Electronic Supplementary MAterial for CrystEngComm This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Delia Haynes' _publ_contact_author_address ; School of Chemistry University of KwaZulu-Natal Westville Campus P. Bag X54001 Durban 4000 Republic of South Africa Current address Department of Chemistry and Polymer Science Stellenbosch University P. Bag X1 Matieland 7602 Republic of South Africa ; _publ_contact_author_email dhaynes@sun.ac.za loop_ _publ_author_name _publ_author_address D.Haynes ; School of Chemistry University of KwaZulu-Natal Westville Campus P. Bag X54001 Durban 4000 Republic of South Africa ; L.Pietersen ; School of Chemistry University of KwaZulu-Natal Westville Campus P. Bag X54001 Durban 4000 Republic of South Africa ; _publ_section_title ; Hydrogen bonding networks in ammonium carboxylate salts: the crystal structures of phenylethylammonium fumarate-fumaric acid, phenylethylammonium succinate-succinic acid and anilinium fumarate-fumaric acid ; data_1 _database_code_depnum_ccdc_archive 'CCDC 665207' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'phenylethylammonium fumarate-fumaric acid' _chemical_melting_point ? _chemical_formula_moiety '2(C8 H12 N), C4 H4 O4, C4 H2 O4' _chemical_formula_sum 'C24 H30 N2 O8' _chemical_formula_weight 474.50 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 9.1871(5) _cell_length_b 10.5741(6) _cell_length_c 12.5960(7) _cell_angle_alpha 81.2810(10) _cell_angle_beta 88.9180(10) _cell_angle_gamma 86.2560(10) _cell_volume 1206.87(12) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 8054 _cell_measurement_theta_min 2.22 _cell_measurement_theta_max 26.36 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.60 _exptl_crystal_size_min 0.41 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.306 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 504 _exptl_absorpt_coefficient_mu 0.098 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9433 _exptl_absorpt_correction_T_max 0.9608 _exptl_absorpt_process_details '(SADABS; Bruker, 2002)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX CCD area-detector' _diffrn_measurement_method \w _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% . _diffrn_reflns_number 13114 _diffrn_reflns_av_R_equivalents 0.0172 _diffrn_reflns_av_sigmaI/netI 0.0187 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.95 _diffrn_reflns_theta_max 26.40 _reflns_number_total 4921 _reflns_number_gt 4552 _reflns_threshold_expression >2\s(I) _computing_data_collection 'SMART (Bruker, 2002)' _computing_cell_refinement 'SAINT (Bruker, 2003)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _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. The NH3+ and COOH hydrogen atoms were located in the difference map. ; _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^)+(0.0568P)^2^+0.3576P] 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 4921 _refine_ls_number_parameters 339 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0362 _refine_ls_R_factor_gt 0.0339 _refine_ls_wR_factor_ref 0.0942 _refine_ls_wR_factor_gt 0.0921 _refine_ls_goodness_of_fit_ref 0.996 _refine_ls_restrained_S_all 0.996 _refine_ls_shift/su_max 0.032 _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 N11 N 0.81710(10) 0.68566(9) 0.13888(7) 0.01722(19) Uani 1 1 d . . . H1 H 0.8827(17) 0.7415(14) 0.1045(12) 0.030(4) Uiso 1 1 d . . . H2 H 0.8565(16) 0.6025(15) 0.1438(11) 0.026(3) Uiso 1 1 d . . . H3 H 0.7330(19) 0.6918(15) 0.1011(13) 0.038(4) Uiso 1 1 d . . . C12 C 0.78400(12) 0.71784(11) 0.24813(9) 0.0195(2) Uani 1 1 d . . . H12A H 0.7141 0.6582 0.2851 0.023 Uiso 1 1 calc R . . H12B H 0.7381 0.8060 0.2421 0.023 Uiso 1 1 calc R . . C14 C 0.89202(12) 0.75312(12) 0.42092(9) 0.0244(2) Uani 1 1 d . . . C13 C 0.92269(12) 0.70844(12) 0.31391(9) 0.0244(2) Uani 1 1 d . . . H13A H 0.9634 0.6185 0.3258 0.029 Uiso 1 1 calc R . . H13B H 0.9961 0.7617 0.2736 0.029 Uiso 1 1 calc R . . C19 C 0.87967(14) 0.66601(14) 0.51435(10) 0.0323(3) Uani 1 1 d . . . H19 H 0.8931 0.5767 0.5115 0.039 Uiso 1 1 calc R . . C16 C 0.83965(16) 0.92466(16) 0.52513(13) 0.0440(4) Uani 1 1 d . . . H16 H 0.8256 1.0138 0.5285 0.053 Uiso 1 1 calc R . . C15 C 0.87210(15) 0.88323(13) 0.42739(11) 0.0333(3) Uani 1 1 d . . . H15 H 