# Electronic Supplementary Material (ESI) for Faraday Discussions # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full 'Faraday Discuss.' _journal_coden_cambridge 0169 loop_ _publ_author_name _publ_author_footnote _publ_author_address J.Stoimenovski . ; School of Chemistry Monash University Wellington Road Clayton Victoria, 3800 Australia ; P.M.Dean . ; School of Chemistry Monash University Wellington Road Clayton Victoria, 3800 Australia ; E.I.Izgorodina . ; School of Chemistry Monash University Wellington Road Clayton Victoria, 3800 Australia ; D.R.MacFarlane . ; School of Chemistry Monash University Wellington Road Clayton Victoria, 3800 Australia ; _publ_contact_author_address ; Department of Chemistry Monash University Wellington Road Clayton Victoria, 3800 Australia ; _publ_contact_author_email pamela.dean@sci.monash.edu.au _publ_contact_author_fax '61 3 990 54597' _publ_contact_author_phone '61 3 990 54535' #TrackingRef '1-%282-hydroxy-ethyl%29-pyrrolidinium+2%2C5-dihydroxy-benzoate.CIF' _publ_contact_author_name 'Dr. Pamela M. Dean' _publ_section_title ; 1-(2-hydroxy-ethyl)-pyrrolidinium 2,5-dihydroxy-benzoate ; data_pyrdhb _database_code_depnum_ccdc_archive 'CCDC 802624' _publ_section_abstract ; 1-2-HEP 2,5 DHB, systematic name 1-(2-hydroxy-ethyl)-pyrrolidinium 2,5-dihydroxy-benzoate, C~6~H~14~N~1~O~1~. C~7~H~5~O~4~, displays interionic N---H...O and O---H...O hydrogen bonding and interanionic O---H...O hydrogen bonding. A C-H...\p ring interaction is also seen. ; _publ_section_comment ; The asymmetric unit consists of a single 1-(2-hydroxy-ethyl)-pyrrolidinium cation and a single 2,5-dihydroxy-benzoate anion (Figure 1). The 1-(2-hydroxy-ethyl)-pyrrolidinium cation adopts the preferred chair conformation with the hydroxyl substituent adopting a gauche conformation with a torsional angle of 62.4 (2) [N1---C5---C6---O1]. The hydrogen (H1N) was located in the fourier difference map at a 0.90(2) \%A distance away from N1. The 2,5-dihydroxy-benzoate anion displays a planar aromatic ring with two hydroxyl groups and a carboxylic acid group displaying standard bond distances and angles (C3A---O3A 1.362(2), C6A O4A 1.371(2), C1A---O1A 1.263(2) and C2A---O1A 1.268(2) \%A respectively). The hydroxy hydrogen atoms was also located and placed in the difference fourier map (O3A---H3AO 0.86(3) and O4A H4AO 0.82(2)). Two main types of hydrogen bonding occurs, strong O...H---O and N...H---O hydrogen bonding and weak interionic C---H...O hydrogen bonding (Table 1, Figure 2 [one intramoleculat bond occurs as indicated by a * in Table 1]). An additional interaction which occurs is an inter-ring C-H...\p interaction (C4-H4B...Cg1, 2.85 \%A, 151 \%, symmetry of the benzoate ring: X,1/2-Y,-1/2+Z). The extended structure (Figure 3) consists of a 'diamandoid' trellis-like structure constructed from the 2,5-dihydroxy-benzoate anions and their hydrogen bonding network. The cations are located within the centres of the 'diamonds' connected by the N---H...O hydrogen bond and inter-ring C-H...\p interaction, thus resulting in two dimensional sheets of anions and cations. ; _publ_section_exptl_prep ; Heptane-2-amine (0.748 g, 6.488 mmol), dissolved in methanol, was slowly added to 2,5-dihydroxybenzoic acid (1.000 g, 6.488 mmol) in methanol solution. The reaction was stirred for 4 hours in an ice bath. Methanol was subsequently removed under vacuum and the resulting opaque solid was dried on a Shlenk line for 5 hours. ; _publ_section_exptl_refinement ; All H atoms were initially located in a difference Fourier map. Thereafter, all H atoms, except the N---H and O---H atoms, were placed in geometrically fixed idealised positions and constrained to ride on their parent atoms with C---H distances in the range 0.95-1.00 \%A and U~iso~(H) = xU~eq~(C), where x = 1.5 for methyl and 1.2 for all other atoms. ; _publ_section_figure_captions ; Figure 1. The asymmetric unit of 1-(2-hydroxy-ethyl)-pyrrolidinium 2,5-dihydroxy-benzoate shown with 50 % thermal ellipsoids, hydrogen atoms as spheres of arbitrary size and numbering scheme. Figure 2, Schematic displaying selected interactions within 1-(2-hydroxy-ethyl)-pyrrolidinium 2,5-dihydroxy-benzoate. Figure 3. Extended packing diagram as viewed down the a-axis highlighting hydrogen bonding in red dashed lines. ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1-(2-hydroxy-ethyl)-pyrrolidinium; 2,5-dihydroxy-benzoate ; _chemical_name_common '1-(2-hydroxy-ethyl)-pyrrolidinium; 2,5-dihydroxy-benzoate' _chemical_melting_point 370 _chemical_formula_moiety 'C6 H14 N1 O1; C7 H5 O4' _chemical_formula_sum 'C13 H19 N O5' _chemical_formula_weight 269.29 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c _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 12.0463(8) _cell_length_b 9.4802(5) _cell_length_c 11.8853(6) _cell_angle_alpha 90.00 _cell_angle_beta 110.191(3) _cell_angle_gamma 90.00 _cell_volume 1273.91(13) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 2431 _cell_measurement_theta_min 2.82 _cell_measurement_theta_max 24.67 _exptl_crystal_description Anhedral _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.50 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.404 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 576 _exptl_absorpt_coefficient_mu 0.108 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9381 _exptl_absorpt_correction_T_max 0.9481 _exptl_absorpt_process_details 'sadabs (Bruker AXS, 2005)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker X8 APEX KAPPA CCD' _diffrn_measurement_method '0.5 deg frames in phi and omega' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14184 _diffrn_reflns_av_R_equivalents 0.0251 _diffrn_reflns_av_sigmaI/netI 0.0220 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.80 _diffrn_reflns_theta_max 27.49 _reflns_number_total 2735 _reflns_number_gt 2316 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker Apex II V 1.0 (Bruker ASX, 2005)' _computing_cell_refinement 'Bruker Apex II V 1.0 (Bruker ASX, 2005)' _computing_data_reduction 'Bruker Apex II V 1.0 (Bruker ASX, 2005)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Pov-ray for windows, version 3.1' _computing_publication_material 'Microsoft Office' _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^)+(0.0632P)^2^+0.5925P] 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 2735 _refine_ls_number_parameters 188 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0512 _refine_ls_R_factor_gt 0.0433 _refine_ls_wR_factor_ref 0.1237 _refine_ls_wR_factor_gt 0.1189 _refine_ls_goodness_of_fit_ref 1.101 _refine_ls_restrained_S_all 1.101 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.22679(11) 0.18123(14) -0.12185(11) 0.0165(3) Uani 1 1 d . . . C2A C 0.29771(13) 0.61401(15) 0.11834(12) 0.0156(3) Uani 1 1 d . . . C5A C 0.38228(13) 0.80657(16) 0.30662(13) 0.0190(3) Uani 1 1 d . . . H5AA H 0.4111 0.8710 0.3714 0.023 Uiso 1 1 calc R . . C7A C 0.41911(13) 0.64195(15) 0.16971(12) 0.0165(3) Uani 1 1 d . . . H7AA H 0.4732 0.5941 0.1408 0.020 Uiso 1 1 calc R . . C4A C 0.26227(14) 0.78037(16) 0.25661(14) 0.0205(3) Uani 1 1 d . . . H4AA H 0.2090 0.8270 0.2873 0.025 Uiso 1 1 calc R . . C3A C 0.21889(13) 0.68606(16) 0.16144(13) 0.0176(3) Uani 1 1 d . . . C6A C 0.46094(13) 0.73868(16) 0.26226(13) 0.0170(3) Uani 1 1 d . . . C4 C 0.33890(14) 0.09157(17) -0.08545(14) 0.0243(4) Uani 1 1 d . . . H4B H 0.3457 0.0419 -0.1560 0.029 Uiso 1 1 calc R . . H4A H 0.4097 0.1516 -0.0503 0.029 Uiso 1 1 calc R . . C3 C 0.32831(18) -0.0134(2) 0.00605(16) 0.0347(4) Uani 1 1 d . . . H3B H 0.3612 -0.1062 -0.0044 0.042 Uiso 1 1 calc R . . H3A H 0.3702 0.0206 0.0886 0.042 Uiso 1 1 calc R . . C1 C 0.15449(16) 0.12717(18) -0.04948(15) 0.0263(4) Uani 1 1 d . . . H1B H 0.0690 0.1292 -0.0971 0.032 Uiso 1 1 calc R . . H1A H 0.1689 0.1840 0.0241 0.032 Uiso 1 1 calc R . . C2 C 0.19773(18) -0.0232(2) -0.01892(18) 0.0390(5) Uani 1 1 d . . . H2A H 0.1812 -0.0574 0.0524 0.047 Uiso 1 1 calc R . . H2B H 0.1597 -0.0875 -0.0870 0.047 Uiso 1 1 calc R . . O3A O 0.09954(9) 0.66736(13) 0.11433(11) 0.0241(3) Uani 1 1 d . . . O1A O 0.32653(9) 0.42712(11) -0.00237(9) 0.0200(3) Uani 1 1 d . . . O2A O 0.14244(10) 0.50129(12) -0.03547(10) 0.0264(3) Uani 1 1 d . . . O4A O 0.58025(9) 0.76416(13) 0.30647(10) 0.0228(3) Uani 1 1 d . . . C5 C 0.16178(14) 0.17721(17) -0.25418(13) 0.0209(3) Uani 1 1 d . . . H5B H 0.1324 0.0802 -0.2775 0.025 Uiso 1 1 calc R . . H5A H 0.2174 0.2006 -0.2962 0.025 Uiso 1 1 calc R . . C1A C 0.25307(13) 0.50751(15) 0.01984(12) 0.0174(3) Uani 1 1 d . . . O1 O 0.09317(12) 0.42082(13) -0.27146(12) 0.0324(3) Uani 1 1 d . . . C6 C 0.05843(14) 0.27854(17) -0.29441(13) 0.0211(3) Uani 1 1 d . . . H6B H 0.0162 0.2663 -0.3815 0.025 Uiso 1 1 calc R . . H6A H 0.0026 0.2550 -0.2526 0.025 Uiso 1 1 calc R . . H4AO H 0.594(2) 0.821(2) 0.362(2) 0.039(6) Uiso 1 1 d . . . H1O H 0.099(2) 0.439(3) -0.200(3) 0.059(8) Uiso 1 1 d . . . H3AO H 0.091(2) 0.611(3) 0.056(2) 0.048(7) Uiso 1 1 d . . . H1N H 0.2503(16) 0.270(2) -0.0984(16) 0.021(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 N1 0.0188(6) 0.0149(6) 0.0150(6) -0.0015(5) 0.0049(5) 0.0010(5) C2A 0.0181(7) 0.0119(7) 0.0141(7) 0.0032(5) 0.0024(5) -0.0002(5) C5A 0.0231(8) 0.0155(7) 0.0174(7) -0.0014(5) 0.0060(6) -0.0033(6) C7A 0.0178(7) 0.0138(7) 0.0172(7) 0.0022(5) 0.0052(6) 0.0015(6) C4A 0.0223(8) 0.0182(8) 0.0224(8) -0.0011(6) 0.0094(6) 0.0018(6) C3A 0.0154(7) 0.0160(7) 0.0194(7) 0.0041(5) 0.0035(6) -0.0003(6) C6A 0.0161(7) 0.0161(7) 0.0162(7) 0.0024(5) 0.0021(5) -0.0028(6) C4 0.0240(8) 0.0241(8) 0.0222(8) -0.0012(6) 0.0048(6) 0.0086(7) C3 0.0458(11) 0.0251(9) 0.0297(9) 0.0055(7) 0.0085(8) 0.0084(8) C1 0.0353(9) 0.0257(9) 0.0230(8) 0.0026(6) 0.0167(7) -0.0008(7) C2 0.0436(11) 0.0328(10) 0.0371(10) 0.0108(8) 0.0094(9) -0.0046(9) O3A 0.0151(5) 0.0259(6) 0.0283(6) -0.0041(5) 0.0039(5) -0.0005(4) O1A 0.0225(6) 0.0163(5) 0.0179(5) -0.0018(4) 0.0026(4) 0.0023(4) O2A 0.0191(6) 0.0260(6) 0.0263(6) -0.0076(5) -0.0023(5) 0.0004(5) O4A 0.0171(5) 0.0244(6) 0.0241(6) -0.0068(5) 0.0036(4) -0.0046(5) C5 0.0212(8) 0.0271(8) 0.0137(7) -0.0027(6) 0.0050(6) 0.0018(6) C1A 0.0216(7) 0.0121(7) 0.0154(7) 0.0024(5) 0.0027(6) 0.0001(6) O1 0.0396(8) 0.0227(6) 0.0250(6) 0.0025(5) -0.0015(6) -0.0019(5) C6 0.0214(7) 0.0235(8) 0.0164(7) -0.0029(6) 0.0039(6) 0.0000(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C5 1.4960(18) . ? N1 C1 1.509(2) . ? N1 C4 1.526(2) . ? N1 H1N 0.90(2) . ? C2A C7A 1.402(2) . ? C2A C3A 1.402(2) . ? C2A C1A 1.498(2) . ? C5A C4A 1.383(2) . ? C5A C6A 1.391(2) . ? C5A H5AA 0.9500 . ? C7A C6A 1.386(2) . ? C7A H7AA 0.9500 . ? C4A C3A 1.394(2) . ? C4A H4AA 0.9500 . ? C3A O3A 1.3624(18) . ? C6A O4A 1.3707(18) . ? C4 C3 1.512(2) . ? C4 H4B 0.9900 . ? C4 H4A 0.9900 . ? C3 C2 1.500(3) . ? C3 H3B 0.9900 . ? C3 H3A 0.9900 . ? C1 C2 1.518(3) . ? C1 H1B 0.9900 . ? C1 H1A 0.9900 . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? O3A H3AO 0.86(3) . ? O1A C1A 1.2629(18) . ? O2A C1A 1.2676(18) . ? O4A H4AO 0.82(2) . ? C5 C6 1.514(2) . ? C5 H5B 0.9900 . ? C5 H5A 0.9900 . ? O1 C6 1.411(2) . ? O1 H1O 0.84(3) . ? C6 H6B 0.9900 . ? C6 H6A 0.9900 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C5 N1 C1 113.26(12) . . ? C5 N1 C4 112.00(11) . . ? C1 N1 C4 106.11(12) . . ? C5 N1 H1N 110.1(12) . . ? C1 N1 H1N 108.8(12) . . ? C4 N1 H1N 106.2(12) . . ? C7A C2A C3A 119.01(13) . . ? C7A C2A C1A 120.45(13) . . ? C3A C2A C1A 120.53(13) . . ? C4A C5A C6A 120.13(14) . . ? C4A C5A H5AA 119.9 . . ? C6A C5A H5AA 119.9 . . ? C6A C7A C2A 120.62(13) . . ? C6A C7A H7AA 119.7 . . ? C2A C7A H7AA 119.7 . . ? C5A C4A C3A 120.49(14) . . ? C5A C4A H4AA 119.8 . . ? C3A C4A H4AA 119.8 . . ? O3A C3A C4A 117.63(13) . . ? O3A C3A C2A 122.55(13) . . ? C4A C3A C2A 119.82(13) . . ? O4A C6A C7A 117.82(13) . . ? O4A C6A C5A 122.30(13) . . ? C7A C6A C5A 119.88(13) . . ? C3 C4 N1 106.53(13) . . ? C3 C4 H4B 110.4 . . ? N1 C4 H4B 110.4 . . ? C3 C4 H4A 110.4 . . ? N1 C4 H4A 110.4 . . ? H4B C4 H4A 108.6 . . ? C2 C3 C4 103.98(14) . . ? C2 C3 H3B 111.0 . . ? C4 C3 H3B 111.0 . . ? C2 C3 H3A 111.0 . . ? C4 C3 H3A 111.0 . . ? H3B C3 H3A 109.0 . . ? N1 C1 C2 103.73(14) . . ? N1 C1 H1B 111.0 . . ? C2 C1 H1B 111.0 . . ? N1 C1 H1A 111.0 . . ? C2 C1 H1A 111.0 . . ? H1B C1 H1A 109.0 . . ? C3 C2 C1 103.83(15) . . ? C3 C2 H2A 111.0 . . ? C1 C2 H2A 111.0 . . ? C3 C2 H2B 111.0 . . ? C1 C2 H2B 111.0 . . ? H2A C2 H2B 109.0 . . ? C3A O3A H3AO 102.9(16) . . ? C6A O4A H4AO 108.8(16) . . ? N1 C5 C6 113.02(12) . . ? N1 C5 H5B 109.0 . . ? C6 C5 H5B 109.0 . . ? N1 C5 H5A 109.0 . . ? C6 C5 H5A 109.0 . . ? H5B C5 H5A 107.8 . . ? O1A C1A O2A 123.41(13) . . ? O1A C1A C2A 118.79(13) . . ? O2A C1A C2A 117.79(13) . . ? C6 O1 H1O 107.7(19) . . ? O1 C6 C5 112.89(13) . . ? O1 C6 H6B 109.0 . . ? C5 C6 H6B 109.0 . . ? O1 C6 H6A 109.0 . . ? C5 C6 H6A 109.0 . . ? H6B C6 H6A 107.8 . . ? 