# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2004 data_global _journal_coden_Cambridge 440 loop_ _publ_author_name 'Ferretti, Valeria' 'Valerio, Bertolasi' 'L. Pretto' _publ_requested_journal 'New J.Chem.(Nouv.J.Chim.)' _publ_contact_author_name 'Dr. Valeria Ferretti' _publ_contact_author_address ; Chemistry Department University of Ferrara via L. Borsari 46 I-44100 Ferrara Italy ; _publ_contact_author_email frt@unife.it _publ_contact_author_phone +39-0532-291132 _publ_contact_author_fax +39-0532-240709 _publ_section_title ; Supramolecular aggregations by means of charge-assisted hydrogen bonds in acid-base adducts containing amidinium cations ; data_polymorphII _database_code_depnum_ccdc_archive 'CCDC 229598' _audit_creation_method SHELXL-97 _chemical_name_systematic ; amidinium (2-hydroxyethoxy)acetate ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C2 H7 N2, C4 H7 O4' _chemical_formula_sum 'C6 H14 N2 O4' _chemical_formula_weight 178.19 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 'P 21/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 8.0430(3) _cell_length_b 11.4270(4) _cell_length_c 10.5020(5) _cell_angle_alpha 90.00 _cell_angle_beta 108.0890(17) _cell_angle_gamma 90.00 _cell_volume 917.51(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293 _cell_measurement_reflns_used 1749 _cell_measurement_theta_min 1.0 _cell_measurement_theta_max 27.5 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.290 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 384 _exptl_absorpt_coefficient_mu 0.108 _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 293 _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method '\f scans and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5856 _diffrn_reflns_av_R_equivalents 0.029 _diffrn_reflns_av_sigmaI/netI 0.0425 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.57 _diffrn_reflns_theta_max 27.49 _reflns_number_total 2093 _reflns_number_gt 1368 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'Kappa CCD server software (Nonius, 1997)' _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR97 (Altomare et al.,1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPIII (Burnett & Johnson, 1996)' _computing_publication_material ; SHELXL-97 (Sheldrick, 1997); PARST (Nardelli, 1983, 1995); WINGX (Farrugia, 1999) ; _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^)+(0.0549P)^2^+0.1701P] 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 2093 _refine_ls_number_parameters 165 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0885 _refine_ls_R_factor_gt 0.0476 _refine_ls_wR_factor_ref 0.1388 _refine_ls_wR_factor_gt 0.1077 _refine_ls_goodness_of_fit_ref 1.123 _refine_ls_restrained_S_all 1.123 _refine_ls_shift/su_max 0.017 _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 O1 O -0.08099(18) 0.04488(11) -0.18741(17) 0.0666(5) Uani 1 1 d . . . O2 O -0.02112(17) -0.14451(11) -0.18221(17) 0.0698(5) Uani 1 1 d . . . O3 O 