# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # 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_UO2(HA)2 _database_code_depnum_ccdc_archive 'CCDC 859445' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Uranyl bis-glutarimidedioxime monohydrate ; _chemical_name_common ; Uranyl bis-glutarimidedioxime monohydrate ; _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H18 N6 O7 U' _chemical_formula_weight 572.33 _exptl_crystal_preparation water loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C -0.0020 0.0020 'WCROMER Program in WinGX L.Kissel & R.H.Pratt Acta Cryst A46 170 1990' H H 0.0000 0.0000 'WCROMER Program in WinGX L.Kissel & R.H.Pratt Acta Cryst A46 170 1990' N N -0.0031 0.0040 'WCROMER Program in WinGX L.Kissel & R.H.Pratt Acta Cryst A46 170 1990' O O -0.0041 0.0074 'WCROMER Program in WinGX L.Kissel & R.H.Pratt Acta Cryst A46 170 1990' U U -8.0145 4.5872 'WCROMER Program in WinGX L.Kissel & R.H.Pratt Acta Cryst A46 170 1990' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pccn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z' '-x, y+1/2, -z+1/2' 'x+1/2, -y, -z+1/2' '-x, -y, -z' 'x-1/2, y-1/2, -z' 'x, -y-1/2, z-1/2' '-x-1/2, y, z-1/2' _cell_length_a 13.0453(11) _cell_length_b 13.9325(12) _cell_length_c 8.0331(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1460.0(2) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 7191 _cell_measurement_theta_min 4.55 _cell_measurement_theta_max 33.48 _exptl_crystal_description plate _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.04 _exptl_crystal_size_mid 0.03 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.604 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1072 _exptl_absorpt_coefficient_mu 6.020 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.74 _exptl_absorpt_correction_T_max 0.88 _exptl_absorpt_process_details 'SADABS 2008/1 Bruker AXS Madison WI USA' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.77490 _diffrn_radiation_type synchrotron _diffrn_radiation_source 'Advanced Light Source station 11.3.1' _diffrn_radiation_monochromator 'silicon 111' _diffrn_measurement_device_type 'Bruker APEX II CCD diffractometer' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% . _diffrn_reflns_number 31749 _diffrn_reflns_av_R_equivalents 0.0734 _diffrn_reflns_av_sigmaI/netI 0.0352 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 4.55 _diffrn_reflns_theta_max 33.60 _reflns_number_total 2227 _reflns_number_gt 1447 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker APEX 2' _computing_cell_refinement 'Bruker SAINT v7.60a' _computing_data_reduction 'Bruker SAINT v7.60a' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL & local programs' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 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. All non-hydrogens where refined anisotropically.The hydrogen atoms were all found in the difference map and allow to refine freely, except those on the water. The distance and angle were restrained and refined using a riding model. ; _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^)+(0.0119P)^2^+4.2956P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2227 _refine_ls_number_parameters 146 