 1 d . . . O4 O 0.9876(3) 0.5423(3) 0.7663(2) 0.0244(6) Uani 1 1 d . . . O5 O 1.3174(3) 0.5359(3) 0.5769(2) 0.0238(6) Uani 1 1 d . . . O6 O 1.4488(3) 0.6752(4) 0.6024(3) 0.0285(6) Uani 1 1 d . . . O7 O 0.6796(3) 0.7365(3) 0.6948(2) 0.0253(6) Uani 1 1 d . . . O8 O 0.6135(3) 0.9022(4) 0.8410(2) 0.0323(7) Uani 1 1 d . . . O9 O 0.5627(3) 1.0093(4) 0.6550(3) 0.0360(8) Uani 1 1 d . . . N1 N 0.8260(4) 0.6538(4) 0.9846(3) 0.0309(8) Uani 1 1 d . . . H1 H 0.8963 0.6348 0.9237 0.037 Uiso 1 1 d R . . N2 N 1.0854(5) 0.7439(5) 0.9244(3) 0.0317(8) Uani 1 1 d . . . C1 C 0.9973(4) 0.6161(4) 0.6726(3) 0.0198(7) Uani 1 1 d . . . C2 C 1.3202(4) 0.6587(4) 0.5983(3) 0.0193(7) Uani 1 1 d . . . C3 C 1.0082(4) 0.7719(4) 0.6541(3) 0.0187(7) Uani 1 1 d . . . C4 C 1.1628(4) 0.7924(5) 0.6219(3) 0.0189(7) Uani 1 1 d . . . C5 C 1.1726(5) 0.9370(5) 0.6071(3) 0.0220(8) Uani 1 1 d . . . H5 H 1.2752 0.9491 0.5882 0.026 Uiso 1 1 calc R . . C6 C 1.0286(5) 1.0641(5) 0.6204(3) 0.0246(8) Uani 1 1 d . . . H6 H 1.0346 1.1613 0.6091 0.029 Uiso 1 1 calc R . . C7 C 0.8762(4) 1.0441(5) 0.6507(3) 0.0226(8) Uani 1 1 d . . . H7 H 0.7802 1.1287 0.6590 0.027 Uiso 1 1 calc R . . C8 C 0.8645(4) 0.8997(4) 0.6690(3) 0.0203(8) Uani 1 1 d . . . C9 C 0.6995(6) 0.6034(6) 0.9984(4) 0.0394(12) Uani 1 1 d . . . H9 H 0.6933 0.5615 0.9388 0.047 Uiso 1 1 calc R . . C10 C 0.5818(6) 0.6154(6) 1.1012(5) 0.0435(13) Uani 1 1 d . . . H10 H 0.4951 0.5797 1.1133 0.052 Uiso 1 1 calc R . . C11 C 0.5919(6) 0.6814(6) 1.1880(4) 0.0408(13) Uani 1 1 d . . . H11 H 0.5111 0.6911 1.2582 0.049 Uiso 1 1 calc R . . C12 C 0.7240(5) 0.7334(6) 1.1698(4) 0.0354(12) Uani 1 1 d . . . H12 H 0.7312 0.7784 1.2273 0.042 Uiso 1 1 calc R . . C13 C 0.8431(5) 0.7167(5) 1.0652(3) 0.0283(9) Uani 1 1 d . . . C14 C 0.9912(5) 0.7628(5) 1.0340(3) 0.0299(10) Uani 1 1 d . . . C15 C 1.0296(6) 0.8189(6) 1.1115(4) 0.0387(12) Uani 1 1 d . . . H15 H 0.9629 0.8279 1.1868 0.046 Uiso 1 1 calc R . . C16 C 1.1685(6) 0.8618(7) 1.0766(4) 0.0437(13) Uani 1 1 d . . . H16 H 1.1956 0.9021 1.1272 0.052 Uiso 1 1 calc R . . C17 C 1.2659(5) 0.8434(6) 0.9646(4) 0.0355(11) Uani 1 1 d . . . H17 H 1.3606 0.8704 0.9384 0.043 Uiso 1 1 calc R . . C18 C 1.2207(6) 0.7844(6) 0.8924(4) 0.0363(11) Uani 1 1 d . . . H18 H 1.2875 0.7719 0.8173 0.044 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 U 0.01386(7) 0.01813(8) 0.02535(8) -0.00475(5) -0.00378(5) -0.00566(5) S1 0.0176(4) 0.0238(5) 0.0267(4) -0.0066(4) -0.0034(3) -0.0056(4) O1 0.0238(13) 0.0252(16) 0.0287(14) 0.0001(12) -0.0036(11) -0.0092(12) O2 0.0202(13) 0.0253(15) 0.0295(14) -0.0002(12) -0.0061(11) -0.0092(11) O3 0.0141(11) 0.0239(14) 0.0268(13) -0.0100(11) -0.0055(10) -0.0041(10) O4 0.0264(13) 0.0192(14) 0.0266(13) -0.0012(11) -0.0053(10) -0.0089(11) O5 0.0195(12) 0.0230(15) 0.0305(14) -0.0098(11) -0.0057(10) -0.0062(11) O6 0.0145(12) 0.0311(17) 0.0429(16) -0.0156(13) -0.0058(11) -0.0067(11) O7 0.0178(12) 0.0259(15) 0.0339(14) -0.0128(12) -0.0021(11) -0.0084(11) O8 0.0313(15) 0.0362(18) 0.0296(15) -0.0118(13) 0.0004(12) -0.0145(13) O9 0.0223(14) 0.0327(18) 0.0489(18) -0.0004(15) -0.0151(13) -0.0021(13) N1 0.0311(18) 0.031(2) 0.0284(17) -0.0010(15) -0.0076(14) -0.0099(16) N2 0.0339(18) 0.037(2) 0.0230(16) -0.0041(15) -0.0045(14) -0.0129(16) C1 0.0118(14) 0.0225(19) 0.0244(17) -0.0057(14) -0.0037(12) -0.0041(13) C2 0.0146(15) 0.0200(18) 0.0268(17) -0.0051(14) -0.0061(13) -0.0077(14) C3 0.0194(16) 0.0213(18) 0.0164(15) -0.0048(13) -0.0049(13) -0.0063(14) C4 0.0143(15) 0.0239(19) 0.0188(16) -0.0043(14) -0.0033(12) -0.0068(14) C5 0.0214(17) 0.025(2) 0.0210(17) -0.0042(14) -0.0039(13) -0.0098(15) C6 0.0289(19) 0.0206(19) 0.0247(18) -0.0025(15) -0.0071(15) -0.0090(15) C7 0.0205(17) 0.0201(19) 0.0259(18) -0.0047(15) -0.0073(14) -0.0032(15) C8 0.0176(16) 0.0208(19) 0.0217(16) -0.0036(14) -0.0048(13) -0.0053(14) C9 0.034(2) 0.039(3) 0.047(3) 0.000(2) -0.013(2) -0.015(2) C10 0.029(2) 0.040(3) 0.057(3) 0.008(2) -0.010(2) -0.014(2) C11 0.028(2) 0.039(3) 0.041(2) 0.005(2) 0.0015(18) -0.009(2) C12 0.032(2) 0.037(3) 0.027(2) -0.0014(19) -0.0049(17) -0.004(2) C13 0.0257(19) 0.027(2) 0.0272(19) 0.0019(16) -0.0090(15) -0.0044(16) C14 0.0253(19) 0.033(2) 0.0258(19) -0.0004(17) -0.0084(15) -0.0033(17) C15 0.037(2) 0.059(3) 0.023(2) -0.004(2) -0.0048(17) -0.021(2) C16 0.040(3) 0.064(4) 0.035(2) -0.009(2) -0.012(2) -0.023(3) C17 0.027(2) 0.045(3) 0.035(2) -0.003(2) -0.0091(17) -0.0129(19) C18 0.033(2) 0.046(3) 0.027(2) -0.0056(19) -0.0046(17) -0.011(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 O2 1.767(3) . ? U O1 1.774(3) . ? U O5 2.346(3) 2_766 ? U O6 2.358(3) 1_455 ? U O7 2.371(3) . ? U O3 2.438(2) 2_766 ? U O3 2.446(3) . ? S1 O9 1.432(3) . ? S1 O8 1.446(3) . ? S1 O7 1.492(3) . ? S1 C8 1.771(4) . ? O3 C1 1.330(5) . ? O3 U 2.438(2) 2_766 ? O4 C1 1.226(4) . ? O5 C2 1.262(5) . ? O5 U 2.346(3) 2_766 ? O6 C2 1.254(5) . ? O6 U 2.358(3) 1_655 ? N1 C13 1.335(6) . ? N1 C9 1.355(6) . ? N1 H1 0.8120 . ? N2 C18 1.341(6) . ? N2 C14 1.349(5) . ? C1 C3 1.495(6) . ? C2 C4 1.501(5) . ? C3 C8 1.398(5) . ? C3 C4 1.407(5) . ? C4 C5 1.389(6) . ? C5 C6 1.396(5) . ? C5 H5 0.9300 . ? C6 C7 1.389(6) . ? C6 H6 0.9300 . ? C7 C8 1.390(6) . ? C7 H7 0.9300 . ? C9 C10 1.360(7) . ? C9 H9 0.9300 . ? C10 C11 1.387(8) . ? C10 H10 0.9300 . ? C11 C12 1.403(7) . ? C11 H11 0.9300 . ? C12 C13 1.380(5) . ? C12 H12 0.9300 . ? C13 C14 1.481(6) . ? C14 C15 1.372(7) . ? C15 C16 1.383(7) . ? C15 H15 0.9300 . ? C16 C17 1.381(6) . ? C16 H16 0.9300 . ? C17 C18 1.375(7) . ? C17 H17 0.9300 . ? C18 H18 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 O2 U O1 178.72(12) . . ? O2 U O5 88.75(13) . 2_766 ? O1 U O5 90.07(13) . 2_766 ? O2 U O6 89.53(11) . 1_455 ? O1 U O6 89.73(12) . 1_455 ? O5 U O6 78.86(10) 2_766 1_455 ? O2 U O7 90.63(13) . . ? O1 U O7 90.23(13) . . ? O5 U O7 156.43(9) 2_766 . ? O6 U O7 77.57(10) 1_455 . ? O2 U O3 87.01(11) . 2_766 ? O1 U O3 93.11(11) . 2_766 ? O5 U O3 71.32(9) 2_766 2_766 ? O6 U O3 150.04(10) 1_455 2_766 ? O7 U O3 132.17(9) . 2_766 ? O2 U O3 92.24(12) . . ? O1 U O3 88.94(12) . . ? O5 U O3 133.02(9) 2_766 . ? O6 U O3 148.08(10) 1_455 . ? O7 U O3 70.55(9) . . ? O3 U O3 61.85(11) 2_766 . ? O9 S1 O8 115.67(19) . . ? O9 S1 O7 112.2(2) . . ? O8 S1 O7 110.39(19) . . ? O9 S1 C8 107.38(19) . . ? O8 S1 C8 104.84(18) . . ? O7 S1 C8 105.58(17) . . ? C1 O3 U 120.3(2) . 2_766 ? C1 O3 U 120.7(2) . . ? U O3 U 118.15(11) 2_766 . ? C2 O5 U 145.1(2) . 2_766 ? C2 O6 U 145.3(3) . 1_655 ? S1 O7 U 144.53(17) . . ? C13 N1 C9 124.5(4) . . ? C13 N1 H1 122.3 . . ? C9 N1 H1 113.0 . . ? C18 N2 C14 116.9(4) . . ? O4 C1 O3 123.5(4) . . ? O4 C1 C3 122.4(4) . . ? O3 C1 C3 114.2(3) . . ? O6 C2 O5 123.3(3) . . ? O6 C2 C4 117.5(4) . . ? O5 C2 C4 119.3(3) . . ? C8 C3 C4 118.9(4) . . ? C8 C3 C1 120.3(3) . . ? C4 C3 C1 120.7(3) . . ? C5 C4 C3 120.7(3) . . ? C5 C4 C2 118.7(3) . . ? C3 C4 C2 120.5(4) . . ? C4 C5 C6 120.0(4) . . ? C4 C5 H5 120.0 . . ? C6 C5 H5 120.0 . . ? C7 C6 C5 119.3(4) . . ? C7 C6 H6 120.3 . . ? C5 C6 H6 120.3 . . ? C6 C7 C8 121.2(3) . . ? C6 C7 H7 119.4 . . ? C8 C7 H7 119.4 . . ? C7 C8 C3 119.8(4) . . ? C7 C8 S1 116.3(3) . . ? C3 C8 S1 123.7(3) . . ? N1 C9 C10 118.7(5) . . ? N1 C9 H9 120.7 . . ? C10 C9 H9 120.7 . . ? C9 C10 C11 119.5(5) . . ? C9 C10 H10 120.2 . . ? C11 C10 H10 120.2 . . ? C10 C11 C12 120.0(4) . . ? C10 C11 H11 120.0 . . ? C12 C11 H11 120.0 . . ? C13 C12 C11 119.0(5) . . ? C13 C12 H12 120.5 . . ? C11 C12 H12 120.5 . . ? N1 C13 C12 118.3(4) . . ? N1 C13 C14 116.4(4) . . ? C12 C13 C14 125.3(4) . . ? N2 C14 C15 122.9(4) . . ? N2 C14 C13 114.9(4) . . ? C15 C14 C13 122.2(4) . . ? C14 C15 C16 119.4(4) . . ? C14 C15 H15 120.3 . . ? C16 C15 H15 120.3 . . ? C17 C16 C15 118.3(5) . . ? C17 C16 H16 120.9 . . ? C15 C16 H16 120.9 . . ? C18 C17 C16 119.0(5) . . ? C18 C17 H17 120.5 . . ? C16 C17 H17 120.5 . . ? N2 C18 C17 123.5(4) . . ? N2 C18 H18 118.2 . . ? C17 C18 H18 118.2 . . ? 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 O4 0.81 2.08 2.814(5) 150.9 . data_2 _database_code_depnum_ccdc_archive 'CCDC 914740' #TrackingRef 'web_deposit_cif_file_0_P.Thuery_1354890695.CIF.