0.33187(16) -0.10335(11) -0.10755(14) 0.0552(4) Uani 1 1 d . . . O4 O 0.1828(2) -0.33249(13) -0.12266(19) 0.0749(5) Uani 1 1 d . . . N1 N -0.4372(3) -0.01775(14) -0.31963(19) 0.0537(5) Uani 1 1 d . . . N2 N -0.3748(2) -0.21106(15) -0.28527(19) 0.0543(4) Uani 1 1 d . . . C1 C -0.4862(2) -0.12745(15) -0.33457(18) 0.0457(4) Uani 1 1 d . . . C2 C -0.6706(3) -0.1568(2) -0.4092(3) 0.0628(6) Uani 1 1 d . . . C3 C 0.0239(2) -0.03920(15) -0.1651(2) 0.0506(5) Uani 1 1 d . . . C4 C 0.2169(3) -0.00837(17) -0.1136(2) 0.0542(5) Uani 1 1 d . . . C5 C 0.3610(3) -0.17780(17) 0.0060(2) 0.0549(5) Uani 1 1 d . . . C6 C 0.3520(3) -0.30240(19) -0.0393(3) 0.0599(6) Uani 1 1 d . . . H2 H 0.121(4) -0.274(3) -0.146(3) 0.105(10) Uiso 1 1 d . . . H11 H -0.524(3) 0.0355(19) -0.350(2) 0.062(6) Uiso 1 1 d . . . H12 H -0.319(4) 0.000(2) -0.273(2) 0.073(7) Uiso 1 1 d . . . H210 H -0.408(3) -0.286(2) -0.299(2) 0.060(6) Uiso 1 1 d . . . H220 H -0.258(3) -0.191(2) -0.245(2) 0.071(7) Uiso 1 1 d . . . H21 H -0.732(4) -0.096(3) -0.452(3) 0.119(11) Uiso 1 1 d . . . H22 H -0.682(4) -0.212(3) -0.470(4) 0.121(12) Uiso 1 1 d . . . H23 H -0.726(4) -0.191(3) -0.351(3) 0.114(11) Uiso 1 1 d . . . H51 H 0.270(3) -0.1589(17) 0.050(2) 0.058(6) Uiso 1 1 d . . . H41 H 0.241(3) 0.056(2) -0.175(2) 0.076(7) Uiso 1 1 d . . . H61 H 0.431(3) -0.313(2) -0.094(3) 0.079(7) Uiso 1 1 d . . . H52 H 0.480(3) -0.1625(18) 0.067(2) 0.072(7) Uiso 1 1 d . . . H42 H 0.242(3) 0.031(2) -0.024(2) 0.070(6) Uiso 1 1 d . . . H62 H 0.381(3) -0.354(2) 0.036(2) 0.069(6) 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 O1 0.0509(8) 0.0386(7) 0.1040(12) -0.0001(7) 0.0147(8) 0.0035(6) O2 0.0434(7) 0.0376(7) 0.1125(13) -0.0075(7) 0.0011(8) -0.0023(6) O3 0.0473(7) 0.0522(8) 0.0694(9) 0.0064(6) 0.0228(7) 0.0009(6) O4 0.0555(9) 0.0401(8) 0.1079(13) -0.0080(8) -0.0054(9) -0.0012(7) N1 0.0482(10) 0.0382(8) 0.0690(11) 0.0006(7) 0.0097(9) -0.0001(7) N2 0.0481(10) 0.0359(8) 0.0785(12) -0.0040(8) 0.0192(9) -0.0017(7) C1 0.0482(10) 0.0404(9) 0.0495(11) -0.0026(7) 0.0167(8) -0.0011(8) C2 0.0515(12) 0.0585(13) 0.0702(15) -0.0038(12) 0.0068(11) -0.0094(11) C3 0.0471(10) 0.0382(9) 0.0629(12) -0.0016(8) 0.0118(9) -0.0019(8) C4 0.0491(11) 0.0407(10) 0.0719(15) -0.0018(9) 0.0173(10) -0.0053(8) C5 0.0450(11) 0.0550(12) 0.0582(12) -0.0006(9) 0.0067(10) -0.0075(9) C6 0.0498(12) 0.0524(11) 0.0711(14) 0.0049(11) 0.0095(11) 0.0036(9) _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 C3 1.252(2) . ? O2 C3 1.253(2) . ? O3 C4 1.415(2) . ? O3 C5 1.424(2) . ? O4 C6 1.413(3) . ? O4 H2 0.82(4) . ? N1 C1 1.309(2) . ? N1 H11 0.91(2) . ? N1 H12 0.95(3) . ? N2 C1 1.302(2) . ? N2 H210 0.90(2) . ? N2 H220 0.93(3) . ? C1 C2 1.485(3) . ? C2 H21 0.89(4) . ? C2 H22 0.88(4) . ? C2 H23 0.95(4) . ? C3 C4 1.518(3) . ? C4 H41 1.03(2) . ? C4 H42 1.01(2) . ? C5 C6 1.496(3) . ? C5 H51 1.00(2) . ? C5 H52 0.98(2) . ? C6 H61 0.99(3) . ? C6 H62 0.95(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 C4 O3 C5 115.58(16) . . ? C6 O4 H2 111(2) . . ? C1 