# Electronic Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and The Centre National de la Recherche Scientifique 2011 data_global _journal_name_full 'New J.Chem.' _journal_coden_Cambridge 0440 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Prof. Rogers, Robin D.' _publ_contact_author_email rdrogers@as.ua.edu _publ_section_title ; Synthesis, limitations, and thermal properties of energetically-substituted, protonated imidazolium picrate and nitrate salts and further comparison with their methylated analogs ; loop_ _publ_author_name M.Smiglak Hines M.Reichert A.Vincek A.Katritzky J.Thrasher ; L.Sun ; P.McCrary P.Beasley S.Kelley R.D.Rogers data_18a _database_code_depnum_ccdc_archive 'CCDC 837939' #TrackingRef '- Protonated ILs CIFs 10-30-11.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H8.50 N8.50 O10.50' _chemical_formula_weight 475.80 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 Pbcn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' '-x, y, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' 'x, -y, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 43.982(11) _cell_length_b 8.850(2) _cell_length_c 9.627(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3747.3(16) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 784 _cell_measurement_theta_min 3.16 _cell_measurement_theta_max 22.31 _exptl_crystal_description fragment _exptl_crystal_colour yellow _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.687 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1936 _exptl_absorpt_coefficient_mu 0.146 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9357 _exptl_absorpt_correction_T_max 0.9741 _exptl_absorpt_process_details 'Bruker AXScale' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 15741 _diffrn_reflns_av_R_equivalents 0.0635 _diffrn_reflns_av_sigmaI/netI 0.0417 _diffrn_reflns_limit_h_min -44 _diffrn_reflns_limit_h_max 48 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.35 _diffrn_reflns_theta_max 23.25 _reflns_number_total 2686 _reflns_number_gt 2074 _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^)+(0.0313P)^2^+12.8907P] 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 2686 _refine_ls_number_parameters 310 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0928 _refine_ls_R_factor_gt 0.0678 _refine_ls_wR_factor_ref 0.1367 _refine_ls_wR_factor_gt 0.1268 _refine_ls_goodness_of_fit_ref 1.065 _refine_ls_restrained_S_all 1.065 _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 O1 O -0.21698(6) -0.2094(3) 1.1042(3) 0.0311(8) Uani 1 1 d . . . H1AA H -0.1998 -0.2756 1.1566 0.047 Uiso 1 1 d . . . O2 O -0.26252(6) -0.0463(3) 1.0257(3) 0.0332(8) Uani 1 1 d . . . O3 O -0.27398(7) -0.0461(4) 0.8100(3) 0.0443(9) Uani 1 1 d . . . O4 O -0.20310(7) -0.1570(4) 0.4626(3) 0.0369(8) Uani 1 1 d . . . O5 O -0.16375(8) -0.2937(4) 0.5088(3) 0.0505(10) Uani 1 1 d . . . O6 O -0.13664(7) -0.3934(4) 0.9787(3) 0.0402(9) Uani 1 1 d . . . O7 O -0.16999(7) -0.3740(4) 1.1411(3) 0.0365(8) Uani 1 1 d . . . O8 O 0.0000 -0.5810(6) 0.2500 0.094(3) Uani 1 2 d S . . H8A H -0.0005 -0.6116 0.3322 0.140 Uiso 0.50 1 d P . . O11 O 0.01431(8) 0.1114(4) 0.3406(4) 0.0481(10) Uani 1 1 d . . . N1 N -0.09052(8) -0.1746(4) 0.3454(4) 0.0260(9) Uani 1 1 d . . . N3 N -0.06183(8) 0.0184(4) 0.4145(4) 0.0283(9) Uani 1 1 d . . . N8 N -0.08537(10) 0.3344(5) 0.2172(4) 0.0465(12) Uani 1 1 d . . . N10 N -0.14227(10) -0.0461(5) 0.0914(5) 0.0557(13) Uani 1 1 d . . . N17 N -0.25668(8) -0.0756(4) 0.9050(4) 0.0262(9) Uani 1 1 d . . . N18 N -0.18633(9) -0.2234(4) 0.5435(4) 0.0320(9) Uani 1 1 d . . . N19 N -0.16137(9) -0.3548(4) 1.0203(4) 0.0298(9) Uani 1 1 d . . . N24 N -0.03943(13) -0.4243(6) 0.0656(5) 0.0558(14) Uani 1 1 d . . . N25 N 0.0000 0.0467(6) 0.2500 0.0311(13) Uani 1 2 d S . . C2 C -0.06777(10) -0.1264(5) 0.4283(4) 0.0258(10) Uani 1 1 d . . . H2A H -0.0571 -0.1906 0.4905 0.031 Uiso 1 1 calc R . . C4 C -0.08209(9) 0.0662(5) 0.3168(4) 0.0238(10) Uani 1 1 d . . . C5 C -0.09993(10) -0.0509(5) 0.2732(4) 0.0263(10) Uani 1 1 d . . . C6 C -0.10253(10) -0.3289(5) 0.3343(5) 0.0354(12) Uani 1 1 d . . . H6A H -0.0929 -0.3931 0.4046 0.053 Uiso 1 1 calc R . . H6B H -0.0981 -0.3692 0.2416 0.053 Uiso 1 1 calc R . . H6C H -0.1246 -0.3274 0.3492 0.053 Uiso 1 1 calc R . . C7 C -0.08357(10) 0.2170(6) 0.2661(4) 0.0290(11) Uani 1 1 d . . . C9 C -0.12351(11) -0.0514(5) 0.1727(5) 0.0346(12) Uani 1 1 d . . . C11 C -0.20905(9) -0.2135(4) 0.9724(4) 0.0217(10) Uani 1 1 d . . . C12 C -0.22794(9) -0.1488(5) 0.8699(4) 0.0227(10) Uani 1 1 d . . . C13 C -0.22032(10) -0.1509(5) 0.7318(4) 0.0246(10) Uani 1 1 d . . . H13A H -0.2332 -0.1048 0.6648 0.030 Uiso 1 1 calc R . . C14 C -0.19385(10) -0.2204(5) 0.6916(4) 0.0248(10) Uani 1 1 d . . . C15 C -0.17456(9) -0.2867(5) 0.7854(5) 0.0265(10) Uani 1 1 d . . . H15A H -0.1563 -0.3338 0.7556 0.032 Uiso 1 1 calc R . . C16 C -0.18239(9) -0.2833(5) 0.9234(4) 0.0234(10) Uani 1 1 d . . . C20 C 0.0000 -0.4311(7) 0.2500 0.0364(18) Uani 1 2 d S . . C21 C -0.01875(10) -0.3481(5) 0.1628(5) 0.0312(11) Uani 1 1 d . . . C22 C -0.01884(9) -0.1933(5) 0.1602(4) 0.0263(11) Uani 1 1 d . . . H22A H -0.0316 -0.1397 0.0979 0.032 Uiso 1 1 calc R . . C23 C 0.0000 -0.1178(6) 0.2500 0.0227(14) Uani 1 2 d S . . O10 O -0.03266(10) -0.5497(7) 0.0265(7) 0.140(3) Uani 1 1 d . . . O9B O -0.06221(15) -0.3603(6) 0.0329(5) 0.103(2) 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 O1 0.0362(18) 0.0350(19) 0.0220(17) 0.0025(14) 0.0013(14) 0.0061(15) O2 0.0338(18) 0.042(2) 0.0236(18) -0.0091(16) 0.0039(14) 0.0045(15) O3 0.046(2) 0.062(2) 0.0254(18) 0.0007(17) -0.0065(16) 0.0249(18) O4 0.051(2) 0.036(2) 0.0242(18) 0.0038(16) 0.0018(16) 0.0061(17) O5 0.058(2) 0.054(2) 0.040(2) 0.0009(18) 0.0194(18) 0.026(2) O6 0.0290(19) 0.045(2) 0.047(2) 0.0005(17) -0.0016(16) 0.0117(16) O7 0.042(2) 0.038(2) 0.030(2) 0.0091(16) -0.0030(16) 0.0037(15) O8 0.110(5) 0.018(3) 0.152(7) 0.000 0.087(5) 0.000 O11 0.050(2) 0.029(2) 0.065(2) -0.0177(18) -0.0083(19) -0.0080(16) N1 0.030(2) 0.020(2) 0.028(2) -0.0005(17) -0.0002(17) 0.0018(16) N3 0.036(2) 0.021(2) 0.027(2) 0.0015(17) -0.0034(17) -0.0016(17) N8 0.077(3) 0.028(3) 0.034(2) 0.002(2) 0.004(2) 0.004(2) N10 0.058(3) 0.036(3) 0.073(3) -0.003(3) -0.033(3) 0.004(2) N17 0.031(2) 0.023(2) 0.024(2) -0.0050(17) 0.0018(18) 0.0018(17) N18 0.043(3) 0.025(2) 0.027(2) -0.0015(19) 0.008(2) -0.001(2) N19 0.033(2) 0.024(2) 0.033(2) 0.0013(18) -0.005(2) -0.0008(18) N24 0.074(4) 0.056(4) 0.037(3) -0.019(3) 0.023(3) -0.043(3) N25 0.035(3) 0.015(3) 0.043(4) 0.000 0.000(3) 0.000 C2 0.028(3) 0.029(3) 0.020(2) 0.000(2) -0.002(2) 0.003(2) C4 0.028(2) 0.022(2) 0.022(2) -0.002(2) 0.000(2) 0.0034(19) C5 0.029(2) 0.025(3) 0.025(2) -0.005(2) -0.003(2) 0.001(2) C6 0.037(3) 0.023(3) 0.047(3) -0.001(2) 0.000(2) -0.001(2) C7 0.039(3) 0.028(3) 0.020(2) -0.004(2) -0.002(2) -0.002(2) C9 0.036(3) 0.024(3) 0.044(3) -0.004(2) -0.009(3) 0.001(2) C11 0.030(3) 0.016(2) 0.020(2) -0.0007(19) -0.0030(19) -0.0054(19) C12 