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C40 H44 N14 Ni2 O34 S2 U2' _chemical_formula_weight 1922.49 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ni Ni 0.3393 1.1124 '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 9.8594(5) _cell_length_b 11.6695(7) _cell_length_c 14.3340(7) _cell_angle_alpha 70.785(3) _cell_angle_beta 77.639(3) _cell_angle_gamma 71.479(2) _cell_volume 1465.57(14) _cell_formula_units_Z 1 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 86462 _cell_measurement_theta_min 2.08 _cell_measurement_theta_max 30.51 _exptl_crystal_description parallelepiped _exptl_crystal_colour 'translucent light yellow' _exptl_crystal_size_max 0.17 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.178 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 926 _exptl_absorpt_coefficient_mu 6.323 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.314 _exptl_absorpt_correction_T_max 0.440 _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 12 \w scans with 2\% steps (767 frames)' _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 86462 _diffrn_reflns_av_R_equivalents 0.0563 _diffrn_reflns_av_sigmaI/netI 0.0644 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.08 _diffrn_reflns_theta_max 30.51 _reflns_number_total 8930 _reflns_number_gt 7782 _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 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^)+(0.0222P)^2^+0.2525P] 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 8930 _refine_ls_number_parameters 424 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0395 _refine_ls_R_factor_gt 0.0302 _refine_ls_wR_factor_ref 0.0661 _refine_ls_wR_factor_gt 0.0641 _refine_ls_goodness_of_fit_ref 1.023 _refine_ls_restrained_S_all 1.023 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 30.51 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.728 _refine_diff_density_min -1.956 _refine_diff_density_rms 0.158 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 0.254032(11) 0.322265(11) 0.443236(8) 0.02401(4) Uani 1 1 d . . . Ni Ni 0.94536(4) 0.26715(4) 1.10855(3) 0.02577(9) Uani 1 1 d . . . S1 S 0.68193(8) 0.19153(7) 0.88397(5) 0.02533(16) Uani 1 1 d . . . O1 O 0.3497(2) 0.1656(2) 0.44234(17) 0.0308(5) Uani 1 1 d . . . O2 O 0.1610(2) 0.4791(2) 0.44170(18) 0.0331(5) Uani 1 1 d . . . O3 O 0.4839(2) 0.3535(2) 0.45194(16) 0.0301(5) Uani 1 1 d . . . O4 O 0.3546(2) 0.2912(3) 0.59467(17) 0.0370(6) Uani 1 1 d . . . O5 O 1.0982(2) 0.2439(2) 0.59131(16) 0.0301(5) Uani 1 1 d . . . O6 O 1.0166(2) 0.2880(2) 0.44872(15) 0.0272(5) Uani 1 1 d . . . O7 O 0.7525(3) 0.2720(2) 0.90221(17) 0.0357(5) Uani 1 1 d . . . O8 O 0.7538(3) 0.0576(2) 0.91788(17) 0.0366(6) Uani 1 1 d . . . O9 O 0.5285(2) 0.2179(2) 0.92130(16) 0.0313(5) Uani 1 1 d . . . O10 O 0.1845(2) 0.3621(2) 0.27484(17) 0.0331(5) Uani 1 1 d . . . O11 O 0.3835(3) 0.4038(2) 0.27136(16) 0.0356(6) Uani 1 1 d . . . O12 O 0.2991(3) 0.4415(2) 0.13212(17) 0.0434(6) Uani 1 1 d . . . O13 O 0.7402(2) 0.3246(2) 1.07449(16) 0.0302(5) Uani 1 1 d . . . H13A H 0.7180 0.3168 1.0279 0.036 Uiso 1 1 d R . . H13B H 0.6793 0.3969 1.0765 0.036 Uiso 1 1 d R . . O14 O 0.9660(2) 0.1007(2) 1.07470(17) 0.0321(5) Uani 1 1 d . . . H14A H 1.0588 0.0408 1.0688 0.039 Uiso 1 1 d R . . H14B H 0.9050 0.0567 1.1256 0.039 Uiso 1 1 d R . . O15 O 1.1835(3) 0.0619(2) 0.78470(19) 0.0478(7) Uani 1 1 d . . . H15A H 1.1920 0.1008 0.7175 0.057 Uiso 1 1 d R . . H15B H 1.2454 0.1017 0.8015 0.057 Uiso 1 1 d R . . O16 O 0.6661(3) -0.1012(2) 1.09706(18) 0.0426(6) Uani 1 1 d . . . H16A H 0.6993 -0.0606 1.0396 0.051 Uiso 1 1 d R . . H16B H 0.5909 -0.1270 1.0938 0.051 Uiso 1 1 d R . . O17 O 0.3999(3) 0.4798(2) 0.8561(2) 0.0443(7) Uani 1 1 d . . . H17A H 0.4302 0.3935 0.8865 0.053 Uiso 1 1 d R . . H17B H 0.4848 0.4962 0.8232 0.053 Uiso 1 1 d R . . N1 N 0.2889(3) 0.4040(3) 0.2223(2) 0.0331(6) Uani 1 1 d . . . N2 N 0.8787(3) 0.1853(2) 1.2535(2) 0.0280(6) Uani 1 1 d . . . N3 N 1.1427(3) 0.1862(2) 1.16263(19) 0.0272(6) Uani 1 1 d . . . N4 N 1.2461(3) 0.0479(3) 1.3084(2) 0.0315(6) Uani 1 1 d . . . N5 N 0.9716(3) 0.0339(3) 1.3982(2) 0.0330(7) Uani 1 1 d . . . N6 N 0.9358(3) 0.4415(2) 1.12823(19) 0.0258(5) Uani 1 1 d . . . N7 N 0.9817(3) 0.6388(2) 1.03554(19) 0.0264(6) Uani 1 1 d . . . C1 C 0.4712(3) 0.3135(3) 0.5459(2) 0.0284(7) Uani 1 1 d . . . C2 C 0.9959(3) 0.2615(3) 0.5428(2) 0.0268(7) Uani 1 1 d . . . C3 C 0.5959(3) 0.2874(3) 0.5995(2) 0.0248(6) Uani 1 1 d . . . C4 C 0.7324(3) 0.2872(3) 0.5470(2) 0.0261(6) Uani 1 1 d . . . H4 H 0.7449 0.3070 0.4779 0.031 Uiso 1 1 calc R . . C5 C 0.8502(3) 0.2572(3) 0.5978(2) 0.0250(6) Uani 1 1 d . . . C6 C 0.8323(3) 0.2272(3) 0.7007(2) 0.0254(6) Uani 1 1 d . . . H6 H 0.9111 0.2063 0.7347 0.030 Uiso 1 1 calc R . . C7 C 0.6956(3) 0.2282(3) 0.7531(2) 0.0235(6) Uani 1 1 d . . . C8 C 0.5779(3) 0.2571(3) 0.7034(2) 0.0269(7) Uani 1 1 d . . . H8 H 0.4873 0.2563 0.7389 0.032 Uiso 1 1 calc R . . C9 C 0.9871(3) 0.1090(3) 1.3069(2) 0.0283(7) Uani 1 1 d . . . C10 C 0.7446(4) 0.1852(3) 1.2957(3) 0.0336(8) Uani 1 1 d . . . H10 H 0.6676 0.2368 1.2608 0.040 Uiso 1 1 calc R . . C11 C 0.7182(4) 0.1091(3) 1.3912(3) 0.0340(8) Uani 1 1 d . . . H11 H 0.6250 0.1079 1.4211 0.041 Uiso 1 1 calc R . . C12 C 0.8358(3) 0.0357(3) 1.4396(2) 0.0305(7) Uani 1 1 d . . . H12 H 0.8207 -0.0151 1.5041 0.037 Uiso 1 1 calc R . . C13 C 1.1362(3) 0.1130(3) 1.2570(2) 0.0287(7) Uani 1 1 d . . . C14 C 1.2759(4) 0.1938(3) 1.1165(2) 0.0325(7) Uani 1 1 d . . . H14 H 1.2861 0.2433 1.0510 0.039 Uiso 1 1 calc R . . C15 C 1.3955(4) 0.1306(3) 1.1641(3) 0.0324(7) Uani 1 1 d . . . H15 H 1.4868 0.1367 1.1325 0.039 Uiso 1 1 calc R . . C16 C 1.3759(4) 0.0571(3) 1.2611(3) 0.0344(8) Uani 1 1 d . . . H16 H 1.4562 0.0124 1.2946 0.041 Uiso 1 1 calc R . . C17 C 0.9772(3) 0.5219(3) 1.0453(2) 0.0248(6) Uani 1 1 d . . . C18 C 0.8977(4) 0.4825(3) 1.2106(2) 0.0318(7) Uani 1 1 d . . . H18 H 0.8675 0.4297 1.2705 0.038 Uiso 1 1 calc R . . C19 C 0.9022(4) 0.5991(3) 1.2087(2) 0.0327(8) Uani 1 1 d . . . H19 H 0.8766 0.6253 1.2662 0.039 Uiso 1 1 calc R . . C20 C 0.9459(3) 0.6770(3) 1.1188(2) 0.0319(7) Uani 1 1 d . . . H20 H 0.9505 0.7565 1.1158 0.038 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 U 0.01813(6) 0.03084(7) 0.02487(6) -0.00932(5) -0.00062(4) -0.00879(4) Ni 0.0256(2) 0.0252(2) 0.02778(19) -0.00852(16) -0.00296(15) -0.00759(16) S1 0.0241(4) 0.0295(4) 0.0238(3) -0.0088(3) -0.0014(3) -0.0087(3) O1 0.0231(11) 0.0309(12) 0.0365(12) -0.0095(10) 0.0000(9) -0.0070(9) O2 0.0271(12) 0.0328(12) 0.0422(13) -0.0165(11) -0.0019(10) -0.0069(10) O3 0.0234(11) 0.0444(14) 0.0264(11) -0.0099(10) -0.0024(9) -0.0151(10) O4 0.0235(11) 0.0600(16) 0.0306(12) -0.0129(11) 0.0011(9) -0.0181(11) O5 0.0186(10) 0.0449(14) 0.0276(11) -0.0078(10) -0.0017(8) -0.0127(10) O6 0.0212(10) 0.0396(12) 0.0260(10) -0.0124(9) -0.0004(8) -0.0133(9) O7 0.0389(14) 0.0473(14) 0.0323(12) -0.0162(11) -0.0020(10) -0.0233(11) O8 0.0378(13) 0.0299(12) 0.0327(12) -0.0049(10) -0.0009(10) -0.0030(10) O9 0.0249(11) 0.0382(13) 0.0303(11) -0.0118(10) 0.0019(9) -0.0089(10) O10 0.0294(12) 0.0415(13) 0.0304(11) -0.0092(10) -0.0035(9) -0.0133(10) O11 0.0342(13) 0.0495(15) 0.0261(11) -0.0069(10) -0.0009(10) -0.0210(11) O12 0.0600(17) 0.0462(15) 0.0269(12) -0.0033(11) -0.0059(11) -0.0251(13) O13 0.0292(12) 0.0337(12) 0.0292(11) -0.0130(10) -0.0058(9) -0.0049(10) O14 0.0293(12) 0.0280(12) 0.0421(13) -0.0144(10) -0.0052(10) -0.0065(9) O15 0.0635(18) 0.0468(16) 0.0425(14) -0.0052(12) -0.0119(13) -0.0315(14) O16 0.0415(15) 0.0549(16) 0.0365(13) -0.0036(12) -0.0081(11) -0.0272(13) O17 0.0347(14) 0.0371(14) 0.0575(16) -0.0180(13) 0.0041(12) -0.0065(11) N1 0.0378(16) 0.0293(14) 0.0319(14) -0.0066(12) -0.0052(12) -0.0100(12) N2 0.0291(14) 0.0277(13) 0.0285(13) -0.0071(11) -0.0029(11) -0.0106(11) N3 0.0275(13) 0.0267(13) 0.0301(13) -0.0105(11) -0.0005(11) -0.0102(11) N4 0.0286(14) 0.0307(14) 0.0346(14) -0.0093(12) -0.0036(11) -0.0072(11) N5 0.0352(16) 0.0313(15) 0.0309(14) -0.0034(12) -0.0039(12) -0.0123(12) N6 0.0251(13) 0.0281(13) 0.0266(13) -0.0091(11) -0.0026(10) -0.0092(11) N7 0.0258(13) 0.0252(13) 0.0312(13) -0.0121(11) -0.0019(10) -0.0075(10) C1 0.0221(15) 0.0383(18) 0.0290(15) -0.0122(14) -0.0032(12) -0.0108(13) C2 0.0218(14) 0.0284(16) 0.0306(15) -0.0102(13) 0.0002(12) -0.0074(12) C3 0.0185(14) 0.0340(16) 0.0269(14) -0.0122(13) -0.0008(11) -0.0114(12) C4 0.0247(15) 0.0305(16) 0.0247(14) -0.0080(13) -0.0001(12) -0.0112(12) C5 0.0226(14) 0.0268(15) 0.0283(15) -0.0100(12) -0.0003(12) -0.0096(12) C6 0.0185(14) 0.0291(16) 0.0302(15) -0.0091(13) -0.0025(11) -0.0082(12) C7 0.0232(14) 0.0271(15) 0.0228(13) -0.0085(12) -0.0019(11) -0.0095(12) C8 0.0230(15) 0.0292(16) 0.0292(15) -0.0085(13) 0.0010(12) -0.0102(12) C9 0.0312(16) 0.0270(16) 0.0294(15) -0.0092(13) -0.0028(13) -0.0108(13) C10 0.0263(16) 0.0352(18) 0.0369(17) -0.0112(15) -0.0025(13) -0.0050(14) C11 0.0283(17) 0.0348(18) 0.0381(18) -0.0127(15) 0.0043(14) -0.0105(14) C12 0.0295(17) 0.0319(17) 0.0305(16) -0.0062(14) 0.0037(13) -0.0163(14) C13 0.0295(16) 0.0279(16) 0.0310(16) -0.0130(13) 0.0009(13) -0.0089(13) C14 0.0307(17) 0.0391(19) 0.0300(16) -0.0141(14) 0.0030(13) -0.0122(14) C15 0.0262(16) 0.0366(18) 0.0380(18) -0.0174(15) 0.0040(13) -0.0112(14) C16 0.0266(16) 0.0369(18) 0.0420(19) -0.0162(15) -0.0032(14) -0.0069(14) C17 0.0206(14) 0.0284(15) 0.0278(15) -0.0111(12) -0.0032(11) -0.0064(12) C18 0.0341(18) 0.0346(18) 0.0280(15) -0.0112(14) -0.0015(13) -0.0100(14) C19 0.0352(18) 0.0347(18) 0.0295(16) -0.0151(14) -0.0003(13) -0.0073(14) C20 0.0298(17) 0.0274(16) 0.0397(18) -0.0156(14) -0.0023(14) -0.0044(13) _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 O2 1.762(2) . ? U O1 1.774(2) . ? U O5 2.433(2) 1_455 ? U O3 2.442(2) . ? U O4 2.450(2) . ? U O6 2.478(2) 1_455 ? U O10 2.506(2) . ? U O11 2.547(2) . ? Ni O13 2.031(2) . ? Ni N2 2.041(3) . ? Ni N3 2.067(3) . ? Ni N7 2.088(3) 2_767 ? Ni O14 2.092(2) . ? Ni N6 2.115(3) . ? S1 O7 1.445(3) . ? S1 O8 1.458(2) . ? S1 O9 1.462(2) . ? S1 C7 1.767(3) . ? O3 C1 1.264(4) . ? O4 C1 1.266(4) . ? O5 C2 1.272(4) . ? O5 U 2.433(2) 1_655 ? O6 C2 1.266(4) . ? O6 U 2.478(2) 1_655 ? O10 N1 1.268(4) . ? O11 N1 1.282(4) . ? O12 N1 1.214(3) . ? O13 H13A 0.7856 . ? O13 H13B 0.8718 . ? O14 H14A 0.9653 . ? O14 H14B 0.9585 . ? O15 H15A 0.9178 . ? O15 H15B 0.9812 . ? O16 H16A 0.8581 . ? O16 H16B 0.8988 . ? O17 H17A 0.9322 . ? O17 H17B 0.9119 . ? N2 C10 1.331(4) . ? N2 C9 1.349(4) . ? N3 C13 1.341(4) . ? N3 C14 1.355(4) . ? N4 C13 1.321(4) . ? N4 C16 1.333(4) . ? N5 C9 1.321(4) . ? N5 C12 1.340(4) . ? N6 C17 1.328(4) . ? N6 C18 1.354(4) . ? N7 C17 1.339(4) . ? N7 C20 1.348(4) . ? N7 Ni 2.088(3) 2_767 ? C1 C3 1.486(4) . ? C2 C5 1.491(4) . ? C3 C4 1.395(4) . ? C3 C8 1.397(4) . ? C4 C5 1.392(4) . ? C4 H4 0.9300 . ? C5 C6 1.383(4) . ? C6 C7 1.393(4) . ? C6 H6 0.9300 . ? C7 C8 1.384(4) . ? C8 H8 0.9300 . ? C9 C13 1.499(4) . ? C10 C11 1.387(5) . ? C10 H10 0.9300 . ? C11 C12 1.372(5) . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? C14 C15 1.363(5) . ? C14 H14 0.9300 . ? C15 C16 1.383(5) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? C17 C17 1.481(6) 2_767 ? C18 C19 1.365(5) . ? C18 H18 0.9300 . ? C19 C20 1.382(5) . ? C19 H19 0.9300 . ? C20 H20 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 O2 U O1 178.80(10) . . ? O2 U O5 90.85(9) . 1_455 ? O1 U O5 90.35(9) . 1_455 ? O2 U O3 92.20(10) . . ? O1 U O3 87.28(10) . . ? O5 U O3 122.38(8) 1_455 . ? O2 U O4 90.77(10) . . ? O1 U O4 89.79(10) . . ? O5 U O4 69.02(8) 1_455 . ? O3 U O4 53.42(7) . . ? O2 U O6 87.19(10) . 1_455 ? O1 U O6 93.41(9) . 1_455 ? O5 U O6 53.20(7) 1_455 1_455 ? O3 U O6 175.50(6) . 1_455 ? O4 U O6 122.12(7) . 1_455 ? O2 U O10 89.77(10) . . ? O1 U O10 89.52(9) . . ? O5 U O10 119.36(8) 1_455 . ? O3 U O10 118.18(7) . . ? O4 U O10 171.60(7) . . ? O6 U O10 66.28(7) 1_455 . ? O2 U O11 89.02(9) . . ? O1 U O11 89.78(9) . . ? O5 U O11 169.80(8) 1_455 . ? O3 U O11 67.81(8) . . ? O4 U O11 121.17(8) . . ? O6 U O11 116.62(8) 1_455 . ? O10 U O11 50.45(8) . . ? O13 Ni N2 90.97(10) . . ? O13 Ni N3 170.54(10) . . ? N2 Ni N3 80.36(11) . . ? O13 Ni N7 91.00(10) . 2_767 ? N2 Ni N7 175.29(12) . 2_767 ? N3 Ni N7 97.93(10) . 2_767 ? O13 Ni O14 87.20(9) . . ? N2 Ni O14 89.44(10) . . ? N3 Ni O14 88.93(10) . . ? N7 Ni O14 94.92(10) 2_767 . ? O13 Ni N6 93.83(10) . . ? N2 Ni N6 96.28(10) . . ? N3 Ni N6 90.89(11) . . ? N7 Ni N6 79.33(10) 2_767 . ? O14 Ni N6 174.17(10) . . ? O7 S1 O8 113.91(16) . . ? O7 S1 O9 112.85(14) . . ? O8 S1 O9 111.32(15) . . ? O7 S1 C7 105.32(15) . . ? O8 S1 C7 105.62(14) . . ? O9 S1 C7 107.13(14) . . ? C1 O3 U 92.86(19) . . ? C1 O4 U 92.44(19) . . ? C2 O5 U 93.74(18) . 1_655 ? C2 O6 U 91.81(19) . 1_655 ? N1 O10 U 98.33(19) . . ? N1 O11 U 95.95(18) . . ? Ni O13 H13A 124.3 . . ? Ni O13 H13B 125.1 . . ? H13A O13 H13B 99.1 . . ? Ni O14 H14A 121.0 . . ? Ni O14 H14B 106.4 . . ? H14A O14 H14B 106.9 . . ? H15A O15 H15B 96.6 . . ? H16A O16 H16B 111.9 . . ? H17A O17 H17B 101.3 . . ? O12 N1 O10 122.8(3) . . ? O12 N1 O11 122.1(3) . . ? O10 N1 O11 115.2(3) . . ? C10 N2 C9 117.5(3) . . ? C10 N2 Ni 127.8(2) . . ? C9 N2 Ni 114.0(2) . . ? C13 N3 C14 116.0(3) . . ? C13 N3 Ni 114.2(2) . . ? C14 N3 Ni 129.8(2) . . ? C13 N4 C16 116.0(3) . . ? C9 N5 C12 116.1(3) . . ? C17 N6 C18 115.7(3) . . ? C17 N6 Ni 113.3(2) . . ? C18 N6 Ni 130.9(2) . . ? C17 N7 C20 116.8(3) . . ? C17 N7 Ni 113.7(2) . 2_767 ? C20 N7 Ni 129.3(2) . 2_767 ? O3 C1 O4 120.6(3) . . ? O3 C1 C3 119.8(3) . . ? O4 C1 C3 119.5(3) . . ? O6 C2 O5 120.1(3) . . ? O6 C2 C5 120.8(3) . . ? O5 C2 C5 119.0(3) . . ? C4 C3 C8 119.7(3) . . ? C4 C3 C1 120.2(3) . . ? C8 C3 C1 120.0(3) . . ? C5 C4 C3 120.1(3) . . ? C5 C4 H4 120.0 . . ? C3 C4 H4 120.0 . . ? C6 C5 C4 120.1(3) . . ? C6 C5 C2 119.0(3) . . ? C4 C5 C2 120.9(3) . . ? C5 C6 C7 119.7(3) . . ? C5 C6 H6 120.1 . . ? C7 C6 H6 120.1 . . ? C8 C7 C6 120.6(3) . . ? C8 C7 S1 122.6(2) . . ? C6 C7 S1 116.7(2) . . ? C7 C8 C3 119.7(3) . . ? C7 C8 H8 120.2 . . ? C3 C8 H8 120.2 . . ? N5 C9 N2 125.5(3) . . ? N5 C9 C13 118.8(3) . . ? N2 C9 C13 115.8(3) . . ? N2 C10 C11 120.9(3) . . ? N2 C10 H10 119.5 . . ? C11 C10 H10 119.5 . . ? C12 C11 C10 117.0(3) . . ? C12 C11 H11 121.5 . . ? C10 C11 H11 121.5 . . ? N5 C12 C11 123.0(3) . . ? N5 C12 H12 118.5 . . ? C11 C12 H12 118.5 . . ? N4 C13 N3 126.6(3) . . ? N4 C13 C9 118.5(3) . . ? N3 C13 C9 114.9(3) . . ? N3 C14 C15 121.4(3) . . ? N3 C14 H14 119.3 . . ? C15 C14 H14 119.3 . . ? C14 C15 C16 117.5(3) . . ? C14 C15 H15 121.3 . . ? C16 C15 H15 121.3 . . ? N4 C16 C15 122.4(3) . . ? N4 C16 H16 118.8 . . ? C15 C16 H16 118.8 . . ? N6 C17 N7 126.4(3) . . ? N6 C17 C17 116.8(4) . 2_767 ? N7 C17 C17 116.8(3) . 2_767 ? N6 C18 C19 122.2(3) . . ? N6 C18 H18 118.9 . . ? C19 C18 H18 118.9 . . ? C18 C19 C20 118.2(3) . . ? C18 C19 H19 120.9 . . ? C20 C19 H19 120.9 . . ? N7 C20 C19 120.6(3) . . ? N7 C20 H20 119.7 . . ? C19 C20 H20 119.7 . . ? 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 O13 H13A O7 0.79 1.97 2.705(3) 155.4 . O13 H13B O17 0.87 1.87 2.648(3) 147.9 2_667 O14 H14A O8 0.97 1.85 2.795(3) 164.9 2_757 O14 H14B O15 0.96 1.86 2.797(4) 166.2 2_757 O15 H15A O5 0.92 2.16 2.981(3) 148.6 . O15 H15B O16 0.98 1.85 2.702(4) 144.0 2_757 O16 H16A O8 0.86 1.93 2.777(3) 169.6 . O16 H16B O9 0.90 1.90 2.777(4) 164.7 2_657 O17 H17A O9 0.93 1.91 2.826(3) 165.8 . O17 H17B O11 0.91 2.01 2.877(4) 157.5 2_666 data_3 _database_code_depnum_ccdc_archive 'CCDC 914741' #TrackingRef 'web_deposit_cif_file_0_P.Thuery_1354890695.CIF.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H19 N O9 S U' _chemical_formula_weight 615.39 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' S S 0.1246 0.1234 '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 9.2111(8) _cell_length_b 13.1733(6) _cell_length_c 16.0964(13) _cell_angle_alpha 84.739(4) _cell_angle_beta 83.029(4) _cell_angle_gamma 87.457(5) _cell_volume 1929.5(2) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 107996 _cell_measurement_theta_min 2.10 _cell_measurement_theta_max 28.70 _exptl_crystal_description platelet _exptl_crystal_colour 'translucent light yellow' _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.118 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1160 _exptl_absorpt_coefficient_mu 8.566 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.468 _exptl_absorpt_correction_T_max 0.773 _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 twelve \w scans with 2\% steps (724 frames)' _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 107996 _diffrn_reflns_av_R_equivalents 0.0684 _diffrn_reflns_av_sigmaI/netI 0.0869 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.10 _diffrn_reflns_theta_max 28.70 _reflns_number_total 9980 _reflns_number_gt 6647 _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. One of the triethylammonium cations (N2, C23-C28) is very badly resolved and the central part of it was restrained to fit the geometry of the other cation (SAME). All non-hydrogen atoms were refined with anisotropic displacement parameters, with restraints for the badly behaving triethylammonium cation. The H atom bound to N1 was found on a Fourier-difference map and all the others (including that of N2) 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 (1.5 for CH~3~). 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^)+(0.0648P)^2^+0.5794P] 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 9980 _refine_ls_number_parameters 474 _refine_ls_number_restraints 142 _refine_ls_R_factor_all 0.0861 _refine_ls_R_factor_gt 0.0490 _refine_ls_wR_factor_ref 0.1353 _refine_ls_wR_factor_gt 0.1233 _refine_ls_goodness_of_fit_ref 1.040 _refine_ls_restrained_S_all 1.038 _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 28.70 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 3.635 _refine_diff_density_min -1.574 _refine_diff_density_rms 0.219 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 0.21976(4) 0.55980(2) 0.256124(17) 0.03334(11) Uani 1 1 d . . . U2 U 0.21970(4) 0.95180(2) 0.227954(16) 0.03205(11) Uani 1 1 d . . . S1 S 0.4406(3) 0.51877(15) -0.13451(12) 0.0358(5) Uani 1 1 d . . . S2 S -0.2411(3) 0.99686(15) 0.55961(12) 0.0352(5) Uani 1 1 d . . . O1 O 0.0821(7) 0.5023(4) 0.2113(3) 0.0399(15) Uani 1 1 d . . . O2 O 0.3580(7) 0.6171(5) 0.3013(4) 0.0456(16) Uani 1 1 d . . . O3 O 0.0810(7) 1.0336(4) 0.1893(3) 0.0399(15) Uani 1 1 d . . . O4 O 0.3564(7) 0.8681(5) 0.2633(3) 0.0425(15) Uani 1 1 d . . . O5 O 0.2184(8) 0.6879(4) 0.1447(4) 0.0462(17) Uani 1 1 d . . . O6 O 0.2132(7) 0.8545(4) 0.1121(3) 0.0357(14) Uani 1 1 d . . . O7 O 0.5988(7) 0.9764(4) -0.1160(3) 0.0424(17) Uani 1 1 d . . . O8 O 0.6378(7) 0.8935(4) -0.2298(3) 0.0408(16) Uani 1 1 d . . . O9 O 0.6022(7) 0.5039(4) -0.1543(3) 0.0395(16) Uani 1 1 d . . . O10 O 0.3818(7) 0.4470(4) -0.0678(3) 0.0382(15) Uani 1 1 d . . . O11 O 0.3672(8) 0.5245(5) -0.2090(4) 0.0524(18) Uani 1 1 d . . . O12 O 0.0435(8) 0.6722(4) 0.3167(4) 0.0452(17) Uani 1 1 d . . . O13 O 0.0367(7) 0.8394(4) 0.2886(3) 0.0371(15) Uani 1 1 d . . . O14 O -0.1329(7) 0.5203(4) 0.6041(3) 0.0394(15) Uani 1 1 d . . . O15 O -0.2904(7) 0.6106(4) 0.6840(3) 0.0400(16) Uani 1 1 d . . . O16 O -0.1645(7) 0.9963(4) 0.6352(3) 0.0352(14) Uani 1 1 d . . . O17 O -0.1808(8) 1.0708(4) 0.4942(4) 0.0426(16) Uani 1 1 d . . . O18 O -0.3977(7) 1.0012(5) 0.5809(4) 0.0492(17) Uani 1 1 d . . . C1 C 0.2468(9) 0.7632(5) 0.0969(4) 0.0238(16) Uani 1 1 d . . . C2 C 0.5771(10) 0.9005(6) -0.1548(5) 0.037(2) Uani 1 1 d . . . C3 C 0.3337(10) 0.7473(6) 0.0123(5) 0.0306(18) Uani 1 1 d . . . C4 C 0.4058(10) 0.8315(6) -0.0326(4) 0.034(2) Uani 1 1 d . . . H4 H 0.3978 0.8955 -0.0119 0.040 Uiso 1 1 calc R . . C5 C 0.4906(9) 0.8153(6) -0.1101(5) 0.0318(19) Uani 1 1 d . . . C6 C 0.4976(10) 0.7208(6) -0.1413(5) 0.034(2) Uani 1 1 d . . . H6 H 0.5501 0.7114 -0.1933 0.040 Uiso 1 1 calc R . . C7 C 0.4254(9) 0.6394(6) -0.0944(4) 0.0286(18) Uani 1 1 d . . . C8 C 0.3451(10) 0.6535(6) -0.0180(5) 0.0317(19) Uani 1 1 d . . . H8 H 0.2985 0.5987 0.0131 0.038 Uiso 1 1 calc R . . C9 C 0.0080(9) 0.7598(6) 0.3353(4) 0.0287(18) Uani 1 1 d . . . C10 C -0.2026(10) 0.6026(6) 0.6167(5) 0.0317(19) Uani 1 1 d . . . C11 C -0.0762(9) 0.7705(6) 0.4206(4) 0.0280(18) Uani 1 1 d . . . C12 C -0.1035(9) 0.6858(6) 0.4760(5) 0.0299(18) Uani 1 1 d . . . H12 H -0.0711 0.6218 0.4600 0.036 Uiso 1 1 calc R . . C13 C -0.1787(9) 0.6942(6) 0.5555(4) 0.0272(17) Uani 