0.8808 0.9443 0.3644 0.040 Uiso 1 1 calc R . . C18 C 0.84790(16) 0.70813(18) 0.61195(11) 0.0439(4) Uani 1 1 d . . . H18 H 0.8401 0.6475 0.6753 0.053 Uiso 1 1 calc R . . C17 C 0.82765(16) 0.83684(19) 0.61744(12) 0.0469(4) Uani 1 1 d . . . H17 H 0.8055 0.8653 0.6843 0.056 Uiso 1 1 calc R . . N21 N 0.66461(10) 0.29779(9) 0.18708(7) 0.01699(19) Uani 1 1 d . . . H4 H 0.6260(15) 0.3813(14) 0.1635(11) 0.026(3) Uiso 1 1 d . . . H5 H 0.5951(17) 0.2427(14) 0.1692(12) 0.030(4) Uiso 1 1 d . . . H6 H 0.7468(18) 0.2819(15) 0.1525(13) 0.034(4) Uiso 1 1 d . . . C22 C 0.68968(12) 0.27747(11) 0.30489(8) 0.0190(2) Uani 1 1 d . . . H22A H 0.7688 0.3306 0.3213 0.023 Uiso 1 1 calc R . . H22B H 0.7206 0.1864 0.3293 0.023 Uiso 1 1 calc R . . C23 C 0.55126(12) 0.31326(11) 0.36453(9) 0.0223(2) Uani 1 1 d . . . H23A H 0.5216 0.4049 0.3415 0.027 Uiso 1 1 calc R . . H23B H 0.4715 0.2616 0.3469 0.027 Uiso 1 1 calc R . . C24 C 0.57620(12) 0.28957(11) 0.48416(9) 0.0214(2) Uani 1 1 d . . . C25 C 0.64383(14) 0.37857(12) 0.53364(10) 0.0275(3) Uani 1 1 d . . . H25 H 0.6683 0.4575 0.4927 0.033 Uiso 1 1 calc R . . C26 C 0.67608(16) 0.35353(14) 0.64224(11) 0.0351(3) Uani 1 1 d . . . H26 H 0.7223 0.4152 0.6752 0.042 Uiso 1 1 calc R . . C27 C 0.64115(16) 0.23896(14) 0.70268(10) 0.0371(3) Uani 1 1 d . . . H27 H 0.6647 0.2212 0.7768 0.044 Uiso 1 1 calc R . . C28 C 0.57190(16) 0.15052(13) 0.65481(11) 0.0366(3) Uani 1 1 d . . . H28 H 0.5468 0.0721 0.6963 0.044 Uiso 1 1 calc R . . C29 C 0.53873(14) 0.17598(12) 0.54592(10) 0.0287(3) Uani 1 1 d . . . H29 H 0.4901 0.1151 0.5137 0.034 Uiso 1 1 calc R . . O31 O -0.06465(8) 0.43655(7) 0.14288(6) 0.01845(17) Uani 1 1 d . . . O32 O 0.10792(8) 0.29612(7) 0.09617(6) 0.01798(17) Uani 1 1 d . . . O33 O 0.37907(8) 0.68782(7) 0.04099(6) 0.01588(16) Uani 1 1 d . . . O34 O 0.55078(8) 0.54874(7) 0.12144(6) 0.01717(16) Uani 1 1 d . . . H7 H 1.001(2) 1.2184(19) 0.0997(16) 0.067(6) Uiso 1 1 d . . . H8 H 0.477(2) 0.7655(18) 0.0280(16) 0.066(6) Uiso 1 1 d . . . C31 C 0.06236(11) 0.40726(9) 0.11513(8) 0.0142(2) Uani 1 1 d . . . C32 C 0.17214(11) 0.50716(9) 0.10122(8) 0.0150(2) Uani 1 1 d . . . H32 H 0.1385 0.5950 0.0901 0.018 Uiso 1 1 calc R . . C33 C 0.31427(11) 0.47761(9) 0.10379(8) 0.0148(2) Uani 1 1 d . . . H33 H 0.3477 0.3897 0.1155 0.018 Uiso 1 1 calc R . . C34 C 0.42434(11) 0.57696(9) 0.08902(8) 0.0139(2) Uani 1 1 d . . . O41 O 0.57415(8) 0.83656(7) 0.02474(6) 0.01686(16) Uani 1 1 d . . . O42 O 0.55268(8) 0.86885(7) -0.15455(6) 0.02068(18) Uani 1 1 d . . . O43 O 0.90837(8) 1.15115(7) 0.10052(6) 0.01781(17) Uani 1 1 d . . . O44 O 0.95280(8) 1.15363(7) -0.07557(6) 0.01848(17) Uani 1 1 d . . . C41 C 0.61019(11) 0.88818(9) -0.07137(8) 0.0152(2) Uani 1 1 d . . . C42 C 0.72982(11) 0.97765(9) -0.07560(8) 0.0160(2) Uani 1 1 d . . . H42 H 0.7802 1.0004 -0.1416 0.019 Uiso 1 1 calc R . . C43 C 0.76772(11) 1.02616(9) 0.00980(8) 0.0158(2) Uani 1 1 d . . . H43 H 0.7177 1.0020 0.0757 0.019 Uiso 1 1 calc R . . C44 C 0.88527(11) 1.11701(9) 0.00728(8) 0.0153(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 N11 0.0143(4) 0.0203(5) 0.0173(4) -0.0029(4) 0.0000(3) -0.0022(4) C12 0.0175(5) 0.0240(5) 0.0174(5) -0.0046(4) 0.0017(4) -0.0017(4) C14 0.0183(5) 0.0360(7) 0.0206(6) -0.0074(5) -0.0016(4) -0.0057(5) C13 0.0198(5) 0.0338(6) 0.0202(5) -0.0062(5) -0.0016(4) -0.0008(5) C19 0.0278(6) 0.0444(8) 0.0241(6) -0.0018(5) -0.0033(5) -0.0052(5) C16 0.0359(8) 0.0540(9) 0.0501(9) -0.0314(8) 0.0032(6) -0.0092(7) C15 0.0340(7) 0.0363(7) 0.0323(7) -0.0105(6) 0.0020(5) -0.0093(5) C18 0.0344(8) 0.0771(12) 0.0202(6) -0.0034(7) -0.0010(5) -0.0128(7) C17 0.0322(7) 0.0866(13) 0.0302(7) -0.0319(8) 0.0043(6) -0.0137(7) N21 0.0151(4) 0.0208(5) 0.0153(4) -0.0033(4) 0.0000(3) -0.0018(4) C22 0.0183(5) 0.0238(5) 0.0146(5) -0.0021(4) -0.0019(4) -0.0010(4) C23 0.0196(5) 0.0293(6) 0.0176(5) -0.0032(4) 0.0004(4) -0.0003(4) C24 0.0212(5) 0.0257(6) 0.0166(5) -0.0035(4) 0.0021(4) 0.0037(4) C25 0.0324(6) 0.0256(6) 0.0243(6) -0.0041(5) -0.0032(5) 0.0015(5) C26 0.0415(8) 0.0385(7) 0.0269(6) -0.0144(6) -0.0096(5) 0.0098(6) C27 0.0494(8) 0.0434(8) 0.0156(6) -0.0056(5) -0.0021(5) 0.0218(6) C28 0.0482(8) 0.0318(7) 0.0248(6) 0.0053(5) 0.0112(6) 0.0090(6) C29 0.0343(7) 0.0262(6) 0.0250(6) -0.0035(5) 0.0059(5) -0.0010(5) O31 