0.028(2) 0.018(2) 0.022(3) -0.0044(19) 0.0008(19) -0.0028(19) C13 0.031(3) 0.019(2) 0.023(2) -0.0015(19) -0.005(2) 0.002(2) C14 0.032(3) 0.021(2) 0.021(2) -0.001(2) 0.000(2) 0.000(2) C15 0.022(2) 0.020(2) 0.038(3) -0.005(2) 0.006(2) -0.0025(19) C16 0.025(2) 0.021(2) 0.024(2) 0.000(2) -0.0031(19) -0.0032(19) C20 0.050(5) 0.012(4) 0.047(4) 0.000 0.027(4) 0.000 C21 0.040(3) 0.026(3) 0.027(3) -0.010(2) 0.010(2) -0.012(2) C22 0.026(2) 0.030(3) 0.023(2) 0.002(2) 0.0026(19) -0.004(2) C23 0.026(3) 0.017(3) 0.025(3) 0.000 0.002(3) 0.000 O10 0.067(3) 0.134(5) 0.221(7) -0.156(5) 0.077(4) -0.064(3) O9B 0.159(5) 0.070(3) 0.081(4) 0.042(3) -0.085(4) -0.069(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 O1 C11 1.317(5) . ? O2 N17 1.217(4) . ? O3 N17 1.218(4) . ? O4 N18 1.223(5) . ? O5 N18 1.219(5) . ? O6 N19 1.208(4) . ? O7 N19 1.236(5) . ? O8 C20 1.326(8) . ? O11 N25 1.219(4) . ? N1 C2 1.350(5) . ? N1 C5 1.361(5) . ? N1 C6 1.468(5) . ? N3 C2 1.315(5) . ? N3 C4 1.364(5) . ? N8 C7 1.143(5) . ? N10 C9 1.138(6) . ? N17 C12 1.460(5) . ? N18 C14 1.464(5) . ? N19 C16 1.458(5) . ? N24 O9B 1.194(7) . ? N24 O10 1.208(6) . ? N24 C21 1.469(6) . ? N25 O11 1.219(4) 3 ? N25 C23 1.456(8) . ? C4 C5 1.366(6) . ? C4 C7 1.422(7) . ? C5 C9 1.418(6) . ? C11 C16 1.407(6) . ? C11 C12 1.411(6) . ? C12 C13 1.372(6) . ? C13 C14 1.372(6) . ? C14 C15 1.371(6) . ? C15 C16 1.373(6) . ? C20 C21 1.388(6) 3 ? C20 C21 1.388(6) . ? C21 C22 1.370(6) . ? C22 C23 1.371(5) . ? C23 C22 1.371(5) 3 ? 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 C2 N1 C5 105.8(3) . . ? C2 N1 C6 127.2(4) . . ? C5 N1 C6 127.0(4) . . ? C2 N3 C4 104.0(4) . . ? O2 N17 O3 122.6(4) . . ? O2 N17 C12 119.9(3) . . ? O3 N17 C12 117.5(3) . . ? O5 N18 O4 124.2(4) . . ? O5 N18 C14 117.4(4) . . ? O4 N18 C14 118.4(4) . . ? O6 N19 O7 123.3(4) . . ? O6 N19 C16 118.8(4) . . ? O7 N19 C16 117.9(4) . . ? O9B N24 O10 124.1(6) . . ? O9B N24 C21 118.0(5) . . ? O10 N24 C21 117.9(6) . . ? O11 N25 O11 123.9(5) . 3 ? O11 N25 C23 118.0(3) . . ? O11 N25 C23 118.0(3) 3 . ? N3 C2 N1 113.3(4) . . ? N3 C4 C5 110.6(4) . . ? N3 C4 C7 123.9(4) . . ? C5 C4 C7 125.5(4) . . ? N1 C5 C4 106.2(4) . . ? N1 C5 C9 124.6(4) . . ? C4 C5 C9 129.2(4) . . ? N8 C7 C4 175.5(5) . . ? N10 C9 C5 177.4(5) . . ? O1 C11 C16 123.8(4) . . ? O1 C11 C12 120.4(4) . . ? C16 C11 C12 115.7(4) . . ? C13 C12 C11 121.9(4) . . ? C13 C12 N17 116.2(4) . . ? C11 C12 N17 121.9(4) . . ? C12 C13 C14 119.1(4) . . ? C15 C14 C13 122.1(4) . . ? C15 C14 N18 119.6(4) . . ? C13 C14 N18 118.3(4) . . ? C14 C15 C16 118.2(4) . . ? C15 C16 C11 122.9(4) . . ? C15 C16 N19 116.8(4) . . ? C11 C16 N19 120.3(4) . . ? O8 C20 C21 122.0(3) . 3 ? O8 C20 C21 122.0(3) . . ? C21 C20 C21 116.0(6) 3 . ? C22 C21 C20 122.8(5) . . ? C22 C21 N24 116.5(5) . . ? C20 C21 N24 120.7(5) . . ? C21 C22 C23 118.3(5) . . ? C22 C23 C22 121.6(6) . 3 ? C22 C23 N25 119.2(3) . . ? C22 C23 N25 119.2(3) 3 . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 23.25 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.739 _refine_diff_density_min -0.685 _refine_diff_density_rms 0.062 data_2a _database_code_depnum_ccdc_archive 'CCDC 837940' #TrackingRef '- Protonated ILs CIFs 10-30-11.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H11 N5 O7' _chemical_formula_weight 325.25 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 Monoclinic _symmetry_space_group_name_H-M Cc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' 'x+1/2, y+1/2, z' 'x+1/2, -y+1/2, z+1/2' _cell_length_a 6.0755(19) _cell_length_b 15.089(5) _cell_length_c 14.771(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.949(5) _cell_angle_gamma 90.00 _cell_volume 1354.0(7) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 937 _cell_measurement_theta_min 2.70 _cell_measurement_theta_max 23.23 _exptl_crystal_description fragment _exptl_crystal_colour yellow _exptl_crystal_size_max 0.86 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.596 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 672 _exptl_absorpt_coefficient_mu 0.136 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8923 _exptl_absorpt_correction_T_max 0.9946 _exptl_absorpt_process_details 'SHELX SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 3030 _diffrn_reflns_av_R_equivalents 0.0147 _diffrn_reflns_av_sigmaI/netI 0.0191 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.70 _diffrn_reflns_theta_max 23.27 _reflns_number_total 1469 _reflns_number_gt 1459 _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^)+(0.0424P)^2^+0.2053P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.7(8) _refine_ls_number_reflns 1469 _refine_ls_number_parameters 213 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0230 _refine_ls_R_factor_gt 0.0228 _refine_ls_wR_factor_ref 0.0593 _refine_ls_wR_factor_gt 0.0590 _refine_ls_goodness_of_fit_ref 1.104 _refine_ls_restrained_S_all 1.103 _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 O1 O 0.1481(2) 0.38813(8) 0.10041(9) 0.0268(3) Uani 1 1 d . . . O2 O -0.0110(2) 0.21612(8) 0.11372(10) 0.0350(4) Uani 1 1 d . . . O3 O -0.0791(3) 0.19080(9) -0.02865(11) 0.0420(4) Uani 1 1 d . . . O4 O -0.7443(2) 0.36497(9) -0.11196(10) 0.0322(3) Uani 1 1 d . . . O5 O -0.7324(2) 0.50652(9) -0.08837(10) 0.0311(3) Uani 1 1 d . . . O6 O -0.0782(2) 0.63751(8) 0.03557(11) 0.0349(4) Uani 1 1 d . . . O7 O 0.1245(2) 0.56342(9) 0.12972(10) 0.0344(4) Uani 1 1 d . . . N1 N 0.7632(3) 0.40282(10) 0.27750(11) 0.0236(4) Uani 1 1 d . . . N3 N 0.4708(3) 0.44707(10) 0.20661(11) 0.0248(4) Uani 1 1 d . . . H3A H 0.354(4) 0.4429(13) 0.1728(16) 0.030 Uiso 1 1 d . . . N4 N -0.0775(3) 0.23894(10) 0.03837(12) 0.0277(4) Uani 1 1 d . . . N5 N -0.6542(3) 0.43160(10) -0.08015(11) 0.0227(4) Uani 1 1 d . . . N6 N -0.0216(3) 0.56740(10) 0.07130(11) 0.0228(4) Uani 1 1 d . . . C2 C 0.5774(3) 0.37523(12) 0.23649(12) 0.0230(4) Uani 1 1 d . . . C4 C 0.5903(3) 0.52180(12) 0.22887(13) 0.0255(4) Uani 1 1 d . . . H4A H 0.5510 0.5813 0.2154 0.050 Uiso 1 1 calc R . . C5 C 0.7735(3) 0.49450(12) 0.27340(14) 0.0258(4) Uani 1 1 d . . . H5A H 0.8877 0.5311 0.2974 0.031 Uiso 1 1 calc R . . C6 C 0.9302(4) 0.34444(15) 0.31706(15) 0.0341(5) Uani 1 1 d . . . H6A H 0.8604 0.3027 0.3585 0.051 Uiso 1 1 calc R . . H6B H 1.0396 0.3799 0.3504 0.051 Uiso 1 1 calc R . . H6C H 1.0028 0.3115 0.2688 0.051 Uiso 1 1 calc R . . C7 C 0.5032(3) 0.28213(12) 0.22800(14) 0.0303(5) Uani 1 1 d . . . H7A H 0.6246 0.2455 0.2063 0.045 Uiso 1 1 calc R . . H7B H 0.3792 0.2788 0.1848 0.045 Uiso 1 1 calc R . . H7C H 0.4566 0.2604 0.2872 0.045 Uiso 1 1 calc R . . C8 C -0.0340(3) 0.40082(12) 0.06248(12) 0.0198(4) Uani 1 1 d . . . C9 C -0.1659(3) 0.32894(11) 0.02665(13) 0.0205(4) Uani 1 1 d . . . C10 C -0.3609(3) 0.33700(12) -0.01924(12) 0.0219(4) Uani 1 1 d . . . H10A H -0.4362 0.2862 -0.0417 0.026 Uiso 1 1 calc R . . C11 C -0.4474(3) 0.42159(11) -0.03239(13) 0.0199(4) Uani 1 1 d . . . C12 C -0.3334(3) 0.49622(12) -0.00181(12) 0.0190(4) Uani 1 1 d . . . H12A H -0.3924 0.5537 -0.0121 0.023 Uiso 1 1 calc R . . C13 C -0.1357(3) 0.48633(12) 0.04313(12) 0.0194(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0203(7) 0.0239(7) 0.0360(8) -0.0008(5) -0.0094(6) 0.0010(6) O2 0.0356(8) 0.0254(8) 0.0434(10) 0.0115(6) -0.0133(7) 0.0011(6) O3 0.0483(10) 0.0244(8) 0.0527(10) -0.0144(7) -0.0129(7) 0.0107(6) O4 0.0273(7) 0.0295(7) 0.0395(8) -0.0078(6) -0.0123(6) -0.0010(6) O5 0.0276(7) 0.0254(7) 0.0400(9) 0.0024(6) -0.0063(6) 0.0087(6) O6 0.0372(9) 0.0158(7) 0.0514(9) 0.0049(6) -0.0072(7) -0.0015(6) O7 0.0313(8) 0.0283(8) 0.0430(9) -0.0033(6) -0.0147(8) -0.0049(6) N1 0.0215(9) 0.0281(8) 0.0210(8) 0.0011(7) -0.0047(6) 0.0000(7) N3 0.0217(9) 0.0284(9) 0.0242(9) -0.0016(7) -0.0019(7) 0.0000(8) N4 0.0221(9) 0.0189(8) 0.0419(10) -0.0001(8) -0.0061(7) 0.0013(7) N5 0.0190(9) 0.0262(10) 0.0229(8) -0.0008(7) -0.0029(7) 0.0025(7) N6 0.0192(9) 0.0207(9) 0.0284(9) -0.0017(6) -0.0006(8) -0.0022(7) C2 0.0214(10) 0.0285(10) 0.0192(10) 0.0005(8) -0.0016(8) 0.0008(9) C4 0.0273(11) 0.0228(10) 0.0264(10) -0.0003(8) -0.0014(9) 0.0007(9) C5 0.0287(11) 0.0264(9) 0.0221(9) -0.0044(9) -0.0006(8) -0.0050(9) C6 0.0287(11) 0.0358(12) 0.0375(12) 0.0034(9) -0.0121(9) 0.0015(9) C7 0.0277(11) 0.0272(11) 0.0358(11) 0.0000(8) -0.0066(9) -0.0023(9) C8 0.0176(11) 0.0213(10) 0.0205(10) 0.0003(7) -0.0007(8) -0.0003(8) C9 0.0200(10) 0.0153(9) 0.0263(10) 0.0020(7) -0.0003(8) 0.0014(7) C10 0.0214(10) 0.0183(9) 0.0259(10) -0.0027(8) -0.0022(8) -0.0018(8) C11 0.0176(10) 0.0223(10) 0.0199(9) -0.0004(7) 0.0004(8) 0.0018(8) C12 0.0214(10) 0.0159(9) 0.0196(9) 0.0010(7) 0.0016(8) 0.0003(8) C13 0.0205(10) 0.0152(9) 0.0224(10) -0.0031(7) 0.0017(8) -0.0023(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 O1 C8 1.247(2) . ? O2 N4 1.227(2) . ? O3 N4 1.228(2) . ? O4 N5 1.234(2) . ? O5 N5 1.231(2) . ? O6 N6 1.229(2) . ? O7 N6 1.229(2) . ? N1 C2 1.338(3) . ? N1 C5 1.386(2) . ? N1 C6 1.458(3) . ? N3 C2 1.334(2) . ? N3 C4 1.378(3) . ? N4 C9 1.469(2) . ? N5 C11 1.439(3) . ? N6 C13 1.463(2) . ? C2 C7 1.480(3) . ? C4 C5 1.348(3) . ? C8 C9 1.444(3) . ? C8 C13 1.457(3) . ? C9 C10 1.361(3) . ? C10 C11 1.393(3) . ? C11 C12 1.394(3) . ? C12 C13 1.371(3) . ? 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 C2 N1 C5 109.21(18) . . ? C2 N1 C6 124.70(16) . . ? C5 N1 C6 126.06(19) . . ? C2 N3 C4 109.56(18) . . ? O3 N4 O2 124.28(16) . . ? O3 N4 C9 117.00(17) . . ? O2 N4 C9 118.71(16) . . ? O5 N5 O4 122.86(18) . . ? O5 N5 C11 118.49(16) . . ? O4 N5 C11 118.64(15) . . ? O6 N6 O7 122.51(15) . . ? O6 N6 C13 118.02(17) . . ? O7 N6 C13 119.47(15) . . ? N3 C2 N1 107.35(16) . . ? N3 C2 C7 126.69(18) . . ? N1 C2 C7 125.95(17) . . ? C5 C4 N3 107.09(17) . . ? C4 C5 N1 106.79(19) . . ? O1 C8 C9 122.16(16) . . ? O1 C8 C13 126.47(16) . . ? C9 C8 C13 111.27(16) . . ? C10 C9 C8 126.07(16) . . ? C10 C9 N4 117.04(16) . . ? C8 C9 N4 116.86(16) . . ? C9 C10 C11 118.36(17) . . ? C10 C11 C12 120.72(18) . . ? C10 C11 N5 119.29(16) . . ? C12 C11 N5 119.97(16) . . ? C13 C12 C11 119.73(16) . . ? C12 C13 C8 123.82(16) . . ? C12 C13 N6 116.99(16) . . ? C8 C13 N6 119.18(17) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 23.27 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.111 _refine_diff_density_min -0.237 _refine_diff_density_rms 0.045 data_2b _database_code_depnum_ccdc_archive 'CCDC 837941' #TrackingRef '- Protonated ILs CIFs 10-30-11.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C5 H9 N3 O3' _chemical_formula_weight 159.15 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 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 7.8630(14) _cell_length_b 13.001(2) _cell_length_c 7.9711(14) _cell_angle_alpha 90.00 _cell_angle_beta 111.871(3) _cell_angle_gamma 90.00 _cell_volume 756.2(2) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 956 _cell_measurement_theta_min 3.13 _cell_measurement_theta_max 23.28 _exptl_crystal_description fragment _exptl_crystal_colour colorless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.398 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 336 _exptl_absorpt_coefficient_mu 0.116 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9638 _exptl_absorpt_correction_T_max 0.9931 _exptl_absorpt_process_details 'SHELX SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 3424 _diffrn_reflns_av_R_equivalents 0.0162 _diffrn_reflns_av_sigmaI/netI 0.0163 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 3.11 _diffrn_reflns_theta_max 23.28 _reflns_number_total 1092 _reflns_number_gt 947 _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^)+(0.0490P)^2^+0.2509P] 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 1092 _refine_ls_number_parameters 105 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0412 _refine_ls_R_factor_gt 0.0343 _refine_ls_wR_factor_ref 0.0918 _refine_ls_wR_factor_gt 0.0877 _refine_ls_goodness_of_fit_ref 1.068 _refine_ls_restrained_S_all 1.068 _refine_ls_shift/su_max 0.045 _refine_ls_shift/su_mean 0.003 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 O1 O 0.25364(18) 1.56243(11) 0.40884(19) 0.0492(4) Uani 1 1 d . . . O2 O 0.43216(18) 1.57380(10) 0.25831(18) 0.0437(4) Uani 1 1 d . . . O3 O 0.31264(17) 1.42781(9) 0.28164(19) 0.0418(4) Uani 1 1 d . . . N1 N 0.78620(19) 1.29400(10) 0.07419(18) 0.0297(4) Uani 1 1 d . . . N3 N 0.5653(2) 1.34081(11) 0.1539(2) 0.0347(4) Uani 1 1 d . . . H3A H 0.491(3) 1.3789(15) 0.199(3) 0.042 Uiso 1 1 d . . . N4 N 0.33347(19) 1.52291(11) 0.31726(19) 0.0313(4) Uani 1 1 d . . . C2 C 0.7212(2) 1.37186(13) 0.1405(2) 0.0283(4) Uani 1 1 d . . . C4 C 0.5300(3) 1.24107(14) 0.0934(3) 0.0386(5) Uani 1 1 d . . . H4A H 0.4275 1.2006 0.0878 0.046 Uiso 1 1 calc R . . C5 C 0.6687(3) 1.21178(13) 0.0436(2) 0.0345(5) Uani 1 1 d . . . H5A H 0.6826 1.1466 -0.0038 0.041 Uiso 1 1 calc R . . C6 C 0.9488(2) 1.29708(14) 0.0266(3) 0.0366(5) Uani 1 1 d . . . H6A H 1.0426 1.3405 0.1133 0.055 Uiso 1 1 calc R . . H6B H 0.9159 1.3255 -0.0953 0.055 Uiso 1 1 calc R . . H6C H 0.9970 1.2273 0.0300 0.055 Uiso 1 1 calc R . . C7 C 0.8026(3) 1.47527(13) 0.1871(3) 0.0386(5) Uani 1 1 d . . . H7A H 0.9294 1.4690 0.2731 0.058 Uiso 1 1 calc R . . H7B H 0.7315 1.5156 0.2420 0.058 Uiso 1 1 calc R . . H7C H 0.8010 1.5099 0.0774 0.058 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 O1 0.0454(8) 0.0552(9) 0.0534(9) -0.0046(7) 0.0259(7) 0.0148(7) O2 0.0471(8) 0.0385(8) 0.0488(8) 0.0040(6) 0.0217(7) -0.0075(6) O3 0.0440(8) 0.0296(7) 0.0571(9) -0.0047(6) 0.0248(7) -0.0047(6) N1 0.0314(8) 0.0285(8) 0.0297(8) 0.0017(6) 0.0120(6) 0.0003(6) N3 0.0364(9) 0.0354(9) 0.0377(9) -0.0013(7) 0.0200(7) -0.0001(7) N4 0.0260(8) 0.0347(9) 0.0297(8) 0.0020(6) 0.0062(7) 0.0050(6) C2 0.0307(9) 0.0290(9) 0.0253(9) 0.0016(7) 0.0103(7) 0.0017(7) C4 0.0422(11) 0.0340(10) 0.0433(11) -0.0015(8) 0.0202(9) -0.0098(8) C5 0.0439(11) 0.0242(9) 0.0357(10) -0.0010(7) 0.0152(9) -0.0043(8) C6 0.0341(10) 0.0372(10) 0.0429(11) -0.0002(8) 0.0195(9) 0.0023(8) C7 0.0412(11) 0.0325(10) 0.0436(11) -0.0057(8) 0.0177(9) -0.0029(8) _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 O1 N4 1.2379(19) . ? O2 N4 1.2379(19) . ? O3 N4 1.2656(18) . ? N1 C2 1.329(2) . ? N1 C5 1.374(2) . ? N1 C6 1.464(2) . ? N3 C2 1.333(2) . ? N3 C4 1.375(2) . ? C2 C7 1.476(2) . ? C4 C5 1.347(3) . ? 