# Supplementary Material (ESI) for Green Chemistry # This journal is © The Royal Society of Chemistry 2006 data_global _journal_name_full 'Green Chemistry' _journal_coden_cambridge 1048 _publ_contact_author_name 'Robin D. Rogers' _publ_contact_author_address ;Center for Green Manufacturing Department of Chemistry The University of Alabama Tuscaloosa, AL 35487 USA ; _publ_contact_author_email rdroger@bama.ua.edu _publ_contact_author_phone 205-348-4323 _publ_contact_author_fax 205-348-0823 loop_ _publ_author_name _publ_author_address M.Smiglak ;Center for Green Manufacturing Department of Chemistry The University of Alabama Tuscaloosa, AL 35487 USA ; S.T.Griffin ;Center for Green Manufacturing Department of Chemistry The University of Alabama Tuscaloosa, AL 35487 USA ; W.M.Reichert ;Center for Green Manufacturing Department of Chemistry The University of Alabama Tuscaloosa, AL 35487 USA ; R.P.Swatloski ;Center for Green Manufacturing Department of Chemistry The University of Alabama Tuscaloosa, AL 35487 USA ; J.D.Holbrey ;The QUILL Research Centre Queen's Univeristy of Belfast BT9 5AG, Northern Ireland UK ; ; A.R.Katritzky ; ;Center for Heterocyclic Compounds Univeristy of Florida Department of Chemistry Gainesville, FL 32611 USA ; 'Hongfang Yang.' ;Center for Heterocyclic Compounds Univeristy of Florida Department of Chemistry Gainesville, FL 32611 USA ; K.Kirichenko ;Center for Heterocyclic Compounds Univeristy of Florida Department of Chemistry Gainesville, FL 32611 USA ; _publ_section_title ; Ionic Liquids via reaction of the zwitterionic 1,3 dimethylimidazolium 2 carboxylate with protic acids. Overcoming synthetic limitations and establishing new halide free protocols for the formation of ILs ; data_4a _database_code_depnum_ccdc_archive 'CCDC 605759' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '2-carboxy-1,3-dimethylimidazolium NO3 H2O' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C6 H11 N3 O6' _chemical_formula_weight 221.18 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 6.430(4) _cell_length_b 6.715(4) _cell_length_c 11.544(7) _cell_angle_alpha 87.486(12) _cell_angle_beta 80.110(12) _cell_angle_gamma 80.82(1) _cell_volume 484.6(5) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 649 _cell_measurement_theta_min 3.26 _cell_measurement_theta_max 23.38 _exptl_crystal_description Rectangular _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.516 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 232 _exptl_absorpt_coefficient_mu 0.136 _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 1913 _diffrn_reflns_av_R_equivalents 0.0389 _diffrn_reflns_av_sigmaI/netI 0.0639 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 3.07 _diffrn_reflns_theta_max 23.38 _reflns_number_total 1303 _reflns_number_gt 1038 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _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^)+(0.1219P)^2^+0.0000P] 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 SHELXL _refine_ls_extinction_coef 0.010(11) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1303 _refine_ls_number_parameters 181 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0928 _refine_ls_R_factor_gt 0.0539 _refine_ls_wR_factor_ref 