1 1 d . . . C14 C -0.2219(9) 0.7899(6) 0.5793(4) 0.0314(19) Uani 1 1 d . . . H14 H -0.2718 0.7970 0.6323 0.038 Uiso 1 1 calc R . . C15 C -0.1911(9) 0.8756(6) 0.5243(5) 0.0317(18) Uani 1 1 d . . . C16 C -0.1209(9) 0.8656(6) 0.4468(4) 0.0287(17) Uani 1 1 d . . . H16 H -0.1020 0.9236 0.4102 0.034 Uiso 1 1 calc R . . N1 N 0.2048(10) 0.2804(6) -0.0797(5) 0.057(2) Uani 1 1 d D . . H1 H 0.2643 0.3231 -0.0753 0.068 Uiso 1 1 d R . . C17 C 0.2614(15) 0.1729(9) -0.0548(9) 0.093(5) Uani 1 1 d D . . H17A H 0.3492 0.1575 -0.0918 0.111 Uiso 1 1 calc R . . H17B H 0.2872 0.1695 0.0020 0.111 Uiso 1 1 calc R . . C19 C 0.1843(12) 0.2957(7) -0.1694(5) 0.051(3) Uani 1 1 d D . . H19A H 0.0987 0.2590 -0.1773 0.061 Uiso 1 1 calc R . . H19B H 0.1619 0.3676 -0.1824 0.061 Uiso 1 1 calc R . . C21 C 0.0849(12) 0.3193(10) -0.0218(6) 0.075(4) Uani 1 1 d D . . H21A H -0.0012 0.2805 -0.0246 0.090 Uiso 1 1 calc R . . H21B H 0.0625 0.3896 -0.0408 0.090 Uiso 1 1 calc R . . C18 C 0.1487(19) 0.0934(10) -0.0596(12) 0.133(8) Uani 1 1 d . . . H18A H 0.0601 0.1099 -0.0249 0.200 Uiso 1 1 calc R . . H18B H 0.1861 0.0274 -0.0401 0.200 Uiso 1 1 calc R . . H18C H 0.1287 0.0926 -0.1167 0.200 Uiso 1 1 calc R . . C20 C 0.3037(13) 0.2653(11) -0.2315(8) 0.086(5) Uani 1 1 d . . . H20A H 0.3917 0.2974 -0.2229 0.128 Uiso 1 1 calc R . . H20B H 0.2792 0.2860 -0.2869 0.128 Uiso 1 1 calc R . . H20C H 0.3188 0.1926 -0.2253 0.128 Uiso 1 1 calc R . . C22 C 0.1139(17) 0.3149(14) 0.0681(7) 0.116(7) Uani 1 1 d D . . H22A H 0.0921 0.2484 0.0952 0.175 Uiso 1 1 calc R . . H22B H 0.0531 0.3654 0.0962 0.175 Uiso 1 1 calc R . . H22C H 0.2149 0.3280 0.0704 0.175 Uiso 1 1 calc R . . N2 N -0.3056(14) 1.2713(11) 0.4240(8) 0.159(3) Uani 1 1 d DU . . H2 H -0.2477 1.2226 0.4549 0.191 Uiso 1 1 d R . . C23 C -0.4627(19) 1.2500(17) 0.4604(10) 0.162(3) Uani 1 1 d DU . . H23A H -0.4907 1.1863 0.4422 0.194 Uiso 1 1 calc R . . H23B H -0.5272 1.3040 0.4394 0.194 Uiso 1 1 calc R . . C25 C -0.258(2) 1.3699(14) 0.4452(12) 0.161(3) Uani 1 1 d DU . . H25A H -0.1568 1.3774 0.4209 0.193 Uiso 1 1 calc R . . H25B H -0.2591 1.3666 0.5057 0.193 Uiso 1 1 calc R . . C27 C -0.2664(19) 1.2479(16) 0.3370(11) 0.162(3) Uani 1 1 d DU . . H27A H -0.3341 1.2865 0.3036 0.194 Uiso 1 1 calc R . . H27B H -0.2845 1.1763 0.3346 0.194 Uiso 1 1 calc R . . C24 C -0.481(2) 1.2434(18) 0.5573(10) 0.159(3) Uani 1 1 d DU . . H24A H -0.3865 1.2365 0.5769 0.238 Uiso 1 1 calc R . . H24B H -0.5375 1.1853 0.5792 0.238 Uiso 1 1 calc R . . H24C H -0.5307 1.3043 0.5761 0.238 Uiso 1 1 calc R . . C26 C -0.344(2) 1.4668(16) 0.4178(13) 0.161(3) Uani 1 1 d DU . . H26A H -0.2891 1.5029 0.3706 0.242 Uiso 1 1 d R . . H26B H -0.3607 1.5096 0.4634 0.242 Uiso 1 1 d R . . H26C H -0.4363 1.4487 0.4022 0.242 Uiso 1 1 d R . . C28 C -0.1106(19) 1.2673(17) 0.2932(13) 0.161(3) Uani 1 1 d DU . . H28A H -0.0861 1.3362 0.2986 0.241 Uiso 1 1 calc R . . H28B H -0.1065 1.2565 0.2347 0.241 Uiso 1 1 calc R . . H28C H -0.0422 1.2211 0.3189 0.241 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 0.0488(2) 0.02380(16) 0.02310(15) -0.00194(11) 0.01411(14) -0.00350(13) U2 0.0487(2) 0.02318(16) 0.02117(15) -0.00352(11) 0.01219(13) -0.00790(13) S1 0.0503(14) 0.0280(10) 0.0268(9) -0.0061(8) 0.0098(9) -0.0060(9) S2 0.0475(14) 0.0284(10) 0.0280(10) -0.0046(8) 0.0051(9) -0.0040(9) O1 0.053(4) 0.030(3) 0.036(3) -0.007(2) 0.004(3) -0.008(3) O2 0.052(4) 0.042(4) 0.042(3) -0.009(3) 0.005(3) -0.013(3) O3 0.056(4) 0.031(3) 0.030(3) 0.000(2) 0.002(3) -0.001(3) O4 0.046(4) 0.050(4) 0.028(3) -0.001(3) 0.003(3) 0.009(3) O5 0.067(5) 0.029(3) 0.034(3) 0.003(2) 0.022(3) 0.007(3) O6 0.054(4) 0.025(3) 0.025(3) -0.006(2) 0.010(3) -0.005(3) O7 0.060(4) 0.031(3) 0.034(3) -0.010(2) 0.017(3) -0.016(3) O8 0.061(4) 0.031(3) 0.027(3) -0.005(2) 0.015(3) -0.016(3) O9 0.050(4) 0.028(3) 0.035(3) -0.007(2) 0.019(3) -0.002(3) O10 0.050(4) 0.027(3) 0.036(3) -0.004(2) 0.009(3) -0.009(3) O11 0.068(5) 0.051(4) 0.040(3) -0.016(3) -0.010(3) 0.001(4) O12 0.063(5) 0.033(3) 0.031(3) 0.002(2) 0.021(3) 0.009(3) O13 0.053(4) 0.030(3) 0.026(3) -0.006(2) 0.011(3) -0.012(3) O14 0.057(4) 0.032(3) 0.023(3) 0.000(2) 0.017(3) 0.005(3) O15 0.060(4) 0.026(3) 0.028(3) 0.003(2) 0.019(3) -0.003(3) O16 0.051(4) 0.028(3) 0.026(3) -0.008(2) 0.008(3) -0.008(3) O17 0.064(5) 0.027(3) 0.033(3) -0.003(2) 0.008(3) -0.003(3) O18 0.043(4) 0.050(4) 0.053(4) -0.013(3) 0.006(3) -0.001(3) C1 0.034(5) 0.023(4) 0.013(3) -0.001(3) 0.001(3) 0.000(3) C2 0.048(6) 0.031(4) 0.027(4) -0.001(3) 0.011(4) -0.004(4) C3 0.040(5) 0.025(4) 0.025(4) -0.002(3) 0.004(3) 0.000(3) C4 0.051(6) 0.025(4) 0.021(4) -0.001(3) 0.011(4) -0.006(4) C5 0.037(5) 0.032(4) 0.025(4) -0.003(3) 0.007(3) -0.011(4) C6 0.047(6) 0.025(4) 0.026(4) -0.004(3) 0.009(4) -0.001(4) C7 0.041(5) 0.026(4) 0.018(3) -0.001(3) 0.002(3) -0.007(3) C8 0.041(5) 0.027(4) 0.027(4) 0.001(3) -0.001(4) -0.008(4) C9 0.035(5) 0.029(4) 0.020(3) -0.007(3) 0.010(3) -0.005(3) C10 0.038(5) 0.031(4) 0.023(4) 0.000(3) 0.007(3) 0.001(4) C11 0.036(5) 0.026(4) 0.019(3) 0.000(3) 0.010(3) -0.008(3) C12 0.035(5) 0.028(4) 0.025(4) -0.007(3) 0.005(3) -0.002(3) C13 0.030(5) 0.031(4) 0.019(3) -0.001(3) 0.001(3) -0.006(3) C14 0.036(5) 0.039(5) 0.019(3) -0.001(3) 0.003(3) -0.005(4) C15 0.032(5) 0.032(4) 0.030(4) -0.011(3) 0.004(3) 0.001(3) C16 0.033(5) 0.028(4) 0.024(4) 0.002(3) -0.001(3) -0.004(3) N1 0.069(7) 0.043(5) 0.059(5) -0.001(4) -0.009(5) -0.023(5) C17 0.075(10) 0.088(11) 0.124(12) 0.019(9) -0.062(9) -0.020(8) C19 0.059(7) 0.050(6) 0.043(5) -0.006(4) -0.004(5) -0.006(5) C21 0.057(8) 0.112(11) 0.057(7) -0.029(7) 0.009(6) -0.024(7) C18 0.131(16) 0.055(9) 0.23(2) 0.032(11) -0.104(15) -0.045(10) C20 0.056(9) 0.120(12) 0.081(9) -0.040(9) 0.027(7) -0.036(8) C22 0.088(12) 0.195(18) 0.075(9) -0.056(11) 0.011(9) -0.064(12) N2 0.127(5) 0.212(6) 0.139(5) -0.032(5) 0.005(5) -0.018(5) C23 0.128(6) 0.216(6) 0.141(6) -0.034(6) 0.004(5) -0.016(5) C25 0.128(6) 0.215(6) 0.140(6) -0.034(6) 0.005(5) -0.016(5) C27 0.129(6) 0.216(6) 0.141(6) -0.034(6) 0.005(5) -0.015(5) C24 0.126(6) 0.214(6) 0.136(6) -0.035(6) 0.005(5) -0.016(5) C26 0.128(6) 0.215(6) 0.140(6) -0.033(6) 0.004(5) -0.016(5) C28 0.126(6) 0.215(6) 0.140(6) -0.034(6) 0.004(5) -0.017(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 1.763(6) . ? U1 O2 1.769(6) . ? U1 O12 2.334(6) . ? U1 O5 2.348(6) . ? U1 O9 2.358(5) 2_665 ? U1 O14 2.453(5) 2_566 ? U1 O15 2.453(6) 2_566 ? U2 O4 1.750(7) . ? U2 O3 1.768(7) . ? U2 O13 2.355(5) . ? U2 O16 2.356(5) 2_576 ? U2 O6 2.365(5) . ? U2 O7 2.457(5) 2_675 ? U2 O8 2.477(5) 2_675 ? S1 O10 1.434(5) . ? S1 O11 1.441(7) . ? S1 O9 1.492(7) . ? S1 C7 1.762(7) . ? S2 O18 1.441(7) . ? S2 O17 1.444(6) . ? S2 O16 1.478(6) . ? S2 C15 1.768(8) . ? O5 C1 1.217(8) . ? O6 C1 1.267(8) . ? O7 C2 1.262(9) . ? O7 U2 2.457(5) 2_675 ? O8 C2 1.278(9) . ? O8 U2 2.477(5) 2_675 ? O9 U1 2.358(5) 2_665 ? O12 C9 1.239(9) . ? O13 C9 1.251(9) . ? O14 C10 1.256(9) . ? O14 U1 2.453(5) 2_566 ? O15 C10 1.280(8) . ? O15 U1 2.453(6) 2_566 ? O16 U2 2.356(5) 2_576 ? C1 C3 1.520(9) . ? C2 C5 1.484(10) . ? C3 C8 1.365(10) . ? C3 C4 1.412(10) . ? C4 C5 1.418(10) . ? C4 H4 0.9300 . ? C5 C6 1.381(10) . ? C6 C7 1.399(10) . ? C6 H6 0.9300 . ? C7 C8 1.380(10) . ? C8 H8 0.9300 . ? C9 C11 1.508(9) . ? C10 C13 1.492(10) . ? C11 C12 1.376(10) . ? C11 C16 1.388(10) . ? C12 C13 1.391(9) . ? C12 H12 0.9300 . ? C13 C14 1.379(11) . ? C14 C15 1.386(11) . ? C14 H14 0.9300 . ? C15 C16 1.348(10) . ? C16 H16 0.9300 . ? N1 C21 1.462(12) . ? N1 C19 1.474(11) . ? N1 C17 1.523(13) . ? N1 H1 0.8160 . ? C17 C18 1.520(16) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C19 C20 1.461(13) . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C21 C22 1.498(9) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? N2 C27 1.459(12) . ? N2 C25 1.472(11) . ? N2 C23 1.522(13) . ? N2 H2 0.9588 . ? C23 C24 1.543(9) . ? C23 H23A 0.9700 . ? C23 H23B 0.9700 . ? C25 C26 1.532(10) . ? C25 H25A 0.9700 . ? C25 H25B 0.9700 . ? C27 C28 1.541(9) . ? C27 H27A 0.9700 . ? C27 H27B 0.9700 . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? C26 H26A 0.9599 . ? C26 H26B 0.9599 . ? C26 H26C 0.9600 . ? C28 H28A 0.9600 . ? C28 H28B 0.9600 . ? C28 H28C 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 O1 U1 O2 179.8(3) . . ? O1 U1 O12 89.6(3) . . ? O2 U1 O12 90.5(3) . . ? O1 U1 O5 86.9(3) . . ? O2 U1 O5 93.3(3) . . ? O12 U1 O5 80.45(19) . . ? O1 U1 O9 89.9(2) . 2_665 ? O2 U1 O9 90.1(3) . 2_665 ? O12 U1 O9 158.4(2) . 2_665 ? O5 U1 O9 78.0(2) . 2_665 ? O1 U1 O14 91.1(2) . 2_566 ? O2 U1 O14 88.7(2) . 2_566 ? O12 U1 O14 73.50(19) . 2_566 ? O5 U1 O14 153.9(2) . 2_566 ? O9 U1 O14 128.1(2) 2_665 2_566 ? O1 U1 O15 87.9(3) . 2_566 ? O2 U1 O15 91.9(3) . 2_566 ? O12 U1 O15 126.68(18) . 2_566 ? O5 U1 O15 152.32(18) . 2_566 ? O9 U1 O15 74.87(18) 2_665 2_566 ? O14 U1 O15 53.33(18) 2_566 2_566 ? O4 U2 O3 178.0(3) . . ? O4 U2 O13 91.1(3) . . ? O3 U2 O13 88.5(2) . . ? O4 U2 O16 89.5(2) . 2_576 ? O3 U2 O16 92.4(2) . 2_576 ? O13 U2 O16 77.19(18) . 2_576 ? O4 U2 O6 89.4(2) . . ? O3 U2 O6 88.5(2) . . ? O13 U2 O6 81.84(17) . . ? O16 U2 O6 158.98(18) 2_576 . ? O4 U2 O7 89.0(2) . 2_675 ? O3 U2 O7 90.6(2) . 2_675 ? O13 U2 O7 155.48(18) . 2_675 ? O16 U2 O7 127.32(18) 2_576 2_675 ? O6 U2 O7 73.65(18) . 2_675 ? O4 U2 O8 94.4(3) . 2_675 ? O3 U2 O8 87.0(3) . 2_675 ? O13 U2 O8 151.22(17) . 2_675 ? O16 U2 O8 74.63(17) 2_576 2_675 ? O6 U2 O8 126.39(17) . 