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 C2 N1 C5 109.29(14) . . ? C2 N1 C6 125.78(14) . . ? C5 N1 C6 124.75(15) . . ? C2 N3 C4 109.20(16) . . ? O2 N4 O1 121.95(15) . . ? O2 N4 O3 118.95(14) . . ? O1 N4 O3 119.09(15) . . ? N1 C2 N3 107.62(15) . . ? N1 C2 C7 126.81(15) . . ? N3 C2 C7 125.55(15) . . ? C5 C4 N3 106.88(17) . . ? C4 C5 N1 107.01(15) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 23.28 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.118 _refine_diff_density_min -0.259 _refine_diff_density_rms 0.038 data_19a _database_code_depnum_ccdc_archive 'CCDC 837942' #TrackingRef '- Protonated ILs CIFs 10-30-11.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '1,3-dimethylimidazolium picrate' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H11 N5 O7' _chemical_formula_weight 325.25 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.2105(15) _cell_length_b 9.615(2) _cell_length_c 10.265(2) _cell_angle_alpha 78.308(3) _cell_angle_beta 82.099(4) _cell_angle_gamma 85.773(4) _cell_volume 689.5(3) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 858 _cell_measurement_theta_min 2.67 _cell_measurement_theta_max 23.32 _exptl_crystal_description platelet _exptl_crystal_colour yellow _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.567 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 336 _exptl_absorpt_coefficient_mu 0.133 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9487 _exptl_absorpt_correction_T_max 0.9921 _exptl_absorpt_process_details 'SHELX SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 3229 _diffrn_reflns_av_R_equivalents 0.0191 _diffrn_reflns_av_sigmaI/netI 0.0290 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.04 _diffrn_reflns_theta_max 23.40 _reflns_number_total 1994 _reflns_number_gt 1635 _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^)+(0.0801P)^2^+0.2773P] 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 1994 _refine_ls_number_parameters 210 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0592 _refine_ls_R_factor_gt 0.0472 _refine_ls_wR_factor_ref 0.1305 _refine_ls_wR_factor_gt 0.1224 _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_restrained_S_all 1.044 _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 O1 O -0.1345(2) 0.63672(16) 0.96676(15) 0.0289(4) Uani 1 1 d . . . O2 O -0.1150(2) 0.47629(19) 0.78108(16) 0.0387(5) Uani 1 1 d . . . O3 O -0.2068(3) 0.26394(18) 0.84279(17) 0.0474(6) Uani 1 1 d . . . O4 O -0.6044(3) 0.11208(19) 1.23788(17) 0.0412(5) Uani 1 1 d . . . O5 O -0.6613(3) 0.2407(2) 1.39089(17) 0.0428(5) Uani 1 1 d . . . O6 O -0.3258(3) 0.6688(2) 1.34202(19) 0.0619(7) Uani 1 1 d . . . O7 O -0.3082(3) 0.7938(2) 1.1424(2) 0.0597(6) Uani 1 1 d . . . N1 N 0.1336(3) 0.7816(2) 0.57182(19) 0.0289(5) Uani 1 1 d . . . N3 N 0.0887(3) 0.9061(2) 0.72691(18) 0.0269(5) Uani 1 1 d . . . N4 N -0.1919(3) 0.3827(2) 0.86571(18) 0.0256(5) Uani 1 1 d . . . N5 N -0.5851(3) 0.2199(2) 1.2813(2) 0.0319(5) Uani 1 1 d . . . N6 N -0.3190(3) 0.6801(2) 1.2205(2) 0.0352(5) Uani 1 1 d . . . C2 C 0.0528(3) 0.7841(2) 0.6953(2) 0.0247(5) Uani 1 1 d . . . H2A H -0.0187 0.7110 0.7518 0.030 Uiso 1 1 calc R . . C4 C 0.1954(3) 0.9835(3) 0.6197(2) 0.0335(6) Uani 1 1 d . . . H4A H 0.2412 1.0748 0.6150 0.040 Uiso 1 1 calc R . . C5 C 0.2232(3) 0.9071(3) 0.5231(2) 0.0349(7) Uani 1 1 d . . . H5A H 0.2920 0.9341 0.4369 0.042 Uiso 1 1 calc R . . C6 C 0.1225(4) 0.6671(3) 0.4986(3) 0.0421(7) Uani 1 1 d . . . H6A H 0.1106 0.5763 0.5622 0.063 Uiso 1 1 calc R . . H6B H 0.2364 0.6627 0.4351 0.063 Uiso 1 1 calc R . . H6C H 0.0130 0.6858 0.4496 0.063 Uiso 1 1 calc R . . C7 C 0.0215(4) 0.9492(3) 0.8548(3) 0.0368(7) Uani 1 1 d . . . H7A H -0.0426 0.8707 0.9163 0.055 Uiso 1 1 calc R . . H7B H -0.0660 1.0321 0.8395 0.055 Uiso 1 1 calc R . . H7C H 0.1281 0.9737 0.8941 0.055 Uiso 1 1 calc R . . C8 C -0.2372(3) 0.5435(2) 1.0345(2) 0.0232(5) Uani 1 1 d . . . C9 C -0.2736(3) 0.4116(2) 0.9952(2) 0.0222(5) Uani 1 1 d . . . C10 C -0.3850(3) 0.3091(2) 1.0742(2) 0.0238(5) Uani 1 1 d . . . H10A H -0.4054 0.2259 1.0427 0.029 Uiso 1 1 calc R . . C11 C -0.4669(3) 0.3273(2) 1.1992(2) 0.0245(5) Uani 1 1 d . . . C12 C -0.4407(3) 0.4489(3) 1.2476(2) 0.0263(6) Uani 1 1 d . . . H12A H -0.4967 0.4598 1.3345 0.032 Uiso 1 1 calc R . . C13 C -0.3333(3) 0.5520(2) 1.1679(2) 0.0248(5) 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 O1 0.0295(9) 0.0268(9) 0.0297(9) -0.0028(7) -0.0006(7) -0.0098(7) O2 0.0493(11) 0.0387(11) 0.0267(9) -0.0049(8) 0.0070(8) -0.0192(9) O3 0.0773(15) 0.0281(10) 0.0362(10) -0.0139(8) 0.0124(9) -0.0138(10) O4 0.0504(12) 0.0335(10) 0.0397(10) -0.0028(9) -0.0016(9) -0.0219(9) O5 0.0457(11) 0.0526(12) 0.0262(10) -0.0009(9) 0.0076(8) -0.0190(9) O6 0.0968(18) 0.0605(14) 0.0372(12) -0.0251(10) -0.0109(11) -0.0142(13) O7 0.0901(17) 0.0352(12) 0.0542(13) -0.0173(10) 0.0138(11) -0.0240(11) N1 0.0311(11) 0.0306(12) 0.0254(11) -0.0041(9) -0.0032(9) -0.0079(9) N3 0.0286(11) 0.0238(11) 0.0290(11) -0.0043(9) -0.0057(8) -0.0054(9) N4 0.0258(11) 0.0257(11) 0.0254(10) -0.0040(9) -0.0038(8) -0.0038(9) N5 0.0307(12) 0.0381(13) 0.0253(11) 0.0013(9) -0.0032(9) -0.0117(10) N6 0.0363(13) 0.0361(13) 0.0362(13) -0.0130(11) -0.0016(9) -0.0099(10) C2 0.0249(13) 0.0261(13) 0.0228(12) -0.0012(10) -0.0027(10) -0.0100(10) C4 0.0353(15) 0.0282(14) 0.0363(14) -0.0003(11) -0.0051(11) -0.0135(11) C5 0.0329(15) 0.0382(15) 0.0300(14) 0.0044(12) -0.0018(11) -0.0128(12) C6 0.0566(18) 0.0423(16) 0.0308(14) -0.0152(12) -0.0021(12) -0.0095(14) C7 0.0463(17) 0.0292(14) 0.0375(14) -0.0132(12) -0.0019(12) -0.0062(12) C8 0.0180(12) 0.0240(12) 0.0275(12) -0.0008(10) -0.0071(9) -0.0031(10) C9 0.0198(12) 0.0258(13) 0.0214(12) -0.0035(10) -0.0039(9) -0.0031(10) C10 0.0223(12) 0.0246(12) 0.0253(12) -0.0033(10) -0.0080(10) -0.0025(10) C11 0.0194(12) 0.0282(13) 0.0239(12) 0.0028(10) -0.0033(9) -0.0091(10) C12 0.0241(13) 0.0341(14) 0.0220(12) -0.0071(10) -0.0052(10) -0.0022(11) C13 0.0236(12) 0.0270(13) 0.0264(12) -0.0083(10) -0.0050(10) -0.0065(10) _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 O1 C8 1.241(3) . ? O2 N4 1.223(2) . ? O3 N4 1.227(2) . ? O4 N5 1.232(3) . ? O5 N5 1.229(3) . ? O6 N6 1.224(3) . ? O7 N6 1.218(3) . ? N1 C2 1.324(3) . ? N1 C5 1.381(3) . ? N1 C6 1.465(3) . ? N3 C2 1.331(3) . ? N3 C4 1.370(3) . ? N3 C7 1.465(3) . ? N4 C9 1.450(3) . ? N5 C11 1.444(3) . ? N6 C13 1.458(3) . ? C4 C5 1.335(4) . ? C8 C9 1.457(3) . ? C8 C13 1.462(3) . ? C9 C10 1.374(3) . ? C10 C11 1.376(3) . ? C11 C12 1.393(3) . ? C12 C13 1.365(3) . ? 