0.0143(4) 0.0172(4) 0.0242(4) -0.0035(3) 0.0022(3) -0.0033(3) O32 0.0151(4) 0.0155(4) 0.0247(4) -0.0064(3) 0.0007(3) -0.0039(3) O33 0.0148(4) 0.0140(3) 0.0186(4) -0.0004(3) -0.0008(3) -0.0039(3) O34 0.0142(4) 0.0172(4) 0.0202(4) -0.0021(3) -0.0013(3) -0.0032(3) C31 0.0150(5) 0.0161(5) 0.0117(4) -0.0014(4) -0.0021(4) -0.0033(4) C32 0.0174(5) 0.0132(5) 0.0146(5) -0.0020(4) 0.0001(4) -0.0035(4) C33 0.0172(5) 0.0135(5) 0.0142(5) -0.0026(4) 0.0001(4) -0.0036(4) C34 0.0152(5) 0.0157(5) 0.0116(4) -0.0043(4) 0.0019(4) -0.0030(4) O41 0.0161(4) 0.0166(4) 0.0176(4) 0.0002(3) -0.0010(3) -0.0057(3) O42 0.0231(4) 0.0212(4) 0.0189(4) -0.0033(3) -0.0027(3) -0.0082(3) O43 0.0161(4) 0.0177(4) 0.0212(4) -0.0063(3) 0.0013(3) -0.0050(3) O44 0.0172(4) 0.0172(4) 0.0212(4) -0.0019(3) 0.0023(3) -0.0054(3) C41 0.0150(5) 0.0120(4) 0.0186(5) -0.0021(4) -0.0006(4) -0.0005(4) C42 0.0146(5) 0.0136(5) 0.0191(5) -0.0002(4) 0.0013(4) -0.0018(4) C43 0.0138(5) 0.0131(5) 0.0201(5) -0.0011(4) 0.0016(4) -0.0016(4) C44 0.0130(5) 0.0115(4) 0.0212(5) -0.0024(4) -0.0003(4) 0.0006(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 N11 C12 1.4882(14) . ? C12 C13 1.5225(15) . ? C14 C19 1.3879(18) . ? C14 C15 1.3905(18) . ? C14 C13 1.5101(16) . ? C19 C18 1.389(2) . ? C16 C17 1.381(2) . ? C16 C15 1.389(2) . ? C18 C17 1.374(2) . ? N21 C22 1.4869(13) . ? C22 C23 1.5206(15) . ? C23 C24 1.5089(15) . ? C24 C29 1.3882(17) . ? C24 C25 1.3889(17) . ? C25 C26 1.3872(18) . ? C26 C27 1.383(2) . ? C27 C28 1.381(2) . ? C28 C29 1.3928(18) . ? O31 C31 1.2449(13) . ? O32 C31 1.2769(13) . ? O33 C34 1.2822(12) . ? O34 C34 1.2413(13) . ? C31 C32 1.4967(13) . ? C32 C33 1.3225(15) . ? C33 C34 1.4944(13) . ? O41 C41 1.2966(13) . ? O42 C41 1.2323(13) . ? O43 C44 1.3048(13) . ? O44 C44 1.2282(13) . ? C41 C42 1.4913(14) . ? C42 C43 1.3214(15) . ? C43 C44 1.4883(14) . ? 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 N11 C12 C13 110.67(9) . . ? C19 C14 C15 118.46(12) . . ? C19 C14 C13 121.13(11) . . ? C15 C14 C13 120.39(11) . . ? C14 C13 C12 110.87(9) . . ? C14 C19 C18 120.64(14) . . ? C17 C16 C15 120.28(15) . . ? C16 C15 C14 120.60(14) . . ? C17 C18 C19 120.47(14) . . ? C18 C17 C16 119.55(13) . . ? N21 C22 C23 110.52(9) . . ? C24 C23 C22 110.33(9) . . ? C29 C24 C25 118.73(11) . . ? C29 C24 C23 120.77(11) . . ? C25 C24 C23 120.43(11) . . ? C26 C25 C24 120.73(12) . . ? C25 C26 C27 120.15(13) . . ? C28 C27 C26 119.68(12) . . ? C27 C28 C29 120.17(13) . . ? C24 C29 C28 120.52(12) . . ? O31 C31 O32 124.62(9) . . ? O31 C31 C32 119.33(9) . . ? O32 C31 C32 116.04(9) . . ? C33 C32 C31 122.39(9) . . ? C32 C33 C34 122.61(9) . . ? O34 C34 O33 124.41(9) . . ? O34 C34 C33 119.81(9) . . ? O33 C34 C33 115.77(9) . . ? O42 C41 O41 124.94(9) . . ? O42 C41 C42 120.59(9) . . ? O41 C41 C42 114.47(9) . . ? C43 C42 C41 121.89(9) . . ? C42 C43 C44 122.92(9) . . ? O44 C44 O43 124.72(9) . . ? O44 C44 C43 121.89(9) . . ? O43 C44 C43 113.38(9) . . ? 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 N11 H3 O41 0.909(17) 2.171(17) 2.9250(12) 139.8(13) . N11 H3 O34 0.909(17) 2.313(16) 2.9513(12) 127.0(13) . N11 H2 O31 0.923(15) 1.855(15) 2.7766(12) 175.9(13) 1_655 N11 H1 O44 0.926(16) 1.929(16) 2.8261(12) 162.3(13) 2_775 N11 H1 O32 0.926(16) 2.617(15) 3.0075(12) 106.0(10) 2_665 N21 H4 O34 0.937(15) 1.861(15) 2.7971(12) 178.0(13) . N21 H6 O31 0.884(17) 2.448(16) 2.9709(12) 118.3(12) 1_655 N21 H5 O42 0.944(16) 1.885(16) 2.8227(12) 171.6(13) 2_665 N21 H6 O43 0.884(17) 2.124(17) 2.9284(12) 150.9(14) 1_545 N21 H5 O33 0.944(16) 2.648(15) 2.8880(12) 95.0(10) 2_665 O41 H8 O33 1.20(2) 1.25(2) 2.4463(10) 174.3(19) . O43 H7 O32 1.14(2) 1.32(2) 2.4599(10) 178.5(19) 1_665 _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 26.40 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.315 _refine_diff_density_min -0.213 _refine_diff_density_rms 0.040 #=== END data_2 _database_code_depnum_ccdc_archive 'CCDC 665208' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'phenylethylamine succinate-succinic acid' _chemical_melting_point ? _chemical_formula_moiety '2(C8 H12 N), C4 H6 O4, C4 H4 O4' _chemical_formula_sum 'C24 H34 N2 O8' _chemical_formula_weight 478.53 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 9.3231(3) _cell_length_b 10.8304(4) _cell_length_c 