2_675 ? O7 U2 O8 53.04(17) 2_675 2_675 ? O10 S1 O11 114.7(4) . . ? O10 S1 O9 111.9(4) . . ? O11 S1 O9 111.8(4) . . ? O10 S1 C7 106.7(3) . . ? O11 S1 C7 108.6(4) . . ? O9 S1 C7 102.2(4) . . ? O18 S2 O17 116.7(4) . . ? O18 S2 O16 111.4(4) . . ? O17 S2 O16 111.0(4) . . ? O18 S2 C15 107.8(4) . . ? O17 S2 C15 106.3(4) . . ? O16 S2 C15 102.5(4) . . ? C1 O5 U1 163.2(6) . . ? C1 O6 U2 135.4(5) . . ? C2 O7 U2 93.8(4) . 2_675 ? C2 O8 U2 92.5(5) . 2_675 ? S1 O9 U1 141.5(4) . 2_665 ? C9 O12 U1 148.9(5) . . ? C9 O13 U2 146.2(6) . . ? C10 O14 U1 93.3(4) . 2_566 ? C10 O15 U1 92.6(5) . 2_566 ? S2 O16 U2 136.5(4) . 2_576 ? O5 C1 O6 125.6(6) . . ? O5 C1 C3 117.6(6) . . ? O6 C1 C3 116.8(6) . . ? O7 C2 O8 120.3(7) . . ? O7 C2 C5 119.3(7) . . ? O8 C2 C5 120.1(7) . . ? C8 C3 C4 121.2(7) . . ? C8 C3 C1 120.7(6) . . ? C4 C3 C1 118.1(6) . . ? C3 C4 C5 117.8(7) . . ? C3 C4 H4 121.1 . . ? C5 C4 H4 121.1 . . ? C6 C5 C4 120.5(7) . . ? C6 C5 C2 120.8(7) . . ? C4 C5 C2 118.6(7) . . ? C5 C6 C7 119.7(7) . . ? C5 C6 H6 120.1 . . ? C7 C6 H6 120.1 . . ? C8 C7 C6 120.4(7) . . ? C8 C7 S1 120.9(5) . . ? C6 C7 S1 118.7(5) . . ? C3 C8 C7 120.4(7) . . ? C3 C8 H8 119.8 . . ? C7 C8 H8 119.8 . . ? O12 C9 O13 124.8(6) . . ? O12 C9 C11 117.2(6) . . ? O13 C9 C11 118.1(6) . . ? O14 C10 O15 120.5(7) . . ? O14 C10 C13 120.5(6) . . ? O15 C10 C13 118.9(7) . . ? C12 C11 C16 118.5(6) . . ? C12 C11 C9 120.2(7) . . ? C16 C11 C9 121.2(6) . . ? C11 C12 C13 121.1(7) . . ? C11 C12 H12 119.4 . . ? C13 C12 H12 119.4 . . ? C14 C13 C12 118.7(7) . . ? C14 C13 C10 120.2(6) . . ? C12 C13 C10 121.0(7) . . ? C13 C14 C15 120.2(7) . . ? C13 C14 H14 119.9 . . ? C15 C14 H14 119.9 . . ? C16 C15 C14 120.2(7) . . ? C16 C15 S2 121.4(6) . . ? C14 C15 S2 118.4(6) . . ? C15 C16 C11 121.2(7) . . ? C15 C16 H16 119.4 . . ? C11 C16 H16 119.4 . . ? C21 N1 C19 115.5(8) . . ? C21 N1 C17 115.1(8) . . ? C19 N1 C17 112.3(8) . . ? C21 N1 H1 97.9 . . ? C19 N1 H1 102.6 . . ? C17 N1 H1 111.9 . . ? C18 C17 N1 112.1(11) . . ? C18 C17 H17A 109.2 . . ? N1 C17 H17A 109.2 . . ? C18 C17 H17B 109.2 . . ? N1 C17 H17B 109.2 . . ? H17A C17 H17B 107.9 . . ? C20 C19 N1 118.6(10) . . ? C20 C19 H19A 107.7 . . ? N1 C19 H19A 107.7 . . ? C20 C19 H19B 107.7 . . ? N1 C19 H19B 107.7 . . ? H19A C19 H19B 107.1 . . ? N1 C21 C22 115.2(11) . . ? N1 C21 H21A 108.5 . . ? C22 C21 H21A 108.5 . . ? N1 C21 H21B 108.5 . . ? C22 C21 H21B 108.5 . . ? H21A C21 H21B 107.5 . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C19 C20 H20A 109.5 . . ? C19 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C19 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C27 N2 C25 115.9(8) . . ? C27 N2 C23 115.4(9) . . ? C25 N2 C23 112.5(8) . . ? C27 N2 H2 103.5 . . ? C25 N2 H2 103.2 . . ? C23 N2 H2 104.4 . . ? N2 C23 C24 111.5(14) . . ? N2 C23 H23A 109.3 . . ? C24 C23 H23A 109.3 . . ? N2 C23 H23B 109.3 . . ? C24 C23 H23B 109.3 . . ? H23A C23 H23B 108.0 . . ? N2 C25 C26 118.3(15) . . ? N2 C25 H25A 107.7 . . ? C26 C25 H25A 107.7 . . ? N2 C25 H25B 107.7 . . ? C26 C25 H25B 107.7 . . ? H25A C25 H25B 107.1 . . ? N2 C27 C28 120.0(13) . . ? N2 C27 H27A 107.3 . . ? C28 C27 H27A 107.3 . . ? N2 C27 H27B 107.3 . . ? C28 C27 H27B 107.3 . . ? H27A C27 H27B 106.9 . . ? C23 C24 H24A 109.5 . . ? C23 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C23 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C25 C26 H26A 109.5 . . ? C25 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C25 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C27 C28 H28A 109.5 . . ? C27 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C27 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 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 N1 H1 O10 0.82 2.02 2.825(9) 169.7 . N2 H2 O17 0.96 2.13 3.011(15) 152.5 . data_4 _database_code_depnum_ccdc_archive 'CCDC 914742' #TrackingRef 'web_deposit_cif_file_0_P.Thuery_1354890695.CIF.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H13 N2 O11.50 S U' _chemical_formula_weight 639.33 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' S S 0.1246 0.1234 '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/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 11.5202(6) _cell_length_b 14.4501(10) _cell_length_c 22.0213(10) _cell_angle_alpha 90.00 _cell_angle_beta 100.470(3) _cell_angle_gamma 90.00 _cell_volume 3604.8(4) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 107052 _cell_measurement_theta_min 2.74 _cell_measurement_theta_max 28.70 _exptl_crystal_description platelet _exptl_crystal_colour 'translucent light yellow' _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.356 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2392 _exptl_absorpt_coefficient_mu 9.186 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.295 _exptl_absorpt_correction_T_max 0.576 _exptl_absorpt_process_details 'SCALEPACK (Otwinowski & Minor, 1997)' _exptl_special_details 'crystal-to-detector distance 35 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 seven \w scans with 2\% steps (487 frames)' _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 107052 _diffrn_reflns_av_R_equivalents 0.0536 _diffrn_reflns_av_sigmaI/netI 0.0727 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 2.74 _diffrn_reflns_theta_max 28.70 _reflns_number_total 9266 _reflns_number_gt 6577 _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. Some of the solvent water molecules are disordered over positions too close to one another and they have been given partial occupancy parameters accordingly, so as to retain also acceptable displacement parameters. All non-hydrogen atoms were refined with anisotropic displacement parameters, with restraints for some solvent water molecules. The H atom bound to N1 was found on a Fourier-difference map, but not those of N3 and the water molecules; the H atom bound to N3 and those bound to C atoms 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^)+(0.0512P)^2^] 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 9266 _refine_ls_number_parameters 532 _refine_ls_number_restraints 24 _refine_ls_R_factor_all 0.0704 _refine_ls_R_factor_gt 0.0420 _refine_ls_wR_factor_ref 0.0989 _refine_ls_wR_factor_gt 0.0913 _refine_ls_goodness_of_fit_ref 0.969 _refine_ls_restrained_S_all 0.970 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 28.70 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 2.568 _refine_diff_density_min -1.382 _refine_diff_density_rms 0.233 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 0.55480(2) 0.220855(18) 0.026124(10) 0.02455(8) Uani 1 1 d . . . U2 U 0.91247(2) 0.256393(18) 0.229449(10) 0.02583(8) Uani 1 1 d . . . S1 S 0.18067(14) 0.15166(12) 0.21101(7) 0.0288(4) Uani 1 1 d . . . S2 S 1.28673(13) 0.32281(12) 0.05315(7) 0.0285(4) Uani 1 1 d . . . O1 O 0.5279(4) 0.1001(3) 0.02123(18) 0.0330(11) Uani 1 1 d . . . O2 O 0.5812(4) 0.3398(3) 0.03122(19) 0.0349(11) Uani 1 1 d . . . O3 O 0.8915(4) 0.1376(4) 0.23435(19) 0.0383(12) Uani 1 1 d . . . O4 O 0.9290(4) 0.3765(3) 0.22536(18) 0.0334(11) Uani 1 1 d . . . O5 O 0.5877(4) 0.2044(4) 0.1345(2) 0.0384(12) Uani 1 1 d . . . O6 O 0.7093(4) 0.2739(3) 0.21039(19) 0.0329(11) Uani 1 1 d . . . O7 O 0.6037(4) 0.2744(3) 0.4215(2) 0.0324(11) Uani 1 1 d . . . O8 O 0.4166(4) 0.2604(3) 0.4285(2) 0.0317(11) Uani 1 1 d . . . O9 O 0.1070(4) 0.2366(3) 0.20802(19) 0.0283(10) Uani 1 1 d . . . O10 O 0.1506(4) 0.0859(3) 0.25460(19) 0.0356(11) Uani 1 1 d . . . O11 O 0.1828(4) 0.1149(3) 0.15011(18) 0.0363(12) Uani 1 1 d . . . O12 O 0.7562(4) 0.1927(3) 0.04210(17) 0.0292(10) Uani 1 1 d . . . O13 O 0.8791(4) 0.2463(4) 0.1227(2) 0.0437(14) Uani 1 1 d . . . O14 O 0.8651(4) 0.2238(3) -0.16665(19) 0.0315(11) Uani 1 1 d . . . O15 O 1.0509(4) 0.2465(3) -0.1726(2) 0.0312(11) Uani 1 1 d . . . O16 O 1.3634(4) 0.2403(3) 0.0496(2) 0.0306(11) Uani 1 1 d . . . O17 O 1.2823(4) 0.3455(4) 0.11571(17) 0.0368(12) Uani 1 1 d . . . O18 O 1.3172(4) 0.3973(3) 0.01531(19) 0.0363(11) Uani 1 1 d . . . O19 O 0.2856(7) -0.0577(5) 0.1472(3) 0.098(2) Uani 1 1 d . . . O20 O 0.5095(7) -0.0255(5) 0.1367(3) 0.097(2) Uani 1 1 d . . . O21 O 1.2300(9) 0.4371(6) 0.2248(4) 0.096(3) Uani 0.75 1 d P . . O22 O 0.9537(16) 0.4890(13) -0.0287(8) 0.036(4) Uani 0.25 1 d PU . . O23 O 0.8242(16) 0.4634(13) 0.0774(9) 0.034(4) Uani 0.34 1 d P . . O24 O 0.8510(14) 0.4646(11) 0.0417(7) 0.042(4) Uani 0.33 1 d PU . . O25 O 0.8675(16) 0.4918(12) 0.0968(8) 0.028(4) Uani 0.33 1 d P . . O26 O 0.9907(8) 0.5370(7) 0.1435(4) 0.066(3) Uani 0.67 1 d PU . . O27 O 1.0650(14) 0.5319(12) 0.0992(7) 0.052(4) Uani 0.33 1 d PU . . N1 N 0.6457(7) 0.4982(6) 0.1291(5) 0.078(3) Uani 1 1 d . . . H1 H 0.7070 0.4809 0.1092 0.093 Uiso 1 1 d R . . N2 N 0.4387(7) 0.5141(5) 0.1714(3) 0.065(2) Uani 1 1 d . . . N3 N 0.7352(9) -0.0445(8) 0.0992(6) 0.113(4) Uani 1 1 d . . . H3 H 0.6643 -0.0530 0.1052 0.136 Uiso 1 1 calc R . . N4 N 0.9557(7) -0.0103(6) 0.0760(5) 0.079(3) Uani 1 1 d . . . C1 C 0.6122(5) 0.2344(5) 0.1880(3) 0.0256(14) Uani 1 1 d . . . C2 C 0.4974(6) 0.2621(4) 0.3958(3) 0.0267(15) Uani 1 1 d . . . C3 C 0.5225(6) 0.2263(5) 0.2292(3) 0.0256(14) Uani 1 1 d . . . C4 C 0.5506(6) 0.2486(4) 0.2912(3) 0.0267(14) Uani 1 1 d . . . H4 H 0.6267 0.2680 0.3079 0.032 Uiso 1 1 calc R . . C5 C 0.4666(6) 0.2424(4) 0.3286(3) 0.0248(14) Uani 1 1 d . . . C6 C 0.3522(5) 0.2149(4) 0.3038(3) 0.0258(14) Uani 1 1 d . . . H6 H 0.2946 0.2123 0.3284 0.031 Uiso 1 1 calc R . . C7 C 0.3253(5) 0.1911(5) 0.2411(3) 0.0275(14) Uani 1 1 d . . . C8 C 0.4091(5) 0.1966(4) 0.2038(3) 0.0245(14) Uani 1 1 d . . . H8 H 0.3902 0.1807 0.1622 0.029 Uiso 1 1 calc R . . C9 C 0.8544(6) 0.2267(5) 0.0668(3) 