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 C3A C2A C7A C6A 0.4(2) . . . . ? C1A C2A C7A C6A -178.90(13) . . . . ? C6A C5A C4A C3A -0.1(2) . . . . ? C5A C4A C3A O3A -178.50(13) . . . . ? C5A C4A C3A C2A 1.9(2) . . . . ? C7A C2A C3A O3A 178.37(13) . . . . ? C1A C2A C3A O3A -2.3(2) . . . . ? C7A C2A C3A C4A -2.1(2) . . . . ? C1A C2A C3A C4A 177.24(13) . . . . ? C2A C7A C6A O4A -178.26(12) . . . . ? C2A C7A C6A C5A 1.4(2) . . . . ? C4A C5A C6A O4A 178.07(13) . . . . ? C4A C5A C6A C7A -1.6(2) . . . . ? C5 N1 C4 C3 -123.41(14) . . . . ? C1 N1 C4 C3 0.65(16) . . . . ? N1 C4 C3 C2 23.16(17) . . . . ? C5 N1 C1 C2 99.39(15) . . . . ? C4 N1 C1 C2 -23.88(16) . . . . ? C4 C3 C2 C1 -38.16(18) . . . . ? N1 C1 C2 C3 38.61(17) . . . . ? C1 N1 C5 C6 66.85(17) . . . . ? C4 N1 C5 C6 -173.18(13) . . . . ? C7A C2A C1A O1A 11.7(2) . . . . ? C3A C2A C1A O1A -167.63(13) . . . . ? C7A C2A C1A O2A -169.69(13) . . . . ? C3A C2A C1A O2A 11.0(2) . . . . ? N1 C5 C6 O1 62.43(17) . . . . ? _diffrn_measured_fraction_theta_max 0.935 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.935 _refine_diff_density_max 0.928 _refine_diff_density_min -0.338 _refine_diff_density_rms 0.051 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 _geom_hbond_publ_flag N1 H1N O1A 0.90(2) 1.91(2) 2.778(2) 162(2) ? y O1 H1O O2A 0.85(3) 1.93(3) 2.766(2) 168(2) ? y O4A H4AO O1A 0.82(2) 1.90(2) 2.695(2) 162(2) 2_655 y O3A H3AO O2A* 0.85(2) 1.76(3) 2.560(2) 154(2) ? y C3 H3A O4A 0.99 2.59 3.378(2) 136 2_645 y C5 H5A O4A 0.99 2.50 3.418(2) 153 3_665 y C6 H6A O3A 0.99 2.48 3.358(2) 148 3_565 y # Attachment 'Adamantan-1-ammonium+2-hydroxybenzoate.CIF' data_hbatri _database_code_depnum_ccdc_archive 'CCDC 802625' _publ_section_abstract ; Adamantylammonium hydroxybenzoate, systematic name; (3s,5s,7s)-adamantan-1-ammonium 2-hydroxybenzoate, C~10~H~18~N~1~. C~7~H~5~O~3~; displays interionic N---H...O hydrogen bonding and interanionic \p...\p ring interactions. In addition a interionic C-H...\p and C-H...O interaction is also seen. ; _publ_section_comment ; The asymmetric unit consists of a single adamantan-1-ammonium cation and a single hydroxybenzoate anion (Figure 1). The adamantan-1-ammonium cation adopts the standard tetrahedral symmetry with all four cyclohexane rings adopting the preferred chair conformation with angles ranging from 108.63 to 109.97 \%. The charged ammonium substituent occurs 1.503(2) \%A from C1. All the ammonium hydrogens were located and placed in the difference map. H3N is the longest (N1---H3N 1.01(2) \%A) with H1N and H2N being shorter (N1---H1N 0.92(2), N1---H2N 0.95(2) \%A). The 2-hydroxybenzoate anion displays a planar aromatic ring with one hydroxyl group and a carboxylic acid group displaying standard bond distances and angles (C3A---O3A 1.351(2), C1A---O1A 1.255(2) and C1A---O2A 1.273(2) \%A respectively). The hydroxy hydrogen atom was also located and placed in the difference fourier map (O3A---H3AO 0.93(2)). Three main types of hydrogen bonding occurs; strong N---H...O bonds, a intramolecular O---H...O bond and a weak C---H...O hydrogen bond (Table 1, Figure 2 [the intramolecular bond is indicated by a * in Table 1]). Additional interactions which occur is a inter-ring C-H...\p interaction (C4-H4A...Cg, 2.67 \%A, 157 \%, symmetry of the benzoate ring: -X,1-Y,1-Z) and a \p...\p interaction (Table 2). The extended structure (Figure 3 and 4) consists of layers of cations and anions constructed from the layered dihydroxybenzoate anions and their hydrogen bonding network to the ammonium substituent of the cation. The cycloalkane moeity of the cation group together, effectively 'sandwiched' between the above mentioned interactions. ; _publ_section_exptl_prep ; Adamantan-1-amine (1.500 g, 9.917 mmol), dissolved in methanol, was slowly added to 2-hydroxybenzoic acid (1.370 g, 9.917 mmol) in methanol solution. The reaction was stirred for 4 hours in an ice bath. Methanol was subsequently removed under vacuum and the resulting white solid was dried on a Shlenk line for 5 hours. ; _publ_section_exptl_refinement ; All H atoms were initially located in a difference Fourier map. Thereafter, all H atoms, except the O---H and N---H atoms, were placed in geometrically fixed idealised positions and constrained to ride on their parent atoms with C---H distances in the range 0.95-1.00 \%A and U~iso~(H) = xU~eq~(C), where x = 1.5 for methyl and 1.2 for all other atoms. ; _publ_section_figure_captions ; Figure 1. The asymmetric unit of adamantylammonium hydroxybenzoate shown with 50 % thermal ellipsoids, hydrogen atoms as spheres of arbitrary size and numbering scheme. Figure 2, Schematic displaying selected interactions within adamantylammonium hydroxybenzoate. Figure 3. Extended packing diagram as viewed down the a-axis highlighting hydrogen bonding in red dashed lines. Figure 3. Extended packing diagram as viewed down the c-axis highlighting hydrogen bonding in red dashed lines. ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; (3s,5s,7s)-adamantan-1-ammonium 2-hydroxybenzoate ; _chemical_name_common '(3s,5s,7s)-adamantan-1-ammonium 2-hydroxybenzoate' _chemical_melting_point ? _chemical_formula_moiety 'C10 H18 N, C7 H5 O3' _chemical_formula_sum 'C17 H23 N O3' _chemical_formula_weight 289.36 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 6.7080(5) _cell_length_b 9.3067(7) _cell_length_c 12.7864(9) _cell_angle_alpha 80.421(5) _cell_angle_beta 76.338(4) _cell_angle_gamma 82.988(4) _cell_volume 761.99(10) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 1725 _cell_measurement_theta_min 2.23 _cell_measurement_theta_max 28.63 _exptl_crystal_description Thin _exptl_crystal_colour translucent _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.261 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 312 _exptl_absorpt_coefficient_mu 0.086 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9583 _exptl_absorpt_correction_T_max 0.9991 _exptl_absorpt_process_details 'sadabs (Bruker AXS, 2005)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker X8 APEX KAPPA CCD' _diffrn_measurement_method '0.5 deg frames in phi and omega' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10562 _diffrn_reflns_av_R_equivalents 0.0387 _diffrn_reflns_av_sigmaI/netI 0.0583 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.96 _diffrn_reflns_theta_max 28.63 _reflns_number_total 3717 _reflns_number_gt 2109 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker Apex II V 1.0 (Bruker ASX, 2005)' _computing_cell_refinement 'Bruker Apex II V 1.0 (Bruker ASX, 2005)' _computing_data_reduction 'Bruker Apex II V 1.0 (Bruker ASX, 2005)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Pov-ray for windows, version 3.1' _computing_publication_material 'Microsoft Office' _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^)+(0.0642P)^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 3717 _refine_ls_number_parameters 206 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0960 _refine_ls_R_factor_gt 0.0503 _refine_ls_wR_factor_ref 0.1366 _refine_ls_wR_factor_gt 0.1170 _refine_ls_goodness_of_fit_ref 0.998 _refine_ls_restrained_S_all 0.998 _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 C2A C 0.0585(2) 0.12982(16) 0.79566(12) 0.0255(3) Uani 1 1 d . . . O2A O 0.35085(15) 0.10614(12) 0.65153(9) 0.0391(3) Uani 1 1 d . . . O1A O 0.05659(16) 0.04709(12) 0.62945(9) 0.0401(3) Uani 1 1 d . . . N1 N 0.2785(2) 0.06658(14) 0.41103(12) 0.0296(3) Uani 1 1 d . . . O3A O 0.37562(17) 0.19407(14) 0.82406(13) 0.0516(4) Uani 1 1 d . . . C1 C 0.2978(2) 0.22107(16) 0.35469(12) 0.0280(4) Uani 1 1 d . . . C7A C -0.1505(2) 0.11628(16) 0.83888(13) 0.0318(4) Uani 1 1 d . . . H7AA H -0.2294 0.0865 0.7969 0.038 Uiso 1 1 calc R . . C3A C 0.1725(2) 0.17745(17) 0.86047(14) 0.0332(4) Uani 1 1 d . . . C7 C 0.4694(2) 0.28475(18) 0.38690(14) 0.0372(4) Uani 1 1 d . . . H7A H 0.5986 0.2264 0.3663 0.045 Uiso 1 1 calc R . . H7B H 0.4389 0.2837 0.4650 0.045 Uiso 1 1 calc R . . C1A C 0.1591(2) 0.09194(16) 0.68597(13) 0.0290(4) Uani 1 1 d . . . C4A C 0.0780(3) 0.20778(19) 0.96404(14) 0.0434(5) Uani 1 1 d . . . H4AA H 0.1538 0.2403 1.0064 0.052 Uiso 1 1 calc R . . C5A C -0.1256(3) 0.19005(19) 1.00386(14) 0.0449(5) Uani 1 1 d . . . H5AA H -0.1868 0.2081 1.0742 0.054 Uiso 1 1 calc R . . C6 C 0.0945(2) 0.31083(18) 0.38995(14) 0.0379(4) Uani 1 1 d . . . H6B H 0.0632 0.3099 0.4681 0.046 Uiso 1 1 calc R . . H6A H -0.0160 0.2693 0.3712 0.046 Uiso 1 1 calc R . . C2 C 0.3467(3) 0.22040(18) 0.23240(13) 0.0364(4) Uani 1 1 d . . . H2B H 0.2381 0.1785 0.2123 0.044 Uiso 1 1 calc R . . H2A H 0.4748 0.1613 0.2107 0.044 Uiso 1 1 calc R . . C6A C -0.2430(3) 0.14580(18) 0.94194(14) 0.0407(4) Uani 1 1 d . . . H6AA H -0.3827 0.1361 0.9695 0.049 Uiso 1 1 calc R . . C9 C 0.2839(3) 0.53351(19) 0.36373(16) 0.0457(5) Uani 1 1 d . . . H9A H 0.2527 0.5336 0.4418 0.055 Uiso 1 1 calc R . . H9B H 0.2949 0.6337 0.3283 0.055 Uiso 1 1 calc R . . C8 C 0.4870(2) 0.44195(19) 0.32909(15) 0.0422(5) Uani 1 1 d . . . H8 H 0.5977 0.4836 0.3491 0.051 Uiso 1 1 calc R . . C10 C 0.5355(3) 0.44342(19) 0.20670(15) 0.0495(5) Uani 1 1 d . . . H10A H 0.6662 0.3876 0.1842 0.059 Uiso 1 1 calc R . . H10B H 0.5467 0.5432 0.1702 0.059 Uiso 1 1 calc R . . C3 C 0.3655(3) 0.37730(19) 0.17490(15) 0.0461(5) Uani 1 1 d . . . H3 H 0.3971 0.3780 0.0960 0.055 Uiso 1 1 calc R . . C5 C 0.1133(3) 0.46831(19) 0.33181(15) 0.0455(5) Uani 1 1 d . . . H5 H -0.0173 0.5269 0.3535 0.055 Uiso 1 1 calc R . . C4 C 0.1616(3) 0.4685(2) 0.20962(16) 0.0529(5) Uani 1 1 d . . . H4A H 0.1713 0.5681 0.1726 0.063 Uiso 1 1 calc R . . H4B H 0.0518 0.4280 0.1895 0.063 Uiso 1 1 calc R . . H1N H 0.406(3) 0.014(2) 0.3982(14) 0.047(5) Uiso 1 1 d . . . H2N H 0.177(3) 0.0241(19) 0.3878(14) 0.049(5) Uiso 1 1 d . . . H3N H 0.227(3) 0.060(2) 0.4924(17) 0.061(6) Uiso 1 1 d . . . H3AO H 0.407(4) 0.178(3) 0.752(2) 0.091(8) 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 C2A 0.0282(8) 0.0232(8) 0.0253(8) -0.0048(7) -0.0060(6) -0.0002(6) O2A 0.0261(6) 0.0441(7) 0.0452(8) -0.0124(6) -0.0009(5) -0.0014(5) O1A 0.0389(7) 0.0524(8) 0.0332(7) -0.0163(6) -0.0059(5) -0.0105(5) N1 0.0262(7) 0.0326(8) 0.0301(9) -0.0080(6) -0.0048(6) -0.0009(6) O3A 0.0329(7) 0.0652(10) 0.0663(10) -0.0274(8) -0.0166(6) -0.0058(6) C1 0.0249(8) 0.0284(9) 0.0303(9) -0.0075(7) -0.0026(6) -0.0023(6) C7A 0.0322(8) 0.0300(9) 0.0332(10) -0.0069(7) -0.0059(7) -0.0022(6) C3A 0.0331(9) 0.0308(9) 0.0390(10) -0.0087(8) -0.0136(7) 0.0015(7) C7 0.0308(9) 0.0411(11) 0.0448(11) -0.0180(8) -0.0107(7) -0.0021(7) C1A 0.0321(8) 0.0233(8) 0.0312(9) -0.0044(7) -0.0075(7) 0.0005(6) C4A 0.0536(11) 0.0459(12) 0.0383(11) -0.0175(9) -0.0208(8) 0.0024(8) C5A 0.0581(12) 0.0455(12) 0.0283(10) -0.0114(9) -0.0043(8) 0.0049(9) C6 0.0260(8) 0.0385(10) 0.0466(11) -0.0107(8) -0.0016(7) 0.0010(7) C2 0.0402(9) 0.0363(10) 0.0329(10) -0.0093(8) -0.0033(7) -0.0079(7) C6A 0.0388(10) 0.0424(11) 0.0359(11) -0.0068(8) 0.0012(7) -0.0016(8) C9 0.0492(11) 0.0351(11) 0.0511(12) -0.0169(9) -0.0015(8) -0.0018(8) C8 0.0358(9) 0.0403(11) 0.0534(12) -0.0163(9) -0.0047(8) -0.0114(7) C10 0.0505(11) 0.0376(11) 0.0544(13) -0.0137(9) 0.0104(9) -0.0135(8) C3 0.0656(12) 0.0385(11) 0.0330(11) -0.0047(9) -0.0042(8) -0.0130(9) C5 0.0356(9) 0.0366(11) 0.0591(13) -0.0094(9) -0.0030(8) 0.0056(7) C4 0.0633(13) 0.0383(11) 0.0612(14) 0.0027(10) -0.0269(10) -0.0081(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 C2A C7A 1.3929(19) . ? C2A C3A 1.404(2) . ? C2A C1A 1.485(2) . ? O2A C1A 1.2727(17) . ? O1A C1A 1.2550(17) . ? N1 C1 1.5031(19) . ? N1 H1N 0.923(18) . ? N1 H2N 0.952(18) . ? N1 H3N 1.01(2) . ? O3A C3A 1.3508(18) . ? O3A H3AO 0.93(2) . ? C1 C2 1.521(2) . ? C1 C6 1.522(2) . ? C1 C7 1.522(2) . ? C7A C6A 1.375(2) . ? C7A H7AA 0.9300 . ? C3A C4A 1.385(2) . ? C7 C8 1.530(2) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C4A C5A 1.361(2) . ? C4A H4AA 0.9300 . ? C5A C6A 1.378(2) . ? C5A H5AA 0.9300 . ? C6 C5 1.535(2) . ? C6 H6B 0.9700 . ? C6 H6A 0.9700 . ? C2 C3 1.527(2) . ? C2 H2B 0.9700 . ? C2 H2A 0.9700 . ? C6A H6AA 0.9300 . ? C9 C5 1.523(2) . ? C9 C8 1.528(2) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C8 C10 1.519(2) . ? C8 H8 0.9800 . ? C10 C3 1.522(2) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C3 C4 1.531(3) . ? C3 H3 0.9800 . ? C5 C4 1.519(3) . ? C5 H5 0.9800 . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? 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 C7A C2A C3A 117.67(14) . . ? C7A C2A C1A 121.39(13) . . ? C3A C2A C1A 120.93(13) . . ? C1 N1 H1N 109.5(10) . . ? C1 N1 H2N 109.8(10) . . ? H1N N1 H2N 112.5(15) . . ? C1 N1 H3N 113.2(11) . . ? H1N N1 H3N 107.4(15) . . ? H2N N1 H3N 104.4(15) . . ? C3A O3A H3AO 105.6(15) . . ? N1 C1 C2 108.90(12) . . ? N1 C1 C6 108.54(12) . . ? C2 C1 C6 110.29(13) . . ? N1 C1 C7 109.39(12) . . ? C2 C1 C7 110.08(12) . . ? C6 C1 C7 109.62(13) . . ? C6A C7A C2A 121.72(15) . . ? C6A C7A H7AA 119.1 . . ? C2A C7A H7AA 119.1 . . ? O3A C3A C4A 118.51(15) . . ? O3A C3A C2A 121.18(15) . . ? C4A C3A C2A 120.30(14) . . ? C1 C7 C8 108.79(13) . . ? C1 C7 H7A 109.9 . . ? C8 C7 H7A 109.9 . . ? C1 C7 H7B 109.9 . . ? C8 C7 H7B 109.9 . . ? H7A C7 H7B 108.3 . . ? O1A C1A O2A 121.37(14) . . ? O1A C1A C2A 120.43(13) . . ? O2A C1A C2A 118.20(13) . . ? C5A C4A C3A 120.02(16) . . ? C5A C4A H4AA 120.0 . . ? C3A C4A H4AA 120.0 . . ? C4A C5A C6A 121.25(16) . . ? C4A C5A H5AA 119.4 . . ? C6A C5A H5AA 119.4 . . ? C1 C6 C5 108.63(12) . . ? C1 C6 H6B 110.0 . . ? C5 C6 H6B 110.0 . . ? C1 C6 H6A 110.0 . . ? C5 C6 H6A 110.0 . . ? H6B C6 H6A 108.3 . . ? C1 C2 C3 109.03(13) . . ? C1 C2 H2B 109.9 . . ? C3 C2 H2B 109.9 . . ? C1 C2 H2A 109.9 . . ? C3 C2 H2A 109.9 . . ? H2B C2 H2A 108.3 . . ? C7A C6A C5A 119.01(16) . . ? C7A C6A H6AA 120.5 . . ? C5A C6A H6AA 120.5 . . ? C5 C9 C8 108.86(14) . . ? C5 C9 H9A 109.9 . . ? C8 C9 H9A 109.9 . . ? C5 C9 H9B 109.9 . . ? C8 C9 H9B 109.9 . . ? H9A C9 H9B 108.3 . . ? C10 C8 C9 109.55(15) . . ? C10 C8 C7 109.88(14) . . ? C9 C8 C7 109.51(13) . . ? C10 C8 H8 109.3 . . ? C9 C8 H8 109.3 . . ? C7 C8 H8 109.3 . . ? C8 C10 C3 109.69(13) . . ? C8 C10 H10A 109.7 . . ? C3 C10 H10A 109.7 . . ? C8 C10 H10B 109.7 . . ? C3 C10 H10B 109.7 . . ? H10A C10 H10B 108.2 . . ? C10 C3 C2 109.96(15) . . ? C10 C3 C4 108.77(15) . . ? C2 C3 C4 109.10(14) . . ? C10 C3 H3 109.7 . . ? C2 C3 H3 109.7 . . ? C4 C3 H3 109.7 . . ? C4 C5 C9 109.97(14) . . ? C4 C5 C6 109.52(15) . . ? C9 C5 C6 109.49(14) . . ? C4 C5 H5 109.3 . . ? C9 C5 H5 109.3 . . ? C6 C5 H5 109.3 . . ? C5 C4 C3 109.71(14) . . ? C5 C4 H4A 109.7 . . ? C3 C4 H4A 109.7 . . ? C5 C4 H4B 109.7 . . ? C3 C4 H4B 109.7 . . ? H4A C4 H4B 108.2 . . ? 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 C3A C2A C7A C6A -1.1(2) . . . . ? C1A C2A C7A C6A 177.49(14) . . . . ? C7A C2A C3A O3A -179.63(14) . . . . ? C1A C2A C3A O3A 1.8(2) . . . . ? C7A C2A C3A C4A 0.7(2) . . . . ? C1A C2A C3A C4A -177.86(14) . . . . ? N1 C1 C7 C8 -179.93(12) . . . . ? C2 C1 C7 C8 60.45(17) . . . . ? C6 C1 C7 C8 -61.03(17) . . . . ? C7A C2A C1A O1A 0.3(2) . . . . ? C3A C2A C1A O1A 178.77(13) . . . . ? C7A C2A C1A O2A -179.67(14) . . . . ? C3A C2A C1A O2A -1.2(2) . . . . ? O3A C3A C4A C5A -179.00(16) . . . . ? C2A C3A C4A C5A 0.7(3) . . . . ? C3A C4A C5A C6A -1.7(3) . . . . ? N1 C1 C6 C5 -179.55(13) . . . . ? C2 C1 C6 C5 -60.33(17) . . . . ? C7 C1 C6 C5 61.03(17) . . . . ? N1 C1 C2 C3 179.77(12) . . . . ? C6 C1 C2 C3 60.77(16) . . . . ? C7 C1 C2 C3 -60.32(17) . . . . ? C2A C7A C6A C5A 0.1(2) . . . . ? C4A C5A C6A C7A 1.4(3) . . . . ? C5 C9 C8 C10 60.03(18) . . . . ? C5 C9 C8 C7 -60.55(18) . . . . ? C1 C7 C8 C10 -59.78(17) . . . . ? C1 C7 C8 C9 60.60(17) . . . . ? C9 C8 C10 C3 -60.92(19) . . . . ? C7 C8 C10 C3 59.43(18) . . . . ? C8 C10 C3 C2 -59.19(19) . . . . ? C8 C10 C3 C4 60.22(19) . . . . ? C1 C2 C3 C10 59.33(17) . . . . ? C1 C2 C3 C4 -59.88(17) . . . . ? C8 C9 C5 C4 -59.75(19) . . . . ? C8 C9 C5 C6 60.64(18) . . . . ? C1 C6 C5 C4 59.80(17) . . . . ? C1 C6 C5 C9 -60.85(18) . . . . ? C9 C5 C4 C3 60.04(19) . . . . ? C6 C5 C4 C3 -60.32(18) . . . . ? C10 C3 C4 C5 -59.70(19) . . . . ? C2 C3 C4 C5 60.25(18) . . . . ? _diffrn_measured_fraction_theta_max 0.947 _diffrn_reflns_theta_full 28.63 _diffrn_measured_fraction_theta_full 0.947 _refine_diff_density_max 0.184 _refine_diff_density_min -0.234 _refine_diff_density_rms 0.048 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 _geom_hbond_publ_flag N1 H1N O2A 0.93(2) 1.90(2) 2.814(2) 168(2) 2_656 y N1 H2N O1A 0.95(2) 1.85(2) 2.784(2) 167(2) 2_556 y N1 H3N O1A 1.01(2) 1.85(2) 2.825(2) 162(2) ? y N1 H3N O2A 1.01(2) 2.49(2) 3.301(2) 138(2) ? y O3A* H3AO O2A 0.93(2) 1.68(3) 2.524(2) 150(3) ? y C10 H10B O3A 0.97 2.58 3.440(2) 148 2_666 y _geom_hbond_footnote_A ; Notes: Where * indicates an intramolecular bond. ; loop_ _geom_extra_tableB_col_1 _geom_extra_tableB_col_2 _geom_extra_tableB_col_3 _geom_extra_tableB_col_4 _geom_extra_tableB_col_5 CgI CgJ Cg...Cg \a 'Symmetry position of CgJ' Cg1 Cg1 3.6528(10) 0 -X,-Y,2-Z _geom_extra_table_head_B ; Geometrical parameters (\%A, \%) of selected inter-ring \p---\p interactions. \a is the dihedral angle between planes I and J, CgI is the centroid of plane I and CgJ the centroid of plane J. ; _geom_table_footnote_B ; Notes: Cg1 is the centroid of ring C2A/C3A/C4A/C5A/C6A/C7A. ; # Attachment 'AdamantylammoniumBenzoate+%281%29.CIF' data_jtmon _database_code_depnum_ccdc_archive 'CCDC 802626' _publ_section_abstract ; Adamantylammonium benzoate,systematic name (3s,5s,7s)-adamantan-1-aminium benzoate C~10~H~18~N~1~. C~7~H~5~O~2~, displays interionic N---H...O hydrogen bonding and interanionic \p...\p ring interactions. In addition a weak intramolecular C---H...O hydrogen bond and an interionic C-H...\p interaction is also seen. ; _publ_section_comment ; The asymmetric unit consists of a single adamantan-1-ammonium cation and a single benzoate anion (Figure 1). The adamantan-1-ammonium cation adopts the standard tetrahedral symmetry with all four cyclohexane rings adopting the preferred chair conformation with with angles ranging from 108.57 to 109.91 \%. The charged ammonium substituent occurs 1.500(4) \%A from C1. All the ammonium hydrogens were located and placed in the difference map. H1N is the longest (N1---H1N 1.1911 \%A) with H2N and H3N being shorter (N1---H2N 0.8757, N1---H3N 0.9907 \%A). The benzoate anion displays a planar aromatic ring with a carboxylic acid group displaying standard bond distances and angles (O1A---C1A 1.262(4) and O2A---C1A 1.244(4) \%A respectively). Two main types of hydrogen bonding occurs, strong N...H---O hydrogen bonding and weak intra-molecular C---H...O (indicated by a * in Table 1) hydrogen bonding (Table 1). Additional interactions which occur are inter-ring \p...\p and C-H...\p interactions (Figure 2 and Tables 2 & 3). The extended structure (Figure 3) consists of layers of hydrogen bonded ionic clusters lying perpendicular to the ac-plane. Each cluster is associated with the other via the inter-ring \p...\p and C-H...\p interactions. ; _publ_section_exptl_prep ; Adamantan-1-amine (1.500 g, 9.917 mmol), dissolved in methanol, was slowly added to benzoic acid (1.211 g, 9.917 mmol) in methanol solution. The reaction was stirred for 4 hours in an ice bath. Methanol was subsequently removed under vacuum and the resulting white powder was dried on a Shlenk line for 5 hours. ; _publ_section_exptl_refinement ; All H atoms were initially located in a difference Fourier map. Thereafter, all H atoms, except the N---H atoms, were placed in geometrically fixed idealised positions and constrained to ride on their parent atoms with C---H distances in the range 0.95-1.00 \%A and U~iso~(H) = xU~eq~(C), where x = 1.5 for methyl and 1.2 for all other atoms. ; _publ_section_figure_captions ; Figure 1. The asymmetric unit of adamantylammonium benzoate shown with 50 % thermal ellipsoids, hydrogen atoms as spheres of arbitrary size and numbering scheme. Figure 2, Schematic displaying selected interactions within adamantylammonium benzoate. Figure 3. Extended packing diagram as viewed down the b-axis highlighting hydrogen bonding in red dashed lines. ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; (3s,5s,7s)-adamantan-1-ammonium benzoate ; _chemical_name_common '(3s,5s,7s)-adamantan-1-ammonium benzoate' _chemical_melting_point 529 _chemical_formula_moiety 'C10 H18 N, C7 H5 O2' _chemical_formula_sum 'C17 H23 N O2' _chemical_formula_weight 273.36 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n _symmetry_space_group_name_Hall '-P 2yn' 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 10.808(2) _cell_length_b 6.5508(13) _cell_length_c 21.104(4) _cell_angle_alpha 90.00 _cell_angle_beta 99.42(3) _cell_angle_gamma 90.00 _cell_volume 1474.0(5) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 4440 _cell_measurement_theta_min ? _cell_measurement_theta_max 30.45 _exptl_crystal_description Needle _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.232 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 592 _exptl_absorpt_coefficient_mu 0.080 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9842 _exptl_absorpt_correction_T_max 0.9921 _exptl_absorpt_process_details 'SORTAV (R.H. Blessing 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Enraf Nonius KAPPA CCD' _diffrn_measurement_method '1 deg frames in phi and omega' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 20392 _diffrn_reflns_av_R_equivalents 0.2416 _diffrn_reflns_av_sigmaI/netI 0.1823 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 1.96 _diffrn_reflns_theta_max 30.45 _reflns_number_total 4440 _reflns_number_gt 1673 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius Collect (Bruker ASX 2005)' _computing_cell_refinement 'HKL2000 (Bruker ASX 2004)' _computing_data_reduction 'HKL2000 (Bruker ASX 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-Seed / POV-Ray' _computing_publication_material 'Microsoft Office 2000' _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^)+(0.1345P)^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 4440 _refine_ls_number_parameters 184 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2600 _refine_ls_R_factor_gt 0.0988 _refine_ls_wR_factor_ref 0.2986 _refine_ls_wR_factor_gt 0.2099 _refine_ls_goodness_of_fit_ref 0.984 _refine_ls_restrained_S_all 0.984 _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 O1A O 0.1275(2) 0.1800(4) 0.18623(11) 0.0381(7) Uani 1 1 d . . . N1 N 0.1418(2) 0.8009(4) 0.24585(12) 0.0266(7) Uani 1 1 d . . . C2 C 0.0629(3) 0.6174(5) 0.33276(15) 0.0298(8) Uani 1 1 d . . . H2A H 0.1504 0.5947 0.3542 0.036 Uiso 1 1 calc R . . H2B H 0.0375 0.5006 0.3038 0.036 Uiso 1 1 calc R . . C1 C 0.0548(3) 0.8141(5) 0.29427(14) 0.0246(7) Uani 1 1 d . . . C8 C -0.0795(3) 0.8477(5) 0.25971(15) 0.0300(8) Uani 1 1 d . . . H8B H -0.1056 0.7326 0.2301 0.036 Uiso 1 1 calc R . . H8A H -0.0842 0.9751 0.2342 0.036 Uiso 1 1 calc R . . C2A C -0.0300(3) 0.2318(5) 0.09449(14) 0.0259(7) Uani 1 1 d . . . O2A O 0.0693(2) 0.4974(4) 0.15982(11) 0.0468(7) Uani 1 1 d . . . C3 C -0.0240(3) 0.6324(5) 0.38334(16) 0.0328(8) Uani 1 1 d . . . H3 H -0.0186 0.5035 0.4090 0.039 Uiso 1 1 calc R . . C4 C 0.0155(3) 0.8126(6) 0.42783(16) 0.0391(9) Uani 1 1 d . . . H4A H 0.1024 0.7919 0.4503 0.047 Uiso 1 1 calc R . . H4B H -0.0402 0.8221 0.4606 0.047 Uiso 1 1 calc R . . C9 C 0.0957(3) 0.9956(5) 0.33872(15) 0.0315(8) Uani 1 1 d . . . H9B H 0.0915 1.1233 0.3134 0.038 Uiso 1 1 calc R . . H9A H 0.1833 0.9761 0.3604 0.038 Uiso 1 1 calc R . . C7 C -0.1664(3) 0.8624(5) 0.31029(16) 0.0354(9) Uani 1 1 d . . . H7 H -0.2547 0.8832 0.2882 0.042 Uiso 1 1 calc R . . C3A C -0.0576(3) 0.0271(5) 0.08431(16) 0.0318(8) Uani 1 1 d . . . H3AA H -0.0167 -0.0723 0.1132 0.038 Uiso 1 1 calc R . . C6A C -0.1758(3) 0.3129(6) -0.00124(17) 0.0417(9) Uani 1 1 d . . . H6AA H -0.2153 0.4113 -0.0309 0.050 Uiso 