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 C2 N1 C5 108.2(2) . . ? C2 N1 C6 125.5(2) . . ? C5 N1 C6 126.3(2) . . ? C2 N3 C4 108.49(19) . . ? C2 N3 C7 124.99(19) . . ? C4 N3 C7 126.52(19) . . ? O2 N4 O3 121.48(18) . . ? O2 N4 C9 120.28(18) . . ? O3 N4 C9 118.21(18) . . ? O5 N5 O4 123.4(2) . . ? O5 N5 C11 118.3(2) . . ? O4 N5 C11 118.26(19) . . ? O7 N6 O6 123.1(2) . . ? O7 N6 C13 118.6(2) . . ? O6 N6 C13 118.2(2) . . ? N1 C2 N3 108.59(19) . . ? C5 C4 N3 107.4(2) . . ? C4 C5 N1 107.3(2) . . ? O1 C8 C9 125.4(2) . . ? O1 C8 C13 123.1(2) . . ? C9 C8 C13 111.46(19) . . ? C10 C9 N4 115.94(19) . . ? C10 C9 C8 123.9(2) . . ? N4 C9 C8 120.20(19) . . ? C9 C10 C11 119.8(2) . . ? C10 C11 C12 121.3(2) . . ? C10 C11 N5 119.6(2) . . ? C12 C11 N5 119.1(2) . . ? C13 C12 C11 118.8(2) . . ? C12 C13 N6 116.5(2) . . ? C12 C13 C8 124.7(2) . . ? N6 C13 C8 118.78(19) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 23.40 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.311 _refine_diff_density_min -0.396 _refine_diff_density_rms 0.062 data_16a _database_code_depnum_ccdc_archive 'CCDC 837943' #TrackingRef '- Protonated ILs CIFs 10-30-11.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H7 N7 O11' _chemical_formula_weight 401.23 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 Monoclinic _symmetry_space_group_name_H-M P2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 6.2866(10) _cell_length_b 11.646(2) _cell_length_c 10.3067(17) _cell_angle_alpha 90.00 _cell_angle_beta 93.367(3) _cell_angle_gamma 90.00 _cell_volume 753.3(2) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 847 _cell_measurement_theta_min 2.64 _cell_measurement_theta_max 23.28 _exptl_crystal_description needle _exptl_crystal_colour yellow _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.769 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 408 _exptl_absorpt_coefficient_mu 0.163 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3527 _diffrn_reflns_av_R_equivalents 0.0143 _diffrn_reflns_av_sigmaI/netI 0.0226 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 1.98 _diffrn_reflns_theta_max 23.29 _reflns_number_total 2075 _reflns_number_gt 1985 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0505P)^2^+1.6312P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.1(10) _refine_ls_number_reflns 2075 _refine_ls_number_parameters 257 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0255 _refine_ls_R_factor_gt 0.0236 _refine_ls_wR_factor_ref 0.0581 _refine_ls_wR_factor_gt 0.0558 _refine_ls_goodness_of_fit_ref 0.506 _refine_ls_restrained_S_all 0.506 _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 N1 N -0.1651(3) 0.60613(16) 0.09333(17) 0.0237(4) Uani 1 1 d . . . N3 N -0.4831(3) 0.68284(16) 0.13296(17) 0.0221(4) Uani 1 1 d . . . N4 N -0.3528(3) 0.54014(18) 0.28512(17) 0.0253(4) Uani 1 1 d . . . N5 N -0.5195(3) 0.81700(18) -0.04609(18) 0.0297(5) Uani 1 1 d . . . N6 N 0.3139(3) 0.52962(18) 0.75480(18) 0.0302(5) Uani 1 1 d . . . N7 N 0.9122(3) 0.28100(18) 0.67537(19) 0.0278(5) Uani 1 1 d . . . N8 N 0.2866(3) 0.26603(17) 0.37381(18) 0.0282(5) Uani 1 1 d . . . O1 O -0.5096(3) 0.55460(14) 0.34677(15) 0.0370(4) Uani 1 1 d . . . H1 H 0.068(5) 0.416(3) 0.441(3) 0.055 Uiso 1 1 d . . . O2 O -0.2097(3) 0.47094(15) 0.31256(16) 0.0359(4) Uani 1 1 d . . . O3 O -0.7022(3) 0.83721(16) -0.01866(17) 0.0411(5) Uani 1 1 d . . . O4 O -0.4261(3) 0.86681(15) -0.13084(16) 0.0403(4) Uani 1 1 d . . . O5 O 0.1092(2) 0.45147(14) 0.51987(15) 0.0288(4) Uani 1 1 d . . . O6 O 0.1827(3) 0.59758(17) 0.70963(18) 0.0470(5) Uani 1 1 d . . . O7 O 0.3756(3) 0.52587(17) 0.87006(15) 0.0416(4) Uani 1 1 d . . . O8 O 1.0027(2) 0.32548(15) 0.77169(15) 0.0334(4) Uani 1 1 d . . . O9 O 0.9888(3) 0.20383(14) 0.61185(17) 0.0343(4) Uani 1 1 d . . . C2 C -0.3344(3) 0.6092(2) 0.1703(2) 0.0217(5) Uani 1 1 d . . . C4 C -0.4031(4) 0.72979(19) 0.0267(2) 0.0225(5) Uani 1 1 d . . . C5 C -0.2088(3) 0.6852(2) -0.0003(2) 0.0246(5) Uani 1 1 d . . . H5A H -0.1234 0.7055 -0.0698 0.030 Uiso 1 1 calc R . . C6 C 0.0338(3) 0.5390(2) 0.1055(2) 0.0322(5) Uani 1 1 d . . . H6A H 0.1226 0.5581 0.0335 0.048 Uiso 1 1 calc R . . H6B H 0.0000 0.4569 0.1029 0.048 Uiso 1 1 calc R . . H6C H 0.1112 0.5574 0.1882 0.048 Uiso 1 1 calc R . . C7 C 0.2988(3) 0.40768(19) 0.5548(2) 0.0221(5) Uani 1 1 d . . . C8 C 0.4093(3) 0.44646(19) 0.6683(2) 0.0239(5) Uani 1 1 d . . . C9 C 0.6083(3) 0.4064(2) 0.7075(2) 0.0246(5) Uani 1 1 d . . . H9A H 0.6805 0.4348 0.7845 0.030 Uiso 1 1 calc R . . C10 C 0.7014(3) 0.3242(2) 0.6328(2) 0.0232(5) Uani 1 1 d . . . O10 O 0.3623(3) 0.18044(16) 0.32710(17) 0.0415(5) Uani 1 1 d . . . O11 O 0.1184(2) 0.31016(15) 0.32940(15) 0.0341(4) Uani 1 1 d . . . C11 C 0.5981(3) 0.2775(2) 0.5232(2) 0.0227(5) Uani 1 1 d . . . H11A H 0.6622 0.2187 0.4749 0.027 Uiso 1 1 calc R . . C12 C 0.3978(3) 0.3196(2) 0.4865(2) 0.0222(5) 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 N1 0.0180(9) 0.0238(11) 0.0290(10) -0.0051(9) -0.0006(7) -0.0004(8) N3 0.0212(9) 0.0200(10) 0.0247(9) -0.0036(8) -0.0014(7) 0.0012(8) N4 0.0292(11) 0.0197(10) 0.0267(9) -0.0017(9) -0.0020(9) -0.0035(10) N5 0.0352(12) 0.0290(12) 0.0244(10) -0.0006(9) -0.0012(9) 0.0038(10) N6 0.0269(11) 0.0290(11) 0.0352(11) -0.0050(10) 0.0067(9) -0.0030(9) N7 0.0217(10) 0.0288(12) 0.0327(11) 0.0104(10) 0.0005(8) -0.0012(9) N8 0.0276(11) 0.0269(12) 0.0298(11) -0.0002(9) 0.0009(8) 0.0011(9) O1 0.0482(11) 0.0289(11) 0.0354(9) 0.0041(8) 0.0165(8) 0.0026(8) O2 0.0320(9) 0.0312(10) 0.0431(10) 0.0096(8) -0.0100(7) 0.0029(8) O3 0.0328(10) 0.0496(12) 0.0407(10) 0.0066(8) 0.0022(8) 0.0175(8) O4 0.0490(11) 0.0381(11) 0.0342(9) 0.0116(8) 0.0047(8) 0.0036(8) O5 0.0229(8) 0.0312(9) 0.0320(9) 0.0006(8) -0.0021(7) 0.0065(7) O6 0.0450(11) 0.0413(12) 0.0541(12) -0.0083(10) -0.0021(9) 0.0186(10) O7 0.0456(10) 0.0504(12) 0.0289(9) -0.0088(9) 0.0042(8) 0.0019(9) O8 0.0260(8) 0.0419(11) 0.0314(9) 0.0048(8) -0.0057(7) -0.0017(8) O9 0.0270(9) 0.0303(11) 0.0457(10) 0.0018(8) 0.0022(8) 0.0077(7) C2 0.0213(11) 0.0196(12) 0.0241(11) -0.0019(9) -0.0003(9) -0.0027(10) C4 0.0232(12) 0.0193(11) 0.0247(12) -0.0014(9) -0.0005(9) -0.0004(9) C5 0.0237(12) 0.0259(12) 0.0242(11) -0.0002(10) 0.0012(9) -0.0030(10) C6 0.0194(11) 0.0325(14) 0.0445(13) -0.0007(13) -0.0009(10) 0.0040(11) C7 0.0206(11) 0.0193(12) 0.0265(11) 0.0070(10) 0.0021(9) -0.0006(9) C8 0.0265(12) 0.0196(12) 0.0262(12) 0.0018(10) 0.0065(9) -0.0013(10) C9 0.0242(11) 0.0254(13) 0.0243(11) 0.0070(10) 0.0007(9) -0.0066(10) C10 0.0201(11) 0.0207(12) 0.0288(12) 0.0077(10) 0.0012(9) -0.0012(9) O10 0.0459(11) 0.0332(11) 0.0439(10) -0.0124(9) -0.0093(8) 0.0116(9) O11 0.0268(9) 0.0400(11) 0.0343(9) -0.0014(8) -0.0078(7) 0.0067(8) C11 0.0240(11) 0.0188(11) 0.0255(12) 0.0059(9) 0.0034(9) 0.0003(10) C12 0.0234(11) 0.0215(11) 0.0217(11) 0.0038(9) 0.0006(9) -0.0043(10) _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 N1 C5 1.350(3) . ? N1 C2 1.365(3) . ? N1 C6 1.474(3) . ? N3 C2 1.310(3) . ? N3 C4 1.348(3) . ? N4 O1 1.216(2) . ? N4 O2 1.228(3) . ? N4 C2 1.441(3) . ? N5 O3 1.221(2) . ? N5 O4 1.227(2) . ? N5 C4 1.437(3) . ? N6 O6 1.216(3) . ? N6 O7 1.229(2) . ? N6 C8 1.468(3) . ? N7 O9 1.227(3) . ? N7 O8 1.229(3) . ? N7 C10 1.461(3) . ? N8 O10 1.216(3) . ? N8 O11 1.239(2) . ? N8 C12 1.459(3) . ? O5 C7 1.326(3) . ? C4 C5 1.370(3) . ? C7 C8 1.400(3) . ? C7 C12 1.410(3) . ? C8 C9 1.374(3) . ? C9 C10 1.381(3) . ? C10 C11 1.380(3) . ? C11 C12 1.384(3) . ? 