12.7030(5) _cell_angle_alpha 80.931(3) _cell_angle_beta 86.268(3) _cell_angle_gamma 88.868(3) _cell_volume 1263.88(8) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 10929 _cell_measurement_theta_min 3.7975 _cell_measurement_theta_max 33.7931 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.65 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.257 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 512 _exptl_absorpt_coefficient_mu 0.094 _exptl_absorpt_correction_T_min 0.9412 _exptl_absorpt_correction_T_max 0.9722 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.29.9 (release 23-03-2006 CrysAlis171 .NET) (compiled Mar 23 2006,23:39:28) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean 8.4190 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 20648 _diffrn_reflns_av_R_equivalents 0.0138 _diffrn_reflns_av_sigmaI/netI 0.0285 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.81 _diffrn_reflns_theta_max 33.89 _reflns_number_total 8647 _reflns_number_gt 6117 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.29.9 (release 23-03-2006 CrysAlis171 .NET) (compiled Mar 23 2006,23:39:28) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.29.9 (release 23-03-2006 CrysAlis171 .NET) (compiled Mar 23 2006,23:39:28) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.29.9 (release 23-03-2006 CrysAlis171 .NET) (compiled Mar 23 2006,23:39:28) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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. The NH3+ and COOH hydrogen atoms were located in the difference map. ; _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^)+(0.0837P)^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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 8647 _refine_ls_number_parameters 339 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0628 _refine_ls_R_factor_gt 0.0439 _refine_ls_wR_factor_ref 0.1374 _refine_ls_wR_factor_gt 0.1309 _refine_ls_goodness_of_fit_ref 1.100 _refine_ls_restrained_S_all 1.100 _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 N11 N 0.81630(10) 0.67585(9) 0.15212(7) 0.02037(17) Uani 1 1 d . . . H1 H 0.8764(15) 0.7346(13) 0.1047(11) 0.033(4) Uiso 1 1 d . . . H2 H 0.8588(16) 0.5928(14) 0.1576(12) 0.036(4) Uiso 1 1 d . . . H3 H 0.7326(18) 0.6612(15) 0.1194(13) 0.045(4) Uiso 1 1 d . . . C12 C 0.78291(11) 0.71748(10) 0.25692(8) 0.0230(2) Uani 1 1 d . . . H12B H 0.7170 0.6572 0.3016 0.028 Uiso 1 1 calc R . . H12A H 0.7338 0.8000 0.2459 0.028 Uiso 1 1 calc R . . C13 C 0.91950(12) 0.72718(13) 0.31436(9) 0.0329(3) Uani 1 1 d . . . H13B H 0.9649 0.6434 0.3293 0.039 Uiso 1 1 calc R . . H13A H 0.9880 0.7828 0.2672 0.039 Uiso 1 1 calc R . . C14 C 0.89017(13) 0.77752(13) 0.41765(9) 0.0317(3) Uani 1 1 d . . . C15 C 0.85581(18) 0.90225(16) 0.41663(14) 0.0522(4) Uani 1 1 d . . . H15 H 0.8521 0.9558 0.3500 0.063 Uiso 1 1 calc R . . C16 C 0.8269(2) 0.9510(2) 0.50921(19) 0.0813(7) Uani 1 1 d . . . H16 H 0.8035 1.0372 0.5060 0.098 Uiso 1 1 calc R . . C17 C 0.8314(2) 0.8771(3) 0.60444(18) 0.0890(9) Uani 1 1 d . . . H17 H 0.8106 0.9112 0.6682 0.107 Uiso 1 1 calc R . . C18 C 0.8657(2) 0.7532(3) 0.61000(13) 0.0866(8) Uani 1 1 d . . . H18 H 0.8690 0.7014 0.6775 0.104 Uiso 1 1 calc R . . C19 C 0.8966(2) 0.70175(19) 0.51493(12) 0.0594(5) Uani 1 1 d . . . H19 H 0.9214 0.6158 0.5184 0.071 Uiso 1 1 calc R . . N21 N 0.64627(10) 0.29566(9) 0.18603(6) 0.01861(17) Uani 1 1 d . . . H4 H 0.7238(17) 0.2711(14) 0.1513(12) 0.037(4) Uiso 1 1 d . . . H5 H 0.6217(16) 0.3819(15) 0.1655(12) 0.036(4) Uiso 1 1 d . . . H6 H 0.5675(14) 0.2420(12) 0.1708(11) 0.027(3) Uiso 1 1 d . . . C22 C 0.67330(11) 0.27366(10) 0.30162(8) 0.0215(2) Uani 1 1 d . . . H22B H 0.7602 0.3197 0.3132 0.026 Uiso 1 1 calc R . . H22A H 0.6913 0.1834 0.3250 0.026 Uiso 1 1 calc R . . C23 C 0.54612(12) 0.31651(12) 0.36793(8) 0.0278(2) Uani 1 1 d . . . H23A H 0.5248 0.4057 0.3424 0.033 Uiso 1 1 calc R . . H23B H 0.4603 0.2673 0.3597 0.033 Uiso 1 1 calc R . . C24 C 0.57889(12) 0.29958(11) 0.48406(8) 0.0270(2) Uani 1 1 d . . . C25 C 0.65299(15) 0.39035(12) 0.52331(10) 0.0376(3) Uani 1 1 d . . . H25 H 0.6781 0.4659 0.4775 0.045 Uiso 1 1 calc R . . C26 C 0.69114(18) 0.37269(14) 0.62864(11) 0.0469(4) Uani 1 1 d . . . H26 H 0.7418 0.4360 0.6543 0.056 Uiso 