0.0274(15) Uani 1 1 d . . . C10 C 0.9717(6) 0.2380(5) -0.1404(3) 0.0272(15) Uani 1 1 d . . . C11 C 0.9466(6) 0.2416(5) 0.0273(3) 0.0262(14) Uani 1 1 d . . . C12 C 0.9174(6) 0.2306(5) -0.0358(3) 0.0262(14) Uani 1 1 d . . . H12 H 0.8413 0.2128 -0.0539 0.031 Uiso 1 1 calc R . . C13 C 1.0016(6) 0.2463(5) -0.0723(3) 0.0270(15) Uani 1 1 d . . . C14 C 1.1166(6) 0.2732(5) -0.0445(3) 0.0282(15) Uani 1 1 d . . . H14 H 1.1737 0.2839 -0.0686 0.034 Uiso 1 1 calc R . . C15 C 1.1437(5) 0.2835(5) 0.0188(3) 0.0266(14) Uani 1 1 d . . . C16 C 1.0609(6) 0.2691(4) 0.0550(3) 0.0255(14) Uani 1 1 d . . . H16 H 1.0800 0.2775 0.0975 0.031 Uiso 1 1 calc R . . C17 C 0.6399(9) 0.4743(6) 0.1880(5) 0.066(3) Uani 1 1 d . . . H17 H 0.7055 0.4528 0.2154 0.079 Uiso 1 1 calc R . . C18 C 0.5325(10) 0.4834(7) 0.2045(4) 0.070(3) Uani 1 1 d . . . H18 H 0.5272 0.4652 0.2444 0.084 Uiso 1 1 calc R . . C19 C 0.4456(8) 0.5357(6) 0.1151(4) 0.057(2) Uani 1 1 d . . . H19 H 0.3770 0.5566 0.0898 0.068 Uiso 1 1 calc R . . C20 C 0.5435(10) 0.5305(6) 0.0900(4) 0.063(3) Uani 1 1 d . . . H20 H 0.5436 0.5472 0.0492 0.076 Uiso 1 1 calc R . . C21 C 0.7580(9) -0.0427(7) 0.0414(6) 0.079(3) Uani 1 1 d . . . H21 H 0.6972 -0.0542 0.0083 0.095 Uiso 1 1 calc R . . C22 C 0.8656(8) -0.0247(6) 0.0309(4) 0.061(2) Uani 1 1 d . . . H22 H 0.8778 -0.0223 -0.0097 0.073 Uiso 1 1 calc R . . C23 C 0.9305(9) -0.0153(7) 0.1349(6) 0.074(3) Uani 1 1 d . . . H23 H 0.9922 -0.0058 0.1679 0.089 Uiso 1 1 calc R . . C24 C 0.8245(8) -0.0328(7) 0.1478(5) 0.064(3) Uani 1 1 d . . . H24 H 0.8122 -0.0368 0.1883 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 0.02215(13) 0.03227(16) 0.01970(12) -0.00115(9) 0.00506(9) -0.00155(10) U2 0.02236(13) 0.03632(17) 0.01933(12) -0.00150(9) 0.00517(9) -0.00232(10) S1 0.0247(8) 0.0342(10) 0.0281(8) -0.0013(7) 0.0060(6) -0.0021(7) S2 0.0209(8) 0.0379(11) 0.0267(8) -0.0023(7) 0.0045(6) -0.0009(7) O1 0.034(3) 0.033(3) 0.032(2) 0.000(2) 0.006(2) -0.002(2) O2 0.035(3) 0.037(3) 0.037(2) 0.001(2) 0.016(2) 0.001(2) O3 0.033(3) 0.046(3) 0.036(3) -0.003(2) 0.008(2) 0.001(2) O4 0.035(3) 0.034(3) 0.033(2) 0.001(2) 0.009(2) 0.001(2) O5 0.025(3) 0.063(4) 0.029(3) -0.001(2) 0.010(2) -0.002(2) O6 0.028(3) 0.046(3) 0.027(2) -0.007(2) 0.009(2) -0.007(2) O7 0.022(2) 0.049(3) 0.025(2) -0.001(2) 0.0033(19) -0.006(2) O8 0.026(3) 0.048(3) 0.023(2) -0.0041(19) 0.010(2) -0.004(2) O9 0.021(2) 0.038(3) 0.027(2) 0.0010(19) 0.0071(19) 0.0001(19) O10 0.031(3) 0.036(3) 0.041(3) 0.007(2) 0.010(2) -0.005(2) O11 0.031(3) 0.047(3) 0.030(2) -0.010(2) 0.0017(19) -0.005(2) O12 0.025(2) 0.041(3) 0.023(2) 0.0017(19) 0.0066(18) -0.007(2) O13 0.021(3) 0.086(4) 0.025(3) -0.013(2) 0.007(2) -0.010(2) O14 0.019(2) 0.054(3) 0.021(2) -0.003(2) 0.0041(19) -0.004(2) O15 0.025(3) 0.049(3) 0.021(2) -0.0028(19) 0.0097(19) -0.001(2) O16 0.028(3) 0.036(3) 0.027(2) 0.0020(19) 0.003(2) -0.001(2) O17 0.036(3) 0.050(4) 0.024(2) -0.007(2) 0.006(2) -0.004(2) O18 0.030(3) 0.040(3) 0.039(3) 0.006(2) 0.005(2) -0.005(2) O19 0.096(6) 0.066(6) 0.132(6) -0.027(5) 0.021(5) 0.014(4) O20 0.128(7) 0.083(6) 0.091(5) 0.004(4) 0.056(5) -0.010(5) O21 0.119(8) 0.057(7) 0.130(7) -0.053(6) 0.073(6) -0.018(6) O22 0.035(5) 0.033(5) 0.043(5) -0.004(3) 0.012(3) 0.005(3) O23 0.036(11) 0.036(12) 0.030(11) 0.015(8) 0.004(8) -0.016(8) O24 0.041(5) 0.037(5) 0.044(5) 0.001(3) 0.003(3) 0.003(3) O25 0.037(11) 0.022(10) 0.029(10) 0.009(7) 0.014(8) 0.000(7) O26 0.070(3) 0.065(4) 0.067(3) 0.011(3) 0.021(3) 0.007(3) O27 0.050(5) 0.051(5) 0.055(5) 0.002(3) 0.008(3) 0.000(3) N1 0.067(6) 0.040(5) 0.134(8) -0.029(5) 0.041(6) -0.011(4) N2 0.083(6) 0.048(5) 0.059(5) -0.006(4) -0.002(4) -0.014(4) N3 0.087(8) 0.096(9) 0.171(10) -0.041(8) 0.064(8) -0.017(6) N4 0.052(5) 0.070(6) 0.108(7) 0.002(5) -0.002(5) 0.007(4) C1 0.018(3) 0.038(4) 0.021(3) 0.002(3) 0.004(3) 0.002(3) C2 0.032(4) 0.029(4) 0.019(3) -0.002(2) 0.005(3) 0.002(3) C3 0.025(3) 0.036(4) 0.017(3) 0.002(3) 0.005(3) 0.002(3) C4 0.018(3) 0.036(4) 0.025(3) 0.002(3) 0.002(3) 0.003(3) C5 0.027(3) 0.031(4) 0.017(3) 0.003(2) 0.005(3) -0.003(3) C6 0.020(3) 0.032(4) 0.026(3) 0.001(3) 0.006(3) 0.001(3) C7 0.025(3) 0.030(4) 0.026(3) 0.002(3) 0.000(3) -0.002(3) C8 0.023(3) 0.029(4) 0.024(3) 0.004(3) 0.010(3) 0.007(3) C9 0.024(3) 0.038(4) 0.021(3) 0.005(3) 0.006(3) 0.005(3) C10 0.031(4) 0.039(4) 0.013(3) 0.003(3) 0.008(3) 0.000(3) C11 0.019(3) 0.038(4) 0.022(3) 0.001(3) 0.003(3) 0.002(3) C12 0.020(3) 0.032(4) 0.028(3) -0.002(3) 0.007(3) 0.002(3) C13 0.022(3) 0.037(4) 0.023(3) 0.006(3) 0.007(3) 0.004(3) C14 0.027(4) 0.033(4) 0.025(3) 0.000(3) 0.007(3) 0.003(3) C15 0.022(3) 0.029(4) 0.029(3) -0.002(3) 0.006(3) -0.004(3) C16 0.027(3) 0.032(4) 0.018(3) 0.003(2) 0.004(3) 0.005(3) C17 0.063(7) 0.039(6) 0.080(7) 0.002(5) -0.027(6) -0.004(5) C18 0.089(8) 0.051(6) 0.060(6) 0.002(5) -0.014(6) -0.015(6) C19 0.061(6) 0.046(6) 0.057(5) -0.012(4) -0.007(5) -0.001(4) C20 0.098(8) 0.037(6) 0.056(5) -0.011(4) 0.014(5) 0.008(5) C21 0.060(7) 0.049(7) 0.121(9) -0.026(6) -0.004(6) -0.011(5) C22 0.057(6) 0.046(6) 0.079(6) 0.008(5) 0.010(5) 0.005(4) C23 0.064(7) 0.043(6) 0.115(9) -0.015(6) 0.018(6) -0.006(5) C24 0.049(6) 0.055(6) 0.089(7) -0.027(5) 0.015(5) -0.017(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag U1 O2 1.746(5) . ? U1 O1 1.773(5) . ? U1 O12 2.319(4) . ? U1 O5 2.360(4) . ? U1 O16 2.371(5) 1_455 ? U1 O8 2.446(4) 4_565 ? U1 O7 2.469(4) 4_565 ? U2 O3 1.739(5) . ? U2 O4 1.751(5) . ? U2 O6 2.315(5) . ? U2 O13 2.317(5) . ? U2 O9 2.390(4) 1_655 ? U2 O15 2.439(4) 4_566 ? U2 O14 2.463(4) 4_566 ? S1 O10 1.438(5) . ? S1 O11 1.447(4) . ? S1 O9 1.487(5) . ? S1 C7 1.772(6) . ? S2 O17 1.426(4) . ? S2 O18 1.443(5) . ? S2 O16 1.494(5) . ? S2 C15 1.777(6) . ? O5 C1 1.238(7) . ? O6 C1 1.273(7) . ? O7 C2 1.265(8) . ? O7 U1 2.469(4) 4_566 ? O8 C2 1.277(8) . ? O8 U1 2.446(4) 4_566 ? O9 U2 2.390(4) 1_455 ? O12 C9 1.262(7) . ? O13 C9 1.245(8) . ? O14 C10 1.275(8) . ? O14 U2 2.463(4) 4_565 ? O15 C10 1.258(8) . ? O15 U2 2.439(4) 4_565 ? O16 U1 2.371(5) 1_655 ? N1 C17 1.355(12) . ? N1 C20 1.406(11) . ? N1 H1 0.9304 . ? N2 C18 1.269(11) . ? N2 C19 1.295(10) . ? N3 C21 1.345(13) . ? N3 C24 1.354(13) . ? N3 H3 0.8600 . ? N4 C22 1.316(11) . ? N4 C23 1.383(12) . ? C1 C3 1.499(8) . ? C2 C5 1.485(8) . ? C2 U1 2.836(6) 4_566 ? C3 C4 1.382(8) . ? C3 C8 1.392(8) . ? C4 C5 1.383(9) . ? C4 H4 0.9300 . ? C5 C6 1.389(9) . ? C6 C7 1.403(8) . ? C6 H6 0.9300 . ? C7 C8 1.379(8) . ? C8 H8 0.9300 . ? C9 C11 1.505(9) . ? C10 C13 1.482(9) . ? C10 U2 2.824(6) 4_565 ? C11 C12 1.379(8) . ? C11 C16 1.404(9) . ? C12 C13 1.385(9) . ? C12 H12 0.9300 . ? C13 C14 1.409(9) . ? C14 C15 1.379(8) . ? C14 H14 0.9300 . ? C15 C16 1.366(9) . ? C16 H16 0.9300 . ? C17 C18 1.358(14) . ? C17 H17 0.9300 . ? C18 H18 0.9300 . ? C19 C20 1.345(12) . ? C19 H19 0.9300 . ? C20 H20 0.9300 . ? C21 C22 1.328(13) . ? C21 H21 0.9300 . ? C22 H22 0.9300 . ? C23 C24 1.327(12) . ? C23 H23 0.9300 . ? C24 H24 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 O2 U1 O1 179.8(2) . . ? O2 U1 O12 90.30(18) . . ? O1 U1 O12 89.73(18) . . ? O2 U1 O5 92.31(19) . . ? O1 U1 O5 87.50(18) . . ? O12 U1 O5 81.76(14) . . ? O2 U1 O16 91.56(18) . 1_455 ? O1 U1 O16 88.34(18) . 1_455 ? O12 U1 O16 158.79(14) . 1_455 ? O5 U1 O16 77.06(15) . 1_455 ? O2 U1 O8 91.44(18) . 4_565 ? O1 U1 O8 88.70(17) . 4_565 ? O12 U1 O8 128.80(14) . 4_565 ? O5 U1 O8 149.19(15) . 4_565 ? O16 U1 O8 72.28(15) 1_455 4_565 ? O2 U1 O7 88.04(17) . 4_565 ? O1 U1 O7 92.16(17) . 4_565 ? O12 U1 O7 75.82(14) . 4_565 ? O5 U1 O7 157.58(15) . 4_565 ? O16 U1 O7 125.36(14) 1_455 4_565 ? O8 U1 O7 53.12(14) 4_565 4_565 ? O3 U2 O4 178.1(2) . . ? O3 U2 O6 88.39(19) . . ? O4 U2 O6 89.91(19) . . ? O3 U2 O13 90.08(19) . . ? O4 U2 O13 90.57(19) . . ? O6 U2 O13 81.19(16) . . ? O3 U2 O9 92.30(19) . 1_655 ? O4 U2 O9 89.62(18) . 1_655 ? O6 U2 O9 158.52(15) . 1_655 ? O13 U2 O9 77.34(16) . 1_655 ? O3 U2 O15 90.23(17) . 4_566 ? O4 U2 O15 90.15(17) . 4_566 ? O6 U2 O15 129.71(15) . 4_566 ? O13 U2 O15 149.09(16) . 4_566 ? O9 U2 O15 71.76(14) 1_655 4_566 ? O3 U2 O14 90.03(18) . 4_566 ? O4 U2 O14 88.68(18) . 4_566 ? O6 U2 O14 76.62(14) . 4_566 ? O13 U2 O14 157.80(16) . 4_566 ? O9 U2 O14 124.83(14) 1_655 4_566 ? O15 U2 O14 53.11(14) 4_566 4_566 ? O10 S1 O11 115.0(3) . . ? O10 S1 O9 111.7(3) . . ? O11 S1 O9 111.6(3) . . ? O10 S1 C7 106.7(3) . . ? O11 S1 C7 106.9(3) . . ? O9 S1 C7 104.0(3) . . ? O17 S2 O18 116.2(3) . . ? O17 S2 O16 111.0(3) . . ? O18 S2 O16 110.9(3) . . ? O17 S2 C15 107.0(3) . . ? O18 S2 C15 107.3(3) . . ? O16 S2 C15 103.5(3) . . ? C1 O5 U1 153.3(5) . . ? C1 O6 U2 144.1(4) . . ? C2 O7 U1 93.2(4) . 4_566 ? C2 O8 U1 93.9(4) . 4_566 ? S1 O9 U2 129.6(3) . 1_455 ? C9 O12 U1 142.2(4) . . ? C9 O13 U2 169.8(5) . . ? C10 O14 U2 92.6(3) . 4_565 ? C10 O15 U2 94.1(4) . 4_565 ? S2 O16 U1 133.5(3) . 