# Supplementary Material (ESI) for New Journal of Chemistry # This journal is (c) The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2007 data_global _journal_coden_Cambridge 440 loop_ _publ_author_name 'Veneta Videnova-Adrabinska' 'Tadeusz Lis' 'Elzbieta Obara' _publ_contact_author_name 'Veneta Videnova-Adrabinska' _publ_contact_author_address ; Chemistry Wroclaw University of Technology 27 Wybrzeze Wyspianskiego St. Wroclaw 50 370 POLAND ; _publ_contact_author_email VENETA@PWR.WROC.PL _publ_requested_journal 'New Journal of Chemistry' _publ_section_title ; Two-dimensional hydrogen-bonded networks in guanidinium hydrogen dicarboxylates ; data_GnHSuc _database_code_depnum_ccdc_archive 'CCDC 631518' _database_code_CSD ? _audit_creation_method SHELXL-97 #CHEMICAL DATA _chemical_name_systematic ; Guanidinium hydrogen butanedicarboxylate' ; _chemical_name_common 'guanidinium hydrogen succinate' _chemical_melting_point ? _chemical_formula_moiety 'C4 H5 O4, C H6 N3' _chemical_formula_sum 'C5 H11 N3 O4' _chemical_formula_weight 177.17 #CRYSTAL DATA 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/c' _symmetry_space_group_name_Hall '-P 2ybc' 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 6.4910(10) _cell_length_b 18.388(4) _cell_length_c 7.2300(10) _cell_angle_alpha 90.00 _cell_angle_beta 112.18(3) _cell_angle_gamma 90.00 _cell_volume 799.1(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.350 _exptl_crystal_size_mid 0.250 _exptl_crystal_size_min 0.100 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.473 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 376 _exptl_absorpt_coefficient_mu 0.127 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; #EXPERIMENTAL DATA _diffrn_ambient_temperature 293(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 'Kuma KM4 CCD' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 2852 _diffrn_reflns_av_R_equivalents 0.1139 _diffrn_reflns_av_sigmaI/netI 0.0855 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -5 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 3.24 _diffrn_reflns_theta_max 24.99 _reflns_number_total 1383 _reflns_number_gt 1158 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'KUMA KM4 software' _computing_cell_refinement 'KUMA KM4 software' _computing_data_reduction 'KUMA KM4 software' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material SHELXL97 #REFINEMENT DATA _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^)+(0.1311P)^2^+0.0577P] 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 refall _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.050(9) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1383 _refine_ls_number_parameters 154 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0669 _refine_ls_R_factor_gt 0.0600 _refine_ls_wR_factor_ref 0.1796 _refine_ls_wR_factor_gt 0.1716 _refine_ls_goodness_of_fit_ref 1.075 _refine_ls_restrained_S_all 1.075 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 #ATOMIC COORDINATES AND THERMAL PARAMETERS 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 C1 C 0.2116(3) 0.62051(8) 0.7036(3) 0.0234(5) Uani 1 1 d . . . C2 C 0.0936(3) 0.69188(9) 0.6951(3) 0.0212(5) Uani 1 1 d . . . H12 H 0.096(3) 0.7153(11) 0.583(3) 0.027(5) Uiso 1 1 d . . . H22 H 0.191(4) 0.7190(13) 0.811(3) 0.042(6) Uiso 1 1 d . . . C3 C -0.1396(3) 0.68402(8) 0.6930(3) 0.0224(5) Uani 1 1 d . . . H13 H -0.140(3) 0.6603(12) 0.818(3) 0.033(5) Uiso 1 1 d . . . H23 H -0.229(4) 0.6522(11) 0.591(3) 0.032(5) Uiso 1 1 d . . . C4 C -0.2613(3) 0.75516(8) 0.6817(3) 0.0213(5) Uani 1 1 d . . . O1 O 0.4144(2) 0.62494(7) 0.7084(2) 0.0369(5) Uani 1 1 d . . . O2 O 0.1270(2) 0.56159(6) 0.7072(2) 0.0419(5) Uani 1 1 d . . . O3 O -0.4591(2) 0.75035(6) 0.6806(2) 0.0331(5) Uani 1 1 d . . . O4 O -0.1715(2) 0.81444(6) 0.6781(2) 0.0321(5) Uani 1 1 d . . . H1 H 0.463(5) 0.6789(16) 0.695(5) 0.073(9) Uiso 1 1 d . . . C10 C 0.3741(3) 0.93678(8) 0.7225(3) 0.0269(5) Uani 1 1 d . . . N1 N 0.2801(4) 0.99822(10) 0.7450(3) 0.0449(6) Uani 1 1 d . . . H11N H 0.162(5) 0.9959(14) 0.758(3) 0.044(7) Uiso 1 1 d . . . H21N H 0.357(5) 1.0375(18) 0.760(4) 0.055(7) Uiso 1 1 d . . . N2 N 0.5754(3) 0.93794(9) 0.7201(3) 0.0366(6) Uani 1 1 d . . . H12N H 0.643(5) 0.9751(17) 0.737(4) 0.054(8) Uiso 1 1 d . . . H22N H 0.641(5) 0.8982(18) 0.698(4) 0.057(8) Uiso 1 1 d . . . N3 N 0.2674(3) 0.87373(9) 0.6994(3) 0.0352(5) Uani 1 1 d . . . H13N H 0.341(4) 0.8353(14) 0.689(3) 0.032(5) Uiso 1 1 d . . . H23N H 0.139(4) 0.8740(12) 0.701(3) 0.037(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 C1 0.0196(10) 0.0152(9) 0.0389(10) -0.0009(6) 0.0150(8) -0.0006(7) C2 0.0174(9) 0.0146(9) 0.0349(10) 0.0016(6) 0.0135(8) 0.0007(6) C3 0.0177(9) 0.0144(9) 0.0370(11) -0.0009(7) 0.0126(8) 0.0007(7) C4 0.0176(9) 0.0165(9) 0.0317(10) 0.0008(6) 0.0115(8) -0.0002(6) O1 0.0227(8) 0.0166(8) 0.0803(11) 0.0040(6) 0.0297(7) 0.0020(5) O2 0.0285(9) 0.0158(8) 0.0893(12) 0.0002(6) 0.0311(8) -0.0012(5) O3 0.0209(8) 0.0174(7) 0.0688(11) 0.0039(5) 0.0259(7) 0.0017(5) O4 0.0238(8) 0.0154(7) 0.0626(10) 0.0014(5) 0.0226(7) -0.0013(5) C10 0.0251(10) 0.0168(9) 0.0405(11) -0.0022(7) 0.0142(8) 0.0000(7) N1 0.0313(11) 0.0222(9) 0.0918(16) -0.0090(8) 0.0351(11) 0.0003(8) N2 0.0262(10) 0.0146(9) 0.0759(14) -0.0060(7) 0.0269(9) -0.0026(6) N3 0.0257(10) 0.0203(10) 0.0648(12) -0.0038(7) 0.0232(9) -0.0034(7) #MOLECULAR GEOMETRY _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 C1 O1 1.307(2) . yes C1 O2 1.219(2) . ? C1 C2 1.509(2) . ? C2 C3 1.515(3) . ? C2 H12 0.92(2) . ? C2 H22 0.97(2) . ? C3 C4 1.514(2) . ? C3 H13 1.01(2) . ? C3 H23 0.95(2) . ? C4 O3 1.284(2) . yes C4 O4 1.241(2) . ? O1 H1 1.06(3) . yes C10 N1 1.323(3) . ? C10 N2 1.313(3) . ? C10 N3 1.328(2) . ? N1 