# Electronic Supplementary Material (ESI) for RSC Advances # This journal is © The Royal Society of Chemistry 2012 data_publication_text _journal_name_full 'RSC Advances' _journal_coden_cambridge 1500 _publ_contact_author_name 'Robin D. Rogers' _publ_contact_author_address ;Center for Green Manufacturing Department of Chemistry/Box 870336 3006D Shelby Hall, 250 Hackberry Lane The University of Alabama Tuscaloosa, AL 35487 ; _publ_contact_author_email RDRogers@as.ua.edu _publ_contact_author_phone +1-205/348-4323 _publ_contact_author_fax '+1-205/348-0823 ' loop_ _publ_author_name _publ_author_address 'Rogers, Robin D.' ;Center for Green Manufacturing Department of Chemistry/Box 870336 3006D Shelby Hall, 250 Hackberry Lane The University of Alabama Tuscaloosa, AL 35487 ; 'Barber, Patrick S.' ;Center for Green Manufacturing Department of Chemistry/Box 870336 250 Hackberry Lane The University of Alabama Tuscaloosa, AL 35487 ; 'Kelley, Steven P.' ;Center for Green Manufacturing Department of Chemistry/Box 870336 250 Hackberry Lane The University of Alabama Tuscaloosa, AL 35487 ; data_[UO2(AO2mim)(NO3)2]H2O _database_code_depnum_ccdc_archive 'CCDC 890413' #TrackingRef '- psb6 07-02-12.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C8 H14 N6 O10 U' _chemical_formula_weight 592.28 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' U U -9.6767 9.6646 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.0282(3) _cell_length_b 13.7694(5) _cell_length_c 14.7200(5) _cell_angle_alpha 90.00 _cell_angle_beta 99.307(2) _cell_angle_gamma 90.00 _cell_volume 1805.80(11) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9341 _cell_measurement_theta_min 2.72 _cell_measurement_theta_max 33.11 _exptl_crystal_description parallelepiped _exptl_crystal_colour red-orange _exptl_crystal_size_max 0.11 _exptl_crystal_size_mid 0.03 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 2.179 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1104 _exptl_absorpt_coefficient_mu 9.047 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4361 _exptl_absorpt_correction_T_max 0.7465 _exptl_absorpt_process_details 'Bruker AXScale' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 36472 _diffrn_reflns_av_R_equivalents 0.0315 _diffrn_reflns_av_sigmaI/netI 0.0193 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.04 _diffrn_reflns_theta_max 30.00 _reflns_number_total 5270 _reflns_number_gt 4691 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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. ; _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^)+(0.0221P)^2^+3.5499P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5270 _refine_ls_number_parameters 235 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0245 _refine_ls_R_factor_gt 0.0199 _refine_ls_wR_factor_ref 0.0504 _refine_ls_wR_factor_gt 0.0485 _refine_ls_goodness_of_fit_ref 1.071 _refine_ls_restrained_S_all 1.071 _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 0.271290(10) 0.860823(7) 0.175150(7) 0.01526(4) Uani 1 1 d . . . C1 C 0.3194(3) 0.8916(2) -0.1011(2) 0.0204(5) Uani 1 1 d . . . H1 H 0.3371 0.9501 -0.0668 0.024 Uiso 1 1 calc R . . C2 C 0.2059(4) 0.7686(3) -0.1772(2) 0.0283(7) Uani 1 1 d . . . H2 H 0.1292 0.7262 -0.2057 0.034 Uiso 1 1 calc R . . C3 C 0.3558(4) 0.7570(3) -0.1738(2) 0.0313(7) Uani 1 1 d . . . H3 H 0.4043 0.7049 -0.1995 0.038 Uiso 1 1 calc R . . C4 C 0.0423(3) 0.8943(2) -0.1160(2) 0.0255(6) Uani 1 1 d . . . H4A H 0.0272 0.8800 -0.0530 0.038 Uiso 1 1 calc R . . H4B H -0.0392 0.8654 -0.1596 0.038 Uiso 1 1 calc R . . H4C H 0.0429 0.9648 -0.1251 0.038 Uiso 1 1 calc R . . C5 C 0.5872(3) 0.8548(2) -0.1080(2) 0.0241(6) Uani 1 1 d . . . H5A H 0.6059 0.9152 -0.0714 0.029 Uiso 1 1 calc R . . H5B H 0.6233 0.8652 -0.1673 0.029 Uiso 1 1 calc R . . C6 C 0.6747(3) 0.7722(2) -0.0565(2) 0.0230(6) Uani 1 1 d . . . H6A H 0.7819 0.7909 -0.0430 0.028 Uiso 1 1 calc R . . H6B H 0.6669 0.7145 -0.0972 0.028 Uiso 1 1 calc R . . C7 C 0.6225(3) 0.7440(2) 0.0339(2) 0.0209(5) Uani 1 1 d . . . H7A H 0.5176 0.7206 0.0201 0.025 Uiso 1 1 calc R . . H7B H 0.6852 0.6896 0.0623 0.025 Uiso 1 1 calc R . . C8 C 0.6306(3) 0.8255(2) 0.10166(19) 0.0185(5) Uani 1 1 d . . . H100 H 0.850(5) 0.839(3) 0.127(3) 0.021(9) Uiso 1 1 d . . . H101 H 0.767(4) 0.900(3) 0.175(2) 0.015(9) Uiso 1 1 d . . . N1 N 0.1861(3) 0.85368(18) -0.13154(18) 0.0204(5) Uani 1 1 d . . . N3 N 0.4242(3) 0.83510(19) -0.12598(18) 0.0212(5) Uani 1 1 d . . . N4 N 0.7641(3) 0.8696(2) 0.1313(2) 0.0233(5) Uani 1 1 d . . . N5 N 0.5076(3) 0.85261(19) 0.12763(18) 0.0210(5) Uani 1 1 d . . . N6 N 0.1107(3) 0.7122(2) 0.0624(2) 0.0349(7) Uani 1 1 d . . . N7 N 0.1416(4) 0.9710(2) 0.3063(2) 0.0353(7) Uani 1 1 d . . . O1 O 0.5129(2) 0.92398(17) 0.19484(15) 0.0242(4) Uani 1 1 d . . . O2 O 0.3295(2) 0.77109(17) 0.26084(15) 0.0256(5) Uani 1 1 d . . . O3 O 0.2079(2) 0.94896(15) 0.08864(14) 0.0214(4) Uani 1 1 d . . . O4 O 0.0644(2) 0.90822(15) 0.25657(15) 0.0217(4) Uani 1 1 d . . . O5 O 0.2767(3) 0.98647(18) 0.29657(17) 0.0298(5) Uani 1 1 d . . . O6 O 0.0729(5) 1.0261(4) 0.3781(4) 0.1008(18) Uani 1 1 d . . . O7 O 0.0430(2) 0.75793(17) 0.11813(17) 0.0280(5) Uani 1 1 d . . . O8 O 0.2437(2) 0.73569(16) 0.05481(16) 0.0238(4) Uani 1 1 d . . . O9 O 0.0360(5) 0.6298(3) 0.0057(4) 0.0806(14) Uani 1 1 d . . . O10 O 0.6637(6) 1.0561(4) 0.3247(3) 0.0990(17) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 U1 0.01120(5) 0.01826(5) 0.01674(5) 0.00049(4) 0.00348(3) 0.00108(4) C1 0.0211(13) 0.0195(13) 0.0201(13) -0.0003(10) 0.0017(10) -0.0002(11) C2 0.0227(15) 0.0295(16) 0.0309(17) -0.0118(13) -0.0013(12) 0.0003(12) C3 0.0228(15) 0.0350(18) 0.0347(18) -0.0167(14) 0.0004(13) 0.0016(13) C4 0.0166(13) 0.0293(15) 0.0304(16) -0.0013(13) 0.0029(11) 0.0050(11) C5 0.0172(13) 0.0315(16) 0.0235(14) 0.0020(12) 0.0030(11) -0.0051(11) C6 0.0154(13) 0.0322(16) 0.0224(14) -0.0037(12) 0.0058(10) 0.0005(11) C7 0.0160(12) 0.0212(13) 0.0260(15) 0.0007(11) 0.0055(10) 0.0023(10) C8 0.0142(12) 0.0224(13) 0.0190(13) 0.0033(10) 0.0032(10) 0.0004(10) N1 0.0175(11) 0.0227(12) 0.0205(12) -0.0012(9) 0.0013(9) 0.0009(9) N3 0.0181(12) 0.0240(12) 0.0208(12) -0.0022(9) 0.0011(9) 0.0002(9) N4 0.0128(11) 0.0304(14) 0.0267(14) -0.0006(11) 0.0031(9) -0.0006(10) N5 0.0129(11) 0.0262(13) 0.0242(12) -0.0036(10) 0.0040(9) -0.0004(9) N6 0.0291(15) 0.0304(15) 0.0437(18) 0.0019(13) 0.0019(13) 0.0027(12) N7 0.0352(16) 0.0360(16) 0.0366(16) -0.0046(13) 0.0121(13) 0.0004(13) O1 0.0170(9) 0.0300(11) 0.0264(11) -0.0077(9) 0.0057(8) -0.0027(8) O2 0.0236(11) 0.0304(12) 0.0234(11) 0.0073(9) 