1_655 ? C17 N1 C20 119.3(9) . . ? C17 N1 H1 123.7 . . ? C20 N1 H1 115.1 . . ? C18 N2 C19 116.2(10) . . ? C21 N3 C24 119.7(10) . . ? C21 N3 H3 120.2 . . ? C24 N3 H3 120.2 . . ? C22 N4 C23 115.3(9) . . ? O5 C1 O6 123.9(6) . . ? O5 C1 C3 119.0(6) . . ? O6 C1 C3 117.0(5) . . ? O7 C2 O8 119.7(6) . . ? O7 C2 C5 120.6(6) . . ? O8 C2 C5 119.5(6) . . ? C4 C3 C8 120.3(6) . . ? C4 C3 C1 121.1(6) . . ? C8 C3 C1 118.6(5) . . ? C3 C4 C5 120.6(6) . . ? C3 C4 H4 119.7 . . ? C5 C4 H4 119.7 . . ? C4 C5 C6 120.0(6) . . ? C4 C5 C2 121.0(6) . . ? C6 C5 C2 118.9(6) . . ? C5 C6 C7 118.7(6) . . ? C5 C6 H6 120.6 . . ? C7 C6 H6 120.6 . . ? C8 C7 C6 121.3(6) . . ? C8 C7 S1 120.5(4) . . ? C6 C7 S1 118.1(5) . . ? C7 C8 C3 119.0(5) . . ? C7 C8 H8 120.5 . . ? C3 C8 H8 120.5 . . ? O13 C9 O12 122.7(6) . . ? O13 C9 C11 118.7(6) . . ? O12 C9 C11 118.5(5) . . ? O15 C10 O14 119.8(5) . . ? O15 C10 C13 120.2(6) . . ? O14 C10 C13 120.0(6) . . ? C12 C11 C16 120.5(6) . . ? C12 C11 C9 119.9(6) . . ? C16 C11 C9 119.6(5) . . ? C11 C12 C13 119.8(6) . . ? C11 C12 H12 120.1 . . ? C13 C12 H12 120.1 . . ? C12 C13 C14 119.8(6) . . ? C12 C13 C10 121.0(6) . . ? C14 C13 C10 119.3(6) . . ? C15 C14 C13 119.4(6) . . ? C15 C14 H14 120.3 . . ? C13 C14 H14 120.3 . . ? C16 C15 C14 121.3(6) . . ? C16 C15 S2 119.4(5) . . ? C14 C15 S2 119.1(5) . . ? C15 C16 C11 119.3(5) . . ? C15 C16 H16 120.4 . . ? C11 C16 H16 120.4 . . ? N1 C17 C18 115.9(8) . . ? N1 C17 H17 122.0 . . ? C18 C17 H17 122.0 . . ? N2 C18 C17 127.0(10) . . ? N2 C18 H18 116.5 . . ? C17 C18 H18 116.5 . . ? N2 C19 C20 125.6(9) . . ? N2 C19 H19 117.2 . . ? C20 C19 H19 117.2 . . ? C19 C20 N1 116.0(8) . . ? C19 C20 H20 122.0 . . ? N1 C20 H20 122.0 . . ? C22 C21 N3 121.1(10) . . ? C22 C21 H21 119.4 . . ? N3 C21 H21 119.4 . . ? N4 C22 C21 122.2(10) . . ? N4 C22 H22 118.9 . . ? C21 C22 H22 118.9 . . ? C24 C23 N4 124.8(10) . . ? C24 C23 H23 117.6 . . ? N4 C23 H23 117.6 . . ? C23 C24 N3 116.8(11) . . ? C23 C24 H24 121.6 . . ? N3 C24 H24 121.6 . . ? 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 O23 0.93 1.65 2.57(2) 172.3 . N1 H1 O24 0.93 2.43 3.345(19) 167.0 . N1 H1 O25 0.93 1.92 2.775(19) 151.2 . N3 H3 O20 0.86 2.07 2.881(12) 157.9 . data_5 _database_code_depnum_ccdc_archive 'CCDC 914743' #TrackingRef 'web_deposit_cif_file_0_P.Thuery_1354890695.CIF.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H32 N2 O24 S2 U2' _chemical_formula_weight 1248.68 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' S S 0.1246 0.1234 '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/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 11.4801(5) _cell_length_b 21.0566(14) _cell_length_c 14.7227(10) _cell_angle_alpha 90.00 _cell_angle_beta 110.471(4) _cell_angle_gamma 90.00 _cell_volume 3334.2(4) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 117844 _cell_measurement_theta_min 2.13 _cell_measurement_theta_max 28.70 _exptl_crystal_description parallelepiped _exptl_crystal_colour 'translucent light yellow' _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.488 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2344 _exptl_absorpt_coefficient_mu 9.928 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.190 _exptl_absorpt_correction_T_max 0.275 _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 six \w scans with 2\% steps (473 frames)' _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 117844 _diffrn_reflns_av_R_equivalents 0.0404 _diffrn_reflns_av_sigmaI/netI 0.0541 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -28 _diffrn_reflns_limit_k_max 28 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.13 _diffrn_reflns_theta_max 28.70 _reflns_number_total 8612 _reflns_number_gt 6355 _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, with restraints on bond lengths and/or displacement parameters for some atoms, particularly in the H~2~DABCO cation. The H atoms bound to O and N atoms were found on a Fourier-difference map, except for those of one water solvent molecule (O24), 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^)+(0.0633P)^2^+4.4106P] 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 8612 _refine_ls_number_parameters 469 _refine_ls_number_restraints 39 _refine_ls_R_factor_all 0.0690 _refine_ls_R_factor_gt 0.0448 _refine_ls_wR_factor_ref 0.1170 _refine_ls_wR_factor_gt 0.1080 _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_restrained_S_all 1.062 _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 28.70 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 2.804 _refine_diff_density_min -2.048 _refine_diff_density_rms 0.208 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 0.10649(2) 0.471199(12) 0.87469(2) 0.02959(9) Uani 1 1 d . . . U2 U 0.39099(2) 0.245483(12) 0.95595(2) 0.02871(9) Uani 1 1 d . . . S1 S 0.15639(17) 0.17825(9) 1.05570(14) 0.0328(4) Uani 1 1 d . . . S2 S -0.38692(17) 0.32739(10) 0.67792(14) 0.0361(4) Uani 1 1 d . . . O1 O -0.0569(4) 0.4714(2) 0.8182(4) 0.0338(12) Uani 1 1 d . . . O2 O 0.2679(4) 0.4660(2) 0.9371(4) 0.0331(12) Uani 1 1 d . . . O3 O 0.3798(5) 0.1676(3) 0.9112(4) 0.0412(13) Uani 1 1 d . . . O4 O 0.4001(5) 0.3229(2) 1.0030(4) 0.0374(12) Uani 1 1 d . . . O5 O 0.0742(5) 0.4233(2) 1.0082(4) 0.0351(12) Uani 1 1 d . . . O6 O -0.1137(5) 0.4425(2) 1.0182(4) 0.0338(11) Uani 1 1 d . . . O7 O -0.4061(5) 0.2576(2) 0.9604(4) 0.0331(12) Uani 1 1 d . . . O8 O -0.3430(6) 0.1650(3) 0.9189(6) 0.0597(18) Uani 1 1 d . . . O9 O 0.2559(4) 0.2168(3) 1.0437(4) 0.0369(12) Uani 1 1 d . . . O10 O 0.1227(5) 0.1248(3) 0.9912(4) 0.0447(14) Uani 1 1 d . . . O11 O 0.1856(5) 0.1609(2) 1.1569(4) 0.0374(12) Uani 1 1 d . . . O12 O 0.1040(5) 0.3602(2) 0.8396(4) 0.0362(12) Uani 1 1 d . . . O13 O 0.1877(4) 0.2642(3) 0.8498(4) 0.0334(12) Uani 1 1 d . . . O14 O -0.0731(5) 0.0734(3) 0.7119(4) 0.0411(13) Uani 1 1 d . . . O15 O -0.2781(5) 0.0870(3) 0.6580(4) 0.0452(14) Uani 1 1 d . . . O16 O -0.4863(5) 0.2872(3) 0.6152(4) 0.0426(14) Uani 1 1 d . . . O17 O -0.4092(5) 0.3419(3) 0.7668(4) 0.0401(13) Uani 1 1 d . . . O18 O -0.3655(5) 0.3831(3) 0.6295(5) 0.0470(14) Uani 1 1 d . . . O19 O 0.1404(6) 0.4573(3) 0.7223(4) 0.0458(14) Uani 1 1 d . . . H19A H 0.1296 0.4224 0.6781 0.055 Uiso 1 1 d R . . H19B H 0.1280 0.4907 0.6740 0.055 Uiso 1 1 d R . . O20 O 0.3931(5) 0.2859(4) 0.8010(4) 0.0592(19) Uani 1 1 d . . . H20A H 0.3116 0.2923 0.7600 0.071 Uiso 1 1 d R . . H20B H 0.4442 0.3090 0.7917 0.071 Uiso 1 1 d R . . O21 O 0.1674(6) 0.0650(3) 0.8373(6) 0.070(2) Uani 1 1 d . . . H21A H 0.1796 0.0916 0.8820 0.084 Uiso 1 1 d R . . H21B H 0.0849 0.0525 0.8102 0.084 Uiso 1 1 d R . . O22 O -0.4214(9) 0.0815(5) 0.4634(7) 0.113(3) Uani 1 1 d . . . H22A H -0.4693 0.1080 0.4868 0.136 Uiso 1 1 d R . . H22B H -0.3914 0.0543 0.5086 0.136 Uiso 1 1 d R . . O23 O -0.2159(8) 0.4557(4) 0.5448(6) 0.089(3) Uani 1 1 d . . . H23A H -0.2610 0.4285 0.5666 0.107 Uiso 1 1 d R . . H23B H -0.1697 0.4746 0.6032 0.107 Uiso 1 1 d R . . O24 O 0.0964(6) 0.5444(3) 0.5855(5) 0.0576(17) Uani 1 1 d . . . N1 N -0.4997(11) 0.0731(6) 0.8182(9) 0.107(4) Uani 1 1 d U . . H1 H -0.4794 0.1026 0.8568 0.129 Uiso 1 1 d R . . N2 N -0.5672(8) 0.0009(4) 0.6685(7) 0.072(3) Uani 1 1 d . . . H2 H -0.5827 -0.0306 0.6303 0.087 Uiso 1 1 d R . . C1 C -0.0304(7) 0.4054(3) 1.0121(5) 0.0316(16) Uani 1 1 d . . . C2 C -0.3237(6) 0.2193(4) 0.9473(5) 0.0328(16) Uani 1 1 d D . . C3 C -0.0542(6) 0.3361(3) 1.0076(5) 0.0276(14) Uani 1 1 d . . . C4 C -0.1735(7) 0.3117(3) 0.9846(5) 0.0313(16) Uani 1 1 d . . . H4 H -0.2406 0.3392 0.9729 0.038 Uiso 1 1 calc R . . C5 C -0.1935(6) 0.2461(3) 0.9787(5) 0.0308(16) Uani 1 1 d D . . C6 C -0.0936(7) 0.2049(3) 0.9977(6) 0.0322(16) Uani 1 1 d . . . H6 H -0.1067 0.1612 0.9924 0.039 Uiso 1 1 calc R . . C7 C 0.0275(7) 0.2296(4) 1.0251(5) 0.0304(15) Uani 1 1 d . . . C8 C 0.0465(7) 0.2949(4) 1.0286(5) 0.0321(16) Uani 1 1 d . . . H8 H 0.1267 0.3110 1.0450 0.039 Uiso 1 1 calc R . . C9 C 0.0964(6) 0.3017(3) 0.8250(5) 0.0288(15) Uani 1 1 d . . . C10 C -0.1702(8) 0.1081(4) 0.6964(6) 0.0411(19) Uani 1 1 d . . . C11 C -0.0299(6) 0.2719(3) 0.7777(5) 0.0282(15) Uani 1 1 d . . . C12 C -0.0386(7) 0.2061(3) 0.7601(5) 0.0295(15) Uani 1 1 d . . . H12 H 0.0331 0.1815 0.7761 0.035 Uiso 1 1 calc R . . C13 C -0.1529(6) 0.1784(3) 0.7193(5) 0.0297(15) Uani 1 1 d . . . C14 C -0.2603(6) 0.2156(3) 0.6941(5) 0.0298(15) Uani 1 1 d . . . H14 H -0.3378 0.1965 0.6667 0.036 Uiso 1 1 calc R . . C15 C -0.2525(6) 0.2806(4) 0.7093(5) 0.0300(15) Uani 1 1 d . . . C16 C -0.1350(7) 0.3094(4) 0.7514(5) 0.0315(16) Uani 1 1 d . . . H16 H -0.1285 0.3530 0.7614 0.038 Uiso 1 1 calc R . . C17 C -0.6009(17) 0.0350(8) 0.8104(15) 0.127(6) Uani 1 1 d U . . H17A H -0.6645 0.0614 0.8207 0.153 Uiso 1 1 calc R . . H17B H -0.5754 0.0040 0.8623 0.153 Uiso 1 1 calc R . . C18 C -0.6597(10) -0.0006(6) 0.7141(10) 0.080(3) Uani 1 1 d U . . H18A H -0.6792 -0.0440 0.7255 0.096 Uiso 1 1 calc R . . H18B H -0.7354 0.0204 0.6737 0.096 Uiso 1 1 calc R . . C19 C -0.3998(13) 0.0307(6) 0.8177(9) 0.091(4) Uani 1 1 d D . . H19C H -0.3727 0.0053 0.8764 0.109 Uiso 1 1 calc R . . H19D H -0.3294 0.0552 0.8152 0.109 Uiso 1 1 calc R . . C20 C -0.4467(14) -0.0112(9) 0.7315(11) 0.122(5) Uani 1 1 d DU . . H20C H -0.3908 -0.0077 0.6953 0.147 Uiso 1 1 calc R . . H20D H -0.4431 -0.0548 0.7538 0.147 Uiso 1 1 calc R . . C21 C -0.5400(15) 0.1132(6) 0.7236(9) 0.102(4) Uani 1 1 d DU . . H21C H -0.6141 0.1375 0.7181 0.122 Uiso 1 1 calc R . . H21D H -0.4745 0.1428 0.7253 0.122 Uiso 1 1 calc R . . C22 C -0.5659(16) 0.0698(7) 0.6387(10) 0.113(5) Uani 1 1 d DU . . H22C H -0.5028 0.0756 0.6097 0.136 Uiso 1 1 calc R . . H22D H -0.6458 0.0805 0.5905 0.136 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 0.03042(15) 0.02592(15) 0.03536(16) -0.00039(11) 0.01517(12) -0.00066(10) U2 0.02613(15) 0.02712(15) 0.03423(16) -0.00082(11) 0.01224(11) -0.00057(10) S1 0.0302(9) 0.0327(10) 0.0373(10) -0.0008(8) 0.0140(8) 0.0003(7) S2 0.0320(9) 0.0396(11) 0.0370(10) -0.0022(8) 0.0124(8) 0.0011(8) O1 0.020(2) 0.034(3) 0.047(3) 0.000(2) 0.010(2) 0.000(2) O2 0.025(2) 0.034(3) 0.043(3) -0.002(2) 0.014(2) -0.001(2) O3 0.037(3) 0.036(3) 0.054(4) -0.009(3) 0.019(3) 0.001(2) O4 0.039(3) 0.025(3) 0.048(3) -0.005(2) 0.014(2) -0.002(2) O5 