1 1 calc R . . C27 C 0.65562(17) 0.26384(14) 0.69568(10) 0.0421(3) Uani 1 1 d . . . H27 H 0.6828 0.2512 0.7674 0.051 Uiso 1 1 calc R . . C28 C 0.58032(16) 0.17281(14) 0.65845(10) 0.0423(3) Uani 1 1 d . . . H28 H 0.5546 0.0979 0.7049 0.051 Uiso 1 1 calc R . . C29 C 0.54196(14) 0.19065(13) 0.55278(10) 0.0361(3) Uani 1 1 d . . . H29 H 0.4901 0.1277 0.5276 0.043 Uiso 1 1 calc R . . O31 O -0.06364(8) 0.44019(7) 0.16174(6) 0.02472(17) Uani 1 1 d . . . O32 O 0.09496(8) 0.32330(7) 0.08289(6) 0.02366(16) Uani 1 1 d . . . C31 C 0.05788(10) 0.42305(9) 0.12042(7) 0.01630(18) Uani 1 1 d . . . C32 C 0.17066(10) 0.52362(9) 0.10848(9) 0.02007(19) Uani 1 1 d . . . H32A H 0.1457 0.5806 0.1608 0.024 Uiso 1 1 calc R . . H32B H 0.1686 0.5732 0.0361 0.024 Uiso 1 1 calc R . . C33 C 0.32171(10) 0.47387(9) 0.12484(8) 0.01673(18) Uani 1 1 d . . . H33B H 0.3412 0.4073 0.0805 0.020 Uiso 1 1 calc R . . H33A H 0.3274 0.4354 0.2005 0.020 Uiso 1 1 calc R . . C34 C 0.43777(10) 0.57213(8) 0.09707(7) 0.01492(17) Uani 1 1 d . . . O33 O 0.40318(7) 0.67537(6) 0.04172(6) 0.01911(15) Uani 1 1 d . . . O34 O 0.56157(7) 0.54661(6) 0.12763(6) 0.02065(15) Uani 1 1 d . . . O41 O 0.59784(8) 0.83009(7) 0.01975(6) 0.02240(16) Uani 1 1 d . . . O42 O 0.57312(8) 0.86629(7) -0.15642(6) 0.02604(17) Uani 1 1 d . . . C41 C 0.63135(10) 0.88676(9) -0.07702(8) 0.01742(18) Uani 1 1 d . . . C42 C 0.75024(11) 0.98096(9) -0.08535(8) 0.02014(19) Uani 1 1 d . . . H42B H 0.7335 1.0488 -0.1454 0.024 Uiso 1 1 calc R . . H42A H 0.8428 0.9397 -0.1022 0.024 Uiso 1 1 calc R . . C43 C 0.76212(10) 1.03798(9) 0.01552(8) 0.01866(19) Uani 1 1 d . . . H43B H 0.6711 1.0824 0.0306 0.022 Uiso 1 1 calc R . . H43A H 0.7746 0.9698 0.0761 0.022 Uiso 1 1 calc R . . C44 C 0.88463(10) 1.12798(8) 0.00891(8) 0.01705(18) Uani 1 1 d . . . O43 O 0.89259(8) 1.17969(7) 0.09419(6) 0.02280(16) Uani 1 1 d . . . O44 O 0.96961(8) 1.14860(7) -0.06961(6) 0.02380(16) Uani 1 1 d . . . H7 H 0.507(2) 0.7558(16) 0.0308(15) 0.069(6) Uiso 1 1 d . . . H8 H 0.991(3) 1.254(2) 0.0935(18) 0.094(7) 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 N11 0.0156(4) 0.0235(4) 0.0231(4) -0.0063(3) -0.0016(3) -0.0020(3) C12 0.0189(5) 0.0284(5) 0.0223(5) -0.0066(4) 0.0004(4) -0.0012(4) C13 0.0236(6) 0.0502(7) 0.0278(5) -0.0143(5) -0.0045(4) 0.0001(5) C14 0.0245(5) 0.0496(7) 0.0227(5) -0.0100(5) -0.0020(4) -0.0067(5) C15 0.0526(9) 0.0603(10) 0.0510(9) -0.0281(8) -0.0131(7) 0.0043(7) C16 0.0623(12) 0.1171(18) 0.0848(15) -0.0761(15) -0.0141(10) 0.0093(11) C17 0.0569(12) 0.166(3) 0.0603(13) -0.0709(16) 0.0151(9) -0.0333(14) C18 0.0799(14) 0.153(2) 0.0231(7) 0.0023(11) 0.0000(8) -0.0539(15) C19 0.0719(11) 0.0718(11) 0.0325(7) 0.0054(7) -0.0134(7) -0.0263(9) N21 0.0179(4) 0.0226(4) 0.0159(4) -0.0040(3) -0.0014(3) -0.0029(3) C22 0.0203(5) 0.0286(5) 0.0159(4) -0.0029(4) -0.0041(3) 0.0000(4) C23 0.0234(5) 0.0427(7) 0.0174(4) -0.0049(4) -0.0027(4) 0.0046(5) C24 0.0265(5) 0.0376(6) 0.0169(4) -0.0057(4) 0.0000(4) 0.0091(5) C25 0.0545(8) 0.0337(6) 0.0255(6) -0.0057(5) -0.0101(5) 0.0059(6) C26 0.0726(10) 0.0429(8) 0.0301(6) -0.0157(6) -0.0192(6) 0.0117(7) C27 0.0603(9) 0.0478(8) 0.0198(5) -0.0102(5) -0.0085(5) 0.0218(7) C28 0.0516(8) 0.0481(8) 0.0235(6) 0.0028(5) 0.0029(5) 0.0093(7) C29 0.0372(7) 0.0446(7) 0.0256(6) -0.0033(5) 0.0006(5) 0.0005(5) O31 0.0172(3) 0.0202(4) 0.0367(4) -0.0067(3) 0.0052(3) -0.0039(3) O32 0.0164(3) 0.0216(4) 0.0358(4) -0.0136(3) 0.0011(3) -0.0060(3) C31 0.0142(4) 0.0166(4) 0.0182(4) -0.0014(3) -0.0033(3) -0.0032(3) C32 0.0141(4) 0.0156(4) 0.0310(5) -0.0041(4) -0.0030(4) -0.0036(3) C33 0.0141(4) 0.0163(4) 0.0193(4) -0.0007(3) -0.0013(3) -0.0045(3) C34 0.0146(4) 0.0164(4) 0.0144(4) -0.0045(3) 0.0006(3) -0.0050(3) O33 0.0180(3) 0.0167(3) 0.0218(3) 0.0013(3) -0.0030(3) -0.0062(3) O34 0.0150(3) 0.0204(3) 0.0266(4) -0.0021(3) -0.0040(3) -0.0047(3) O41 0.0237(4) 0.0216(3) 0.0213(3) 0.0012(3) -0.0044(3) -0.0109(3) O42 0.0280(4) 0.0298(4) 0.0213(4) -0.0042(3) -0.0046(3) -0.0131(3) C41 0.0166(4) 0.0147(4) 0.0212(4) -0.0029(3) -0.0022(3) -0.0031(3) C42 0.0201(5) 0.0191(4) 0.0210(4) -0.0004(4) -0.0032(3) -0.0089(4) C43 0.0144(4) 0.0156(4) 0.0268(5) -0.0064(4) 0.0013(3) -0.0053(3) C44 0.0132(4) 0.0124(4) 0.0261(5) -0.0039(3) -0.0027(3) -0.0010(3) O43 0.0178(3) 0.0233(4) 