H11N 0.81(3) . ? N1 H21N 0.86(3) . ? N2 H12N 0.80(3) . ? N2 H22N 0.89(3) . ? N3 H13N 0.87(3) . ? N3 H23N 0.84(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 O2 C1 O1 120.83(15) . . ? O2 C1 C2 123.21(16) . . ? O1 C1 C2 115.95(13) . . ? C1 C2 C3 114.03(14) . . ? C1 C2 H12 105.5(12) . . ? C3 C2 H12 112.4(12) . . ? C1 C2 H22 104.9(14) . . ? C3 C2 H22 112.1(13) . . ? H12 C2 H22 107.4(18) . . ? C4 C3 C2 114.66(14) . . ? C4 C3 H13 104.1(12) . . ? C2 C3 H13 112.1(12) . . ? C4 C3 H23 109.6(13) . . ? C2 C3 H23 112.5(13) . . ? H13 C3 H23 102.9(17) . . ? O3 C4 O4 122.48(14) . . ? O3 C4 C3 116.17(14) . . ? O4 C4 C3 121.33(16) . . ? C1 O1 H1 113.0(15) . . ? N2 C10 N1 119.68(18) . . ? N2 C10 N3 119.10(17) . . ? N1 C10 N3 121.2(2) . . ? C10 N1 H11N 118.1(18) . . ? C10 N1 H21N 117(2) . . ? H11N N1 H21N 124(3) . . ? C10 N2 H12N 120(2) . . ? C10 N2 H22N 122.5(19) . . ? H12N N2 H22N 117(3) . . ? C10 N3 H13N 116.2(16) . . ? C10 N3 H23N 117.8(16) . . ? H13N N3 H23N 126(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2 C1 C2 C3 0.4(3) . . . . ? O1 C1 C2 C3 -179.11(16) . . . . ? C1 C2 C3 C4 -179.22(15) . . . . ? O4 C4 C3 C2 -1.2(3) . . . . ? O3 C4 C3 C2 -179.68(15) . . . . ? 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 O1 H1 O3 1.06(3) 1.43(3) 2.4813(19) 177(3) 1_655 N1 H11N O2 0.81(3) 2.32(3) 3.025(3) 146(2) 2_556 N1 H21N O1 0.86(3) 2.14(3) 2.995(2) 172(3) 2_656 N2 H12N O2 0.80(3) 2.11(3) 2.900(2) 170(3) 2_656 N2 H22N O4 0.89(3) 2.00(3) 2.885(2) 172(3) 1_655 N3 H13N O3 0.87(3) 2.05(3) 2.915(2) 175(2) 1_655 N3 H23N O4 0.84(3) 2.25(3) 3.000(2) 150(2) . _diffrn_measured_fraction_theta_max 1.0 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 0.281 _refine_diff_density_min -0.357 _refine_diff_density_rms 0.098 #============================================== data_2 _database_code_depnum_ccdc_archive 'CCDC 631519' #============================================== _database_code_CSD ? _audit_creation_method SHELXL-97 #CHEMICAL DATA _chemical_name_systematic ; guanidinium hydrogen E-butenedicarboxylate ; _chemical_name_common 'guanidinium hydrogen fumarate' _chemical_melting_point ? _chemical_formula_moiety 'C4 H3 O4, C H6 N3 ' _chemical_formula_sum 'C5 H9 N3 O4 ' _chemical_formula_weight 175.14 #CRYSTAL DATA 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 P21/m _symmetry_space_group_name_Hall '-P 2yb' _symmetry_Int_Tables_number 11 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, 1/2+y, -z' '-x, -y, -z' 'x, 1/2-y, z' _cell_length_a 3.696(3) _cell_length_b 18.824(5) _cell_length_c 5.496(2) _cell_angle_alpha 90.00 _cell_angle_beta 94.76(4) _cell_angle_gamma 90.00 _cell_volume 381.1(5) _cell_formula_units_Z 2 _cell_measurement_temperature 297 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 10.90 _cell_measurement_theta_max 30.19 _exptl_crystal_description 'thick needle' _exptl_crystal_colour