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0437 _refine_ls_R_factor_gt 0.0258 _refine_ls_wR_factor_ref 0.0650 _refine_ls_wR_factor_gt 0.0565 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.038 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group U1 U 0.0000 0.5000 0.0000 0.01201(7) Uani 1 2 d S . . O3 O 0.0721(2) 0.59718(19) -0.0852(3) 0.0172(6) Uani 1 1 d . . . O1 O -0.1265(2) 0.6109(2) 0.1427(3) 0.0182(6) Uani 1 1 d . . . N1 N -0.1029(3) 0.6524(2) 0.2913(4) 0.0170(7) Uani 1 1 d . . . H1N H -0.159(4) 0.690(3) 0.330(6) 0.027(13) Uiso 1 1 d . . . O2 O 0.1499(2) 0.4399(2) 0.1461(3) 0.0184(6) Uani 1 1 d . . . N2 N 0.1849(3) 0.4792(3) 0.2888(5) 0.0185(7) Uani 1 1 d . . . H2N H 0.241(3) 0.452(3) 0.317(5) 0.013(11) Uiso 1 1 d . . . N3 N 0.0431(2) 0.5686(2) 0.2877(4) 0.0168(6) Uani 1 1 d . . . C1 C -0.0183(3) 0.6324(3) 0.3661(5) 0.0158(8) Uani 1 1 d . . . C2 C 0.0070(3) 0.6803(3) 0.5287(5) 0.0170(8) Uani 1 1 d . . . H2A H -0.032(4) 0.642(4) 0.620(7) 0.041(15) Uiso 1 1 d . . . H2B H -0.030(4) 0.742(5) 0.529(6) 0.034(15) Uiso 1 1 d . . . C3 C 0.1231(3) 0.6865(3) 0.5485(5) 0.0189(8) Uani 1 1 d . . . H3A H 0.140(3) 0.709(3) 0.658(5) 0.013(11) Uiso 1 1 d . . . H3B H 0.154(4) 0.737(4) 0.467(6) 0.045(16) Uiso 1 1 d . . . C4 C 0.1690(3) 0.5869(3) 0.5252(5) 0.0172(8) Uani 1 1 d . . . H4A H 0.148(3) 0.542(3) 0.612(6) 0.020(12) Uiso 1 1 d . . . H4B H 0.244(4) 0.587(4) 0.520(5) 0.033(15) Uiso 1 1 d . . . C5 C 0.1325(3) 0.5439(3) 0.3648(5) 0.0162(8) Uani 1 1 d . . . O1W O 0.2500 0.2500 0.0299(5) 0.0234(9) Uani 1 2 d SD . . H1WA H 0.221(4) 0.290(2) -0.025(4) 0.028 Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 U1 0.00925(10) 0.01408(10) 0.01268(10) -0.00021(7) 0.00079(7) -0.00075(7) O3 0.0151(13) 0.0188(14) 0.0178(14) 0.0009(11) 0.0023(11) -0.0021(11) O1 0.0155(13) 0.0234(15) 0.0156(13) -0.0058(11) 0.0008(11) -0.0016(11) N1 0.0159(16) 0.0187(17) 0.0164(16) -0.0002(13) -0.0020(13) 0.0003(13) O2 0.0149(13) 0.0229(15) 0.0174(13) -0.0060(12) -0.0046(11) 0.0034(11) N2 0.0139(16) 0.0235(18) 0.0180(16) -0.0013(14) -0.0030(14) 0.0020(13) N3 0.0136(15) 0.0209(17) 0.0157(15) -0.0021(13) 0.0008(13) 0.0011(13) C1 0.0171(19) 0.0170(19) 0.0133(18) 0.0007(14) 0.0009(14) 0.0003(14) C2 0.017(2) 0.0198(19) 0.0146(18) -0.0028(14) -0.0018(15) -0.0012(16) C3 0.0170(19) 0.020(2) 0.0194(19) -0.0016(16) -0.0023(16) -0.0024(16) C4 0.0176(19) 0.023(2) 0.0112(18) -0.0018(15) -0.0012(14) 0.0038(16) C5 0.0164(19) 0.0188(19) 0.0135(18) -0.0010(15) -0.0018(15) 0.0005(15) O1W 0.018(2) 0.024(2) 0.028(2) 0.000 0.000 -0.0014(18) _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 O3 1.785(3) . ? U1 O3 1.785(3) 5_565 ? U1 O1 2.535(3) . ? U1 O1 2.535(3) 5_565 ? U1 O2 2.429(3) . ? U1 O2 2.429(3) 5_565 ? U1 N3 2.563(3) . ? U1 N3 2.563(3) 5_565 ? O1 N1 1.361(4) . ? N1 H1N 0.95(5) . ? N1 C1 1.288(5) . ? O2 N2 1.350(4) . ? N2 H2N 0.86(4) . ? N2 C5 1.285(5) . ? N3 C1 1.351(5) . ? N3 C5 1.365(5) . ? C1 C2 1.503(6) . ? C2 H2A 1.04(6) . ? C2 H2B 0.99(6) . ? C2 C3 1.526(6) . ? C3 H3A 0.96(4) . ? C3 H3B 1.05(6) . ? C3 C4 1.524(6) . ? C4 H4A 0.97(5) . ? C4 H4B 0.99(6) . ? C4 C5 1.499(5) . ? O1W H1WA 0.813(16) . ? 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 O3 U1 O3 180.0 . 