0.0056(8) 0.0056(9) O3 0.0207(10) 0.0217(10) 0.0220(10) 0.0025(8) 0.0043(8) 0.0016(8) O4 0.0188(9) 0.0219(10) 0.0260(11) -0.0058(8) 0.0082(8) -0.0033(8) O5 0.0210(11) 0.0373(13) 0.0326(12) -0.0145(10) 0.0087(9) -0.0062(9) O6 0.085(3) 0.113(4) 0.117(4) -0.067(3) 0.055(3) -0.018(3) O7 0.0164(10) 0.0325(12) 0.0361(13) -0.0093(10) 0.0071(9) -0.0009(9) O8 0.0185(10) 0.0230(10) 0.0307(12) -0.0065(9) 0.0065(8) -0.0019(8) O9 0.063(3) 0.062(2) 0.113(4) -0.034(2) 0.004(2) -0.0144(19) O10 0.098(3) 0.133(5) 0.062(3) -0.019(3) 0.001(2) -0.047(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag U1 O2 1.783(2) . ? U1 O3 1.785(2) . ? U1 O1 2.322(2) . ? U1 N5 2.353(2) . ? U1 O8 2.455(2) . ? U1 O4 2.465(2) . ? U1 O5 2.482(2) . ? U1 O7 2.530(2) . ? U1 N7 2.851(3) . ? U1 N6 2.875(3) . ? C1 N3 1.322(4) . ? C1 N1 1.323(4) . ? C2 C3 1.356(4) . ? C2 N1 1.376(4) . ? C3 N3 1.376(4) . ? C4 N1 1.464(4) . ? C5 N3 1.477(4) . ? C5 C6 1.516(4) . ? C6 C7 1.532(4) . ? C7 C8 1.495(4) . ? C8 N5 1.287(4) . ? C8 N4 1.357(4) . ? N5 O1 1.390(3) . ? N6 O8 1.266(4) . ? N6 O7 1.267(4) . ? N6 O9 1.503(5) . ? N7 O4 1.266(4) . ? N7 O5 1.269(4) . ? N7 O6 1.514(5) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 U1 O3 178.35(10) . . ? O2 U1 O1 90.44(9) . . ? O3 U1 O1 91.19(9) . . ? O2 U1 N5 89.95(10) . . ? O3 U1 N5 91.27(9) . . ? O1 U1 N5 34.58(8) . . ? O2 U1 O8 90.46(10) . . ? O3 U1 O8 88.80(9) . . ? O1 U1 O8 109.66(7) . . ? N5 U1 O8 75.09(8) . . ? O2 U1 O4 89.97(9) . . ? O3 U1 O4 89.20(8) . . ? O1 U1 O4 127.62(7) . . ? N5 U1 O4 162.20(8) . . ? O8 U1 O4 122.71(7) . . ? O2 U1 O5 90.26(10) . . ? O3 U1 O5 90.37(9) . . ? O1 U1 O5 74.96(7) . . ? N5 U1 O5 109.54(8) . . ? O8 U1 O5 175.32(7) . . ? O4 U1 O5 52.66(7) . . ? O2 U1 O7 88.73(10) . . ? O3 U1 O7 89.66(9) . . ? O1 U1 O7 161.71(7) . . ? N5 U1 O7 127.13(8) . . ? O8 U1 O7 52.08(7) . . ? O4 U1 O7 70.66(7) . . ? O5 U1 O7 123.31(7) . . ? O2 U1 N7 89.78(10) . . ? O3 U1 N7 90.10(10) . . ? O1 U1 N7 101.33(8) . . ? N5 U1 N7 135.91(9) . . ? O8 U1 N7 149.00(8) . . ? O4 U1 N7 26.29(8) . . ? O5 U1 N7 26.37(8) . . ? O7 U1 N7 96.94(8) . . ? O2 U1 N6 88.76(10) . . ? O3 U1 N6 89.93(9) . . ? O1 U1 N6 135.59(8) . . ? N5 U1 N6 101.01(9) . . ? O8 U1 N6 25.98(8) . . ? O4 U1 N6 96.78(8) . . ? O5 U1 N6 149.43(8) . . ? O7 U1 N6 26.13(8) . . ? N7 U1 N6 123.06(9) . . ? N3 C1 N1 109.0(3) . . ? C3 C2 N1 106.9(3) . . ? C2 C3 N3 106.8(3) . . ? N3 C5 C6 112.0(2) . . ? C5 C6 C7 114.5(2) . . ? C8 C7 C6 113.6(2) . . ? N5 C8 N4 122.6(3) . . ? N5 C8 C7 117.7(3) . . ? N4 C8 C7 119.7(3) . . ? C1 N1 C2 108.6(3) . . ? C1 N1 C4 125.2(3) . . ? C2 N1 C4 126.2(3) . . ? C1 N3 C3 108.7(3) . . ? C1 N3 C5 125.4(3) . . ? C3 N3 C5 125.9(3) . . ? C8 N5 O1 119.0(2) . . ? C8 N5 U1 165.9(2) . . ? O1 N5 U1 71.52(13) . . ? O8 N6 O7 119.6(3) . . ? O8 N6 O9 119.4(3) . . ? O7 N6 O9 121.0(3) . . ? O8 N6 U1 58.15(16) . . ? O7 N6 U1 61.56(16) . . ? O9 N6 U1 176.0(2) . . ? O4 N7 O5 119.9(3) . . ? O4 N7 O6 119.8(3) . . ? O5 N7 O6 120.3(3) . . ? O4 N7 U1 59.56(15) . . ? O5 N7 U1 60.36(16) . . ? O6 N7 U1 177.8(3) . . ? N5 O1 U1 73.90(13) . . ? N7 O4 U1 94.15(17) . . ? N7 O5 U1 93.27(18) . . ? N6 O7 U1 92.32(18) . . ? N6 O8 U1 95.87(19) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 1.023 _refine_diff_density_min -1.087 _refine_diff_density_rms 0.122