0.038(3) 0.030(3) 0.041(3) 0.003(2) 0.019(2) -0.006(2) O6 0.038(3) 0.032(3) 0.035(3) -0.003(2) 0.017(2) 0.004(2) O7 0.026(3) 0.039(3) 0.036(3) 0.000(2) 0.013(2) 0.000(2) O8 0.039(3) 0.051(4) 0.093(5) -0.025(4) 0.028(3) -0.010(3) O9 0.029(3) 0.041(3) 0.047(3) 0.005(3) 0.020(2) 0.000(2) O10 0.041(3) 0.034(3) 0.057(4) -0.016(3) 0.015(3) 0.002(2) O11 0.045(3) 0.035(3) 0.034(3) 0.006(2) 0.016(2) 0.000(2) O12 0.039(3) 0.028(3) 0.042(3) -0.004(2) 0.016(2) -0.007(2) O13 0.026(3) 0.037(3) 0.038(3) 0.001(2) 0.012(2) 0.002(2) O14 0.050(3) 0.028(3) 0.046(3) -0.002(2) 0.018(3) -0.001(2) O15 0.053(4) 0.037(3) 0.046(3) -0.008(3) 0.018(3) -0.014(3) O16 0.030(3) 0.060(4) 0.036(3) -0.014(3) 0.009(2) 0.001(3) O17 0.038(3) 0.043(3) 0.039(3) -0.005(3) 0.014(2) 0.005(2) O18 0.038(3) 0.048(4) 0.058(4) 0.012(3) 0.020(3) 0.007(3) O19 0.073(4) 0.032(3) 0.042(3) -0.002(3) 0.032(3) 0.000(3) O20 0.031(3) 0.103(6) 0.047(4) 0.032(4) 0.017(3) 0.006(3) O21 0.058(4) 0.062(5) 0.080(5) -0.017(4) 0.012(4) 0.003(3) O22 0.131(8) 0.105(8) 0.109(8) -0.007(6) 0.049(7) 0.033(7) O23 0.117(7) 0.095(6) 0.080(6) -0.023(5) 0.067(5) -0.043(5) O24 0.066(4) 0.054(4) 0.056(4) 0.011(3) 0.027(3) 0.007(3) N1 0.098(7) 0.115(8) 0.107(7) -0.031(6) 0.035(6) 0.002(6) N2 0.060(6) 0.056(6) 0.080(7) 0.009(5) -0.002(5) -0.010(4) C1 0.042(4) 0.030(4) 0.025(4) 0.002(3) 0.014(3) -0.005(3) C2 0.028(4) 0.038(4) 0.036(4) 0.007(3) 0.015(3) 0.000(3) C3 0.029(3) 0.030(4) 0.027(4) -0.003(3) 0.014(3) 0.000(3) C4 0.034(4) 0.028(4) 0.036(4) 0.000(3) 0.017(3) 0.004(3) C5 0.026(4) 0.040(4) 0.029(4) 0.001(3) 0.012(3) -0.002(3) C6 0.036(4) 0.025(4) 0.039(4) -0.002(3) 0.017(3) -0.002(3) C7 0.035(4) 0.030(4) 0.025(4) 0.001(3) 0.009(3) 0.002(3) C8 0.034(4) 0.037(4) 0.029(4) -0.003(3) 0.014(3) -0.007(3) C9 0.031(4) 0.030(4) 0.028(4) 0.001(3) 0.013(3) -0.001(3) C10 0.045(5) 0.029(4) 0.048(5) -0.004(4) 0.015(4) 0.001(4) C11 0.034(4) 0.026(4) 0.026(4) 0.000(3) 0.013(3) -0.001(3) C12 0.030(3) 0.028(4) 0.033(4) 0.000(3) 0.014(3) 0.006(3) C13 0.031(4) 0.024(4) 0.035(4) -0.005(3) 0.014(3) -0.005(3) C14 0.028(3) 0.032(4) 0.029(4) 0.001(3) 0.011(3) -0.003(3) C15 0.027(3) 0.036(4) 0.026(4) -0.005(3) 0.009(3) -0.001(3) C16 0.034(4) 0.030(4) 0.031(4) -0.007(3) 0.013(3) -0.006(3) C17 0.150(9) 0.104(9) 0.176(10) -0.021(7) 0.119(8) -0.045(7) C18 0.046(5) 0.087(7) 0.109(8) 0.028(6) 0.028(5) -0.010(5) C19 0.096(10) 0.094(10) 0.071(8) -0.008(7) 0.013(7) 0.044(8) C20 0.095(8) 0.156(10) 0.119(9) -0.032(8) 0.041(7) -0.001(7) C21 0.137(9) 0.061(6) 0.076(7) 0.017(6) -0.001(6) -0.006(6) C22 0.131(9) 0.111(9) 0.111(9) 0.017(7) 0.059(7) -0.004(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 1.761(5) . ? U1 O1 1.766(5) . ? U1 O5 2.351(5) . ? U1 O6 2.389(5) 3_567 ? U1 O12 2.392(5) . ? U1 O19 2.425(6) . ? U1 O14 2.461(5) 2_556 ? U2 O3 1.754(5) . ? U2 O4 1.760(5) . ? U2 O7 2.321(5) 1_655 ? U2 O13 2.343(5) . ? U2 O16 2.377(5) 4_666 ? U2 O9 2.417(5) . ? U2 O20 2.442(6) . ? S1 O10 1.435(6) . ? S1 O11 1.455(6) . ? S1 O9 1.461(5) . ? S1 C7 1.759(7) . ? S2 O18 1.439(6) . ? S2 O17 1.451(6) . ? S2 O16 1.460(6) . ? S2 C15 1.752(7) . ? O5 C1 1.279(8) . ? O6 C1 1.261(9) . ? O6 U1 2.389(5) 3_567 ? O7 C2 1.308(9) . ? O7 U2 2.321(5) 1_455 ? O8 C2 1.209(9) . ? O12 C9 1.247(9) . ? O13 C9 1.261(8) . ? O14 C10 1.285(9) . ? O14 U1 2.461(5) 2_546 ? O15 C10 1.249(10) . ? O16 U2 2.377(5) 4_465 ? O19 H19A 0.9602 . ? O19 H19B 0.9752 . ? O20 H20A 0.9291 . ? O20 H20B 0.8104 . ? O21 H21A 0.8382 . ? O21 H21B 0.9276 . ? O22 H22A 0.9286 . ? O22 H22B 0.8540 . ? O23 H23A 0.9023 . ? O23 H23B 0.9269 . ? N1 C17 1.383(17) . ? N1 C19 1.455(15) . ? N1 C21 1.554(17) . ? N1 H1 0.8185 . ? N2 C20 1.393(17) . ? N2 C18 1.441(14) . ? N2 C22 1.517(17) . ? N2 H2 0.8474 . ? C1 C3 1.482(10) . ? C2 C5 1.510(7) . ? C3 C4 1.390(10) . ? C3 C8 1.393(10) . ? C4 C5 1.398(10) . ? C4 H4 0.9300 . ? C5 C6 1.386(10) . ? C6 C7 1.405(10) . ? C6 H6 0.9300 . ? C7 C8 1.390(10) . ? C8 H8 0.9300 . ? C9 C11 1.508(10) . ? C10 C13 1.517(10) . ? C11 C16 1.379(10) . ? C11 C12 1.407(10) . ? C12 C13 1.368(10) . ? C12 H12 0.9300 . ? C13 C14 1.395(10) . ? C14 C15 1.385(10) . ? C14 H14 0.9300 . ? C15 C16 1.410(10) . ? C16 H16 0.9300 . ? C17 C18 1.54(2) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C19 C20 1.483(9) . ? C19 H19C 0.9700 . ? C19 H19D 0.9700 . ? C20 H20C 0.9700 . ? C20 H20D 0.9700 . ? C21 C22 1.493(9) . ? C21 H21C 0.9700 . ? C21 H21D 0.9700 . ? C22 H22C 0.9700 . ? C22 H22D 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 O2 U1 O1 175.3(2) . . ? O2 U1 O5 89.0(2) . . ? O1 U1 O5 86.7(2) . . ? O2 U1 O6 85.1(2) . 3_567 ? O1 U1 O6 95.5(2) . 3_567 ? O5 U1 O6 75.73(18) . 3_567 ? O2 U1 O12 89.0(2) . . ? O1 U1 O12 88.3(2) . . ? O5 U1 O12 76.59(18) . . ? O6 U1 O12 151.78(18) 3_567 . ? O2 U1 O19 89.7(2) . . ? O1 U1 O19 93.0(2) . . ? O5 U1 O19 147.64(19) . . ? O6 U1 O19 136.32(18) 3_567 . ? O12 U1 O19 71.06(18) . . ? O2 U1 O14 105.6(2) . 2_556 ? O1 U1 O14 78.9(2) . 2_556 ? O5 U1 O14 140.05(18) . 2_556 ? O6 U1 O14 68.92(18) 3_567 2_556 ? O12 U1 O14 138.95(19) . 2_556 ? O19 U1 O14 70.90(19) . 2_556 ? O3 U2 O4 178.5(3) . . ? O3 U2 O7 93.1(2) . 1_655 ? O4 U2 O7 88.1(2) . 1_655 ? O3 U2 O13 89.0(2) . . ? O4 U2 O13 90.9(2) . . ? O7 U2 O13 139.07(18) 1_655 . ? O3 U2 O16 92.3(2) . 4_666 ? O4 U2 O16 87.0(2) . 4_666 ? O7 U2 O16 76.20(18) 1_655 4_666 ? O13 U2 O16 144.61(18) . 4_666 ? O3 U2 O9 89.5(2) . . ? O4 U2 O9 89.0(2) . . ? O7 U2 O9 146.91(19) 1_655 . ? O13 U2 O9 73.91(18) . . ? O16 U2 O9 70.74(18) 4_666 . ? O3 U2 O20 89.9(3) . . ? O4 U2 O20 91.5(3) . . ? O7 U2 O20 69.54(19) 1_655 . ? O13 U2 O20 69.59(18) . . ? O16 U2 O20 145.74(18) 4_666 . ? O9 U2 O20 143.49(18) . . ? O10 S1 O11 113.2(4) . . ? O10 S1 O9 113.3(4) . . ? O11 S1 O9 110.7(3) . . ? O10 S1 C7 107.7(3) . . ? O11 S1 C7 106.7(3) . . ? O9 S1 C7 104.6(3) . . ? O18 S2 O17 112.9(4) . . ? O18 S2 O16 113.0(4) . . ? O17 S2 O16 110.3(3) . . ? O18 S2 C15 107.6(3) . . ? O17 S2 C15 107.3(3) . . ? O16 S2 C15 105.2(3) . . ? C1 O5 U1 126.1(5) . . ? C1 O6 U1 131.7(5) . 3_567 ? C2 O7 U2 134.3(4) . 1_455 ? S1 O9 U2 151.5(4) . . ? C9 O12 U1 175.1(5) . . ? C9 O13 U2 146.3(5) . . ? C10 O14 U1 115.9(5) . 2_546 ? S2 O16 U2 148.7(4) . 4_465 ? U1 O19 H19A 134.1 . . ? U1 O19 H19B 124.0 . . ? H19A O19 H19B 96.0 . . ? U2 O20 H20A 108.8 . . ? U2 O20 H20B 127.7 . . ? H20A O20 H20B 115.3 . . ? H21A O21 H21B 113.1 . . ? H22A O22 H22B 104.2 . . ? H23A O23 H23B 99.0 . . ? C17 N1 C19 106.6(14) . . ? C17 N1 C21 105.2(13) . . ? C19 N1 C21 108.6(12) . . ? C17 N1 H1 121.5 . . ? C19 N1 H1 115.8 . . ? C21 N1 H1 97.7 . . ? C20 N2 C18 114.1(11) . . ? C20 N2 C22 105.1(12) . . ? C18 N2 C22 103.8(10) . . ? C20 N2 H2 103.2 . . ? C18 N2 H2 105.9 . . ? C22 N2 H2 125.3 . . ? O6 C1 O5 124.6(7) . . ? O6 C1 C3 118.7(6) . . ? O5 C1 C3 116.7(6) . . ? O8 C2 O7 125.3(6) . . ? O8 C2 C5 120.0(7) . . ? O7 C2 C5 114.4(7) . . ? C4 C3 C8 119.6(7) . . ? C4 C3 C1 121.8(6) . . ? C8 C3 C1 118.6(6) . . ? C3 C4 C5 120.5(6) . . ? C3 C4 H4 119.7 . . ? C5 C4 H4 119.7 . . ? C6 C5 C4 119.9(6) . . ? C6 C5 C2 119.2(7) . . ? C4 C5 C2 120.8(6) . . ? C5 C6 C7 119.5(7) . . ? C5 C6 H6 120.2 . . ? C7 C6 H6 120.2 . . ? C8 C7 C6 120.2(7) . . ? C8 C7 S1 119.4(5) . . ? C6 C7 S1 120.4(6) . . ? C7 C8 C3 120.1(6) . . ? C7 C8 H8 120.0 . . ? C3 C8 H8 120.0 . . ? O12 C9 O13 124.6(6) . . ? O12 C9 C11 119.3(6) . . ? O13 C9 C11 116.1(6) . . ? O15 C10 O14 122.6(7) . . ? O15 C10 C13 118.7(7) . . ? O14 C10 C13 118.6(7) . . ? C16 C11 C12 120.9(6) . . ? C16 C11 C9 119.8(7) . . ? C12 C11 C9 119.4(6) . . ? C13 C12 C11 119.7(6) . . ? C13 C12 H12 120.2 . . ? C11 C12 H12 120.2 . . ? C12 C13 C14 120.1(6) . . ? C12 C13 C10 122.9(7) . . ? C14 C13 C10 116.9(6) . . ? C15 C14 C13 120.6(6) . . ? C15 C14 H14 119.7 . . ? C13 C14 H14 119.7 . . ? C14 C15 C16 119.6(6) . . ? C14 C15 S2 120.8(5) . . ? C16 C15 S2 119.5(6) . . ? C11 C16 C15 119.1(7) . . ? C11 C16 H16 120.5 . . ? C15 C16 H16 120.5 . . ? N1 C17 C18 116.3(13) . . ? N1 C17 H17A 108.2 . . ? C18 C17 H17A 108.2 . . ? N1 C17 H17B 108.2 . . ? C18 C17 H17B 108.2 . . ? H17A C17 H17B 107.4 . . ? N2 C18 C17 105.2(10) . . ? N2 C18 H18A 110.7 . . ? C17 C18 H18A 110.7 . . ? N2 C18 H18B 110.7 . . ? C17 C18 H18B 110.7 . . ? H18A C18 H18B 108.8 . . ? N1 C19 C20 108.5(12) . . ? N1 C19 H19C 110.0 . . ? C20 C19 H19C 110.0 . . ? N1 C19 H19D 110.0 . . ? C20 C19 H19D 110.0 . . ? H19C C19 H19D 108.4 . . ? N2 C20 C19 116.1(13) . . ? N2 C20 H20C 108.3 . . ? C19 C20 H20C 108.3 . . ? N2 C20 H20D 108.3 . . ? C19 C20 H20D 108.3 . . ? H20C C20 H20D 107.4 . . ? C22 C21 N1 109.0(11) . . ? C22 C21 H21C 109.9 . . ? N1 C21 H21C 109.9 . . ? C22 C21 H21D 109.9 . . ? N1 C21 H21D 109.9 . . ? H21C C21 H21D 108.3 . . ? C21 C22 N2 111.3(11) . . ? C21 C22 H22C 109.4 . . ? N2 C22 H22C 109.4 . . ? C21 C22 H22D 109.4 . . ? N2 C22 H22D 109.4 . . ? H22C C22 H22D 108.0 . . ? 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 O19 H19A O11 0.96 1.93 2.783(7) 146.4 4_565 O19 H19B O24 0.98 1.67 2.640(9) 175.2 . O20 H20A O11 0.93 1.96 2.809(8) 151.8 4_565 O20 H20B O17 0.81 1.97 2.757(8) 163.7 1_655 O21 H21A O10 0.84 2.06 2.792(9) 146.1 . O21 H21B O14 0.93 1.93 2.738(9) 143.8 . O21 H21B O1 0.93 2.48 2.949(9) 111.3 2_546 O22 H22A O4 0.93 2.16 3.068(11) 165.4 4_465 O22 H22B O15 0.85 2.24 2.762(12) 119.8 . O22 H22B O2 0.85 2.30 3.060(11) 147.5 2_546 O23 H23A O18 0.90 2.00 2.887(9) 168.7 . O23 H23B O21 0.93 2.09 2.818(11) 134.3 2_556 N1 H1 O8 0.82 2.00 2.705(14) 143.2 . N1 H1 O3 0.82 2.46 3.013(13) 126.2 1_455 N2 H2 O22 0.85 1.76 2.575(14) 160.0 3_456