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 C5 N1 C2 105.35(17) . . ? C5 N1 C6 123.96(18) . . ? C2 N1 C6 130.61(19) . . ? C2 N3 C4 102.16(18) . . ? O1 N4 O2 125.2(2) . . ? O1 N4 C2 117.31(19) . . ? O2 N4 C2 117.53(19) . . ? O3 N5 O4 124.7(2) . . ? O3 N5 C4 118.19(19) . . ? O4 N5 C4 117.07(19) . . ? O6 N6 O7 124.2(2) . . ? O6 N6 C8 119.27(18) . . ? O7 N6 C8 116.54(19) . . ? O9 N7 O8 124.19(19) . . ? O9 N7 C10 117.98(19) . . ? O8 N7 C10 117.8(2) . . ? O10 N8 O11 122.62(19) . . ? O10 N8 C12 119.01(18) . . ? O11 N8 C12 118.37(19) . . ? N3 C2 N1 114.4(2) . . ? N3 C2 N4 121.10(19) . . ? N1 C2 N4 124.47(19) . . ? N3 C4 C5 113.0(2) . . ? N3 C4 N5 120.5(2) . . ? C5 C4 N5 126.5(2) . . ? N1 C5 C4 105.09(18) . . ? O5 C7 C8 119.8(2) . . ? O5 C7 C12 124.07(19) . . ? C8 C7 C12 116.11(19) . . ? C9 C8 C7 122.4(2) . . ? C9 C8 N6 116.27(19) . . ? C7 C8 N6 121.33(19) . . ? C8 C9 C10 118.7(2) . . ? C11 C10 C9 122.4(2) . . ? C11 C10 N7 119.0(2) . . ? C9 C10 N7 118.5(2) . . ? C10 C11 C12 117.5(2) . . ? C11 C12 C7 122.86(19) . . ? C11 C12 N8 116.9(2) . . ? C7 C12 N8 120.23(18) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 23.29 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.100 _refine_diff_density_min -0.181 _refine_diff_density_rms 0.034 data_1b _database_code_depnum_ccdc_archive 'CCDC 837944' #TrackingRef '- Protonated ILs CIFs 10-30-11.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '1-methyl-3-H-imidazolium nitrate' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C4 H7 N3 O3' _chemical_formula_weight 145.13 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 Monoclinic _symmetry_space_group_name_H-M P2(1)/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 8.957(7) _cell_length_b 9.917(7) _cell_length_c 7.143(6) _cell_angle_alpha 90.00 _cell_angle_beta 96.046(12) _cell_angle_gamma 90.00 _cell_volume 630.9(8) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 862 _cell_measurement_theta_min 2.29 _cell_measurement_theta_max 23.20 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.88 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.528 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 304 _exptl_absorpt_coefficient_mu 0.131 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8934 _exptl_absorpt_correction_T_max 0.9883 _exptl_absorpt_process_details 'SHELX SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 2862 _diffrn_reflns_av_R_equivalents 0.0224 _diffrn_reflns_av_sigmaI/netI 0.0223 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 2.29 _diffrn_reflns_theta_max 23.34 _reflns_number_total 906 _reflns_number_gt 773 _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^)+(0.0521P)^2^+0.3409P] 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 906 _refine_ls_number_parameters 95 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0415 _refine_ls_R_factor_gt 0.0347 _refine_ls_wR_factor_ref 0.0929 _refine_ls_wR_factor_gt 0.0880 _refine_ls_goodness_of_fit_ref 0.985 _refine_ls_restrained_S_all 0.985 _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 N1 N 0.19518(16) 0.65742(14) 0.2245(2) 0.0206(4) Uani 1 1 d . . . N3 N 0.38338(18) 0.77845(15) 0.1626(2) 0.0249(4) Uani 1 1 d . . . H3A H 0.471(2) 0.802(2) 0.123(3) 0.030 Uiso 1 1 d . . . C5 C 0.1560(2) 0.78965(17) 0.2460(3) 0.0238(5) Uani 1 1 d . . . H5A H 0.0632 0.8218 0.2818 0.029 Uiso 1 1 calc R . . C4 C 0.2736(2) 0.86564(18) 0.2072(2) 0.0258(5) Uani 1 1 d . . . H4A H 0.2793 0.9613 0.2101 0.031 Uiso 1 1 calc R . . C2 C 0.3338(2) 0.65355(18) 0.1740(2) 0.0242(5) Uani 1 1 d . . . H2A H 0.3882 0.5742 0.1501 0.029 Uiso 1 1 calc R . . C6 C 0.0972(2) 0.54201(17) 0.2461(3) 0.0276(5) Uani 1 1 d . . . H6A H 0.1304 0.4654 0.1743 0.041 Uiso 1 1 calc R . . H6B H -0.0062 0.5656 0.1989 0.041 Uiso 1 1 calc R . . H6C H 0.1016 0.5175 0.3795 0.041 Uiso 1 1 calc R . . N4 N 0.71807(18) 0.75521(15) 0.0000(2) 0.0263(4) Uani 1 1 d . . . O1 O 0.64177(14) 0.85915(12) 0.02792(19) 0.0327(4) Uani 1 1 d . . . O2 O 0.84585(15) 0.76803(14) -0.0507(2) 0.0368(4) Uani 1 1 d . . . O3 O 0.66295(16) 0.64208(13) 0.02323(19) 0.0365(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0206(8) 0.0212(8) 0.0204(8) 0.0002(6) 0.0036(6) 0.0000(6) N3 0.0212(9) 0.0295(9) 0.0246(9) -0.0011(6) 0.0055(7) -0.0045(7) C5 0.0237(10) 0.0210(10) 0.0270(11) 0.0006(8) 0.0046(8) 0.0033(8) C4 0.0295(11) 0.0208(10) 0.0276(11) -0.0001(8) 0.0046(8) -0.0001(8) C2 0.0231(10) 0.0251(10) 0.0247(10) -0.0020(7) 0.0044(8) 0.0016(8) C6 0.0280(11) 0.0223(10) 0.0332(11) 0.0003(8) 0.0066(8) -0.0053(8) N4 0.0277(10) 0.0282(10) 0.0235(9) -0.0021(7) 0.0059(7) -0.0028(7) O1 0.0280(8) 0.0232(7) 0.0489(9) -0.0006(6) 0.0139(6) 0.0008(6) O2 0.0256(8) 0.0423(9) 0.0453(10) -0.0073(6) 0.0172(7) -0.0044(6) O3 0.0452(9) 0.0221(8) 0.0445(9) 0.0003(6) 0.0156(7) -0.0067(6) _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 N1 C2 1.330(3) . ? N1 C5 1.370(2) . ? N1 C6 1.460(2) . ? N3 C2 1.321(2) . ? N3 C4 1.372(2) . ? C5 C4 1.347(3) . ? N4 O2 1.243(2) . ? N4 O3 1.244(2) . ? N4 O1 1.264(2) . ? 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 C2 N1 C5 108.38(15) . . ? C2 N1 C6 126.51(15) . . ? C5 N1 C6 125.06(15) . . ? C2 N3 C4 108.84(16) . . ? C4 C5 N1 107.30(16) . . ? C5 C4 N3 106.86(17) . . ? N3 C2 N1 108.61(15) . . ? O2 N4 O3 121.45(15) . . ? O2 N4 O1 119.49(15) . . ? O3 N4 O1 119.06(16) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 23.34 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.169 _refine_diff_density_min -0.322 _refine_diff_density_rms 0.064 # Attachment '- Protonated ILs CIFs 10-30-11.cif' data_1a _database_code_depnum_ccdc_archive 'CCDC 837945' #TrackingRef '- Protonated ILs CIFs 10-30-11.