colorless _exptl_crystal_size_max 0.600 _exptl_crystal_size_mid 0.350 _exptl_crystal_size_min 0.300 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.526 _exptl_crystal_density_method ? _exptl_crystal_F_000 184 _exptl_absorpt_coefficient_mu 0.132 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; \q scan width 0.60 +0.35tan\q%, \q scan rate 4.1\% per min. ; #EXPERIMENTAL DATA _diffrn_ambient_temperature 297 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'X-ray tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type Enraf-Nonius _diffrn_measurement_method 'w scan' _diffrn_standards_number 3 _diffrn_standards_interval_time '60 min' _diffrn_standards_decay_% 0 _diffrn_reflns_number 2539 _diffrn_reflns_av_R_equivalents 0.032 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 2.8 _diffrn_reflns_theta_max 29.95 _reflns_number_total 1153 _reflns_number_gt 986 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'MITHRIL DIRDIF' _computing_structure_refinement TEXSAN _computing_molecular_graphics 'PLATON (Utrecht University 2003)' _computing_publication_material 'PLATON (Utrecht University 2003)' #REFINEMENT DATA _refine_special_details ; ? ; _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=4Fo^2^\s^2^(Fo^2^)' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method TEXSAN _refine_ls_extinction_coef ? _refine_ls_extinction_expression ? _refine_ls_number_reflns 1153 _refine_ls_number_parameters 78 _refine_ls_number_restraints 0 _refine_ls_R_factor_gt 0.053 _refine_ls_wR_factor_ref 0.067 _refine_ls_goodness_of_fit_ref 2.17 _refine_ls_shift/su_max 0.00 _refine_diff_density_max 0.30 _refine_diff_density_min -0.56 #ATOMIC COORDINATES AND THERMAL PARAMETERS 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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.7312(3) 0.06795(5) 0.7248(2) 2.04(4) Bani 1 d . . . C2 C 0.5854(3) 0.00104(5) 0.6088(2) 2.19(4) Bani 1 d . . . H2C H 0.623(5) -0.041(1) 0.704(4) 4.2(4) Biso 1 d . . . O1 O 0.9281(2) 0.06094(4) 0.9301(1) 2.65(4) Bani 1 d . . . O2 O 0.6671(3) 0.12595(4) 0.6294(2) 3.22(4) Bani 1 d . . . H1 H 0.93(1) 0.014(2) 0.972(7) 3.4(7) Biso 0.5 d PD . . C10 C 1.1587(5) 0.25 1.0825(3) 2.38(5) Bani 1 d . . . N1 N 1.2455(4) 0.18872(6) 1.1899(2) 3.74(5) Bani 1 d . . . H11N H 1.352(7) 0.190(1) 1.334(5) 6.1(6) Biso 1 d . . . H21N H 1.156(6) 0.149(1) 1.111(4) 4.8(4) Biso 1 d . . . N2 N 0.9882(4) 0.25 0.8619(3) 3.00(6) Bani 1 d . . . H12N H 0.896(5) 0.209(1) 0.796(3) 3.8(3) Biso 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_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 C1 0.0309(5) 0.0213(4) 0.0233(5) -0.0014(3) -0.0000(4) -0.0006(3) C2 0.0355(5) 0.0194(4) 0.0259(5) -0.0027(4) -0.0122(4) -0.0002(3) O1 0.0462(5) 0.0235(4) 0.0270(5) -0.0021(3) -0.0200(4) 0.0000(2) O2 0.0586(6) 0.0209(4) 0.0380(5) -0.0026(3) -0.0244(4) 0.0032(3) C10 