5_565 ? O3 U1 O1 93.09(11) . . ? O3 U1 O1 86.91(11) 5_565 . ? O3 U1 O1 93.09(11) 5_565 5_565 ? O3 U1 O1 86.91(11) . 5_565 ? O3 U1 O2 91.30(11) . . ? O3 U1 O2 91.30(11) 5_565 5_565 ? O3 U1 O2 88.70(11) . 5_565 ? O3 U1 O2 88.70(11) 5_565 . ? O3 U1 N3 86.97(11) . . ? O3 U1 N3 86.97(11) 5_565 5_565 ? O3 U1 N3 93.03(11) . 5_565 ? O3 U1 N3 93.03(11) 5_565 . ? O1 U1 O1 180.0 . 5_565 ? O1 U1 O2 121.05(9) . . ? O1 U1 O2 58.95(9) . 5_565 ? O1 U1 O2 121.05(9) 5_565 5_565 ? O1 U1 O2 58.95(9) 5_565 . ? O1 U1 N3 60.50(9) . . ? O1 U1 N3 119.50(9) . 5_565 ? O1 U1 N3 60.50(9) 5_565 5_565 ? O1 U1 N3 119.50(9) 5_565 . ? O2 U1 O2 180.0 . 5_565 ? O2 U1 N3 61.10(10) . . ? O2 U1 N3 61.10(10) 5_565 5_565 ? O2 U1 N3 118.90(10) . 5_565 ? O2 U1 N3 118.90(10) 5_565 . ? N3 U1 N3 180.00(6) . 5_565 ? U1 O1 N1 120.5(2) . . ? O1 N1 H1N 110(3) . . ? O1 N1 C1 120.8(3) . . ? H1N N1 C1 129(3) . . ? U1 O2 N2 122.9(2) . . ? O2 N2 H2N 110(3) . . ? O2 N2 C5 120.5(3) . . ? H2N N2 C5 130(3) . . ? U1 N3 C1 122.4(3) . . ? U1 N3 C5 120.1(2) . . ? C1 N3 C5 117.4(3) . . ? N1 C1 N3 115.6(4) . . ? N1 C1 C2 119.8(4) . . ? N3 C1 C2 124.6(4) . . ? C1 C2 H2A 106(3) . . ? C1 C2 H2B 106(3) . . ? C1 C2 C3 109.5(3) . . ? H2A C2 H2B 102(4) . . ? H2A C2 C3 116(3) . . ? H2B C2 C3 116(4) . . ? C2 C3 H3A 110(2) . . ? C2 C3 H3B 111(3) . . ? C2 C3 C4 109.0(4) . . ? H3A C3 H3B 105(4) . . ? H3A C3 C4 109(3) . . ? H3B C3 C4 113(3) . . ? C3 C4 H4A 113(3) . . ? C3 C4 H4B 113(3) . . ? C3 C4 C5 110.2(3) . . ? H4A C4 H4B 108(4) . . ? H4A C4 C5 106(3) . . ? H4B C4 C5 107(3) . . ? N2 C5 N3 114.6(4) . . ? N2 C5 C4 121.3(4) . . ? N3 C5 C4 124.1(4) . . ? 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 H1N O1W 0.95(5) 1.84(5) 2.756(4) 161(4) 3 N2 H2N O1 0.86(4) 1.96(4) 2.816(4) 174(4) 4_565 N2 H2N N1 0.86(4) 2.64(4) 3.382(5) 144(4) 4_565 O1W H1WA O1 0.813(16) 2.070(15) 2.876(3) 171(5) 5_565 O1W H1WA O2 0.813(16) 2.66(2) 3.095(3) 115(3) . _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 33.60 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.531 _refine_diff_density_min -0.590 _refine_diff_density_rms 0.151 data_H2A _database_code_depnum_ccdc_archive 'CCDC 859853' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ; Glutarimidedioxime ; _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C5 H9 N3 O2' _chemical_formula_weight 143.15 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pbam loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' '-x+1/2, y+1/2, -z' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x, y, -z' 'x-1/2, -y-1/2, z' '-x-1/2, y-1/2, z' _cell_length_a 7.1205(7) _cell_length_b 14.1467(13) _cell_length_c 13.5789(12) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1367.8(2) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 7149 _cell_measurement_theta_min 3.12 _cell_measurement_theta_max 33.36 _exptl_crystal_description lath _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.390 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 608 _exptl_absorpt_coefficient_mu 0.109 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.94 _exptl_absorpt_correction_T_max 0.95 _exptl_absorpt_process_details 'SADABS 2008/1 Bruker AXS Madison WI USA' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.77490 _diffrn_radiation_type synchrotron _diffrn_radiation_source 