N1 H11 115.6(13) . . ? C1 N1 H12 119.1(14) . . ? H11 N1 H12 125(2) . . ? C1 N2 H210 120.1(14) . . ? C1 N2 H220 118.0(14) . . ? H210 N2 H220 121(2) . . ? N2 C1 N1 120.71(19) . . ? N2 C1 C2 119.68(18) . . ? N1 C1 C2 119.62(19) . . ? C1 C2 H21 114(2) . . ? C1 C2 H22 114(2) . . ? H21 C2 H22 106(3) . . ? C1 C2 H23 110(2) . . ? H21 C2 H23 111(3) . . ? H22 C2 H23 102(3) . . ? O1 C3 O2 124.23(17) . . ? O1 C3 C4 116.33(16) . . ? O2 C3 C4 119.44(16) . . ? O3 C4 C3 114.84(15) . . ? O3 C4 H41 108.8(13) . . ? C3 C4 H41 108.3(13) . . ? O3 C4 H42 111.2(13) . . ? C3 C4 H42 108.9(13) . . ? H41 C4 H42 104.2(18) . . ? O3 C5 C6 108.85(18) . . ? O3 C5 H51 107.5(12) . . ? C6 C5 H51 112.4(11) . . ? O3 C5 H52 108.1(13) . . ? C6 C5 H52 108.5(13) . . ? H51 C5 H52 111.4(18) . . ? O4 C6 C5 111.77(18) . . ? O4 C6 H61 106.3(15) . . ? C5 C6 H61 109.1(14) . . ? O4 C6 H62 107.8(14) . . ? C5 C6 H62 110.3(14) . . ? H61 C6 H62 112(2) . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.169 _refine_diff_density_min -0.162 _refine_diff_density_rms 0.038 data_polimorphI _database_code_depnum_ccdc_archive 'CCDC 229599' _audit_creation_method SHELXL-97 _chemical_name_systematic ; amidinium (2-hydroxyethoxy)acetate ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C2 H7 N2, C4 H7 O4' _chemical_formula_sum 'C6 H14 N2 O4' _chemical_formula_weight 178.19 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' O O 0.0106 0.0060 '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' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/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 10.4290(4) _cell_length_b 7.7270(3) _cell_length_c 11.8840(6) _cell_angle_alpha 90.00 _cell_angle_beta 101.7890(14) _cell_angle_gamma 90.00 _cell_volume 937.47(7) _cell_formula_units_Z 4 _cell_measurement_temperature 293 _cell_measurement_reflns_used 2542 _cell_measurement_theta_min 1.0 _cell_measurement_theta_max 30.0 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.263 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 384 _exptl_absorpt_coefficient_mu 0.105 _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 293 _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method '\f scans and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8956 _diffrn_reflns_av_R_equivalents 0.032 _diffrn_reflns_av_sigmaI/netI 0.0398 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.37 _diffrn_reflns_theta_max 29.00 _reflns_number_total 2491 _reflns_number_gt 1544 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'Kappa CCD server software (Nonius, 1997)' _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR97 (Altomare et al.,1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPIII (Burnett & Johnson, 1996)' _computing_publication_material ; SHELXL-97 (Sheldrick, 1997); PARST (Nardelli, 1983, 1995); WINGX (Farrugia, 1999) ; _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^)+(0.0512P)^2^+0.1550P] 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 