0.0324(7) 0.0239(6) 0.0320(7) 0.0000 -0.0101(5) 0.0000 N1 0.0657(8) 0.0275(5) 0.0438(6) -0.0004(5) -0.0254(6) 0.0069(4) N2 0.0512(9) 0.0213(6) 0.0372(7) 0.0000 -0.0220(6) 0.0000 #MOLECULAR GEOMETRY 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 C1 O1 1.298(1) . ? C1 O2 1.226(1) . ? C1 C2 1.492(1) . ? C2 C2 1.306(2) 3_656 ? C2 H2C 0.96(2) . ? O1 H1 0.92(4) . ? N1 C10 1.323(1) . ? N1 H11N 0.85(3) . ? N1 H21N 0.91(2) . ? N2 C10 1.319(2) . ? N2 H12N 0.91(2) . ? N2 H12N 0.91(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 O1 C1 O2 122.48(9) . . ? O1 C1 C2 116.25(9) . . ? O2 C1 C2 121.3(1) . . ? C1 C2 C2 123.1(1) . . ? C1 C2 H2C 116(1) . . ? C2 C2 H2C 121(1) . . ? C1 O1 H1 108(2) . . ? N1 C10 N1 121.4(2) . . ? N2 C10 N1 119.30(8) . . ? N2 C10 N1 119.30(8) . . ? C10 N1 H11N 117(2) . . ? C10 N1 H21N 116(1) . . ? H11N N1 H21N 126(3) . . ? C10 N2 H12N 120(1) . . ? C10 N2 H12N 120(1) . . ? H12N N2 H12N 117(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 O1 H1 O1 0.91(4) 1.58(4) 2.464(2) 161(4) 3_757 N1 H11N O2 0.85(3) 2.26(2) 3.006(3) 145.2(17) 1_656 N1 H21N O1 0.92(2) 2.07(2) 2.987(3) 177(2) . N2 H12N O2 0.907(18) 1.967(18) 2.871(3) 174.3(18) . #============================================== data_3 _database_code_depnum_ccdc_archive 'CCDC 631520' #============================================== _database_code_CSD ? _audit_creation_method SHELXL-97 #CHEMICAL DATA _chemical_name_systematic ; 'Guanidinium hydrogen pentanedicarboxylate' ; _chemical_name_common 'guanidinium hydrogen adipate' _chemical_melting_point ? _chemical_formula_moiety 'C5 H7 O4, C H6 N3' _chemical_formula_sum 'C6 H13 N3 O4' _chemical_formula_weight 191.19 #CRYSTAL DATA 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' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.284(2) _cell_length_b 8.501(3) _cell_length_c 10.466(4) _cell_angle_alpha 69.10(3) _cell_angle_beta 77.91(3) _cell_angle_gamma 89.42(3) _cell_volume 428.4(3) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.600 _exptl_crystal_size_mid 0.400 _exptl_crystal_size_min 0.200 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.482 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 204 _exptl_absorpt_coefficient_mu 0.124 _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 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'KUMA KM4 CCD' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 6197 _diffrn_reflns_av_R_equivalents 0.0215 _diffrn_reflns_av_sigmaI/netI 0.0177 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.89 _diffrn_reflns_theta_max 27.99 _reflns_number_total 2040 _reflns_number_gt 1848 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'KUMA KM4 software' _computing_cell_refinement 'KUMA KM4 software' _computing_data_reduction 'KUMA KM4 software' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek,2003)' _computing_publication_material ? _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^)+(0.0380P)^2^+0.1470P] 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 0.038(7) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2040 _refine_ls_number_parameters 169 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0346 _refine_ls_R_factor_gt 0.0305 _refine_ls_wR_factor_ref 0.0809 _refine_ls_wR_factor_gt 0.0783 _refine_ls_goodness_of_fit_ref 1.075 _refine_ls_restrained_S_all 1.075 _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 C1 C 0.25826(18) 0.35469(12) 0.44237(10) 0.01112(19) Uani 1 1 d . . . C2 C 0.23167(18) 0.52538(12) 0.33481(10) 0.01146(19) Uani 1 1 d . . . H12 H 0.183(2) 0.6006(17) 0.3867(14) 0.015(3) Uiso 1 1 d . . . H22 H 0.406(3) 0.5678(17) 0.2763(14) 0.019(3) Uiso 1 1 d . . . C3 C 0.04237(18) 0.53101(12) 0.24206(10) 0.01171(19) Uani 1 1 d . . . H13 H 0.102(2) 0.4689(16) 0.1801(14) 0.014(3) Uiso 1 1 d . . . H23 H -0.128(3) 0.4790(16) 0.2995(14) 0.015(3) Uiso 1 1 d . . . C4 C 0.02425(19) 0.71597(12) 0.15586(10) 0.0122(2) Uani 1 1 d . . . H14 H -0.049(2) 0.7768(17) 0.2165(14) 0.016(3) Uiso 1 1 d . . . H24 H 0.198(3) 0.7701(17) 0.1070(14) 0.017(3) Uiso 1 1 d . . . C5 C -0.13861(18) 0.75144(12) 0.04684(10) 0.0118(2) Uani 1 1 d . . . O1 O 0.41826(14) 0.35469(9) 0.52181(7) 0.01463(17) Uani 1 1 d . . . O2 O 0.13562(14) 0.22581(9) 0.45475(8) 0.01591(17) Uani 1 1 d . . . O3 O -0.13830(14) 0.90917(9) -0.03153(8) 0.01586(17) Uani 1 1 d . . . O4 O -0.26449(14) 0.63769(9) 0.03514(8) 0.01585(18) Uani 1 1 d . . . H1 H 0.5000 0.5000 0.5000 0.060(8) Uiso 1 2 d S . . H3 H 0.0000 1.0000 0.0000 0.066(9) Uiso 1 2 d S . . C10 C 0.39099(18) -0.11740(12) 0.74278(10) 0.0126(2) Uani 1 1 d . . . N1 N 0.53820(18) 0.01169(11) 0.73805(10) 0.0169(2) Uani 1 1 d . . . H11N H 0.638(3) -0.0068(18) 0.7956(16) 0.022(3) Uiso 1 1 d . . . H21N H 0.535(3) 0.109(2) 0.6729(17) 0.027(4) Uiso 1 1 d . . . N2 N 0.23526(17) -0.09128(11) 0.65360(9) 0.01565(19) Uani 1 1 d . . . H12N H 0.223(3) 0.014(2) 0.5933(17) 0.030(4) Uiso 1 1 d . . . H22N H 0.133(3) -0.1743(19) 0.6538(15) 0.024(4) Uiso 1 1 d . . . N3 N 0.40252(17) -0.27024(11) 0.83722(9) 0.01452(19) Uani 1 1 d . . . H13N H 0.303(3) -0.359(2) 0.8456(15) 0.024(3) Uiso 1 1 d . . . H23N H 0.513(3) -0.2867(19) 0.8948(16) 0.027(4) 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 C1 0.0113(4) 0.0112(4) 0.0109(4) -0.0034(3) -0.0039(3) 0.0019(3) C2 0.0131(4) 0.0097(4) 0.0116(4) -0.0023(3) -0.0055(3) 0.0007(3) C3 0.0135(4) 0.0101(4) 0.0119(4) -0.0027(3) -0.0060(3) 0.0011(3) C4 0.0149(4) 0.0104(4) 0.0121(4) -0.0031(3) -0.0067(3) 0.0011(3) C5 0.0120(4) 0.0119(4) 0.0112(4) -0.0032(3) -0.0037(3) 0.0018(3) O1 0.0181(4) 0.0111(3) 0.0158(3) -0.0024(3) -0.0105(3) 0.0005(3) O2 0.0192(4) 0.0110(3) 0.0179(4) -0.0023(3) -0.0100(3) -0.0005(3) O3 0.0209(4) 0.0104(3) 0.0167(4) -0.0014(3) -0.0114(3) 