'Advanced Light Source station 11.3.1' _diffrn_radiation_monochromator 'silicon 111' _diffrn_measurement_device_type 'Bruker APEX II CCD diffractometer' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% . _diffrn_reflns_number 32395 _diffrn_reflns_av_R_equivalents 0.0328 _diffrn_reflns_av_sigmaI/netI 0.0122 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.14 _diffrn_reflns_theta_max 33.07 _reflns_number_total 2072 _reflns_number_gt 1769 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker APEX 2' _computing_cell_refinement 'Bruker SAINT v7.60a' _computing_data_reduction 'Bruker SAINT v7.60a' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL & local programs' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 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. All non-hydrogen atoms were refined anisotropically. Hydrogen atoms on carbon atoms were place geometrically and refined using a riding model. All other hydrogen atoms were found in the difference map and allowed to refine freely. ; _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^)+(0.0627P)^2^+0.6130P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens mixed _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef . _refine_ls_number_reflns 2072 _refine_ls_number_parameters 111 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0508 _refine_ls_R_factor_gt 0.0446 _refine_ls_wR_factor_ref 0.1336 _refine_ls_wR_factor_gt 0.1290 _refine_ls_goodness_of_fit_ref 1.145 _refine_ls_restrained_S_all 1.145 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1A O 0.68320(14) 0.40570(6) 0.15400(7) 0.0234(2) Uani 1 1 d . . . H1OA H 0.607(3) 0.3951(16) 0.2105(19) 0.058(7) Uiso 1 1 d . . . N1A N 0.73902(16) 0.50098(8) 0.17088(7) 0.0213(2) Uani 1 1 d . . . N3A N 0.7586(2) 0.49961(11) 0.0000 0.0184(3) Uani 1 2 d S . . H2NA H 0.708(4) 0.442(2) 0.0000 0.032(7) Uiso 1 2 d S . . C1A C 0.77590(17) 0.54333(9) 0.09002(8) 0.0183(2) Uani 1 1 d . . . C2A C 0.83881(19) 0.64519(9) 0.09189(9) 0.0228(3) Uani 1 1 d . . . H2AA H 0.9776 0.6481 0.0942 0.027 Uiso 1 1 calc R . . H2AB H 0.7890 0.6767 0.1515 0.027 Uiso 1 1 calc R . . C3A C 0.7678(3) 0.69618(13) 0.0000 0.0236(4) Uani 1 2 d S . . H3AA H 0.8133 0.7623 0.0000 0.028 Uiso 1 2 calc SR . . H3AB H 0.6288 0.6972 0.0000 0.028 Uiso 1 2 calc SR . . O1B O 0.69252(13) 0.59167(7) 0.34588(7) 0.0227(2) Uani 1 1 d . . . H1OB H 0.724(3) 0.5570(17) 0.2942(18) 0.050(6) Uiso 1 1 d . . . N1B N 0.50240(16) 0.61691(8) 0.32884(7) 0.0212(2) Uani 1 1 d . . . N3B N 0.5028(2) 0.62358(10) 0.5000 0.0182(3) Uani 1 2 d S . . H2NB H 0.623(4) 0.6023(18) 0.5000 0.030(6) Uiso 1 2 d S . . C1B C 0.41580(18) 0.63303(8) 0.41003(8) 0.0183(2) Uani 1 1 d . . . C2B C 0.21438(19) 0.66376(10) 0.40796(9) 0.0236(3) Uani 1 1 d . . . H2BA H 0.1523 0.6378 0.3486 0.028 Uiso 1 1 calc R . . H2BB H 0.2078 0.7336 0.4046 0.028 Uiso 1 1 calc R . . C3B C 0.1123(3) 0.62918(14) 0.5000 0.0265(4) Uani 1 2 d S . . H3BA H 0.1075 0.5592 0.5000 0.032 Uiso 1 2 calc SR . . H3BB H -0.0182 0.6533 0.5000 0.032 Uiso 1 2 calc SR . . 