2491 _refine_ls_number_parameters 165 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0924 _refine_ls_R_factor_gt 0.0465 _refine_ls_wR_factor_ref 0.1343 _refine_ls_wR_factor_gt 0.1042 _refine_ls_goodness_of_fit_ref 1.084 _refine_ls_restrained_S_all 1.084 _refine_ls_shift/su_max 0.008 _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 O1 O 0.09759(13) -0.17056(16) 0.26200(14) 0.0743(4) Uani 1 1 d . . . O2 O -0.10245(12) -0.26213(17) 0.26497(11) 0.0656(4) Uani 1 1 d . . . O3 O 0.06751(11) 0.12040(14) 0.37033(10) 0.0546(3) Uani 1 1 d . . . O4 O 0.24098(12) 0.29694(17) 0.56647(12) 0.0617(4) Uani 1 1 d . . . N1 N 0.15843(16) -0.4923(2) 0.17324(13) 0.0559(4) Uani 1 1 d . . . N2 N -0.05924(15) -0.5517(2) 0.12997(13) 0.0533(4) Uani 1 1 d . . . C1 C 0.06185(17) -0.5949(2) 0.12977(13) 0.0484(4) Uani 1 1 d . . . C2 C 0.0885(3) -0.7640(3) 0.0790(2) 0.0650(5) Uani 1 1 d . . . C3 C -0.01281(17) -0.1504(2) 0.28296(14) 0.0505(4) Uani 1 1 d . . . C4 C -0.04644(17) 0.0205(2) 0.33205(17) 0.0515(4) Uani 1 1 d . . . C5 C 0.04096(19) 0.2814(2) 0.41839(16) 0.0524(4) Uani 1 1 d . . . C6 C 0.1665(2) 0.3733(2) 0.46510(17) 0.0578(5) Uani 1 1 d . . . H1 H 0.1433(18) -0.390(3) 0.2045(17) 0.060(5) Uiso 1 1 d . . . H2 H -0.125(2) -0.629(3) 0.1026(18) 0.072(6) Uiso 1 1 d . . . H3 H -0.0778(18) -0.456(3) 0.1672(17) 0.061(5) Uiso 1 1 d . . . H4 H 0.239(2) -0.523(3) 0.1751(17) 0.066(6) Uiso 1 1 d . . . H5 H 0.194(2) 0.294(3) 0.618(2) 0.082(7) Uiso 1 1 d . . . H40 H -0.0914(18) -0.003(2) 0.3957(17) 0.064(5) Uiso 1 1 d . . . H41 H -0.105(2) 0.080(3) 0.2750(18) 0.072(6) Uiso 1 1 d . . . H50 H -0.0094(16) 0.258(2) 0.4797(15) 0.049(4) Uiso 1 1 d . . . H51 H -0.0142(19) 0.350(3) 0.3605(17) 0.067(5) Uiso 1 1 d . . . H60 H 0.2228(19) 0.373(2) 0.4076(18) 0.068(6) Uiso 1 1 d . . . H61 H 0.149(2) 0.500(3) 0.4833(17) 0.077(6) Uiso 1 1 d . . . H21 H 0.170(3) -0.761(4) 0.053(3) 0.115(9) Uiso 1 1 d . . . H22 H 0.093(3) -0.852(4) 0.129(3) 0.121(10) Uiso 1 1 d . . . H23 H 0.030(3) -0.788(4) 0.011(3) 0.132(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 O1 0.0577(8) 0.0597(7) 0.1125(12) -0.0298(7) 0.0336(8) -0.0074(6) O2 0.0632(8) 0.0689(8) 0.0699(9) -0.0209(6) 0.0259(6) -0.0164(6) O3 0.0521(7) 0.0467(6) 0.0677(8) -0.0117(5) 0.0187(6) 0.0025(5) O4 0.0506(7) 0.0734(8) 0.0632(8) -0.0056(6) 0.0169(6) 0.0027(6) N1 0.0500(9) 0.0543(8) 0.0646(10) -0.0067(7) 0.0147(7) 0.0020(7) N2 0.0545(9) 0.0532(8) 0.0531(9) -0.0025(7) 0.0131(7) -0.0028(7) C1 0.0585(10) 0.0459(8) 0.0417(8) 0.0054(6) 0.0126(7) 0.0035(7) C2 0.0803(15) 0.0477(10) 0.0679(14) -0.0023(9) 0.0177(12) 0.0067(9) C3 0.0535(10) 0.0518(9) 0.0481(9) -0.0030(7) 0.0149(8) -0.0022(7) C4 0.0458(9) 0.0528(9) 0.0561(10) -0.0010(8) 0.0109(8) 0.0043(7) C5 0.0641(11) 0.0438(8) 0.0509(10) 0.0016(7) 0.0154(9) 0.0143(8) C6 0.0721(12) 0.0410(9) 0.0644(12) -0.0015(8) 0.0241(10) 0.0021(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 C3 1.2366(19) . ? O2 C3 1.258(2) . ? O3 C4 1.412(2) . ? O3 C5 1.4195(19) . ? O4 