0.0299(4) -0.0120(3) 0.0010(3) -0.0074(3) O44 0.0218(4) 0.0233(4) 0.0267(4) -0.0057(3) 0.0032(3) -0.0102(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 N11 C12 1.4840(13) . ? C12 C13 1.5217(15) . ? C13 C14 1.5055(16) . ? C14 C19 1.375(2) . ? C14 C15 1.380(2) . ? C15 C16 1.372(2) . ? C16 C17 1.344(4) . ? C17 C18 1.366(3) . ? C18 C19 1.418(3) . ? N21 C22 1.4872(12) . ? C22 C23 1.5174(15) . ? C23 C24 1.5081(14) . ? C24 C25 1.3851(18) . ? C24 C29 1.3872(18) . ? C25 C26 1.3900(17) . ? C26 C27 1.374(2) . ? C27 C28 1.381(2) . ? C28 C29 1.3947(17) . ? O31 C31 1.2403(12) . ? O32 C31 1.2806(12) . ? C31 C32 1.5125(13) . ? C32 C33 1.5131(13) . ? C33 C34 1.5183(12) . ? C34 O34 1.2535(11) . ? C34 O33 1.2712(12) . ? O41 C41 1.3058(12) . ? O42 C41 1.2280(11) . ? C41 C42 1.5086(13) . ? C42 C43 1.5186(13) . ? C43 C44 1.5057(13) . ? C44 O44 1.2274(12) . ? C44 O43 1.3023(12) . ? 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 N11 C12 C13 110.82(9) . . ? C14 C13 C12 112.04(10) . . ? C19 C14 C15 118.22(14) . . ? C19 C14 C13 121.51(14) . . ? C15 C14 C13 120.27(13) . . ? C16 C15 C14 121.81(19) . . ? C17 C16 C15 120.2(2) . . ? C16 C17 C18 120.35(17) . . ? C17 C18 C19 120.00(18) . . ? C14 C19 C18 119.39(19) . . ? N21 C22 C23 111.08(8) . . ? C24 C23 C22 110.16(8) . . ? C25 C24 C29 118.43(11) . . ? C25 C24 C23 120.50(11) . . ? C29 C24 C23 121.00(11) . . ? C24 C25 C26 121.05(13) . . ? C27 C26 C25 120.07(14) . . ? C26 C27 C28 119.77(12) . . ? C27 C28 C29 120.12(13) . . ? C24 C29 C28 120.55(13) . . ? O31 C31 O32 123.36(9) . . ? O31 C31 C32 120.65(9) . . ? O32 C31 C32 115.96(8) . . ? C31 C32 C33 113.99(8) . . ? C32 C33 C34 114.21(8) . . ? O34 C34 O33 123.90(8) . . ? O34 C34 C33 118.82(8) . . ? O33 C34 C33 117.26(8) . . ? O42 C41 O41 123.90(9) . . ? O42 C41 C42 121.38(9) . . ? O41 C41 C42 114.72(8) . . ? C41 C42 C43 113.68(8) . . ? C44 C43 C42 113.73(8) . . ? O44 C44 O43 123.68(9) . . ? O44 C44 C43 122.47(9) . . ? O43 C44 C43 113.85(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 N11 H3 O41 0.936(17) 2.431(16) 3.0318(12) 121.9(12) . N11 H3 O34 0.936(17) 2.027(17) 2.8391(11) 144.2(14) . N11 H2 O31 0.970(15) 1.786(15) 2.7548(12) 177.6(13) 1_655 N11 H1 O44 0.965(15) 1.916(15) 2.8190(12) 154.8(12) 2_775 N11 H1 O32 0.965(15) 2.555(14) 3.0441(12) 111.5(10) 2_665 N21 H5 O34 0.957(15) 1.859(16) 2.8137(12) 176.3(13) . N21 H4 O31 0.881(16) 2.748(15) 3.1252(11) 107.3(11) 1_655 N21 H6 O42 0.993(14) 1.813(14) 2.8020(11) 174.0(12) 2_665 N21 H4 O43 0.881(16) 2.000(16) 2.8656(12) 167.3(14) 1_545 N21 H6 O33 0.993(14) 2.705(13) 2.9262(11) 92.8(8) 2_665 O41 H7 O33 1.163(19) 1.304(19) 2.4670(9) 178.0(17) . _diffrn_measured_fraction_theta_max 0.846 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 0.477 _refine_diff_density_min -0.427 _refine_diff_density_rms 0.051 #=== END data_3 _database_code_depnum_ccdc_archive 'CCDC 665209' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'anilinium fumarate-fumaric acid' _chemical_melting_point ? _chemical_formula_moiety '2(C6H8N) , C4H4O4, C4H2O4' _chemical_formula_sum 'C20 H22 N2 O8' _chemical_formula_weight 418.40 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 9.2426(11) _cell_length_b 10.3797(12) _cell_length_c 10.4421(12) _cell_angle_alpha 83.590(2) _cell_angle_beta 89.104(2) _cell_angle_gamma 85.167(2) _cell_volume 991.9(2) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 1502 _cell_measurement_theta_min 2.63 _cell_measurement_theta_max 25.79 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.58 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.401 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 440 _exptl_absorpt_coefficient_mu 0.109 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9392 _exptl_absorpt_correction_T_max 0.9935 _exptl_absorpt_process_details '(SADABS; Bruker, 2002)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX CCD area-detector' _diffrn_measurement_method \w _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% . _diffrn_reflns_number 6027 _diffrn_reflns_av_R_equivalents 0.0203 _diffrn_reflns_av_sigmaI/netI 0.0452 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.96 _diffrn_reflns_theta_max 26.38 _reflns_number_total 3938 _reflns_number_gt 3103 