0.0007(3) O4 0.0184(4) 0.0125(3) 0.0174(4) -0.0031(3) -0.0098(3) -0.0003(3) C10 0.0125(4) 0.0129(4) 0.0127(4) -0.0047(4) -0.0034(3) 0.0019(3) N1 0.0207(4) 0.0121(4) 0.0193(4) -0.0036(4) -0.0111(4) -0.0012(3) N2 0.0191(4) 0.0115(4) 0.0168(4) -0.0023(3) -0.0099(3) -0.0008(3) N3 0.0162(4) 0.0116(4) 0.0161(4) -0.0026(3) -0.0084(3) -0.0001(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O2 1.2309(13) . ? C1 O1 1.3041(12) . ? C1 C2 1.5131(14) . ? C2 C3 1.5223(14) . ? C2 H12 0.978(13) . ? C2 H22 0.982(14) . ? C3 C4 1.5220(14) . ? C3 H13 0.977(13) . ? C3 H23 0.979(13) . ? C4 C5 1.5145(14) . ? C4 H14 0.973(13) . ? C4 H24 0.980(14) . ? C5 O3 1.2983(13) . ? C5 O4 1.2346(13) . ? O1 H1 1.2381(8) . ? O3 H3 1.2383(8) . ? C10 N2 1.3296(13) . ? C10 N1 1.3320(14) . ? C10 N3 1.3327(14) . ? N1 H11N 0.853(16) . ? N1 H21N 0.870(16) . ? N2 H12N 0.903(17) . ? N2 H22N 0.892(16) . ? N3 H13N 0.892(16) . ? N3 H23N 0.897(17) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 C1 O1 122.59(9) . . ? O2 C1 C2 122.35(9) . . ? O1 C1 C2 115.06(8) . . ? C1 C2 C3 116.58(8) . . ? C1 C2 H12 106.3(8) . . ? C3 C2 H12 110.5(8) . . ? C1 C2 H22 107.1(8) . . ? C3 C2 H22 109.8(8) . . ? H12 C2 H22 106.0(11) . . ? C4 C3 C2 107.05(8) . . ? C4 C3 H13 110.1(8) . . ? C2 C3 H13 111.3(8) . . ? C4 C3 H23 110.8(8) . . ? C2 C3 H23 110.4(8) . . ? H13 C3 H23 107.3(11) . . ? C5 C4 C3 116.27(8) . . ? C5 C4 H14 106.0(8) . . ? C3 C4 H14 110.6(8) . . ? C5 C4 H24 107.2(8) . . ? C3 C4 H24 110.1(8) . . ? H14 C4 H24 106.1(11) . . ? O4 C5 O3 122.78(9) . . ? O4 C5 C4 121.91(9) . . ? O3 C5 C4 115.30(9) . . ? C1 O1 H1 111.33(7) . . ? C5 O3 H3 111.24(7) . . ? N2 C10 N1 119.44(9) . . ? N2 C10 N3 121.34(9) . . ? N1 C10 N3 119.22(9) . . ? C10 N1 H11N 118.6(10) . . ? C10 N1 H21N 118.0(10) . . ? H11N N1 H21N 123.3(14) . . ? C10 N2 H12N 120.5(10) . . ? C10 N2 H22N 122.1(9) . . ? H12N N2 H22N 117.3(14) . . ? C10 N3 H13N 121.8(10) . . ? C10 N3 H23N 120.3(10) . . ? H13N N3 H23N 117.9(14) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2 C1 C2 C3 0.47(14) . . . . ? O1 C1 C2 C3 -178.80(8) . . . . ? C1 C2 C3 C4 173.33(8) . . . . ? C2 C3 C4 C5 175.33(8) . . . . ? C3 C4 C5 O4 4.95(14) . . . . ? C3 C4 C5 O3 -175.82(8) . . . . ? 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 O1 H1 O1 1.24 1.24 2.4761(17) 180.0 2_666 O3 H3 O3 1.24 1.24 2.4765(16) 180.0 2_575 N1 H11N O3 0.853(16) 2.268(16) 3.1136(16) 171.4(13) 1_646 N1 H21N O1 0.870(16) 2.292(17) 3.1434(17) 166.0(13) . N2 H12N O2 0.903(17) 1.990(17) 2.8814(17) 169.0(14) . N2 H22N O2 0.892(16) 2.131(16) 2.8872(14) 142.1(13) 2_556 N3 H13N O4 0.892(16) 2.238(15) 2.9554(17) 137.2(12) 2_556 N3 H23N O4 0.897(17) 1.999(17) 2.8881(15) 170.7(14) 1_646 _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 27.99 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.387 _refine_diff_density_min -0.220 _refine_diff_density_rms 0.041