C6 1.422(2) . ? O4 H5 0.86(2) . ? N1 C1 1.303(2) . ? N1 H1 0.90(2) . ? N1 H4 0.87(2) . ? N2 C1 1.307(2) . ? N2 H2 0.92(2) . ? N2 H3 0.90(2) . ? C1 C2 1.489(2) . ? C2 H21 0.97(3) . ? C2 H22 0.90(3) . ? C2 H23 0.93(4) . ? C3 C4 1.514(2) . ? C4 H40 0.99(2) . ? C4 H41 0.94(2) . ? C5 C6 1.493(3) . ? C5 H50 0.998(18) . ? C5 H51 0.96(2) . ? C6 H60 0.99(2) . ? C6 H61 1.02(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 C4 O3 C5 112.83(12) . . ? C6 O4 H5 108.8(15) . . ? C1 N1 H1 120.8(12) . . ? C1 N1 H4 120.5(13) . . ? H1 N1 H4 118.7(17) . . ? C1 N2 H2 119.2(13) . . ? C1 N2 H3 121.0(12) . . ? H2 N2 H3 119.0(18) . . ? N1 C1 N2 120.90(16) . . ? N1 C1 C2 120.08(17) . . ? N2 C1 C2 119.03(17) . . ? C1 C2 H21 111.2(17) . . ? C1 C2 H22 112.4(19) . . ? H21 C2 H22 108(3) . . ? C1 C2 H23 112.9(19) . . ? H21 C2 H23 101(2) . . ? H22 C2 H23 111(3) . . ? O1 C3 O2 124.71(15) . . ? O1 C3 C4 119.08(15) . . ? O2 C3 C4 116.20(15) . . ? O3 C4 C3 110.79(13) . . ? O3 C4 H40 110.8(11) . . ? C3 C4 H40 108.5(11) . . ? O3 C4 H41 110.2(12) . . ? C3 C4 H41 108.7(12) . . ? H40 C4 H41 107.8(16) . . ? O3 C5 C6 109.77(14) . . ? O3 C5 H50 108.0(10) . . ? C6 C5 H50 111.6(10) . . ? O3 C5 H51 109.5(11) . . ? C6 C5 H51 110.8(11) . . ? H50 C5 H51 107.1(15) . . ? O4 C6 C5 113.80(15) . . ? O4 C6 H60 106.6(12) . . ? C5 C6 H60 110.0(12) . . ? O4 C6 H61 107.9(11) . . ? C5 C6 H61 110.3(12) . . ? H60 C6 H61 107.9(16) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 29.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.204 _refine_diff_density_min -0.151 _refine_diff_density_rms 0.036 data_amidiniumacetate _database_code_depnum_ccdc_archive 'CCDC 229600' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Amidinium acetate ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C2 H7 N2+, C2 H3 O2-' _chemical_formula_sum 'C4 H10 N2 O2' _chemical_formula_weight 118.13 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' O O 0.0106 0.0060 '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' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P n m a' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z+1/2' '-x, y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z-1/2' 'x, -y-1/2, z' _cell_length_a 10.0507(4) _cell_length_b 9.2132(5) _cell_length_c 7.7953(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 721.84(7) _cell_formula_units_Z 4 _cell_measurement_temperature 293 _cell_measurement_reflns_used 1207 _cell_measurement_theta_min 1.0 _cell_measurement_theta_max 30.0 _exptl_crystal_description prism _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.087 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 256 _exptl_absorpt_coefficient_mu 0.087 _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 293 _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method '\f scans and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8271 _diffrn_reflns_av_R_equivalents 0.038 _diffrn_reflns_av_sigmaI/netI 0.0275 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 