1 1 calc R . . C7A C -0.0902(3) 0.3744(5) 0.05153(16) 0.0337(8) Uani 1 1 d . . . H7AA H -0.0725 0.5155 0.0583 0.040 Uiso 1 1 calc R . . C10 C -0.1590(3) 0.6646(5) 0.34975(16) 0.0369(9) Uani 1 1 d . . . H10B H -0.2156 0.6738 0.3821 0.044 Uiso 1 1 calc R . . H10A H -0.1860 0.5475 0.3212 0.044 Uiso 1 1 calc R . . C5A C -0.2036(3) 0.1085(6) -0.01060(17) 0.0419(10) Uani 1 1 d . . . H5AA H -0.2630 0.0659 -0.0464 0.050 Uiso 1 1 calc R . . C5 C 0.0080(3) 1.0101(5) 0.38894(16) 0.0367(9) Uani 1 1 d . . . H5 H 0.0340 1.1276 0.4184 0.044 Uiso 1 1 calc R . . C1A C 0.0617(3) 0.3096(5) 0.15149(15) 0.0269(8) Uani 1 1 d . . . C6 C -0.1271(3) 1.0430(6) 0.35462(17) 0.0401(9) Uani 1 1 d . . . H6B H -0.1841 1.0552 0.3867 0.048 Uiso 1 1 calc R . . H6A H -0.1323 1.1708 0.3293 0.048 Uiso 1 1 calc R . . C4A C -0.1448(3) -0.0331(6) 0.03207(16) 0.0384(9) Uani 1 1 d . . . H4AA H -0.1642 -0.1738 0.0257 0.046 Uiso 1 1 calc R . . H2N H 0.1308 0.6933 0.2210 0.039(11) Uiso 1 1 d R . . H3N H 0.1381 0.9282 0.2203 0.039(10) Uiso 1 1 d R . . H1N H 0.2435 0.7690 0.2756 0.098(16) Uiso 1 1 d 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 O1A 0.0323(13) 0.0430(16) 0.0356(14) 0.0113(12) -0.0044(11) -0.0043(11) N1 0.0282(14) 0.0288(16) 0.0232(14) -0.0034(13) 0.0052(11) -0.0017(12) C2 0.0320(18) 0.029(2) 0.0290(18) -0.0005(15) 0.0050(14) 0.0032(15) C1 0.0239(15) 0.0265(18) 0.0232(16) 0.0012(14) 0.0033(13) -0.0001(13) C8 0.0272(17) 0.036(2) 0.0260(17) 0.0024(15) 0.0024(13) 0.0001(14) C2A 0.0228(15) 0.035(2) 0.0200(15) -0.0010(14) 0.0054(12) -0.0001(14) O2A 0.0572(17) 0.0375(17) 0.0401(16) -0.0116(13) -0.0084(12) 0.0004(13) C3 0.0368(19) 0.032(2) 0.0307(18) 0.0056(15) 0.0084(15) 0.0008(15) C4 0.038(2) 0.051(3) 0.0286(18) -0.0035(18) 0.0085(15) -0.0016(18) C9 0.0325(18) 0.032(2) 0.0302(18) -0.0045(15) 0.0051(14) -0.0028(15) C7 0.0236(17) 0.046(2) 0.036(2) 0.0019(17) 0.0042(14) 0.0036(15) C3A 0.0291(18) 0.036(2) 0.0300(18) -0.0012(16) 0.0049(14) 0.0033(15) C6A 0.040(2) 0.047(3) 0.035(2) 0.0066(19) -0.0014(16) 0.0056(18) C7A 0.0340(19) 0.034(2) 0.0314(19) 0.0007(15) -0.0003(15) 0.0022(15) C10 0.0355(19) 0.044(2) 0.0330(19) -0.0005(17) 0.0119(15) -0.0062(17) C5A 0.040(2) 0.053(3) 0.0305(19) -0.0104(18) -0.0015(16) 0.0019(19) C5 0.047(2) 0.034(2) 0.0309(19) -0.0079(16) 0.0108(16) -0.0031(17) C1A 0.0259(16) 0.032(2) 0.0251(17) 0.0003(15) 0.0115(13) 0.0009(15) C6 0.041(2) 0.041(2) 0.042(2) 0.0014(18) 0.0187(17) 0.0102(17) C4A 0.037(2) 0.036(2) 0.041(2) -0.0116(18) 0.0029(17) -0.0005(16) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1A C1A 1.262(4) . ? N1 C1 1.500(4) . ? N1 H2N 0.8757 . ? N1 H3N 0.9907 . ? N1 H1N 1.1911 . ? C2 C1 1.518(4) . ? C2 C3 1.536(4) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C1 C8 1.529(4) . ? C1 C9 1.534(4) . ? C8 C7 1.536(4) . ? C8 H8B 0.9900 . ? C8 H8A 0.9900 . ? C2A C3A 1.383(4) . ? C2A C7A 1.387(4) . ? C2A C1A 1.516(4) . ? O2A C1A 1.244(4) . ? C3 C4 1.525(5) . ? C3 C10 1.529(5) . ? C3 H3 1.0000 . ? C4 C5 1.527(5) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C9 C5 1.536(5) . ? C9 H9B 0.9900 . ? C9 H9A 0.9900 . ? C7 C6 1.525(5) . ? C7 C10 1.535(5) . ? C7 H7 1.0000 . ? C3A C4A 1.385(4) . ? C3A H3AA 0.9500 . ? C6A C5A 1.379(5) . ? C6A C7A 1.386(5) . ? C6A H6AA 0.9500 . ? C7A H7AA 0.9500 . ? C10 H10B 0.9900 . ? C10 H10A 0.9900 . ? C5A C4A 1.374(5) . ? C5A H5AA 0.9500 . ? C5 C6 1.535(5) . ? C5 H5 1.0000 . ? C6 H6B 0.9900 . ? C6 H6A 0.9900 . ? C4A H4AA 0.9500 . ? 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 H2N 114.6 . . ? C1 N1 H3N 110.4 . . ? H2N N1 H3N 111.2 . . ? C1 N1 H1N 106.2 . . ? H2N N1 H1N 101.4 . . ? H3N N1 H1N 112.7 . . ? C1 C2 C3 109.2(3) . . ? C1 C2 H2A 109.8 . . ? C3 C2 H2A 109.8 . . ? C1 C2 H2B 109.8 . . ? C3 C2 H2B 109.8 . . ? H2A C2 H2B 108.3 . . ? N1 C1 C2 109.1(2) . . ? N1 C1 C8 109.6(2) . . ? C2 C1 C8 110.2(2) . . ? N1 C1 C9 108.1(2) . . ? C2 C1 C9 110.2(3) . . ? C8 C1 C9 109.6(2) . . ? C1 C8 C7 108.6(3) . . ? C1 C8 H8B 110.0 . . ? C7 C8 H8B 110.0 . . ? C1 C8 H8A 110.0 . . ? C7 C8 H8A 110.0 . . ? H8B C8 H8A 108.4 . . ? C3A C2A C7A 119.0(3) . . ? C3A C2A C1A 123.0(3) . . ? C7A C2A C1A 117.9(3) . . ? C4 C3 C10 109.2(3) . . ? C4 C3 C2 109.6(3) . . ? C10 C3 C2 109.4(3) . . ? C4 C3 H3 109.5 . . ? C10 C3 H3 109.5 . . ? C2 C3 H3 109.5 . . ? C3 C4 C5 109.9(3) . . ? C3 C4 H4A 109.7 . . ? C5 C4 H4A 109.7 . . ? C3 C4 H4B 109.7 . . ? C5 C4 H4B 109.7 . . ? H4A C4 H4B 108.2 . . ? C1 C9 C5 108.7(3) . . ? C1 C9 H9B 109.9 . . ? C5 C9 H9B 109.9 . . ? C1 C9 H9A 109.9 . . ? C5 C9 H9A 109.9 . . ? H9B C9 H9A 108.3 . . ? C6 C7 C10 109.7(3) . . ? C6 C7 C8 109.5(3) . . ? C10 C7 C8 109.9(3) . . ? C6 C7 H7 109.2 . . ? C10 C7 H7 109.2 . . ? C8 C7 H7 109.2 . . ? C2A C3A C4A 120.1(3) . . ? C2A C3A H3AA 120.0 . . ? C4A C3A H3AA 120.0 . . ? C5A C6A C7A 119.9(3) . . ? C5A C6A H6AA 120.1 . . ? C7A C6A H6AA 120.1 . . ? C6A C7A C2A 120.6(3) . . ? C6A C7A H7AA 119.7 . . ? C2A C7A H7AA 119.7 . . ? C3 C10 C7 109.2(3) . . ? C3 C10 H10B 109.8 . . ? C7 C10 H10B 109.8 . . ? C3 C10 H10A 109.8 . . ? C7 C10 H10A 109.8 . . ? H10B C10 H10A 108.3 . . ? C4A C5A C6A 119.7(3) . . ? C4A C5A H5AA 120.2 . . ? C6A C5A H5AA 120.2 . . ? C4 C5 C6 109.6(3) . . ? C4 C5 C9 109.5(3) . . ? C6 C5 C9 109.3(3) . . ? C4 C5 H5 109.5 . . ? C6 C5 H5 109.5 . . ? C9 C5 H5 109.5 . . ? O2A C1A O1A 124.4(3) . . ? O2A C1A C2A 117.6(3) . . ? O1A C1A C2A 117.9(3) . . ? C7 C6 C5 109.2(3) . . ? C7 C6 H6B 109.8 . . ? C5 C6 H6B 109.8 . . ? C7 C6 H6A 109.8 . . ? C5 C6 H6A 109.8 . . ? H6B C6 H6A 108.3 . . ? C5A C4A C3A 120.7(3) . . ? C5A C4A H4AA 119.6 . . ? C3A C4A H4AA 119.6 . . ? 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 C3 C2 C1 N1 178.8(2) . . . . ? C3 C2 C1 C8 -60.8(3) . . . . ? C3 C2 C1 C9 60.2(3) . . . . ? N1 C1 C8 C7 -179.5(3) . . . . ? C2 C1 C8 C7 60.4(3) . . . . ? C9 C1 C8 C7 -61.0(3) . . . . ? C1 C2 C3 C4 -59.5(3) . . . . ? C1 C2 C3 C10 60.2(3) . . . . ? C10 C3 C4 C5 -60.2(3) . . . . ? C2 C3 C4 C5 59.6(4) . . . . ? N1 C1 C9 C5 -179.6(3) . . . . ? C2 C1 C9 C5 -60.4(3) . . . . ? C8 C1 C9 C5 61.0(3) . . . . ? C1 C8 C7 C6 60.9(3) . . . . ? C1 C8 C7 C10 -59.7(3) . . . . ? C7A C2A C3A C4A -0.4(5) . . . . ? C1A C2A C3A C4A 178.3(3) . . . . ? C5A C6A C7A C2A 1.3(5) . . . . ? C3A C2A C7A C6A -0.6(5) . . . . ? C1A C2A C7A C6A -179.5(3) . . . . ? C4 C3 C10 C7 60.2(4) . . . . ? C2 C3 C10 C7 -59.7(3) . . . . ? C6 C7 C10 C3 -60.5(3) . . . . ? C8 C7 C10 C3 60.0(4) . . . . ? C7A C6A C5A C4A -0.8(5) . . . . ? C3 C4 C5 C6 59.9(3) . . . . ? C3 C4 C5 C9 -60.0(4) . . . . ? C1 C9 C5 C4 59.7(3) . . . . ? C1 C9 C5 C6 -60.3(3) . . . . ? C3A C2A C1A O2A -172.3(3) . . . . ? C7A C2A C1A O2A 6.5(4) . . . . ? C3A C2A C1A O1A 9.6(4) . . . . ? C7A C2A C1A O1A -171.7(3) . . . . ? C10 C7 C6 C5 59.8(3) . . . . ? C8 C7 C6 C5 -60.9(4) . . . . ? C4 C5 C6 C7 -59.4(4) . . . . ? C9 C5 C6 C7 60.6(4) . . . . ? C6A C5A C4A C3A -0.2(5) . . . . ? C2A C3A C4A C5A 0.9(5) . . . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 30.45 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.335 _refine_diff_density_min -0.411 _refine_diff_density_rms 0.097 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 _geom_hbond_publ_flag N1 H1N O1A 1.19 1.60 2.780(3) 169 2_555 y N1 H2N O2A 0.87 1.86 2.720(4) 165 ? y N1 H3N O1A 0.99 1.80 2.777(4) 170 1_565 y C7A H7AA O2A* 0.95 2.42 2.749(4) 100 ? y _geom_hbond_footnote_A ; Notes: Where * indicates an intramolecular bond. ; loop_ _geom_extra_tableA_col_1 _geom_extra_tableA_col_2 _geom_extra_tableA_col_3 _geom_extra_tableA_col_4 _geom_extra_tableA_col_5 _geom_extra_tableA_col_6 X--H CgJ H..Cg X-H..Cg X..Cg 'Symmetry position of CgJ' C10--H10B Cg1 2.61 173 3.594(4) -1/2-X,1/2+Y,1/2-Z _geom_extra_table_head_A ; Geometrical parameters (\%A, \%) of selected inter-ring C-H...\p interactions. The CgJ refer to the Ring Centre-of-Gravity ; _geom_table_footnote_A ; Notes: Cg1 is the centroid of ring C2A/C3A/C4A/C5A/C6A/C7A. ; loop_ _geom_extra_tableB_col_1 _geom_extra_tableB_col_2 _geom_extra_tableB_col_3 _geom_extra_tableB_col_4 _geom_extra_tableB_col_5 CgI CgJ Cg...Cg \a 'Symmetry position of CgJ' Cg1 Cg1 3.992(2) 0 -X,-Y,-Z Cg1 Cg1 5.443(2) 0 -X,1-Y,-Z _geom_extra_table_head_B ; Geometrical parameters (\%A, \%) of selected inter-ring \p---\p interactions. \a is the dihedral angle between planes I and J, CgI is the centroid of plane I and CgJ the centroid of plane J. ; _geom_table_footnote_B ; Notes: Cg1 is the centroid of ring C2A/C3A/C4A/C5A/C6A/C7A. ; # Attachment 'AdamantylammoniumDihydroxybenzoate.CIF' data_jellym _database_code_depnum_ccdc_archive 'CCDC 802627' _publ_section_abstract ; Adamantylammonium dihydroxybenzoate, systematic name; (3s,5s,7s)-adamantan-1-aminium 2,5-dihydroxybenzoate, C~10~H~18~N~1~. C~7~H~5~O~4~; displays interionic N---H...O hydrogen bonding and interanionic O---H...O and \p...\p ring interactions. In addition a interionic C-H...\p interaction is also seen. ; _publ_section_comment ; The asymmetric unit consists of a single adamantan-1-ammonium cation and a single dihydroxybenzoate anion (Figure 1). The adamantan-1-ammonium cation adopts the standard tetrahedral symmetry with all four cyclohexane rings adopting the preferred chair conformation with angles ranging from 108.36 to 110.35 \%. The charged ammonium substituent occurs 1.503(4) \%A from C1. All the ammonium hydrogens were located and placed in the difference map. H2N is the longest (N1---H2N 1.09(4) \%A) with H1N and H3N being shorter (N1---H1N 1.03(4), N1---H3N 0.91(4) \%A). The 2,5-dihydroxy-benzoate anion displays a planar aromatic ring with two hydroxyl groups and a carboxylic acid group displaying standard bond distances and angles (C3A---O3A 1.360(4), C6A O4A 1.366(4), C1A---O1A 1.248(4) and C1A---O2A 1.270(4) \%A respectively). The hydroxy hydrogen atoms were also located and placed in the difference fourier map (O3A---H3AO 1.08(4) and O4A H4AO 0.98(4)). Two main types of hydrogen bonding occurs, strong O---H...O and N---H...O hydrogen bonding (Table 1, Figure 2 [one intramoleculat bond occurs as indicated by a * in Table 1]). Additional interactions which occur is a inter-ring C-H...\p interaction (C6-H6B...Cg, 2.72 \%A, 172 \%, symmetry of the benzoate ring: 1-X,1-Y,1-Z) and \p...\p interactions (Table 2). The extended structure (Figure 3) consists of sheets of groups of cations and anions constructed from the layered dihydroxybenzoate anions and their hydrogen bonding network to the ammonium substituent of the cation. ; _publ_section_exptl_prep ; Adamantan-1-amine (1.472 g, 9.733 mmol), dissolved in methanol, was slowly added to 2,5-dihydroxybenzoic acid (1.500 g, 9.733 mmol) in methanol solution. The reaction was stirred for 4 hours in an ice bath. Methanol was subsequently removed under vacuum and the resulting white powder was dried on a Shlenk line for 5 hours. ; _publ_section_exptl_refinement ; All H atoms were initially located in a difference Fourier map. Thereafter, all H atoms, except the O---H and N---H atoms, were placed in geometrically fixed idealised positions and constrained to ride on their parent atoms with C---H distances in the range 0.95-1.00 \%A and U~iso~(H) = xU~eq~(C), where x = 1.5 for methyl and 1.2 for all other atoms. ; _publ_section_figure_captions ; Figure 1. The asymmetric unit of adamantylammonium dihydroxybenzoate shown with 50 % thermal ellipsoids, hydrogen atoms as spheres of arbitrary size and numbering scheme. Figure 2, Schematic displaying selected interactions within adamantylammonium dihydroxybenzoate. Figure 3. Extended packing diagram as viewed down the b-axis highlighting hydrogen bonding in red dashed lines. ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; (3s,5s,7s)-adamantan-1-ammonium 2,5-dihydroxybenzoate ; _chemical_name_common '(3s,5s,7s)-adamantan-1-ammonium 2,5-dihydroxybenzoate' _chemical_melting_point ? _chemical_formula_moiety 'C10 H18 N, C7 H5 O4' _chemical_formula_sum 'C17 H23 N O4' _chemical_formula_weight 305.36 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/n _symmetry_space_group_name_Hall ' -P 2yn' 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 12.157(3) _cell_length_b 6.9992(17) _cell_length_c 17.778(4) _cell_angle_alpha 90.00 _cell_angle_beta 92.728(14) _cell_angle_gamma 90.00 _cell_volume 1511.0(6) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 2095 _cell_measurement_theta_min 3.13 _cell_measurement_theta_max 21.45 _exptl_crystal_description Anhedral _exptl_crystal_colour Translucent _exptl_crystal_size_max 0.02 _exptl_crystal_size_mid 0.02 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.342 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 656 _exptl_absorpt_coefficient_mu 0.095 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9981 _exptl_absorpt_correction_T_max 0.9990 _exptl_absorpt_process_details 'sadabs (Bruker AXS, 2005)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker X8 APEX KAPPA CCD' _diffrn_measurement_method '0.5 deg frames in phi and omega' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 25942 _diffrn_reflns_av_R_equivalents 0.2325 _diffrn_reflns_av_sigmaI/netI 0.1087 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 3.13 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2647 _reflns_number_gt 1266 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker Apex II V 1.0 (Bruker ASX, 2005)' _computing_cell_refinement 'Bruker Apex II V 1.0 (Bruker ASX, 2005)' _computing_data_reduction 'Bruker Apex II V 1.0 (Bruker ASX, 2005)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Pov-ray for windows, version 3.1' _computing_publication_material 'Microsoft Office' _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^)+(0.0905P)^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 2647 _refine_ls_number_parameters 219 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1465 _refine_ls_R_factor_gt 0.0712 _refine_ls_wR_factor_ref 0.1864 _refine_ls_wR_factor_gt 0.1530 _refine_ls_goodness_of_fit_ref 0.906 _refine_ls_restrained_S_all 0.906 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.9550(2) 0.7191(5) 0.55584(19) 0.0264(8) Uani 1 1 d . . . C1 C 0.8368(3) 0.7076(5) 0.5766(2) 0.0248(9) Uani 1 1 d . . . C10 C 0.7756(3) 0.8810(5) 0.5443(2) 0.0327(10) Uani 1 1 d . . . H10A H 0.7800 0.8833 0.4899 0.039 Uiso 1 1 calc R . . H10B H 0.8089 0.9971 0.5645 0.039 Uiso 1 1 calc R . . C2 C 0.7857(3) 0.5273(5) 0.5432(2) 0.0326(10) Uani 1 1 d . . . H2A H 0.8255 0.4163 0.5626 0.039 Uiso 1 1 calc R . . H2B H 0.7901 0.5289 0.4889 0.039 Uiso 1 1 calc R . . C8 C 0.6028(3) 0.6891(6) 0.5321(2) 0.0411(11) Uani 1 1 d . . . H8A H 0.6056 0.6908 0.4776 0.049 Uiso 1 1 calc R . . H8B H 0.5263 0.6818 0.5449 0.049 Uiso 1 1 calc R . . C5 C 0.6599(3) 0.5116(6) 0.6487(2) 0.0418(11) Uani 1 1 d . . . H5A H 0.6990 0.4006 0.6688 0.050 Uiso 1 1 calc R . . H5B H 0.5837 0.5023 0.6623 0.050 Uiso 1 1 calc R . . C7 C 0.6550(3) 0.8702(5) 0.5650(2) 0.0368(10) Uani 1 1 d . . . H7 H 0.6151 0.9821 0.5449 0.044 Uiso 1 1 calc R . . C3 C 0.8332(3) 0.7055(5) 0.6614(2) 0.0340(10) Uani 1 1 d . . . H3A H 0.8668 0.8208 0.6823 0.041 Uiso 1 1 calc R . . H3B H 0.8737 0.5963 0.6818 0.041 Uiso 1 1 calc R . . C9 C 0.6656(3) 0.5164(6) 0.5639(2) 0.0364(10) Uani 1 1 d . . . H9 H 0.6325 0.3995 0.5426 0.044 Uiso 1 1 calc R . . C4 C 0.7117(3) 0.6939(6) 0.6824(2) 0.0396(11) Uani 1 1 d . . . H4 H 0.7075 0.6919 0.7373 0.048 Uiso 1 1 calc R . . C6 C 0.6500(3) 0.8667(6) 0.6503(2) 0.0439(11) Uani 1 1 d . . . H6A H 0.6826 0.9826 0.6713 0.053 Uiso 1 1 calc R . . H6B H 0.5738 0.8615 0.6640 0.053 Uiso 1 1 calc R . . O3A O 0.6008(2) 0.5759(3) 0.24842(15) 0.0336(7) Uani 1 1 d . . . O2A O 0.5493(2) 0.4488(3) 0.11990(14) 0.0351(7) Uani 1 1 d . . . O1A O 0.54677(19) 0.1376(3) 0.09731(14) 0.0308(7) Uani 1 1 d . . . O4A O 0.6707(2) -0.1566(4) 0.34995(15) 0.0360(7) Uani 1 1 d . . . C2A C 0.5984(3) 0.2404(5) 0.22140(19) 0.0244(9) Uani 1 1 d . . . C7A C 0.6163(3) 0.0556(5) 0.24841(19) 0.0246(9) Uani 1 1 d . . . H7AA H 0.6035 -0.0475 0.2162 0.030 Uiso 1 1 calc R . . C4A C 0.6558(3) 0.3582(5) 0.3450(2) 0.0294(9) Uani 1 1 d . . . H4AA H 0.6689 0.4602 0.3778 0.035 Uiso 1 1 calc R . . C5A C 0.6733(3) 0.1750(5) 0.3699(2) 0.0285(9) Uani 1 1 d . . . H5AA H 0.6992 0.1528 0.4192 0.034 Uiso 1 1 calc R . . C1A C 0.5623(3) 0.2764(5) 0.1406(2) 0.0278(9) Uani 1 1 d . . . C3A C 0.6185(3) 0.3924(5) 0.2710(2) 0.0261(9) Uani 1 1 d . . . C6A C 0.6523(3) 0.0225(5) 0.3215(2) 0.0274(9) Uani 1 1 d . . . H1N H 0.963(3) 0.695(5) 0.499(3) 0.064(14) Uiso 1 1 d . . . H2N H 0.998(3) 0.593(6) 0.578(2) 0.064(13) Uiso 1 1 d . . . H3N H 0.985(4) 0.836(6) 0.566(2) 0.066(15) Uiso 1 1 d . . . H4AO H 0.648(3) -0.250(5) 0.311(2) 0.057(13) Uiso 1 1 d . . . H3AO H 0.581(3) 0.555(5) 0.189(2) 0.046(11) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0177(19) 0.035(2) 0.027(2) -0.0040(16) 0.0059(14) -0.0026(16) C1 0.013(2) 0.035(2) 0.027(2) -0.0011(18) 0.0048(16) -0.0019(16) C10 0.028(2) 0.038(2) 0.033(2) 0.0038(19) 0.0058(18) 0.0035(18) C2 0.027(3) 0.035(2) 0.036(2) -0.0058(18) 0.0029(18) -0.0042(17) C8 0.020(2) 0.066(3) 0.037(3) -0.003(2) 0.0026(18) -0.002(2) C5 0.028(3) 0.054(3) 0.044(3) 0.010(2) 0.002(2) -0.003(2) C7 0.027(2) 0.042(2) 0.042(3) 0.004(2) 0.0033(19) 0.0097(19) C3 0.023(2) 0.049(2) 0.030(2) 0.0032(19) 0.0027(17) 0.0012(18) C9 0.020(2) 0.045(3) 0.045(3) -0.003(2) 0.0035(19) -0.0084(19) C4 0.029(3) 0.068(3) 0.023(2) 0.002(2) 0.0072(18) 0.002(2) C6 0.025(2) 0.061(3) 0.046(3) -0.008(2) 0.009(2) 0.001(2) O3A 0.0378(17) 0.0287(15) 0.0339(17) -0.0009(13) -0.0031(13) 0.0001(12) O2A 0.0348(17) 0.0330(17) 0.0369(17) 0.0059(14) -0.0041(13) 0.0038(12) O1A 0.0291(16) 0.0323(15) 0.0309(16) -0.0051(13) 0.0004(12) -0.0057(12) O4A 0.0447(18) 0.0301(16) 0.0326(16) 0.0016(14) -0.0044(13) 0.0024(13) C2A 0.017(2) 0.030(2) 0.026(2) -0.0023(18) 0.0048(16) -0.0023(15) C7A 0.019(2) 0.033(2) 0.022(2) 0.0007(18) 0.0028(16) -0.0007(16) C4A 0.023(2) 0.035(2) 0.029(2) -0.0018(19) -0.0004(17) 0.0013(18) C5A 0.024(2) 0.035(2) 0.026(2) 0.0031(19) -0.0016(17) 0.0039(17) C1A 0.012(2) 0.038(2) 0.034(3) 0.003(2) 0.0071(17) -0.0029(17) C3A 0.018(2) 0.028(2) 0.033(2) 0.0043(19) 0.0052(17) 0.0054(16) C6A 0.023(2) 0.026(2) 0.034(3) 0.0026(19) 0.0048(18) 0.0040(16) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C1 1.503(4) . ? N1 H1N 1.03(4) . ? N1 H2N 1.09(4) . ? N1 H3N 0.91(4) . ? C1 C3 1.510(5) . ? C1 C2 1.515(5) . ? C1 C10 1.522(5) . ? C10 C7 1.530(5) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C2 C9 1.525(5) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C8 C7 1.523(5) . ? C8 C9 1.524(5) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C5 C9 1.512(5) . ? C5 C4 1.532(5) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C7 C6 1.520(5) . ? C7 H7 0.9800 . ? C3 C4 1.543(5) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C9 H9 0.9800 . ? C4 C6 1.519(5) . ? C4 H4 0.9800 . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? O3A C3A 1.360(4) . ? O3A H3AO 1.08(4) . ? O2A C1A 1.270(4) . ? O2A H3AO 1.47(4) . ? O1A C1A 1.248(4) . ? O4A C6A 1.366(4) . ? O4A H4AO 0.98(4) . ? C2A C7A 1.393(5) . ? C2A C3A 1.396(5) . ? C2A C1A 1.504(5) . ? C7A C6A 1.371(5) . ? C7A H7AA 0.9300 . ? C4A C5A 1.370(5) . ? C4A C3A 1.392(5) . ? C4A H4AA 0.9300 . ? C5A C6A 1.387(5) . ? C5A H5AA 0.9300 . ? 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 111(2) . . ? C1 N1 H2N 108(2) . . ? H1N N1 H2N 99(3) . . ? C1 N1 H3N 112(3) . . ? H1N N1 H3N 107(4) . . ? H2N N1 H3N 118(3) . . ? N1 C1 C3 108.6(3) . . ? N1 C1 C2 109.1(3) . . ? C3 C1 C2 110.6(3) . . ? N1 C1 C10 108.7(3) . . ? C3 C1 C10 110.3(3) . . ? C2 C1 C10 109.4(3) . . ? C1 C10 C7 109.0(3) . . ? C1 C10 H10A 109.9 . . ? C7 C10 H10A 109.9 . . ? C1 C10 H10B 109.9 . . ? C7 C10 H10B 109.9 . . ? H10A C10 H10B 108.3 . . ? C1 C2 C9 109.0(3) . . ? C1 C2 H2A 109.9 . . ? C9 C2 H2A 109.9 . . ? C1 C2 H2B 109.9 . . ? C9 C2 H2B 109.9 . . ? H2A C2 H2B 108.3 . . ? C7 C8 C9 109.0(3) . . ? C7 C8 H8A 109.9 . . ? C9 C8 H8A 109.9 . . ? C7 C8 H8B 109.9 . . ? C9 C8 H8B 109.9 . . ? H8A C8 H8B 108.3 . . ? C9 C5 C4 109.4(3) . . ? C9 C5 H5A 109.8 . . ? C4 C5 H5A 109.8 . . ? C9 C5 H5B 109.8 . . ? C4 C5 H5B 109.8 . . ? H5A C5 H5B 108.2 . . ? C6 C7 C8 109.6(3) . . ? C6 C7 C10 109.0(3) . . ? C8 C7 C10 109.5(3) . . ? C6 C7 H7 109.6 . . ? C8 C7 H7 109.6 . . ? C10 C7 H7 109.6 . . ? C1 C3 C4 108.4(3) . . ? C1 C3 H3A 110.0 . . ? C4 C3 H3A 110.0 . . ? C1 C3 H3B 110.0 . . ? C4 C3 H3B 110.0 . . ? H3A C3 H3B 108.4 . . ? C5 C9 C8 110.0(3) . . ? C5 C9 C2 109.4(3) . . ? C8 C9 C2 109.8(3) . . ? C5 C9 H9 109.2 . . ? C8 C9 H9 109.2 . . ? C2 C9 H9 109.2 . . ? C6 C4 C5 109.3(3) . . ? C6 C4 C3 109.2(3) . . ? C5 C4 C3 109.3(3) . . ? C6 C4 H4 109.7 . . ? C5 C4 H4 109.7 . . ? C3 C4 H4 109.7 . . ? C4 C6 C7 110.2(3) . . ? C4 C6 H6A 109.6 . . ? C7 C6 H6A 109.6 . . ? C4 C6 H6B 109.6 . . ? C7 C6 H6B 109.6 . . ? H6A C6 H6B 108.1 . . ? C3A O3A H3AO 100.7(19) . . ? C1A O2A H3AO 102.3(14) . . ? C6A O4A H4AO 108(2) . . ? C7A C2A C3A 118.0(3) . . ? C7A C2A C1A 121.2(3) . . ? C3A C2A C1A 120.7(3) . . ? C6A C7A C2A 121.4(3) . . ? C6A C7A H7AA 119.3 . . ? C2A C7A H7AA 119.3 . . ? C5A C4A C3A 120.3(3) . . ? C5A C4A H4AA 119.9 . . ? C3A C4A H4AA 119.9 . . ? C4A C5A C6A 120.0(3) . . ? C4A C5A H5AA 120.0 . . ? C6A C5A H5AA 120.0 . . ? O1A C1A O2A 123.3(3) . . ? O1A C1A C2A 119.2(3) . . ? O2A C1A C2A 117.6(3) . . ? O3A C3A C4A 118.8(3) . . ? O3A C3A C2A 120.8(3) . . ? C4A C3A C2A 120.4(3) . . ? O4A C6A C7A 123.0(3) . . ? O4A C6A C5A 117.0(3) . . ? C7A C6A C5A 119.9(3) . . ? 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 N1 C1 C10 C7 179.9(3) . . . . ? C3 C1 C10 C7 -61.1(4) . . . . ? C2 C1 C10 C7 60.8(4) . . . . ? N1 C1 C2 C9 -179.7(3) . . . . ? C3 C1 C2 C9 60.9(4) . . . . ? C10 C1 C2 C9 -60.9(4) . . . . ? C9 C8 C7 C6 -59.7(4) . . . . ? C9 C8 C7 C10 59.8(4) . . . . ? C1 C10 C7 C6 59.5(4) . . . . ? C1 C10 C7 C8 -60.3(4) . . . . ? N1 C1 C3 C4 179.9(3) . . . . ? C2 C1 C3 C4 -60.4(4) . . . . ? C10 C1 C3 C4 60.9(4) . . . . ? C4 C5 C9 C8 -60.2(4) . . . . ? C4 C5 C9 C2 60.5(4) . . . . ? C7 C8 C9 C5 60.4(4) . . . . ? C7 C8 C9 C2 -60.0(4) . . . . ? C1 C2 C9 C5 -60.2(4) . . . . ? C1 C2 C9 C8 60.6(4) . . . . ? C9 C5 C4 C6 59.1(4) . . . . ? C9 C5 C4 C3 -60.2(4) . . . . ? C1 C3 C4 C6 -60.0(4) . . . . ? C1 C3 C4 C5 59.5(4) . . . . ? C5 C4 C6 C7 -59.1(4) . . . . ? C3 C4 C6 C7 60.3(4) . . . . ? C8 C7 C6 C4 59.8(4) . . . . ? C10 C7 C6 C4 -60.0(4) . . . . ? C3A C2A C7A C6A 0.1(5) . . . . ? C1A C2A C7A C6A 178.1(3) . . . . ? C3A C4A C5A C6A -0.9(5) . . . . ? C7A C2A C1A O1A 1.0(5) . . . . ? C3A C2A C1A O1A 178.9(3) . . . . ? C7A C2A C1A O2A -179.0(3) . . . . ? C3A C2A C1A O2A -1.1(5) . . . . ? C5A C4A C3A O3A 179.3(3) . . . . ? C5A C4A C3A C2A 0.1(5) . . . . ? C7A C2A C3A O3A -178.9(3) . . . . ? C1A C2A C3A O3A 3.2(5) . . . . ? C7A C2A C3A C4A 0.3(5) . . . . ? C1A C2A C3A C4A -177.6(3) . . . . ? C2A C7A C6A O4A 180.0(3) . . . . ? C2A C7A C6A C5A -1.0(5) . . . . ? C4A C5A C6A O4A -179.5(3) . . . . ? C4A C5A C6A C7A 1.3(5) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.493 _refine_diff_density_min -0.320 _refine_diff_density_rms 0.095 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 _geom_hbond_publ_flag N1 H1N O1A 1.03(5) 1.76(5) 2.781(4) 170(3) 2_655 y N1 H2N O1A 1.09(4) 1.75(4) 2.818(4) 166(3) 4_555 y N1 H3N O2A 0.91(4) 1.93(4) 2.809(4) 162(3) 4_565 y O4A H4AO O3A 0.98(3) 1.73(4) 2.709(4) 175(4) 1_545 y O3A* H3AO O2A 1.08(4) 1.47(4) 2.504(4) 157(3) ? y _geom_hbond_footnote_A ; Notes: Where * indicates an intramolecular bond. ; loop_ _geom_extra_tableB_col_1 _geom_extra_tableB_col_2 _geom_extra_tableB_col_3 _geom_extra_tableB_col_4 _geom_extra_tableB_col_5 CgI CgJ Cg...Cg \a 'Symmetry position of CgJ' Cg1 Cg1 4.805(2) 5 3/2-X,-1/2+Y,1/2-Z Cg1 Cg1 4.806(2) 5 3/2-X,1/2+Y,1/2-Z _geom_extra_table_head_B ; Geometrical parameters (\%A, \%) of selected inter-ring \p---\p interactions. \a is the dihedral angle between planes I and J, CgI is the centroid of plane I and CgJ the centroid of plane J. ; _geom_table_footnote_B ; Notes: Cg1 is the centroid of ring C2A/C3A/C4A/C5A/C6A/C7A. ; # Attachment 'Hydroxyethylpyrrolidinium+Benzoate.CIF' data_pyrmon _database_code_depnum_ccdc_archive 'CCDC 802628' _publ_section_abstract ; 1-(2-hydroxyethyl)pyrrolidin-1-ium benzoate, C~6~H~14~N~1~O~1~. C~7~H~5~O~2~, displays interionic N---H...O, C---H...O and O---H...O hydrogen bonding and interanionic C---H...O hydrogen bonding. A \p...