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '1-methyl-3-H-imidazolium picrate' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H9 N5 O7' _chemical_formula_weight 311.22 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 Monoclinic _symmetry_space_group_name_H-M P2(1)/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 8.018(2) _cell_length_b 5.8847(15) _cell_length_c 27.215(7) _cell_angle_alpha 90.00 _cell_angle_beta 94.798(5) _cell_angle_gamma 90.00 _cell_volume 1279.7(6) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 720 _cell_measurement_theta_min 2.85 _cell_measurement_theta_max 23.19 _exptl_crystal_description needle _exptl_crystal_colour yellow _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.615 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 640 _exptl_absorpt_coefficient_mu 0.139 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9438 _exptl_absorpt_correction_T_max 0.9944 _exptl_absorpt_process_details 'SHELX SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 5553 _diffrn_reflns_av_R_equivalents 0.0509 _diffrn_reflns_av_sigmaI/netI 0.0585 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 2.55 _diffrn_reflns_theta_max 23.31 _reflns_number_total 1841 _reflns_number_gt 1352 _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^)+(0.0396P)^2^+1.6319P] 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 1841 _refine_ls_number_parameters 203 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0909 _refine_ls_R_factor_gt 0.0580 _refine_ls_wR_factor_ref 0.1216 _refine_ls_wR_factor_gt 0.1107 _refine_ls_goodness_of_fit_ref 1.072 _refine_ls_restrained_S_all 1.072 _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 N1 N 0.6145(3) 0.6182(5) 0.15321(11) 0.0229(7) Uani 1 1 d . . . H3A H 0.435(4) 1.016(7) 0.1108(13) 0.027 Uiso 1 1 d . . . N3 N 0.4943(4) 0.9021(6) 0.11562(12) 0.0272(8) Uani 1 1 d . . . C2 C 0.5244(4) 0.8042(6) 0.15875(14) 0.0258(9) Uani 1 1 d . . . H2A H 0.4877 0.8577 0.1890 0.031 Uiso 1 1 calc R . . C4 C 0.5656(4) 0.7766(6) 0.08072(14) 0.0257(9) Uani 1 1 d . . . H4A H 0.5623 0.8090 0.0465 0.031 Uiso 1 1 calc R . . C5 C 0.6417(4) 0.5975(6) 0.10423(13) 0.0237(9) Uani 1 1 d . . . H5A H 0.7024 0.4800 0.0897 0.028 Uiso 1 1 calc R . . C6 C 0.6679(5) 0.4585(6) 0.19255(13) 0.0325(10) Uani 1 1 d . . . H6A H 0.6832 0.5399 0.2240 0.049 Uiso 1 1 calc R . . H6B H 0.7740 0.3880 0.1854 0.049 Uiso 1 1 calc R . . H6C H 0.5825 0.3406 0.1946 0.049 Uiso 1 1 calc R . . O1 O 0.3036(3) 1.2372(4) 0.14343(9) 0.0272(7) Uani 1 1 d . . . O2 O 0.3462(4) 1.2134(5) 0.04609(9) 0.0398(8) Uani 1 1 d . . . O3 O 0.2338(4) 1.4661(5) -0.00180(10) 0.0619(11) Uani 1 1 d . . . O4 O -0.0651(4) 2.0910(5) 0.05176(10) 0.0411(8) Uani 1 1 d . . . O5 O -0.1250(3) 2.1162(5) 0.12755(10) 0.0377(7) Uani 1 1 d . . . O6 O 0.3022(4) 1.5247(6) 0.23920(10) 0.0566(9) Uani 1 1 d . . . O7 O 0.0701(4) 1.3492(7) 0.23210(11) 0.0674(11) Uani 1 1 d . . . N4 N 0.2625(4) 1.3861(5) 0.03918(11) 0.0275(8) Uani 1 1 d . . . N5 N -0.0566(4) 2.0217(5) 0.09410(12) 0.0259(7) Uani 1 1 d . . . N6 N 0.1739(4) 1.4729(5) 0.21590(11) 0.0278(8) Uani 1 1 d . . . C8 C 0.2237(4) 1.4128(6) 0.12943(13) 0.0218(9) Uani 1 1 d . . . C9 C 0.1955(4) 1.5013(6) 0.08043(13) 0.0204(8) Uani 1 1 d . . . C10 C 0.1055(4) 1.6978(6) 0.06939(13) 0.0222(9) Uani 1 1 d . . . H10 H 0.0906 1.7506 0.0363 0.027 Uiso 1 1 calc R . . C11 C 0.0379(4) 1.8159(6) 0.10622(13) 0.0207(9) Uani 1 1 d . . . C12 C 0.0569(4) 1.7452(6) 0.15497(13) 0.0222(9) Uani 1 1 d . . . H12 H 0.0093 1.8280 0.1803 0.027 Uiso 1 1 calc R . . C13 C 0.1466(4) 1.5519(6) 0.16485(12) 0.0199(8) 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 N1 0.0232(17) 0.0187(16) 0.0267(18) 0.0017(15) 0.0012(14) 0.0048(14) N3 0.0288(19) 0.0222(18) 0.030(2) 0.0004(17) 0.0005(16) 0.0060(15) C2 0.027(2) 0.025(2) 0.026(2) -0.0065(19) 0.0041(18) 0.0033(18) C4 0.026(2) 0.028(2) 0.023(2) -0.0030(19) 0.0052(18) 0.0055(18) C5 0.023(2) 0.024(2) 0.025(2) -0.0057(19) 0.0056(17) 0.0044(17) C6 0.037(2) 0.030(2) 0.030(2) 0.0022(19) 0.0015(19) 0.0112(19) O1 0.0318(15) 0.0234(15) 0.0261(15) 0.0021(12) 0.0016(12) 0.0120(12) O2 0.0571(18) 0.0335(17) 0.0297(16) -0.0009(13) 0.0080(14) 0.0274(15) O3 0.106(3) 0.061(2) 0.0206(17) 0.0128(16) 0.0172(17) 0.051(2) O4 0.0555(19) 0.0326(16) 0.0353(18) 0.0123(14) 0.0044(15) 0.0179(14) O5 0.0417(17) 0.0325(16) 0.0398(17) -0.0047(15) 0.0087(15) 0.0185(14) O6 0.061(2) 0.072(2) 0.0336(18) 0.0066(17) -0.0186(17) -0.0153(19) O7 0.050(2) 0.109(3) 0.044(2) 0.035(2) 0.0073(17) -0.011(2) N4 0.0329(19) 0.0258(19) 0.024(2) 0.0001(16) 0.0056(16) 0.0088(16) N5 0.0272(17) 0.0216(18) 0.029(2) 0.0022(17) 0.0033(15) 0.0037(15) N6 0.032(2) 0.0254(18) 0.026(2) 0.0016(16) 0.0043(17) 0.0079(16) C8 0.021(2) 0.019(2) 0.025(2) -0.0015(17) -0.0020(17) 0.0015(16) C9 0.023(2) 0.0176(19) 0.021(2) -0.0030(17) 0.0044(16) 0.0049(16) C10 0.023(2) 0.025(2) 0.018(2) 0.0044(17) -0.0011(17) -0.0019(17) C11 0.021(2) 0.0161(19) 0.025(2) -0.0011(17) 0.0009(17) 0.0028(16) C12 0.020(2) 0.022(2) 0.026(2) -0.0062(18) 0.0056(17) 0.0023(16) C13 0.026(2) 0.022(2) 0.0122(19) 0.0012(16) -0.0002(16) -0.0010(16) _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 N1 C2 1.327(4) . ? N1 C5 1.374(4) . ? N1 C6 1.462(4) . ? N3 C2 1.312(5) . ? N3 C4 1.365(5) . ? C4 C5 1.352(5) . ? O1 C8 1.258(4) . ? O2 N4 1.224(4) . ? O3 N4 1.215(4) . ? O4 N5 1.219(4) . ? O5 N5 1.233(4) . ? O6 N6 1.202(4) . ? O7 N6 1.216(4) . ? N4 C9 1.452(4) . ? N5 C11 1.452(4) . ? N6 C13 1.464(4) . ? C8 C9 1.432(5) . ? C8 C13 1.442(5) . ? C9 C10 1.383(5) . ? C10 C11 1.368(5) . ? C11 C12 1.387(5) . ? C12 C13 1.361(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 C2 N1 C5 108.4(3) . . ? C2 N1 C6 125.2(3) . . ? C5 N1 C6 126.4(3) . . ? C2 N3 C4 109.2(3) . . ? N3 C2 N1 108.8(3) . . ? C5 C4 N3 106.9(3) . . ? C4 C5 N1 106.7(3) . . ? O3 N4 O2 121.5(3) . . ? O3 N4 C9 118.4(3) . . ? O2 N4 C9 120.2(3) . . ? O4 N5 O5 123.6(3) . . ? O4 N5 C11 118.7(3) . . ? O5 N5 C11 117.6(3) . . ? O6 N6 O7 122.8(3) . . ? O6 N6 C13 118.3(3) . . ? O7 N6 C13 118.8(3) . . ? O1 C8 C9 128.1(3) . . ? O1 C8 C13 120.0(3) . . ? C9 C8 C13 111.9(3) . . ? C10 C9 C8 123.0(3) . . ? C10 C9 N4 116.3(3) . . ? C8 C9 N4 120.7(3) . . ? C11 C10 C9 119.8(3) . . ? C10 C11 C12 122.0(3) . . ? C10 C11 N5 119.2(3) . . ? C12 C11 N5 118.7(3) . . ? C13 C12 C11 117.0(3) . . ? C12 C13 C8 126.2(3) . . ? C12 C13 N6 119.2(3) . . ? C8 C13 N6 114.6(3) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 23.31 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.419 _refine_diff_density_min -0.328 _refine_diff_density_rms 0.054 data_20a _database_code_depnum_ccdc_archive 'CCDC 837946' #TrackingRef '- Protonated ILs CIFs 10-30-11.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H13 N5 O7' _chemical_formula_weight 339.27 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.250(2) _cell_length_b 9.107(3) _cell_length_c 11.946(4) _cell_angle_alpha 83.270(5) _cell_angle_beta 74.608(5) _cell_angle_gamma 79.684(5) _cell_volume 746.1(4) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 815 _cell_measurement_theta_min 2.99 _cell_measurement_theta_max 23.21 _exptl_crystal_description fragment _exptl_crystal_colour yellow _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.510 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 352 _exptl_absorpt_coefficient_mu 0.126 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9488 _exptl_absorpt_correction_T_max 0.9850 _exptl_absorpt_process_details 'SHELX SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 3389 _diffrn_reflns_av_R_equivalents 0.0118 _diffrn_reflns_av_sigmaI/netI 0.0192 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.28 _diffrn_reflns_theta_max 23.23 _reflns_number_total 2111 _reflns_number_gt 1870 _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 fullcycle _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0490P)^2^+0.2837P] 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 