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 O1A 0.0330(5) 0.0199(4) 0.0173(4) -0.0002(3) 0.0052(3) -0.0017(4) N1A 0.0277(5) 0.0204(5) 0.0158(5) -0.0029(4) 0.0027(4) -0.0008(4) N3A 0.0258(7) 0.0171(6) 0.0123(6) 0.000 0.000 -0.0012(5) C1A 0.0202(5) 0.0198(5) 0.0149(5) -0.0030(4) 0.0005(4) 0.0022(4) C2A 0.0266(6) 0.0202(5) 0.0215(6) -0.0042(4) 0.0010(4) -0.0014(5) C3A 0.0256(8) 0.0173(8) 0.0279(9) 0.000 0.000 0.0017(6) O1B 0.0250(4) 0.0272(5) 0.0158(4) -0.0048(3) -0.0004(3) 0.0023(4) N1B 0.0255(5) 0.0217(5) 0.0163(5) -0.0028(4) -0.0030(4) 0.0016(4) N3B 0.0218(7) 0.0196(7) 0.0132(6) 0.000 0.000 0.0015(5) C1B 0.0250(6) 0.0146(5) 0.0153(5) -0.0009(4) -0.0030(4) -0.0004(4) C2B 0.0259(6) 0.0247(6) 0.0203(6) -0.0020(4) -0.0041(4) 0.0041(5) C3B 0.0215(8) 0.0267(9) 0.0313(9) 0.000 0.000 -0.0007(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 O1A H1OA 0.95(3) . ? O1A N1A 1.4240(14) . ? N1A C1A 1.2782(16) . ? N3A H2NA 0.89(3) . ? N3A C1A 1.3754(13) . ? N3A C1A 1.3754(13) 6 ? C1A C2A 1.5092(17) . ? C2A H2AA 0.9900 . ? C2A H2AB 0.9900 . ? C2A C3A 1.5274(16) . ? C3A C2A 1.5274(16) 6 ? C3A H3AA 0.9900 . ? C3A H3AB 0.9900 . ? O1B H1OB 0.88(2) . ? O1B N1B 1.4191(15) . ? N1B C1B 1.2837(16) . ? N3B H2NB 0.91(3) . ? N3B C1B 1.3763(13) . ? N3B C1B 1.3763(13) 6_556 ? C1B C2B 1.4989(18) . ? C2B H2BA 0.9900 . ? C2B H2BB 0.9900 . ? C2B C3B 1.5263(17) . ? C3B C2B 1.5264(17) 6_556 ? C3B H3BA 0.9900 . ? C3B H3BB 0.9900 . ? 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 H1OA O1A N1A 100.3(14) . . ? O1A N1A C1A 111.27(10) . . ? H2NA N3A C1A 116.6(2) . . ? H2NA N3A C1A 116.6(2) . 6 ? C1A N3A C1A 125.41(15) . 6 ? N1A C1A N3A 122.30(12) . . ? N1A C1A C2A 119.61(10) . . ? N3A C1A C2A 118.09(11) . . ? C1A C2A H2AA 109.7 . . ? C1A C2A H2AB 109.7 . . ? C1A C2A C3A 109.81(11) . . ? H2AA C2A H2AB 108.2 . . ? H2AA C2A C3A 109.7 . . ? H2AB C2A C3A 109.7 . . ? C2A C3A C2A 109.55(14) . 6 ? C2A C3A H3AA 109.8 . . ? C2A C3A H3AA 109.8 6 . ? C2A C3A H3AB 109.8 . . ? C2A C3A H3AB 109.8 6 . ? H3AA C3A H3AB 108.2 . . ? H1OB O1B N1B 104.5(15) . . ? O1B N1B C1B 111.28(10) . . ? H2NB N3B C1B 117.19(14) . . ? H2NB N3B C1B 117.19(14) . 6_556 ? C1B N3B C1B 125.15(15) . 6_556 ? N1B C1B N3B 121.93(12) . . ? N1B C1B C2B 119.67(10) . . ? N3B C1B C2B 118.40(11) . . ? C1B C2B H2BA 109.6 . . ? C1B C2B H2BB 109.6 . . ? C1B C2B C3B 110.32(11) . . ? H2BA C2B H2BB 108.1 . . ? H2BA C2B C3B 109.6 . . ? H2BB C2B C3B 109.6 . . ? C2B C3B C2B 109.93(15) . 6_556 ? C2B C3B H3BA 109.7 . . ? C2B C3B H3BA 109.7 6_556 . ? C2B C3B H3BB 109.7 . . ? C2B C3B H3BB 109.7 6_556 . ? H3BA C3B H3BB 108.2 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1A N1A C1A N3A 0.97(18) . . . . ? O1A N1A C1A C2A -179.70(10) . . . . ? C1A N3A C1A N1A 172.52(10) 6 . . . ? C1A N3A C1A C2A -6.8(2) 6 . . . ? N1A C1A C2A C3A -147.23(12) . . . . ? N3A C1A C2A C3A 32.14(17) . . . . ? C1A C2A C3A C2A -57.23(18) . . . 6 ? O1B N1B C1B N3B -1.45(17) . . . . ? O1B N1B C1B C2B 178.10(10) . . . . ? C1B N3B C1B N1B -175.10(9) 6_556 . . . ? C1B N3B C1B C2B 5.3(2) 6_556 . . . ? N1B C1B C2B C3B 149.65(12) . . . . ? N3B C1B C2B C3B -30.78(17) . . . . ? C1B C2B C3B C2B 55.73(18) . . . 6_556 ? 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 O1A H1OA N1B 0.95(3) 1.79(3) 2.7358(14) 170(2) 2_665 O1B H1OB N1A 0.88(2) 1.86(3) 2.7207(14) 165(2) . _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.449 _refine_diff_density_min -0.185 _refine_diff_density_rms 0.054