\p ring interaction is also seen. ; _publ_section_comment ; The asymmetric unit consists of a single 1-(2-hydroxy-ethyl)-pyrrolidinium cation and a single benzoate anion (Figure 1). The 1-(2-hydroxy-ethyl)-pyrrolidinium cation adopts the preferred chair conformation with the hydroxyl substituent adopting a gauche conformation with a torsional angle of -66.3(2) \% [N1---C5---C6---O1], which is not the energetically favoured conformation. The hydrogen (H1N) was located in the fourier difference map at a 1.06(4) \%A distance away from N1. The benzoate anion displays a planar aromatic ring with one carboxylic acid group displaying standard bond distances and angles (C1A---O1A 1.257(2) and C1A---O2A 1.261(2) \%A respectively). Three main types of hydrogen bonding occurs, strong O---H...O and N---H...O hydrogen bonding and weak interionic C---H...O hydrogen bonding (Table 1, Figure 2). A \p...\p interaction is also seen (Table 2). The extended structure (Figure 3) consists of distinct layers of cations and anions, which are connected by the above mentioned hydrogen bonds. The aromatic moeities are grouped together via the \p...\p interaction and the charged centres are clearly grouped and linked via hydrogen bonding (Figure 4). ; _publ_section_exptl_prep ; 1-(2-hydroxyethyl)-pyrrolidine (0.979 g, 8.501 mmol), dissolved in methanol, was slowly added to benzoic acid (1.038 g, 8.501 mmol) in methanol solution. The reaction was stirred for 4 hours in an ice bath. Methanol was subsequently removed under vacuum and the resulting yellow solid was dried on a Shlenk line for 5 hours. ; _publ_section_exptl_refinement ; All H atoms were initially located in a difference Fourier map. Thereafter, all H atoms, except the N---H and O---H atoms, were placed in geometrically fixed idealised positions and constrained to ride on their parent atoms with C---H distances in the range 0.95-1.00 \%A and U~iso~(H) = xU~eq~(C), where x = 1.5 for methyl and 1.2 for all other atoms. ; _publ_section_figure_captions ; Figure 1. The asymmetric unit of 1-(2-hydroxy-ethyl)-pyrrolidinium benzoate shown with 50 % thermal ellipsoids, hydrogen atoms as spheres of arbitrary size and numbering scheme. Figure 2, Schematic displaying selected interactions within 1-(2-hydroxy-ethyl)-pyrrolidinium benzoate. Figure 3. Extended packing diagram as viewed down the c-axis highlighting hydrogen bonding in red dashed lines. Figure 4. Extended packing diagram as viewed down the a-axis highlighting hydrogen bonding in red dashed lines. ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1-(2-hydroxyethyl)pyrrolidin-1-ium benzoate ; _chemical_name_common '1-(2-hydroxyethyl)pyrrolidin-1-ium benzoate' _chemical_melting_point ? _chemical_formula_moiety 'C6 H14 N O, C7 H5 O2' _chemical_formula_sum 'C13 H19 N O3' _chemical_formula_weight 237.29 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 'C2/c ' _symmetry_space_group_name_Hall ' -C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 19.760(4) _cell_length_b 11.178(2) _cell_length_c 11.485(2) _cell_angle_alpha 90.00 _cell_angle_beta 95.28(1) _cell_angle_gamma 90.00 _cell_volume 2525.9(7) _cell_formula_units_Z 8 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 1724 _cell_measurement_theta_min 2.69 _cell_measurement_theta_max 20.06 _exptl_crystal_description anhedral _exptl_crystal_colour yellow _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.248 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1024 _exptl_absorpt_coefficient_mu 0.088 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9826 _exptl_absorpt_correction_T_max 0.9826 _exptl_absorpt_process_details 'sadabs (Bruker AXS, 2005)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker X8 APEX KAPPA CCD' _diffrn_measurement_method '0.5 deg frames in phi and omega' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16525 _diffrn_reflns_av_R_equivalents 0.0661 _diffrn_reflns_av_sigmaI/netI 0.0682 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.69 _diffrn_reflns_theta_max 28.45 _reflns_number_total 3152 _reflns_number_gt 1676 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker Apex II V 1.0 (Bruker ASX, 2005)' _computing_cell_refinement 'Bruker Apex II V 1.0 (Bruker ASX, 2005)' _computing_data_reduction 'Bruker Apex II V 1.0 (Bruker ASX, 2005)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Pov-ray for windows, version 3.1' _computing_publication_material 'Microsoft Office' _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^)+(0.0570P)^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 3152 _refine_ls_number_parameters 158 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1095 _refine_ls_R_factor_gt 0.0494 _refine_ls_wR_factor_ref 0.1312 _refine_ls_wR_factor_gt 0.1098 _refine_ls_goodness_of_fit_ref 0.999 _refine_ls_restrained_S_all 0.999 _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 O2A O 0.15506(6) 0.23557(10) 0.79772(10) 0.0411(3) Uani 1 1 d . . . O1A O 0.22717(6) 0.28472(10) 0.66732(10) 0.0436(3) Uani 1 1 d . . . O1 O 0.18219(6) -0.20488(10) 0.64121(11) 0.0491(4) Uani 1 1 d . . . N1 N 0.30678(6) -0.06656(11) 0.58757(11) 0.0335(3) Uani 1 1 d . . . C2A C 0.11844(8) 0.21267(13) 0.59740(14) 0.0336(4) Uani 1 1 d . . . C3A C 0.13424(9) 0.20345(13) 0.48291(14) 0.0369(4) Uani 1 1 d . . . H3AA H 0.1794 0.2181 0.4643 0.044 Uiso 1 1 calc R . . C1A C 0.17097(8) 0.24600(13) 0.69441(15) 0.0339(4) Uani 1 1 d . . . C4 C 0.31957(8) 0.02385(15) 0.68317(13) 0.0381(4) Uani 1 1 d . . . H4A H 0.2964 0.0011 0.7527 0.046 Uiso 1 1 calc R . . H4B H 0.3037 0.1042 0.6565 0.046 Uiso 1 1 calc R . . C3 C 0.39607(9) 0.02180(16) 0.71020(15) 0.0441(5) Uani 1 1 d . . . H3A H 0.4095 -0.0376 0.7719 0.053 Uiso 1 1 calc R . . H3B H 0.4131 0.1015 0.7366 0.053 Uiso 1 1 calc R . . C1 C 0.36295(8) -0.04432(15) 0.51128(14) 0.0425(5) Uani 1 1 d . . . H1B H 0.3512 0.0226 0.4566 0.051 Uiso 1 1 calc R . . H1A H 0.3719 -0.1167 0.4655 0.051 Uiso 1 1 calc R . . C5 C 0.23817(8) -0.06143(16) 0.52255(15) 0.0444(5) Uani 1 1 d . . . H5A H 0.2359 -0.1208 0.4583 0.053 Uiso 1 1 calc R . . H5B H 0.2314 0.0189 0.4870 0.053 Uiso 1 1 calc R . . C6 C 0.18158(9) -0.08598(15) 0.59860(17) 0.0491(5) Uani 1 1 d . . . H6B H 0.1856 -0.0301 0.6657 0.059 Uiso 1 1 calc R . . H6A H 0.1375 -0.0705 0.5530 0.059 Uiso 1 1 calc R . . C7A C 0.05275(10) 0.19311(19) 0.62217(18) 0.0602(6) Uani 1 1 d . . . H7AA H 0.0417 0.1983 0.7008 0.072 Uiso 1 1 calc R . . C2 C 0.42412(9) -0.01300(17) 0.59498(16) 0.0503(5) Uani 1 1 d . . . H2B H 0.4495 0.0546 0.5642 0.060 Uiso 1 1 calc R . . H2A H 0.4550 -0.0825 0.6066 0.060 Uiso 1 1 calc R . . C4A C 0.08440(10) 0.17298(17) 0.39560(16) 0.0551(5) Uani 1 1 d . . . H4AA H 0.0955 0.1646 0.3173 0.066 Uiso 1 1 calc R . . C5A C 0.01867(12) 0.1548(2) 0.42230(19) 0.0827(8) Uani 1 1 d . . . H5AA H -0.0157 0.1343 0.3622 0.099 Uiso 1 1 calc R . . C6A C 0.00273(11) 0.1662(2) 0.5349(2) 0.0890(9) Uani 1 1 d . . . H6AA H -0.0428 0.1555 0.5530 0.107 Uiso 1 1 calc R . . H1N H 0.3157 -0.1522 0.6248 0.063(5) Uiso 1 1 d R . . H1O H 0.2152 -0.2079 0.7106 0.085(8) Uiso 1 1 d 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 O2A 0.0480(8) 0.0454(7) 0.0309(7) -0.0030(5) 0.0080(6) -0.0095(5) O1A 0.0327(7) 0.0558(8) 0.0433(7) -0.0049(6) 0.0087(6) -0.0059(5) O1 0.0459(8) 0.0452(7) 0.0548(9) 0.0049(6) -0.0022(7) -0.0076(6) N1 0.0362(8) 0.0359(8) 0.0284(7) 0.0008(6) 0.0026(6) 0.0016(6) C2A 0.0321(10) 0.0362(9) 0.0330(10) -0.0036(7) 0.0062(8) -0.0005(7) C3A 0.0407(10) 0.0343(9) 0.0364(10) 0.0006(7) 0.0070(8) -0.0007(7) C1A 0.0347(10) 0.0297(8) 0.0381(10) -0.0026(7) 0.0079(8) 0.0014(7) C4 0.0439(11) 0.0393(9) 0.0320(9) -0.0031(7) 0.0079(8) -0.0014(8) C3 0.0423(11) 0.0507(10) 0.0395(10) -0.0010(8) 0.0051(8) -0.0091(8) C1 0.0503(11) 0.0466(10) 0.0328(10) 0.0002(8) 0.0155(9) -0.0010(8) C5 0.0419(11) 0.0454(10) 0.0437(10) 0.0055(8) -0.0088(9) 0.0008(8) C6 0.0371(10) 0.0484(11) 0.0599(12) 0.0072(9) -0.0057(9) -0.0010(8) C7A 0.0405(12) 0.0999(17) 0.0417(12) -0.0145(11) 0.0128(10) -0.0159(11) C2 0.0441(11) 0.0605(12) 0.0481(11) 0.0010(9) 0.0141(9) -0.0024(9) C4A 0.0642(14) 0.0672(13) 0.0341(11) -0.0032(9) 0.0060(10) -0.0101(11) C5A 0.0608(16) 0.138(2) 0.0480(14) -0.0109(14) -0.0046(12) -0.0356(15) C6A 0.0443(13) 0.165(3) 0.0579(15) -0.0200(16) 0.0055(12) -0.0396(15) _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 O2A C1A 1.2605(19) . ? O1A C1A 1.2573(19) . ? O1 C6 1.4159(19) . ? O1 H1O 0.9834 . ? N1 C5 1.4876(19) . ? N1 C4 1.4965(19) . ? N1 C1 1.497(2) . ? N1 H1N 1.0568 . ? C2A C7A 1.372(2) . ? C2A C3A 1.383(2) . ? C2A C1A 1.498(2) . ? C3A C4A 1.382(2) . ? C3A H3AA 0.9500 . ? C4 C3 1.515(2) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C3 C2 1.531(2) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C1 C2 1.515(2) . ? C1 H1B 0.9900 . ? C1 H1A 0.9900 . ? C5 C6 1.506(2) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 H6B 0.9900 . ? C6 H6A 0.9900 . ? C7A C6A 1.375(3) . ? C7A H7AA 0.9500 . ? C2 H2B 0.9900 . ? C2 H2A 0.9900 . ? C4A C5A 1.377(3) . ? C4A H4AA 0.9500 . ? C5A C6A 1.365(3) . ? C5A H5AA 0.9500 . ? C6A H6AA 0.9500 . ? 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 C6 O1 H1O 107.2 . . ? C5 N1 C4 115.27(12) . . ? C5 N1 C1 112.98(12) . . ? C4 N1 C1 103.48(12) . . ? C5 N1 H1N 110.4 . . ? C4 N1 H1N 107.7 . . ? C1 N1 H1N 106.4 . . ? C7A C2A C3A 119.08(16) . . ? C7A C2A C1A 119.31(16) . . ? C3A C2A C1A 121.60(15) . . ? C4A C3A C2A 120.01(16) . . ? C4A C3A H3AA 120.0 . . ? C2A C3A H3AA 120.0 . . ? O1A C1A O2A 124.56(16) . . ? O1A C1A C2A 117.96(15) . . ? O2A C1A C2A 117.47(14) . . ? N1 C4 C3 103.77(13) . . ? N1 C4 H4A 111.0 . . ? C3 C4 H4A 111.0 . . ? N1 C4 H4B 111.0 . . ? C3 C4 H4B 111.0 . . ? H4A C4 H4B 109.0 . . ? C4 C3 C2 105.10(13) . . ? C4 C3 H3A 110.7 . . ? C2 C3 H3A 110.7 . . ? C4 C3 H3B 110.7 . . ? C2 C3 H3B 110.7 . . ? H3A C3 H3B 108.8 . . ? N1 C1 C2 104.97(12) . . ? N1 C1 H1B 110.8 . . ? C2 C1 H1B 110.8 . . ? N1 C1 H1A 110.8 . . ? C2 C1 H1A 110.8 . . ? H1B C1 H1A 108.8 . . ? N1 C5 C6 113.13(13) . . ? N1 C5 H5A 109.0 . . ? C6 C5 H5A 109.0 . . ? N1 C5 H5B 109.0 . . ? C6 C5 H5B 109.0 . . ? H5A C5 H5B 107.8 . . ? O1 C6 C5 112.85(14) . . ? O1 C6 H6B 109.0 . . ? C5 C6 H6B 109.0 . . ? O1 C6 H6A 109.0 . . ? C5 C6 H6A 109.0 . . ? H6B C6 H6A 107.8 . . ? C2A C7A C6A 120.95(18) . . ? C2A C7A H7AA 119.5 . . ? C6A C7A H7AA 119.5 . . ? C1 C2 C3 106.02(14) . . ? C1 C2 H2B 110.5 . . ? C3 C2 H2B 110.5 . . ? C1 C2 H2A 110.5 . . ? C3 C2 H2A 110.5 . . ? H2B C2 H2A 108.7 . . ? C5A C4A C3A 119.91(18) . . ? C5A C4A H4AA 120.0 . . ? C3A C4A H4AA 120.0 . . ? C6A C5A C4A 120.1(2) . . ? C6A C5A H5AA 119.9 . . ? C4A C5A H5AA 119.9 . . ? C5A C6A C7A 119.9(2) . . ? C5A C6A H6AA 120.1 . . ? C7A C6A H6AA 120.1 . . ? 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 C7A C2A C3A C4A -1.1(2) . . . . ? C1A C2A C3A C4A -179.73(15) . . . . ? C7A C2A C1A O1A -167.12(16) . . . . ? C3A C2A C1A O1A 11.5(2) . . . . ? C7A C2A C1A O2A 11.4(2) . . . . ? C3A C2A C1A O2A -169.93(14) . . . . ? C5 N1 C4 C3 -164.87(13) . . . . ? C1 N1 C4 C3 -41.02(15) . . . . ? N1 C4 C3 C2 29.34(17) . . . . ? C5 N1 C1 C2 162.06(14) . . . . ? C4 N1 C1 C2 36.73(16) . . . . ? C4 N1 C5 C6 -62.36(18) . . . . ? C1 N1 C5 C6 178.95(13) . . . . ? N1 C5 C6 O1 -66.29(19) . . . . ? C3A C2A C7A C6A -0.8(3) . . . . ? C1A C2A C7A C6A 177.88(19) . . . . ? N1 C1 C2 C3 -18.24(18) . . . . ? C4 C3 C2 C1 -6.84(19) . . . . ? C2A C3A C4A C5A 1.7(3) . . . . ? C3A C4A C5A C6A -0.4(4) . . . . ? C4A C5A C6A C7A -1.5(4) . . . . ? C2A C7A C6A C5A 2.1(4) . . . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 28.45 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.197 _refine_diff_density_min -0.195 _refine_diff_density_rms 0.044 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 _geom_hbond_publ_flag N1 H1N O2A 1.06 1.61 2.6483(18) 165 6_546 y O1 H1O O1A 0.98 1.72 2.7078(18) 179 6_546 y C3A H3AA O1A 0.95 2.49 3.371(2) 154 7_556 y C1 H1A O1 0.99 2.53 3.382(2) 145 7_546 y C4 H4B O1A 0.99 2.53 3.436(2) 152 ? y loop_ _geom_extra_tableB_col_1 _geom_extra_tableB_col_2 _geom_extra_tableB_col_3 _geom_extra_tableB_col_4 _geom_extra_tableB_col_5 CgI CgJ Cg...Cg \a 'Symmetry position of CgJ' Cg1 Cg1 4.9166(15) 0 -X,-Y,1-Z _geom_extra_table_head_B ; Geometrical parameters (\%A, \%) of selected inter-ring \p---\p interactions. \a is the dihedral angle between planes I and J, CgI is the centroid of plane I and CgJ the centroid of plane J. ; _geom_table_footnote_B ; Notes: Cg1 is the centroid of ring C2A/C3A/C4A/C5A/C6A/C7A. ; # Attachment 'heptan-2-ammonium+2%2C5-dihydroxybenzoate.CIF' data_jel43mon _database_code_depnum_ccdc_archive 'CCDC 802629' _publ_section_abstract ; Heptan-2-ammonium 2,5-dihydroxybenzoate , C~7~H~18~N~1~. C~7~H~5~O~4~, displays interionic N---H...O and interanionic O---H...O and C-H...O hydrogen bonding. Interring interactions are also seen. ; _publ_section_comment ; The asymmetric unit consists of a single heptan-2-ammonium cation and a single 2,5-dihydroxy-benzoate anion (Figure 1). The alkyl end of the heptan-2-ammonium cation adopts a gauche conformation with a torsional angle of 69.5(5) [C4---C5---C6---C7], the ammonium end displays a trans conformation [C4---C3---C2---C1, -178.9(4)]. The hydrogen atoms of the ammonium substituent, with a standard terahedral arrangment, were located in the fourier difference map [N1 H1N 0.97(4); N1 H2N 0.97(4); N1 H3N 0.88(4) \%A]. The 2,5-dihydroxy-benzoate anion displays a planar aromatic ring with two hydroxyl groups and a carboxylic acid group displaying standard bond distances and angles (C3A---O3A 1.359(4), C6A---O4A 1.377(4), C1A---O1A 1.255(4) and C1A---O2A 1.276(4) \%A respectively). The hydroxy hydrogen atoms was also located and placed in the difference fourier map (O3A---H3AO 0.82(5) and O4A---H4AO 0.99(4)). Three main types of hydrogen bonding occurs, strong O...H---O and N...H---O hydrogen bonding and weak interanionic C---H...O hydrogen bonding (Table 1, Figure 2 [one intramoleculat bond occurs as indicated by a * in Table 1]). Additional interactions which also occurs is an inter-ring C-H...\p and \p...\p interactions (C3-H3B...Cg1, 2.78 \%A, 156 \%, symmetry of the benzoate ring: 1-X,1-Y,1-Z; Cg1...Cg1, 3.819(2) \%A, 0 \%, symmetry of the benzoate ring: 1-X,-Y,2-Z). The extended structure (Figure 3) consists of tightly interlayered cationic and anionic chains constructed from the hydrogen bonding and interring interaction network. ; _publ_section_exptl_prep ; Heptane-2-amine (0.748 g, 6.488 mmol), dissolved in methanol, was slowly added to 2,5-dihydroxybenzoic acid (1.000 g, 6.488 mmol) in methanol solution. The reaction was stirred for 4 hours in an ice bath. Methanol was subsequently removed under vacuum and the resulting opaque solid was dried on a Shlenk line for 5 hours. ; _publ_section_exptl_refinement ; All H atoms were initially located in a difference Fourier map. Thereafter, all H atoms, except the N---H and O---H atoms, were placed in geometrically fixed idealised positions and constrained to ride on their parent atoms with C---H distances in the range 0.95-1.00 \%A and U~iso~(H) = xU~eq~(C), where x = 1.5 for methyl and 1.2 for all other atoms. ; _publ_section_figure_captions ; Figure 1. The asymmetric unit of heptan-2-ammonium 2,5-dihydroxybenzoate shown with 50 % thermal ellipsoids, hydrogen atoms as spheres of arbitrary size and numbering scheme. Figure 2, Packing diagram as viewed down the b-axis, displaying selected interactions within heptan-2-ammonium 2,5-dihydroxybenzoate. Figure 3. Extended packing diagram as viewed down the a-axis. ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; heptan-2-ammonium 2,5-dihydroxybenzoate ; _chemical_name_common 'heptan-2-ammonium 2,5-dihydroxybenzoate' _chemical_melting_point ? _chemical_formula_moiety 'C7 H18 N, C7 H5 O4' _chemical_formula_sum 'C14 H23 N O4' _chemical_formula_weight 269.33 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P2(1)/n ' _symmetry_space_group_name_Hall '-P 2yn' 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 10.165(1) _cell_length_b 12.302(1) _cell_length_c 11.254(1) _cell_angle_alpha 90.00 _cell_angle_beta 97.111(7) _cell_angle_gamma 90.00 _cell_volume 1396.4(2) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 2321 _cell_measurement_theta_min 2.55 _cell_measurement_theta_max 22.21 _exptl_crystal_description small _exptl_crystal_colour translucent _exptl_crystal_size_max 0.02 _exptl_crystal_size_mid 0.01 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.281 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 584 _exptl_absorpt_coefficient_mu 0.093 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9981 _exptl_absorpt_correction_T_max 0.9991 _exptl_absorpt_process_details 'sadabs (Bruker AXS, 2005)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker X8 APEX KAPPA CCD' _diffrn_measurement_method '0.5 deg frames in phi and omega' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18233 _diffrn_reflns_av_R_equivalents 0.1593 _diffrn_reflns_av_sigmaI/netI 0.1773 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.88 _diffrn_reflns_theta_max 28.52 _reflns_number_total 3512 _reflns_number_gt 1745 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker Apex II V 1.0 (Bruker ASX, 2005)' _computing_cell_refinement 'Bruker Apex II V 1.0 (Bruker ASX, 2005)' _computing_data_reduction 'Bruker Apex II V 1.0 (Bruker ASX, 2005)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Pov-ray for windows, version 3.1' _computing_publication_material 'Microsoft Office' _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^)+(0.0540P)^2^+1.0740P] 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 3512 _refine_ls_number_parameters 194 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2183 _refine_ls_R_factor_gt 0.1050 _refine_ls_wR_factor_ref 0.2021 _refine_ls_wR_factor_gt 0.1686 _refine_ls_goodness_of_fit_ref 1.067 _refine_ls_restrained_S_all 1.067 _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 O2A O 0.1822(2) 0.1955(2) 0.7382(2) 0.0325(7) Uani 1 1 d . . . O1A O 0.1416(2) 0.0330(2) 0.6545(2) 0.0246(7) Uani 1 1 d . . . O4A O 0.5393(3) -0.1927(2) 0.8268(2) 0.0287(7) Uani 1 1 d . . . O3A O 0.4074(3) 0.2404(2) 0.8526(3) 0.0313(7) Uani 1 1 d . . . C3A C 0.4372(4) 0.1339(3) 0.8388(3) 0.0248(9) Uani 1 1 d . . . C2A C 0.3471(3) 0.0606(3) 0.7773(3) 0.0195(9) Uani 1 1 d . . . C5A C 0.5941(4) -0.0110(3) 0.8839(3) 0.0249(9) Uani 1 1 d . . . H5A H 0.6786 -0.0354 0.9192 0.030 Uiso 1 1 calc R . . C7A C 0.3845(4) -0.0481(3) 0.7715(3) 0.0241(9) Uani 1 1 d . . . H7A H 0.3253 -0.0981 0.7286 0.029 Uiso 1 1 calc R . . C6A C 0.5042(4) -0.0845(3) 0.8258(3) 0.0249(9) Uani 1 1 d . . . C4A C 0.5608(4) 0.0964(3) 0.8902(3) 0.0241(9) Uani 1 1 d . . . H4A H 0.6227 0.1461 0.9301 0.029 Uiso 1 1 calc R . . C1A C 0.2150(4) 0.0976(3) 0.7185(3) 0.0234(9) Uani 1 1 d . . . N1 N 0.1067(3) 0.8974(3) 0.4479(3) 0.0243(8) Uani 1 1 d . . . C4 C 0.3823(4) 0.8008(3) 0.4464(4) 0.0295(10) Uani 1 1 d . . . H4B H 0.3215 0.7659 0.4971 0.035 Uiso 1 1 calc R . . H4C H 0.3743 0.7619 0.3688 0.035 Uiso 1 1 calc R . . C3 C 0.3433(4) 0.9200(3) 0.4254(4) 0.0298(10) Uani 1 1 d . . . H3A H 0.3575 0.9581 0.5035 0.036 Uiso 1 1 calc R . . H3B H 0.4045 0.9527 0.3736 0.036 Uiso 1 1 calc R . . C2 C 0.2038(4) 0.9419(3) 0.3698(4) 0.0280(10) Uani 1 1 d . . . H2 H 0.1891 0.9046 0.2903 0.034 Uiso 1 1 calc R . . C5 C 0.5239(4) 0.7927(3) 0.5072(4) 0.0309(10) Uani 1 1 d . . . H5B H 0.5322 0.8379 0.5805 0.037 Uiso 1 1 calc R . . H5C H 0.5838 0.8237 0.4530 0.037 Uiso 1 1 calc R . . C1 C 0.1764(4) 1.0625(3) 0.3509(4) 0.0318(10) Uani 1 1 d . . . H1A H 0.1911 1.1002 0.4281 0.048 Uiso 1 1 calc R . . H1B H 0.0842 1.0728 0.3154 0.048 Uiso 1 1 calc R . . H1C H 0.2361 1.0922 0.2970 0.048 Uiso 1 1 calc R . . C6 C 0.5705(4) 0.6780(3) 0.5416(4) 0.0307(10) Uani 1 1 d . . . H6A H 0.6561 0.6824 0.5940 0.037 Uiso 1 1 calc R . . H6B H 0.5053 0.6435 0.5882 0.037 Uiso 1 1 calc R . . C7 C 0.5877(5) 0.6072(4) 0.4352(4) 0.0441(12) Uani 1 1 d . . . H1 H 0.5019 0.5979 0.3861 0.066 Uiso 1 1 calc R . . H7B H 0.6221 0.5361 0.4631 0.066 Uiso 1 1 calc R . . H7C H 0.6502 0.6418 0.3873 0.066 Uiso 1 1 calc R . . H1N H 0.017(4) 0.916(3) 0.414(3) 0.026(11) Uiso 1 1 d . . . H2N H 0.124(4) 0.931(3) 0.527(4) 0.035(12) Uiso 1 1 d . . . H3N H 0.112(4) 0.827(4) 0.457(3) 0.030(12) Uiso 1 1 d . . . H4AO H 0.466(4) -0.242(4) 0.798(4) 0.048(13) Uiso 1 1 d . . . H3AO H 0.332(5) 0.244(4) 0.817(4) 0.061(18) 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 O2A 0.0324(17) 0.0166(16) 0.0456(18) -0.0045(13) -0.0068(14) 0.0034(12) O1A 0.0238(15) 0.0218(15) 0.0262(14) -0.0043(12) -0.0052(12) 0.0014(11) O4A 0.0280(17) 0.0185(16) 0.0370(17) 0.0027(13) -0.0068(13) 0.0027(13) O3A 0.0321(19) 0.0193(17) 0.0395(18) -0.0050(13) -0.0072(14) 0.0011(13) C3A 0.032(3) 0.020(2) 0.022(2) -0.0004(17) 0.0030(18) -0.0017(18) C2A 0.021(2) 0.021(2) 0.0176(19) 0.0019(16) 0.0043(16) -0.0001(16) C5A 0.019(2) 0.033(3) 0.022(2) 0.0041(18) -0.0020(17) -0.0037(18) C7A 0.026(2) 0.021(2) 0.024(2) -0.0022(17) -0.0012(17) -0.0040(17) C6A 0.023(2) 0.024(2) 0.027(2) 0.0047(18) -0.0004(17) 0.0053(18) C4A 0.021(2) 0.026(2) 0.025(2) -0.0036(17) -0.0013(16) -0.0067(18) C1A 0.026(2) 0.021(2) 0.023(2) 0.0058(17) 0.0008(17) -0.0026(18) N1 0.022(2) 0.021(2) 0.029(2) 0.0007(16) -0.0019(15) -0.0004(15) C4 0.030(2) 0.028(2) 0.030(2) -0.0008(19) 0.0012(18) 0.0038(19) C3 0.030(2) 0.028(2) 0.030(2) 0.0040(18) 0.0002(18) 0.0004(18) C2 0.027(2) 0.029(2) 0.028(2) 0.0034(18) 0.0013(18) -0.0030(18) C5 0.029(2) 0.036(3) 0.028(2) 0.0018(19) 0.0049(18) 0.0000(19) C1 0.033(3) 0.026(2) 0.035(2) 0.0085(19) -0.0021(19) 0.0004(18) C6 0.029(2) 0.032(3) 0.031(2) 0.0031(19) 0.0036(18) 0.0072(19) C7 0.054(3) 0.040(3) 0.038(3) 0.002(2) 0.004(2) 0.020(2) _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 O2A C1A 1.276(4) . ? O1A C1A 1.255(4) . ? O4A C6A 1.377(4) . ? O4A H4AO 0.99(4) . ? O3A C3A 1.359(4) . ? O3A H3AO 0.82(5) . ? C3A C4A 1.395(5) . ? C3A C2A 1.405(5) . ? C2A C7A 1.393(5) . ? C2A C1A 1.493(5) . ? C5A C4A 1.368(5) . ? C5A C6A 1.389(5) . ? C5A H5A 0.9500 . ? C7A C6A 1.368(5) . ? C7A H7A 0.9500 . ? C4A H4A 0.9500 . ? N1 C2 1.504(5) . ? N1 H1N 0.97(4) . ? N1 H2N 0.97(4) . ? N1 H3N 0.88(4) . ? C4 C5 1.519(5) . ? C4 C3 1.529(5) . ? C4 H4B 0.9900 . ? C4 H4C 0.9900 . ? C3 C2 1.502(5) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C2 C1 1.519(5) . ? C2 H2 1.0000 . ? C5 C6 1.523(5) . ? C5 H5B 0.9900 . ? C5 H5C 0.9900 . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C6 C7 1.508(5) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 H1 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? 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 C6A O4A H4AO 114(2) . . ? C3A O3A H3AO 101(3) . . ? O3A C3A C4A 118.3(3) . . ? O3A C3A C2A 122.3(3) . . ? C4A C3A C2A 119.4(4) . . ? C7A C2A C3A 118.3(3) . . ? C7A C2A C1A 120.5(3) . . ? C3A C2A C1A 121.2(3) . . ? C4A C5A C6A 120.0(3) . . ? C4A C5A H5A 120.0 . . ? C6A C5A H5A 120.0 . . ? C6A C7A C2A 121.7(4) . . ? C6A C7A H7A 119.1 . . ? C2A C7A H7A 119.1 . . ? C7A C6A O4A 122.4(3) . . ? C7A C6A C5A 119.6(4) . . ? O4A C6A C5A 118.0(3) . . ? C5A C4A C3A 120.9(3) . . ? C5A C4A H4A 119.5 . . ? C3A C4A H4A 119.5 . . ? O1A C1A O2A 123.2(3) . . ? O1A C1A C2A 120.0(3) . . ? O2A C1A C2A 116.8(3) . . ? C2 N1 H1N 110(2) . . ? C2 N1 H2N 109(2) . . ? H1N N1 H2N 108(3) . . ? C2 N1 H3N 113(3) . . ? H1N N1 H3N 109(3) . . ? H2N N1 H3N 108(3) . . ? C5 C4 C3 110.2(3) . . ? C5 C4 H4B 109.6 . . ? C3 C4 H4B 109.6 . . ? C5 C4 H4C 109.6 . . ? C3 C4 H4C 109.6 . . ? H4B C4 H4C 108.1 . . ? C2 C3 C4 116.7(3) . . ? C2 C3 H3A 108.1 . . ? C4 C3 H3A 108.1 . . ? C2 C3 H3B 108.1 . . ? C4 C3 H3B 108.1 . . ? H3A C3 H3B 107.3 . . ? C3 C2 N1 110.2(3) . . ? C3 C2 C1 112.4(3) . . ? N1 C2 C1 108.3(3) . . ? C3 C2 H2 108.6 . . ? N1 C2 H2 108.6 . . ? C1 C2 H2 108.6 . . ? C4 C5 C6 115.0(3) . . ? C4 C5 H5B 108.5 . . ? C6 C5 H5B 108.5 . . ? C4 C5 H5C 108.5 . . ? C6 C5 H5C 108.5 . . ? H5B C5 H5C 107.5 . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C7 C6 C5 113.3(3) . . ? C7 C6 H6A 108.9 . . ? C5 C6 H6A 108.9 . . ? C7 C6 H6B 108.9 . . ? C5 C6 H6B 108.9 . . ? H6A C6 H6B 107.7 . . ? C6 C7 H1 109.5 . . ? C6 C7 H7B 109.5 . . ? H1 C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? H1 C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? 