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2002)' _computing_cell_refinement 'SAINT (Bruker, 2003)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _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. The NH3+ and COOH hydrogen atoms were located in the difference map. ; _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^)+(0.0542P)^2^+0.2506P] 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 3938 _refine_ls_number_parameters 303 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0587 _refine_ls_R_factor_gt 0.0438 _refine_ls_wR_factor_ref 0.1096 _refine_ls_wR_factor_gt 0.1000 _refine_ls_goodness_of_fit_ref 1.006 _refine_ls_restrained_S_all 1.006 _refine_ls_shift/su_max 0.052 _refine_ls_shift/su_mean 0.004 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 O31 O -0.06328(13) 0.45012(12) 0.16137(12) 0.0153(3) Uani 1 1 d . . . O32 O 0.11013(13) 0.30253(12) 0.10804(12) 0.0153(3) Uani 1 1 d . . . O33 O 0.37904(13) 0.69369(11) 0.05622(12) 0.0141(3) Uani 1 1 d . . . O34 O 0.55167(13) 0.55027(12) 0.14674(12) 0.0154(3) Uani 1 1 d . . . H7 H 0.471(3) 0.758(3) 0.039(3) 0.066(9) Uiso 1 1 d . . . H8 H 1.006(3) 1.232(3) 0.107(3) 0.079(10) Uiso 1 1 d . . . C31 C 0.06402(19) 0.41760(17) 0.13211(16) 0.0119(4) Uani 1 1 d . . . C32 C 0.17403(19) 0.51522(17) 0.12066(16) 0.0129(4) Uani 1 1 d . . . H32 H 0.1413 0.6050 0.1103 0.015 Uiso 1 1 calc R . . C33 C 0.31527(19) 0.48217(17) 0.12435(16) 0.0130(4) Uani 1 1 d . . . H33 H 0.3481 0.3925 0.1368 0.016 Uiso 1 1 calc R . . C34 C 0.42512(18) 0.58029(17) 0.10977(16) 0.0119(4) Uani 1 1 d . . . O41 O 0.57638(13) 0.83688(12) 0.03006(11) 0.0143(3) Uani 1 1 d . . . O42 O 0.54589(13) 0.86542(12) -0.18405(12) 0.0178(3) Uani 1 1 d . . . O43 O 0.91042(13) 1.16227(12) 0.10877(12) 0.0150(3) Uani 1 1 d . . . O44 O 0.95147(13) 1.14766(12) -0.10181(12) 0.0146(3) Uani 1 1 d . . . C41 C 0.60754(18) 0.88614(17) -0.08492(17) 0.0129(4) Uani 1 1 d . . . C42 C 0.72667(18) 0.97523(16) -0.09396(17) 0.0136(4) Uani 1 1 d . . . H42 H 0.7727 0.9951 -0.1749 0.016 Uiso 1 1 calc R . . C43 C 0.77025(18) 1.02736(16) 0.00724(17) 0.0127(4) Uani 1 1 d . . . H43 H 0.7252 1.0053 0.0882 0.015 Uiso 1 1 calc R . . C44 C 0.88598(18) 1.11852(16) 0.00030(17) 0.0123(4) Uani 1 1 d . . . N11 N 0.81980(18) 0.70470(16) 0.17512(15) 0.0151(3) Uani 1 1 d . . . H1 H 0.893(3) 0.758(2) 0.137(2) 0.043(7) Uiso 1 1 d . . . H2 H 0.854(2) 0.613(2) 0.167(2) 0.033(6) Uiso 1 1 d . . . H3 H 0.734(3) 0.721(3) 0.129(3) 0.053(8) Uiso 1 1 d . . . C12 C 0.79669(19) 0.72253(17) 0.31151(17) 0.0145(4) Uani 1 1 d . . . C13 C 0.9036(2) 0.67160(19) 0.39857(18) 0.0210(4) Uani 1 1 d . . . H13 H 0.9882 0.6239 0.3706 0.025 Uiso 1 1 calc R . . C14 C 0.8854(2) 0.6911(2) 0.52682(19) 0.0268(5) Uani 1 1 d . . . H14 H 0.9583 0.6570 0.5874 0.032 Uiso 1 1 calc R . . C15 C 0.7614(2) 0.7600(2) 0.56734(19) 0.0254(5) Uani 1 1 d . . . H15 H 0.7491 0.7731 0.6556 0.030 Uiso 1 1 calc R . . C16 C 0.6561(2) 0.8095(2) 0.47934(19) 0.0251(5) Uani 1 1 d . . . H16 H 0.5711 0.8567 0.5074 0.030 Uiso 1 1 calc R . . C17 C 0.6725(2) 0.79135(19) 0.34976(18) 0.0202(4) Uani 1 1 d . . . H17 H 0.5998 0.8256 0.2891 0.024 Uiso 1 1 calc R . . N21 N 0.66778(18) 0.29739(16) 0.22251(14) 0.0144(3) Uani 1 1 d . . . H4 H 0.631(2) 0.382(2) 0.195(2) 0.036(6) Uiso 1 1 d . . . H5 H 0.752(3) 0.273(2) 0.176(2) 0.033(6) Uiso 1 1 d . . . H6 H 0.590(3) 0.239(3) 0.200(2) 0.053(8) Uiso 1 1 d . . . C22 C 0.69432(18) 0.28056(18) 0.36167(16) 0.0139(4) Uani 1 1 d . . . C23 C 0.6652(2) 0.38427(18) 0.43212(18) 0.0182(4) Uani 1 1 d . . . H23 H 0.6304 0.4671 0.3909 0.022 Uiso 1 1 calc R . . C24 C 0.6874(2) 0.3661(2) 0.56402(18) 0.0221(4) Uani 1 1 d . . . H24 H 0.6677 0.4369 0.6138 0.027 Uiso 1 1 calc R . . C25 C 0.7381(2) 0.2452(2) 0.62343(19) 0.0250(5) Uani 1 1 d . . . H25 H 0.7523 0.2328 0.7140 0.030 Uiso 1 1 calc R . . C26 C 0.7681(2) 0.1429(2) 0.55111(19) 0.0279(5) Uani 1 1 d . . . H26 H 0.8042 0.0604 0.5921 0.034 Uiso 1 1 calc R . . C27 C 0.7460(2) 0.15925(19) 0.41898(19) 0.0226(4) Uani 1 1 d . . . H27 H 0.7660 0.0887 0.3690 0.027 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 O31 0.0111(6) 0.0160(7) 0.0192(7) -0.0033(5) 0.0017(5) -0.0026(5) O32 0.0124(6) 0.0137(7) 0.0211(7) -0.0059(5) 0.0013(5) -0.0032(5) O33 0.0124(6) 0.0122(6) 0.0175(7) 0.0014(5) -0.0005(5) -0.0039(5) O34 