0.1792 _refine_ls_wR_factor_gt 0.1394 _refine_ls_goodness_of_fit_ref 1.152 _refine_ls_restrained_S_all 1.152 _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 1.6295(4) 0.1903(3) 0.1983(2) 0.0278(7) Uani 1 1 d . . . N3 N 1.4312(4) 0.2714(3) 0.3665(2) 0.0279(7) Uani 1 1 d . . . N4 N 0.2932(4) 0.8395(4) 0.2925(2) 0.0293(7) Uani 1 1 d . . . O1 O 1.2862(4) 0.3629(3) 0.07846(18) 0.0465(8) Uani 1 1 d . . . O2 O 1.0925(4) 0.4583(3) 0.25198(19) 0.0357(7) Uani 1 1 d . . . H2A H 0.980(10) 0.527(8) 0.201(4) 0.099(17) Uiso 1 1 d . . . O3 O 0.2733(4) 0.8957(3) 0.19085(17) 0.0432(8) Uani 1 1 d . . . O4 O 0.4574(4) 0.7193(3) 0.31079(18) 0.0404(7) Uani 1 1 d . . . O5 O 0.1534(4) 0.8975(3) 0.37808(18) 0.0404(7) Uani 1 1 d . . . O1W O 0.8080(4) 0.6486(4) 0.1473(2) 0.0431(7) Uani 1 1 d . . . H1O H 0.793(9) 0.631(7) 0.069(5) 0.088(16) Uiso 1 1 d . . . H2O H 0.694(7) 0.672(6) 0.191(4) 0.053(12) Uiso 1 1 d . . . C2 C 1.4346(5) 0.2791(4) 0.2494(2) 0.0251(8) Uani 1 1 d . . . C4 C 1.6263(5) 0.1770(5) 0.3873(3) 0.0333(8) Uani 1 1 d . . . H4A H 1.653(6) 0.158(5) 0.460(3) 0.039(9) Uiso 1 1 d . . . C5 C 1.7486(5) 0.1271(5) 0.2836(3) 0.0314(8) Uani 1 1 d . . . H5A H 1.879(6) 0.065(5) 0.269(3) 0.028(9) Uiso 1 1 d . . . C6 C 1.7106(7) 0.1599(6) 0.0721(3) 0.0389(9) Uani 1 1 d . . . H6A H 1.851(8) 0.103(6) 0.066(4) 0.061(12) Uiso 1 1 d . . . H6B H 1.648(6) 0.062(5) 0.046(3) 0.043(10) Uiso 1 1 d . . . H6C H 1.694(7) 0.302(6) 0.029(3) 0.064(11) Uiso 1 1 d . . . C7 C 1.2619(5) 0.3706(4) 0.1843(3) 0.0282(8) Uani 1 1 d . . . C8 C 1.2528(6) 0.3458(5) 0.4598(3) 0.0349(9) Uani 1 1 d . . . H8A H 1.211(6) 0.484(5) 0.449(3) 0.042(10) Uiso 1 1 d . . . H8B H 1.115(8) 0.261(6) 0.454(3) 0.074(12) Uiso 1 1 d . . . H8C H 1.298(7) 0.325(5) 0.532(4) 0.054(11) Uiso 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 0.0281(16) 0.0297(14) 0.0247(14) 0.0019(10) -0.0067(11) -0.0001(11) N3 0.0324(17) 0.0303(14) 0.0203(13) 0.0024(10) -0.0061(11) -0.0020(11) N4 0.0307(16) 0.0317(14) 0.0266(14) 0.0023(11) -0.0081(12) -0.0053(11) O1 0.0498(17) 0.0615(16) 0.0239(14) 0.0027(10) -0.0132(11) 0.0111(12) O2 0.0283(13) 0.0467(14) 0.0298(13) 0.0015(10) -0.0083(10) 0.0040(10) O3 0.0534(17) 0.0564(16) 0.0211(13) 0.0089(10) -0.0122(11) -0.0082(12) O4 0.0299(14) 0.0488(14) 0.0384(14) 0.0058(10) -0.0074(10) 0.0059(10) O5 0.0367(15) 0.0532(14) 0.0269(12) -0.0031(10) -0.0056(10) 0.0074(10) O1W 0.0298(15) 0.0639(17) 0.0320(15) 0.0003(11) -0.0118(12) 0.0101(11) C2 0.0281(18) 0.0246(15) 0.0218(15) 0.0028(11) -0.0046(12) -0.0026(12) C4 0.039(2) 0.0340(17) 0.0282(19) 0.0073(13) -0.0150(15) -0.0022(13) C5 0.0250(18) 0.0326(17) 0.0372(19) 0.0026(13) -0.0127(15) 0.0011(14) C6 0.038(2) 0.045(2) 0.0283(18) -0.0045(15) 0.0001(15) 0.0046(17) C7 0.0294(18) 0.0299(16) 0.0257(17) 0.0029(12) -0.0087(13) -0.0025(12) C8 0.043(2) 0.038(2) 0.0198(18) 0.0007(13) -0.0017(15) 0.0021(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 1.347(4) . ? N1 C5 1.362(4) . ? N1 C6 1.472(4) . ? N3 C2 1.347(4) . ? N3 C4 1.367(4) . ? N3 C8 1.472(4) . ? N4 O3 1.239(3) . ? N4 O5 1.246(3) . ? N4 O4 1.265(3) . ? O1 C7 1.208(4) . ? O2 C7 1.298(4) . ? C2 C7 1.484(5) . ? C4 C5 1.339(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 108.9(2) . . ? C2 N1 C6 128.0(3) . . ? C5 