2111 _refine_ls_number_parameters 238 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0400 _refine_ls_R_factor_gt 0.0352 _refine_ls_wR_factor_ref 0.0913 _refine_ls_wR_factor_gt 0.0887 _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_restrained_S_all 1.054 _refine_ls_shift/su_max 0.075 _refine_ls_shift/su_mean 0.003 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 O1 O 0.50638(18) -0.23605(14) 0.79435(11) 0.0351(3) Uani 1 1 d . A . O4 O 0.12238(18) 0.13288(14) 0.41967(11) 0.0370(3) Uani 1 1 d . . . O5 O 0.2364(2) -0.07348(15) 0.33449(11) 0.0425(4) Uani 1 1 d . . . O6 O 0.67782(19) -0.45099(15) 0.52009(12) 0.0402(3) Uani 1 1 d . . . O7 O 0.5105(2) -0.50139(14) 0.69542(12) 0.0436(4) Uani 1 1 d . . . N1 N 0.1482(2) -0.62965(16) 1.09796(13) 0.0296(4) Uani 1 1 d . . . N3 N 0.2162(2) -0.40857(16) 1.09131(13) 0.0310(4) Uani 1 1 d . . . N4 N 0.2898(2) 0.06292(18) 0.79738(14) 0.0384(4) Uani 1 1 d . . . N5 N 0.2104(2) 0.00354(17) 0.41711(13) 0.0303(4) Uani 1 1 d . . . N6 N 0.5533(2) -0.41531(16) 0.60885(13) 0.0316(4) Uani 1 1 d . . . C2 C 0.1316(2) -0.51596(19) 1.16204(15) 0.0287(4) Uani 1 1 d . . . C4 C 0.2873(3) -0.4565(2) 0.98041(16) 0.0341(4) Uani 1 1 d . . . H4A H 0.3537 -0.4022 0.9136 0.041 Uiso 1 1 calc R . . C5 C 0.2443(3) -0.5945(2) 0.98527(16) 0.0330(4) Uani 1 1 d . . . H5A H 0.2749 -0.6566 0.9223 0.040 Uiso 1 1 calc R . . C6 C 0.0819(3) -0.7737(2) 1.14068(19) 0.0429(5) Uani 1 1 d . . . H6A H 0.1511 -0.8492 1.0859 0.064 Uiso 0.50 1 calc PR . . H6B H -0.0575 -0.7634 1.1476 0.064 Uiso 0.50 1 calc PR . . H6C H 0.1078 -0.8048 1.2171 0.064 Uiso 0.50 1 calc PR . . H6D H -0.0168 -0.7624 1.2145 0.064 Uiso 0.50 1 calc PR . . H6E H 0.1917 -0.8482 1.1528 0.064 Uiso 0.50 1 calc PR . . H6F H 0.0264 -0.8068 1.0833 0.064 Uiso 0.50 1 calc PR . . C7 C 0.0318(3) -0.5077(2) 1.28688(16) 0.0412(5) Uani 1 1 d . . . H7A H 0.0597 -0.6049 1.3287 0.062 Uiso 1 1 calc R . . H7B H -0.1081 -0.4816 1.2956 0.062 Uiso 1 1 calc R . . H7C H 0.0778 -0.4310 1.3191 0.062 Uiso 1 1 calc R . . C8 C 0.2375(3) -0.2641(2) 1.1248(2) 0.0460(5) Uani 1 1 d . . . H8A H 0.2937 -0.2031 1.0551 0.069 Uiso 0.50 1 calc PR . . H8B H 0.3229 -0.2804 1.1778 0.069 Uiso 0.50 1 calc PR . . H8C H 0.1102 -0.2121 1.1638 0.069 Uiso 0.50 1 calc PR . . H8D H 0.1908 -0.2606 1.2094 0.069 Uiso 0.50 1 calc PR . . H8E H 0.1616 -0.1833 1.0866 0.069 Uiso 0.50 1 calc PR . . H8F H 0.3743 -0.2516 1.1006 0.069 Uiso 0.50 1 calc PR . . C9 C 0.4314(2) -0.18341(19) 0.71324(15) 0.0273(4) Uani 1 1 d . . . C10 C 0.3247(2) -0.03405(19) 0.70362(15) 0.0278(4) Uani 1 1 d . A . C11 C 0.2561(2) 0.02604(19) 0.60851(15) 0.0276(4) Uani 1 1 d . . . H11A H 0.1894 0.1258 0.6069 0.033 Uiso 1 1 calc R A . C12 C 0.2847(2) -0.05941(19) 0.51556(15) 0.0259(4) Uani 1 1 d . A . C13 C 0.3849(2) -0.20519(19) 0.51582(15) 0.0273(4) Uani 1 1 d . . . H13A H 0.4072 -0.2630 0.4509 0.033 Uiso 1 1 calc R A . C14 C 0.4500(2) -0.26267(18) 0.61109(15) 0.0265(4) Uani 1 1 d . A . O2A O 0.2989(7) 0.0088(4) 0.8962(3) 0.0826(13) Uani 0.50 1 d P A 1 O3A O 0.2521(4) 0.1953(3) 0.7779(3) 0.0479(8) Uani 0.50 1 d P A 1 O2B O 0.2502(4) 0.0078(3) 0.8960(2) 0.0462(7) Uani 0.50 1 d P A 2 O3B O 0.2939(4) 0.2013(3) 0.7692(2) 0.0430(7) Uani 0.50 1 d P A 2 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 O1 0.0385(7) 0.0383(7) 0.0311(7) 0.0045(6) -0.0138(6) -0.0092(6) O4 0.0343(7) 0.0332(8) 0.0425(8) 0.0071(6) -0.0135(6) -0.0033(6) O5 0.0520(9) 0.0467(8) 0.0333(8) -0.0049(6) -0.0195(7) -0.0047(7) O6 0.0363(8) 0.0414(8) 0.0386(8) -0.0099(6) -0.0049(7) 0.0029(6) O7 0.0552(9) 0.0311(7) 0.0406(8) 0.0080(6) -0.0110(7) -0.0051(6) N1 0.0261(8) 0.0316(8) 0.0320(9) 0.0001(7) -0.0109(7) -0.0028(6) N3 0.0296(8) 0.0313(8) 0.0321(9) 0.0013(7) -0.0109(7) -0.0022(6) N4 0.0438(10) 0.0386(10) 0.0327(10) -0.0070(7) -0.0093(8) -0.0034(7) N5 0.0264(8) 0.0342(9) 0.0312(9) 0.0041(7) -0.0087(6) -0.0090(7) N6 0.0325(9) 0.0305(8) 0.0333(9) -0.0007(7) -0.0116(8) -0.0045(7) C2 0.0225(9) 0.0332(10) 0.0291(10) 0.0016(8) -0.0089(7) 0.0002(7) C4 0.0274(10) 0.0471(12) 0.0259(10) 0.0051(8) -0.0074(8) -0.0048(8) C5 0.0272(10) 0.0453(12) 0.0267(10) -0.0058(8) -0.0088(8) -0.0006(8) C6 0.0447(12) 0.0368(11) 0.0505(13) 0.0036(9) -0.0161(10) -0.0126(9) C7 0.0395(11) 0.0484(12) 0.0304(11) -0.0005(9) -0.0053(9) 0.0005(9) C8 0.0499(13) 0.0320(11) 0.0579(14) -0.0039(9) -0.0180(11) -0.0042(9) C9 0.0240(9) 0.0317(10) 0.0257(10) 0.0032(8) -0.0038(8) -0.0103(7) C10 0.0271(9) 0.0311(10) 0.0244(9) -0.0032(7) -0.0020(7) -0.0082(7) C11 0.0208(9) 0.0272(9) 0.0326(10) 0.0002(8) -0.0028(7) -0.0053(7) C12 0.0225(9) 0.0297(9) 0.0261(9) 0.0019(7) -0.0066(7) -0.0076(7) C13 0.0256(9) 0.0294(10) 0.0274(10) -0.0026(7) -0.0036(7) -0.0100(7) C14 0.0237(9) 0.0248(9) 0.0296(10) 0.0011(7) -0.0041(7) -0.0060(7) O2A 0.147(4) 0.060(2) 0.042(2) -0.0132(16) -0.041(2) 0.015(2) O3A 0.0598(19) 0.0319(17) 0.0542(19) -0.0090(13) -0.0204(15) 0.0006(13) O2B 0.0619(19) 0.0531(17) 0.0176(15) -0.0026(12) 0.0003(12) -0.0088(14) O3B 0.0566(18) 0.0306(16) 0.0445(17) -0.0127(12) -0.0131(14) -0.0072(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 O1 C9 1.241(2) . ? O4 N5 1.2346(19) . ? O5 N5 1.232(2) . ? O6 N6 1.230(2) . ? O7 N6 1.2276(19) . ? N1 C2 1.329(2) . ? N1 C5 1.372(2) . ? N1 C6 1.467(2) . ? N3 C2 1.339(2) . ? N3 C4 1.380(2) . ? N3 C8 1.464(3) . ? N4 O3A 1.197(3) . ? N4 O2B 1.207(3) . ? N4 O2A 1.239(4) . ? N4 O3B 1.269(3) . ? N4 C10 1.449(2) . ? N5 C12 1.439(2) . ? N6 C14 1.456(2) . ? C2 C7 1.479(3) . ? C4 C5 1.339(3) . ? C9 C10 1.448(2) . ? C9 C14 1.454(2) . ? C10 C11 1.376(2) . ? C11 C12 1.380(3) . ? C12 C13 1.395(2) . ? C13 C14 1.360(2) . ? 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 C2 N1 C5 109.57(15) . . ? C2 N1 C6 125.84(16) . . ? C5 N1 C6 124.55(16) . . ? C2 N3 C4 109.32(15) . . ? C2 N3 C8 126.33(16) . . ? C4 N3 C8 124.32(16) . . ? O3A N4 O2B 120.17(19) . . ? O3A N4 O2A 120.7(2) . . ? O2B N4 O2A 16.7(2) . . ? O3A N4 O3B 13.83(15) . . ? O2B N4 O3B 124.9(2) . . ? O2A N4 O3B 120.9(2) . . ? O3A N4 C10 119.1(2) . . ? O2B N4 C10 117.91(19) . . ? O2A N4 C10 120.1(2) . . ? O3B N4 C10 117.08(18) . . ? O5 N5 O4 122.93(15) . . ? O5 N5 C12 118.90(15) . . ? O4 N5 C12 118.17(15) . . ? O7 N6 O6 123.69(15) . . ? O7 N6 C14 118.17(15) . . ? O6 N6 C14 118.14(15) . . ? N1 C2 N3 107.06(15) . . ? N1 C2 C7 126.33(17) . . ? N3 C2 C7 126.58(17) . . ? C5 C4 N3 106.63(16) . . ? C4 C5 N1 107.42(16) . . ? O1 C9 C10 125.36(16) . . ? O1 C9 C14 123.65(16) . . ? C10 C9 C14 110.91(15) . . ? C11 C10 C9 124.31(16) . . ? C11 C10 N4 116.32(15) . . ? C9 C10 N4 119.35(15) . . ? C10 C11 C12 119.62(16) . . ? C11 C12 C13 120.90(16) . . ? C11 C12 N5 119.29(15) . . ? C13 C12 N5 119.82(15) . . ? C14 C13 C12 118.46(16) . . ? C13 C14 C9 125.75(16) . . ? C13 C14 N6 117.12(15) . . ? C9 C14 N6 117.10(15) . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 23.23 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.238 _refine_diff_density_min -0.233 _refine_diff_density_rms 0.040