0.0127(6) 0.0168(7) 0.0166(7) -0.0009(5) -0.0019(5) -0.0022(5) C31 0.0137(9) 0.0145(9) 0.0075(8) -0.0010(7) -0.0016(7) -0.0006(7) C32 0.0168(9) 0.0118(9) 0.0105(8) -0.0011(7) -0.0007(7) -0.0034(7) C33 0.0163(9) 0.0123(9) 0.0108(9) -0.0019(7) 0.0015(7) -0.0041(7) C34 0.0143(9) 0.0133(9) 0.0092(8) -0.0050(7) 0.0034(7) -0.0025(7) O41 0.0130(6) 0.0153(7) 0.0147(6) 0.0005(5) -0.0003(5) -0.0046(5) O42 0.0185(7) 0.0214(7) 0.0150(7) -0.0045(5) -0.0015(5) -0.0080(5) O43 0.0143(6) 0.0153(7) 0.0171(7) -0.0054(5) 0.0010(5) -0.0056(5) O44 0.0135(6) 0.0147(6) 0.0158(7) -0.0005(5) 0.0017(5) -0.0038(5) C41 0.0119(9) 0.0117(9) 0.0150(9) -0.0021(7) 0.0001(7) 0.0013(7) C42 0.0123(9) 0.0125(9) 0.0155(9) 0.0007(7) 0.0017(7) -0.0022(7) C43 0.0115(9) 0.0104(8) 0.0157(9) 0.0007(7) 0.0029(7) -0.0015(7) C44 0.0111(9) 0.0092(9) 0.0161(9) -0.0017(7) -0.0003(7) 0.0025(7) N11 0.0130(8) 0.0184(9) 0.0142(8) -0.0019(6) 0.0011(6) -0.0032(7) C12 0.0158(9) 0.0154(9) 0.0134(9) -0.0008(7) 0.0024(7) -0.0082(7) C13 0.0183(10) 0.0250(11) 0.0194(10) -0.0028(8) -0.0001(8) -0.0008(8) C14 0.0302(12) 0.0322(12) 0.0180(10) -0.0003(9) -0.0054(9) -0.0051(9) C15 0.0367(12) 0.0280(11) 0.0135(10) -0.0045(8) 0.0058(8) -0.0123(9) C16 0.0250(11) 0.0256(11) 0.0256(11) -0.0061(9) 0.0117(9) -0.0042(9) C17 0.0176(10) 0.0238(10) 0.0196(10) -0.0032(8) 0.0017(8) -0.0025(8) N21 0.0123(8) 0.0191(9) 0.0119(8) -0.0024(7) 0.0001(6) -0.0011(7) C22 0.0109(9) 0.0211(10) 0.0100(9) -0.0007(7) -0.0003(7) -0.0047(7) C23 0.0176(10) 0.0185(10) 0.0185(10) -0.0022(8) -0.0003(7) -0.0015(8) C24 0.0251(11) 0.0271(11) 0.0159(10) -0.0083(8) 0.0016(8) -0.0045(9) C25 0.0285(11) 0.0344(12) 0.0121(9) -0.0010(8) -0.0016(8) -0.0050(9) C26 0.0392(13) 0.0238(11) 0.0187(10) 0.0035(8) -0.0025(9) 0.0027(9) C27 0.0298(11) 0.0192(10) 0.0190(10) -0.0041(8) 0.0008(8) 0.0001(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 O31 C31 1.240(2) . ? O32 C31 1.284(2) . ? O33 C34 1.287(2) . ? O34 C34 1.241(2) . ? C31 C32 1.489(2) . ? C32 C33 1.322(2) . ? C33 C34 1.492(2) . ? O41 C41 1.289(2) . ? O42 C41 1.237(2) . ? O43 C44 1.296(2) . ? O44 C44 1.238(2) . ? C41 C42 1.492(2) . ? C42 C43 1.323(2) . ? C43 C44 1.482(2) . ? N11 C12 1.467(2) . ? C12 C17 1.378(3) . ? C12 C13 1.384(2) . ? C13 C14 1.382(3) . ? C14 C15 1.386(3) . ? C15 C16 1.376(3) . ? C16 C17 1.391(3) . ? N21 C22 1.466(2) . ? C22 C23 1.376(3) . ? C22 C27 1.383(3) . ? C23 C24 1.385(3) . ? C24 C25 1.385(3) . ? C25 C26 1.377(3) . ? C26 C27 1.387(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 O31 C31 O32 124.18(16) . . ? O31 C31 C32 120.08(15) . . ? O32 C31 C32 115.73(15) . . ? C33 C32 C31 122.73(16) . . ? C32 C33 C34 122.54(16) . . ? O34 C34 O33 124.14(16) . . ? O34 C34 C33 120.43(15) . . ? O33 C34 C33 115.43(15) . . ? O42 C41 O41 124.98(16) . . ? O42 C41 C42 119.70(15) . . ? O41 C41 C42 115.32(15) . . ? C43 C42 C41 122.04(16) . . ? C42 C43 C44 123.13(16) . . ? O44 C44 O43 124.69(16) . . ? O44 C44 C43 121.27(15) . . ? O43 C44 C43 114.04(15) . . ? C17 C12 C13 121.59(17) . . ? C17 C12 N11 120.00(16) . . ? C13 C12 N11 118.38(17) . . ? C14 C13 C12 119.08(18) . . ? C13 C14 C15 120.26(18) . . ? C16 C15 C14 119.79(18) . . ? C15 C16 C17 120.81(19) . . ? C12 C17 C16 118.47(18) . . ? C23 C22 C27 121.72(17) . . ? C23 C22 N21 119.65(16) . . ? C27 C22 N21 118.62(17) . . ? C22 C23 C24 119.03(17) . . ? C25 C24 C23 120.16(18) . . ? C26 C25 C24 119.96(18) . . ? C25 C26 C27 120.63(18) . . ? C22 C27 C26 118.50(18) . . ? 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 N11 H3 O41 0.93(3) 2.03(3) 2.892(2) 154(2) . N11 H3 O34 0.93(3) 2.53(3) 3.098(2) 120(2) . N11 H2 O31 0.99(2) 1.80(2) 2.787(2) 173(2) 1_655 N11 H1 O44 0.96(3) 1.82(3) 2.764(2) 167(2) 2_775 N11 H1 O32 0.96(3) 2.71(2) 3.025(2) 99.9(16) 2_665 N21 H4 O34 0.93(2) 1.86(2) 2.785(2) 177(2) . N21 H5 O31 0.94(2) 2.61(2) 3.080(2) 111.8(16) 1_655 N21 H6 O42 1.02(3) 1.75(3) 2.767(2) 172(2) 2_665 N21 H5 O43 0.94(2) 1.96(2) 2.858(2) 160.0(19) 1_545 N21 H5 O33 0.94(2) 2.70(2) 2.9393(19) 95.1(15) 2_665 O43 H8 O32 1.18(3) 1.26(3) 2.4447(16) 177(3) 1_665 _diffrn_measured_fraction_theta_max 0.968 _diffrn_reflns_theta_full 26.38 _diffrn_measured_fraction_theta_full 0.968 _refine_diff_density_max 0.273 _refine_diff_density_min -0.255 _refine_diff_density_rms 0.054