N1 C6 123.1(3) . . ? C2 N3 C4 108.2(2) . . ? C2 N3 C8 128.0(3) . . ? C4 N3 C8 123.8(3) . . ? O3 N4 O5 121.4(3) . . ? O3 N4 O4 119.8(2) . . ? O5 N4 O4 118.8(2) . . ? N1 C2 N3 107.4(3) . . ? N1 C2 C7 124.5(3) . . ? N3 C2 C7 128.1(3) . . ? C5 C4 N3 108.1(3) . . ? C4 C5 N1 107.4(3) . . ? O1 C7 O2 125.7(3) . . ? O1 C7 C2 120.8(3) . . ? O2 C7 C2 113.4(3) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O2 H2A O1W 1.04(6) 1.48(6) 2.513(3) 170(4) . O1W H1O O1 0.94(6) 1.86(6) 2.782(4) 168(5) 2_765 O1W H2O O4 0.81(5) 1.86(5) 2.673(4) 171(4) . C4 H4A O5 0.89(4) 2.40(4) 3.250(4) 161(3) 2_766 C5 H5A O5 0.87(4) 2.44(4) 3.144(4) 139(3) 1_745 C6 H6C O1 1.06(4) 2.53(4) 3.579(5) 171(3) 2_865 C8 H8C O4 0.93(5) 2.57(5) 3.465(5) 161(3) 2_766 _diffrn_measured_fraction_theta_max 0.919 _diffrn_reflns_theta_full 23.38 _diffrn_measured_fraction_theta_full 0.919 _refine_diff_density_max 0.356 _refine_diff_density_min -0.384 _refine_diff_density_rms 0.092 data_5a _database_code_depnum_ccdc_archive 'CCDC 605760' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '4-carboxy-1,3-dimethylimidazolium nitrate' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C6 H9 N3 O5' _chemical_formula_weight 203.16 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 6.628(2) _cell_length_b 11.910(4) _cell_length_c 11.538(4) _cell_angle_alpha 90.00 _cell_angle_beta 104.508(7) _cell_angle_gamma 90.00 _cell_volume 881.7(5) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 537 _cell_measurement_theta_min 2.50 _cell_measurement_theta_max 23.24 _exptl_crystal_description flat _exptl_crystal_colour colorless _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.531 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 424 _exptl_absorpt_coefficient_mu 0.134 _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 3851 _diffrn_reflns_av_R_equivalents 0.0315 _diffrn_reflns_av_sigmaI/netI 0.0407 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.50 _diffrn_reflns_theta_max 23.27 _reflns_number_total 1264 _reflns_number_gt 1000 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _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^)+(0.0515P)^2^+0.4373P] 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 SHELXL _refine_ls_extinction_coef 0.0053(18) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1264 _refine_ls_number_parameters 164 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0625 _refine_ls_R_factor_gt 0.0448 _refine_ls_wR_factor_ref 0.1067 _refine_ls_wR_factor_gt 0.1004 _refine_ls_goodness_of_fit_ref 1.074 _refine_ls_restrained_S_all 1.074 _refine_ls_shift/su_max 0.018 _refine_ls_shift/su_mean 0.001 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 -0.2501(3) 0.29762(18) 0.48033(18) 0.0245(6) Uani 1 1 d . . . N3 N -0.2474(3) 0.41223(18) 0.33541(18) 0.0233(6) Uani 1 1 d . . . N4 N -0.2486(3) 0.88650(19) 0.65590(19) 0.0275(6) Uani 1 1 d . . . O1 O -0.2725(3) 0.65910(16) 0.35088(17) 0.0394(6) Uani 1 1 d . . . O2 O -0.2349(3) 0.63633(18) 0.54748(16) 0.0321(5) Uani 1 1 d . . . H2O H -0.235(5) 0.708(4) 0.551(3) 0.073(13) Uiso 1 1 d . . . O3 O -0.2078(3) 0.98148(16) 0.69948(18) 0.0388(6) Uani 1 1 d . . . O4 O -0.1732(3) 0.85409(17) 0.57080(17) 0.0395(6) Uani 1 1 d . . . O5 O -0.3656(3) 0.82288(18) 0.69370(18) 0.0422(6) Uani 1 1 d . . . C2 C -0.2455(4) 0.3055(2) 0.3663(2) 0.0264(7) Uani 1 1 d . . . H2A H -0.236(4) 0.240(2) 0.317(2) 0.027(7) Uiso 1 1 d . . . C4 C -0.2537(4) 0.4766(2) 0.4347(2) 0.0223(6) Uani 1 1 d . . . C5 C -0.2547(4) 0.4038(2) 0.5248(2) 0.0240(7) Uani 1 1 d . . . H5A H -0.257(4) 0.418(2) 0.605(2) 0.023(7) Uiso 1 1 d . . . C6 C -0.2519(6) 0.1921(3) 0.5468(3) 0.0358(8) Uani 1 1 d . . . H6C H -0.405(6) 0.174(3) 0.546(3) 0.069(11) Uiso 1 1 d . . . H6B H -0.186(5) 0.199(3) 0.628(4) 0.071(12) Uiso 1 1 d . . . H6A H -0.200(6) 0.137(3) 0.509(3) 0.073(13) Uiso 1 1 d . . . C7 C -0.2277(6) 0.4512(3) 0.2173(2) 0.0298(7) Uani 1 1 d . . . H7C H -0.349(5) 0.496(3) 0.185(3) 0.038(9) Uiso 1 1 d . . . H7B H -0.102(4) 0.490(2) 0.224(2) 0.023(7) Uiso 1 1 d . . . H7A H -0.221(4) 0.386(3) 0.169(3) 0.035(8) Uiso 1 1 d . . . C8 C -0.2548(4) 0.6004(2) 0.4379(2) 0.0243(6) 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 0.0271(13) 0.0214(13) 0.0240(13) 0.0002(10) 0.0047(9) -0.0019(10) N3 0.0256(13) 0.0224(14) 0.0216(12) 0.0001(10) 0.0050(9) -0.0009(10) N4 0.0316(14) 0.0247(14) 0.0245(13) 0.0015(11) 0.0040(11) 0.0020(11) O1 0.0672(15) 0.0251(12) 0.0250(11) 0.0045(9) 0.0096(10) 0.0000(10) O2 0.0464(13) 0.0241(13) 0.0261(12) -0.0042(9) 0.0096(9) 0.0006(10) O3 0.0546(14) 0.0199(12) 0.0446(13) -0.0087(9) 0.0178(10) -0.0051(10) O4 0.0545(14) 0.0369(13) 0.0328(12) -0.0063(9) 0.0215(10) 0.0008(10) O5 0.0496(14) 0.0376(13) 0.0428(13) -0.0029(10) 0.0183(10) -0.0177(11) C2 0.0240(16) 0.0264(18) 0.0271(17) -0.0038(13) 0.0034(12) -0.0005(13) C4 0.0210(14) 0.0247(15) 0.0197(13) -0.0019(12) 0.0026(10) -0.0010(12) C5 0.0261(16) 0.0234(16) 0.0223(15) -0.0018(12) 0.0055(12) -0.0011(12) C6 0.049(2) 0.0236(17) 0.0332(19) 0.0052(15) 0.0074(16) -0.0018(16) C7 0.035(2) 0.0329(19) 0.0230(16) 0.0015(14) 0.0107(14) -0.0042(16) C8 0.0216(14) 0.0272(15) 0.0233(15) -0.0026(13) 0.0040(11) -0.0017(12) _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(3) . ? N1 C5 1.369(4) . ? N1 C6 1.474(4) . ? N3 C2 1.319(4) . ? N3 C4 1.387(3) . ? N3 C7 1.476(3) . ? N4 O5 1.239(3) . ? N4 O3 1.240(3) . ? N4 O4 1.269(3) . ? O1 C8 1.205(3) . ? O2 C8 1.310(3) . ? C4 C5 1.355(4) . ? C4 C8 1.476(4) . ? 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(2) . . ? C2 N1 C6 125.5(2) . . ? C5 N1 C6 126.1(2) . . ? C2 N3 C4 108.0(2) . . ? C2 N3 C7 123.7(2) . . ? C4 N3 C7 128.1(2) . . ? O5 N4 O3 120.5(2) . . ? O5 N4 O4 119.3(2) . . ? O3 N4 O4 120.2(2) . . ? N3 C2 N1 109.5(2) . . ? C5 C4 N3 106.7(2) . . ? C5 C4 C8 128.2(2) . . ? N3 C4 C8 125.1(2) . . ? C4 C5 N1 107.3(2) . . ? O1 C8 O2 125.5(3) . . ? O1 C8 C4 124.0(2) . . ? O2 C8 C4 110.5(2) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O2 H2O O4 0.86(4) 1.79(4) 2.629(3) 167(4) . C2 H2A O1 0.98(3) 2.17(3) 3.079(3) 153(2) 2_445 C7 H7C O3 0.96(3) 2.44(3) 3.238(4) 140(2) 4_575 C5 H5A O3 0.94(3) 2.45(3) 3.381(4) 171(2) 2_446 O2 H2O O5 0.86(4) 2.46(4) 3.044(3) 126(3) . C6 H6B O5 0.93(4) 2.48(4) 3.290(4) 145(3) 2_446 C5 H5A O5 0.94(3) 2.53(3) 3.288(4) 138(2) 2_446 _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 23.27 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.227 _refine_diff_density_min -0.163 _refine_diff_density_rms 0.054