3.42 _diffrn_reflns_theta_max 27.99 _reflns_number_total 919 _reflns_number_gt 590 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'Kappa CCD server software (Nonius, 1997)' _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR97 (Altomare et al.,1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPIII (Burnett & Johnson, 1996)' _computing_publication_material ; SHELXL-97 (Sheldrick, 1997); PARST (Nardelli, 1983, 1995); WINGX (Farrugia, 1999) ; _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^)+(0.1136P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 919 _refine_ls_number_parameters 65 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0745 _refine_ls_R_factor_gt 0.0516 _refine_ls_wR_factor_ref 0.1710 _refine_ls_wR_factor_gt 0.1486 _refine_ls_goodness_of_fit_ref 1.020 _refine_ls_restrained_S_all 1.020 _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 0.33861(14) 0.13091(11) 0.65616(14) 0.0759(5) Uani 1 1 d . . . N1 N 0.21348(15) 0.12721(13) 0.33243(17) 0.0673(5) Uani 1 1 d . . . C1 C 0.18275(19) 0.2500 0.2608(2) 0.0580(5) Uani 1 2 d S . . C2 C 0.1103(4) 0.2500 0.0934(4) 0.0865(8) Uani 1 2 d S . . C3 C 0.3705(2) 0.2500 0.7188(2) 0.0602(6) Uani 1 2 d S . . C4 C 0.4563(4) 0.2500 0.8776(5) 0.1035(10) Uani 1 2 d S . . H1N H 0.1964(17) 0.045(2) 0.282(2) 0.085(5) Uiso 1 1 d . . . H2N H 0.2478(16) 0.1248(17) 0.443(3) 0.079(4) Uiso 1 1 d . . . H41 H 0.122(4) 0.169(3) 0.026(4) 0.166(12) Uiso 1 1 d . . . H21 H 0.425(4) 0.328(4) 0.961(5) 0.197(17) Uiso 1 1 d . . . H22 H 0.536(9) 0.2500 0.847(7) 0.22(3) Uiso 1 2 d S . . H42 H 0.036(8) 0.2500 0.111(9) 0.19(3) Uiso 1 2 d S . . 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 0.1165(10) 0.0510(6) 0.0602(7) 0.0067(4) -0.0123(5) -0.0034(5) N1 0.0968(10) 0.0495(7) 0.0557(8) -0.0044(5) -0.0069(6) 0.0001(5) C1 0.0701(11) 0.0561(10) 0.0477(10) 0.000 -0.0001(7) 0.000 C2 0.105(2) 0.0913(18) 0.0631(14) 0.000 -0.0236(13) 0.000 C3 0.0705(11) 0.0606(11) 0.0494(10) 0.000 0.0004(8) 0.000 C4 0.108(2) 0.121(2) 0.0814(18) 0.000 -0.0356(17) 0.000 _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 C3 1.2429(14) . ? N1 C1 1.2989(15) . ? N1 H1N 0.87(2) . ? N1 H2N 0.93(2) . ? C1 N1 1.2989(15) 8_565 ? C1 C2 1.494(3) . ? C2 H41 0.92(3) . ? C2 H42 0.76(8) . ? C3 O1 1.2429(14) 8_565 ? C3 C4 1.508(3) . ? C4 H21 1.02(4) . ? C4 H22 0.84(8) . ? 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 C1 N1 H1N 121.0(11) . . ? C1 N1 H2N 120.5(10) . . ? H1N N1 H2N 118.3(15) . . ? N1 C1 N1 121.14(19) 8_565 . ? N1 C1 C2 119.43(9) 8_565 . ? N1 C1 C2 119.43(9) . . ? C1 C2 H41 116(2) . . ? C1 C2 H42 109(5) . . ? H41 C2 H42 103(4) . . ? O1 C3 O1 123.96(19) . 8_565 ? O1 C3 C4 118.01(9) . . ? O1 C3 C4 118.01(9) 8_565 . ? C3 C4 H21 110(2) . . ? C3 C4 H22 108(4) . . ? H21 C4 H22 119(3) . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 27.99 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.202 _refine_diff_density_min -0.222 _refine_diff_density_rms 0.042