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 O3A C3A C2A C7A -177.7(4) . . . . ? C4A C3A C2A C7A 0.9(5) . . . . ? O3A C3A C2A C1A 2.9(5) . . . . ? C4A C3A C2A C1A -178.5(3) . . . . ? C3A C2A C7A C6A 1.4(5) . . . . ? C1A C2A C7A C6A -179.1(4) . . . . ? C2A C7A C6A O4A 176.1(4) . . . . ? C2A C7A C6A C5A -3.1(6) . . . . ? C4A C5A C6A C7A 2.3(6) . . . . ? C4A C5A C6A O4A -176.8(3) . . . . ? C6A C5A C4A C3A 0.0(6) . . . . ? O3A C3A C4A C5A 177.0(3) . . . . ? C2A C3A C4A C5A -1.6(6) . . . . ? C7A C2A C1A O1A -6.3(5) . . . . ? C3A C2A C1A O1A 173.1(3) . . . . ? C7A C2A C1A O2A 172.9(3) . . . . ? C3A C2A C1A O2A -7.7(5) . . . . ? C5 C4 C3 C2 -177.8(3) . . . . ? C4 C3 C2 N1 60.1(5) . . . . ? C4 C3 C2 C1 -178.9(4) . . . . ? C3 C4 C5 C6 175.4(3) . . . . ? C4 C5 C6 C7 69.5(5) . . . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 28.52 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.255 _refine_diff_density_min -0.322 _refine_diff_density_rms 0.068 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 _geom_hbond_publ_flag O4A H4AO O2A 0.98(4) 1.70(4) 2.662(4) 167(4) 2_546 y N1 H1N O1A 0.97(4) 1.81(4) 2.777(4) 173(3) 3_566 y O3A* H3AO O2A 0.82(5) 1.77(5) 2.544(4) 157(5) ? y N1 H2N O1A 0.98(4) 1.90(4) 2.848(4) 163(4) 1_565 y N1 H3N O3A 0.87(5) 2.42(4) 2.979(5) 122(3) 2_556 y N1 H3N O4A 0.87(5) 2.27(4) 2.905(4) 130(3) 4_454 y C7A H7A O2A 0.95 2.57 3.225(4) 126 2_546 y # Attachment 'hydroxyethylpyrrolidiniumhydroxybenzoate.CIF' data_hbamon _database_code_depnum_ccdc_archive 'CCDC 802630' _publ_section_abstract ; 1-(2-hydroxyethyl)pyrrolidin-1-ium 2-hydroxybenzoate, C~6~H~14~N~1~O~1~. C~7~H~5~O~3~, displays interionic N---H...O, C---H...O and O---H...O hydrogen bonding and interanionic C---H...O hydrogen bonding. C-H...\p and \p...\p ring interactions are also seen. ; _publ_section_comment ; The asymmetric unit consists of a single 1-(2-hydroxy-ethyl)-pyrrolidinium cation and a single 2-hydroxybenzoate anion (Figure 1). The 1-(2-hydroxy-ethyl)-pyrrolidinium cation adopts a slightly twisted ring conformation with the hydroxyl substituent adopting a gauche conformation with a torsional angle of 62.9(3) \% [N1---C5---C6---O1], both of which are not the energetically favoured conformation. The hydrogen (H1N) was located in the fourier difference map at a 0.91(4) \%A distance away from N1. The 2-hydroxybenzoate anion displays a planar aromatic ring with one hydroxyl group and a carboxylic acid group displaying standard bond distances and angles (C3A---O3A 1.355(3), C1A---O1A 1.249(3) and C1A---O2A 1.279(3) \%A respectively). The hydroxy hydrogen atoms was also located and placed in the difference fourier map (O3A---H3AO 0.96(3). Three main types of hydrogen bonding occurs, strong O...H---O and N...H---O hydrogen bonding and weak interionic C---H...O hydrogen bonding (Table 1, Figure 2 [one intramoleculat bond occurs as indicated by a * in Table 1]). Additional interactions which occur are inter-ring C-H...\p and weak \p...\p interactions (Tables 2 and 3). The extended structure (Figure 3) consists of a 'zig-zag' arrangement, constructed from alternating groups of cations and anions, which are connected by the above mentioned hydrogen bonds. The aromatic moeities are grouped together with the charged centres grouped and linked via hydrogen bonding (Figure 4). ; _publ_section_exptl_prep ; 1-(2-hydroxyethyl)-pyrrolidine (1.251 g, 10.860 mmol), dissolved in methanol, was slowly added to 2-hydroxybenzoic acid (1.500 g, 10.860 mmol) in methanol solution. The reaction was stirred for 4 hours in an ice bath. Methanol was subsequently removed under vacuum and the resulting yellow solid was dried on a Shlenk line for 5 hours. ; _publ_section_exptl_refinement ; All H atoms were initially located in a difference Fourier map. Thereafter, all H atoms, except the N---H and O---H atoms, were placed in geometrically fixed idealised positions and constrained to ride on their parent atoms with C---H distances in the range 0.95-1.00 \%A and U~iso~(H) = xU~eq~(C), where x = 1.5 for methyl and 1.2 for all other atoms. ; _publ_section_figure_captions ; Figure 1. The asymmetric unit of 1-(2-hydroxy-ethyl)-pyrrolidinium 2-hydroxybenzoate shown with 50 % thermal ellipsoids, hydrogen atoms as spheres of arbitrary size and numbering scheme. Figure 2, Schematic displaying selected interactions within 1-(2-hydroxy-ethyl)-pyrrolidinium 2-hydroxybenzoate. Figure 3. Extended packing diagram as viewed down the a-axis highlighting hydrogen bonding in red dashed lines. Figure 4. Extended packing diagram as viewed down the b-axis highlighting hydrogen bonding in red dashed lines. ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1-(2-hydroxyethyl)pyrrolidin-1-ium 2-hydroxybenzoate ; _chemical_name_common '1-(2-hydroxyethyl)pyrrolidin-1-ium 2-hydroxybenzoate' _chemical_melting_point ? _chemical_formula_moiety 'C6 H14 N O, C7 H5 O3' _chemical_formula_sum 'C13 H19 N O4' _chemical_formula_weight 253.29 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P2(1)/c ' _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 11.668(2) _cell_length_b 9.365(1) _cell_length_c 12.161(2) _cell_angle_alpha 90.00 _cell_angle_beta 107.290(4) _cell_angle_gamma 90.00 _cell_volume 1268.9(3) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 1042 _cell_measurement_theta_min 2.79 _cell_measurement_theta_max 20.88 _exptl_crystal_description triangular _exptl_crystal_colour translucent _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.326 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 544 _exptl_absorpt_coefficient_mu 0.098 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9807 _exptl_absorpt_correction_T_max 0.9807 _exptl_absorpt_process_details 'sadabs (Bruker AXS, 2005)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker X8 APEX KAPPA CCD' _diffrn_measurement_method '0.5 deg frames in phi and omega' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9186 _diffrn_reflns_av_R_equivalents 0.0534 _diffrn_reflns_av_sigmaI/netI 0.0768 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.84 _diffrn_reflns_theta_max 28.34 _reflns_number_total 3126 _reflns_number_gt 1558 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker Apex II V 1.0 (Bruker ASX, 2005)' _computing_cell_refinement 'Bruker Apex II V 1.0 (Bruker ASX, 2005)' _computing_data_reduction 'Bruker Apex II V 1.0 (Bruker ASX, 2005)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Pov-ray for windows, version 3.1' _computing_publication_material 'Microsoft Office' _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^)+(0.1005P)^2^+0.0349P] 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 3126 _refine_ls_number_parameters 175 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1383 _refine_ls_R_factor_gt 0.0703 _refine_ls_wR_factor_ref 0.2210 _refine_ls_wR_factor_gt 0.1851 _refine_ls_goodness_of_fit_ref 1.072 _refine_ls_restrained_S_all 1.072 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O3A O 0.11258(16) 0.1736(2) 0.60312(17) 0.0439(5) Uani 1 1 d . . . O2A O 0.14050(15) -0.0056(2) 0.45867(15) 0.0440(5) Uani 1 1 d . . . O1A O 0.32267(17) -0.0856(2) 0.46823(18) 0.0513(6) Uani 1 1 d . . . C3A C 0.2338(2) 0.1795(3) 0.6446(2) 0.0342(6) Uani 1 1 d . . . C1A C 0.2548(2) -0.0040(3) 0.5011(2) 0.0364(6) Uani 1 1 d . . . C2A C 0.3073(2) 0.0981(3) 0.5970(2) 0.0339(6) Uani 1 1 d . . . C4A C 0.2839(3) 0.2683(3) 0.7382(2) 0.0491(8) Uani 1 1 d . . . H4AA H 0.2330 0.3228 0.7703 0.059 Uiso 1 1 calc R . . C7A C 0.4316(2) 0.1122(3) 0.6431(3) 0.0489(8) Uani 1 1 d . . . H7AA H 0.4834 0.0605 0.6103 0.059 Uiso 1 1 calc R . . C6A C 0.4796(3) 0.2011(4) 0.7365(3) 0.0667(12) Uani 1 1 d . . . H6AA H 0.5642 0.2098 0.7680 0.080 Uiso 1 1 calc R . . C5A C 0.4040(4) 0.2776(4) 0.7839(3) 0.0616(10) Uani 1 1 d . . . H5AA H 0.4372 0.3369 0.8489 0.074 Uiso 1 1 calc R . . N1 N 0.7830(2) 0.1729(3) 0.13429(19) 0.0357(6) Uani 1 1 d . . . O1 O 0.9166(2) 0.4176(2) 0.26853(19) 0.0577(7) Uani 1 1 d . . . C6 C 0.9517(3) 0.2747(3) 0.2906(2) 0.0455(8) Uani 1 1 d . . . H6B H 0.9954 0.2641 0.3735 0.055 Uiso 1 1 calc R . . H6A H 1.0078 0.2498 0.2465 0.055 Uiso 1 1 calc R . . C5 C 0.8483(2) 0.1719(3) 0.2596(2) 0.0415(7) Uani 1 1 d . . . H5B H 0.8787 0.0743 0.2826 0.050 Uiso 1 1 calc R . . H5A H 0.7918 0.1969 0.3032 0.050 Uiso 1 1 calc R . . C4 C 0.6728(3) 0.0773(3) 0.1019(3) 0.0464(7) Uani 1 1 d . . . H4B H 0.6657 0.0244 0.1701 0.056 Uiso 1 1 calc R . . H4A H 0.5990 0.1345 0.0698 0.056 Uiso 1 1 calc R . . C1 C 0.8596(2) 0.1271(3) 0.0602(2) 0.0411(7) Uani 1 1 d . . . H1A H 0.8828 0.2108 0.0219 0.049 Uiso 1 1 calc R . . H1B H 0.9334 0.0791 0.1075 0.049 Uiso 1 1 calc R . . C2 C 0.7864(3) 0.0286(6) -0.0250(4) 0.1023(18) Uani 1 1 d . . . H2A H 0.7536 0.0783 -0.0996 0.123 Uiso 1 1 calc R . . H2B H 0.8363 -0.0522 -0.0365 0.123 Uiso 1 1 calc R . . C3 C 0.6910(4) -0.0230(5) 0.0140(3) 0.0822(14) Uani 1 1 d . . . H3B H 0.7108 -0.1193 0.0479 0.099 Uiso 1 1 calc R . . H3A H 0.6167 -0.0300 -0.0515 0.099 Uiso 1 1 calc R . . H3AO H 0.103(3) 0.105(4) 0.542(3) 0.056(9) Uiso 1 1 d . . . H1N H 0.754(3) 0.260(4) 0.108(3) 0.059(10) Uiso 1 1 d . . . H1O H 0.898(3) 0.436(4) 0.201(3) 0.056(10) 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 O3A 0.0392(11) 0.0425(14) 0.0539(12) -0.0097(9) 0.0200(9) 0.0003(9) O2A 0.0362(11) 0.0420(14) 0.0515(11) -0.0135(9) 0.0096(8) 0.0008(9) O1A 0.0469(12) 0.0346(13) 0.0812(14) -0.0079(10) 0.0327(11) 0.0039(9) C3A 0.0389(15) 0.0257(15) 0.0374(13) 0.0033(11) 0.0103(11) -0.0058(12) C1A 0.0377(15) 0.0256(16) 0.0503(15) 0.0009(12) 0.0198(12) 0.0003(12) C2A 0.0334(14) 0.0247(16) 0.0430(14) 0.0082(11) 0.0106(11) -0.0011(11) C4A 0.073(2) 0.0290(18) 0.0452(16) -0.0004(12) 0.0167(15) -0.0090(15) C7A 0.0387(16) 0.0343(19) 0.071(2) 0.0168(14) 0.0127(14) -0.0025(13) C6A 0.0430(19) 0.056(2) 0.079(2) 0.0297(19) -0.0156(17) -0.0238(17) C5A 0.076(2) 0.043(2) 0.0538(18) 0.0062(15) 0.0000(18) -0.0227(18) N1 0.0424(13) 0.0237(14) 0.0488(13) 0.0018(10) 0.0256(11) -0.0020(10) O1 0.0884(17) 0.0378(15) 0.0449(12) -0.0050(10) 0.0169(12) -0.0102(11) C6 0.0635(19) 0.0379(19) 0.0379(14) 0.0003(12) 0.0192(13) -0.0040(14) C5 0.0537(17) 0.0338(18) 0.0448(15) 0.0036(12) 0.0264(13) 0.0008(13) C4 0.0413(16) 0.0333(18) 0.0731(19) 0.0034(15) 0.0298(14) -0.0079(13) C1 0.0461(17) 0.0387(18) 0.0468(15) -0.0046(12) 0.0266(13) -0.0027(13) C2 0.073(3) 0.138(5) 0.112(3) -0.082(3) 0.052(2) -0.053(3) C3 0.101(3) 0.090(3) 0.071(2) -0.035(2) 0.048(2) -0.058(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 O3A C3A 1.355(3) . ? O3A H3AO 0.96(3) . ? O2A C1A 1.279(3) . ? O1A C1A 1.249(3) . ? C3A C4A 1.391(4) . ? C3A C2A 1.395(4) . ? C1A C2A 1.491(4) . ? C2A C7A 1.397(4) . ? C4A C5A 1.349(4) . ? C4A H4AA 0.9500 . ? C7A C6A 1.385(5) . ? C7A H7AA 0.9500 . ? C6A C5A 1.387(6) . ? C6A H6AA 0.9500 . ? C5A H5AA 0.9500 . ? N1 C5 1.487(3) . ? N1 C1 1.508(3) . ? N1 C4 1.520(3) . ? N1 H1N 0.91(4) . ? O1 C6 1.402(4) . ? O1 H1O 0.80(3) . ? C6 C5 1.502(4) . ? C6 H6B 0.9900 . ? C6 H6A 0.9900 . ? C5 H5B 0.9900 . ? C5 H5A 0.9900 . ? C4 C3 1.485(5) . ? C4 H4B 0.9900 . ? C4 H4A 0.9900 . ? C1 C2 1.458(4) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 C3 1.417(5) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 H3B 0.9900 . ? C3 H3A 0.9900 . ? 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 C3A O3A H3AO 100.9(18) . . ? O3A C3A C4A 117.9(3) . . ? O3A C3A C2A 121.7(2) . . ? C4A C3A C2A 120.4(3) . . ? O1A C1A O2A 123.2(3) . . ? O1A C1A C2A 119.4(2) . . ? O2A C1A C2A 117.4(2) . . ? C3A C2A C7A 118.3(3) . . ? C3A C2A C1A 121.0(2) . . ? C7A C2A C1A 120.7(3) . . ? C5A C4A C3A 120.5(3) . . ? C5A C4A H4AA 119.7 . . ? C3A C4A H4AA 119.7 . . ? C6A C7A C2A 120.3(3) . . ? C6A C7A H7AA 119.8 . . ? C2A C7A H7AA 119.8 . . ? C7A C6A C5A 119.9(3) . . ? C7A C6A H6AA 120.0 . . ? C5A C6A H6AA 120.0 . . ? C4A C5A C6A 120.4(3) . . ? C4A C5A H5AA 119.8 . . ? C6A C5A H5AA 119.8 . . ? C5 N1 C1 113.3(2) . . ? C5 N1 C4 113.5(2) . . ? C1 N1 C4 106.5(2) . . ? C5 N1 H1N 113(2) . . ? C1 N1 H1N 106(2) . . ? C4 N1 H1N 104(2) . . ? C6 O1 H1O 112(3) . . ? O1 C6 C5 113.4(2) . . ? O1 C6 H6B 108.9 . . ? C5 C6 H6B 108.9 . . ? O1 C6 H6A 108.9 . . ? C5 C6 H6A 108.9 . . ? H6B C6 H6A 107.7 . . ? N1 C5 C6 112.5(2) . . ? N1 C5 H5B 109.1 . . ? C6 C5 H5B 109.1 . . ? N1 C5 H5A 109.1 . . ? C6 C5 H5A 109.1 . . ? H5B C5 H5A 107.8 . . ? C3 C4 N1 105.5(2) . . ? C3 C4 H4B 110.6 . . ? N1 C4 H4B 110.6 . . ? C3 C4 H4A 110.6 . . ? N1 C4 H4A 110.6 . . ? H4B C4 H4A 108.8 . . ? C2 C1 N1 106.2(2) . . ? C2 C1 H1A 110.5 . . ? N1 C1 H1A 110.5 . . ? C2 C1 H1B 110.5 . . ? N1 C1 H1B 110.5 . . ? H1A C1 H1B 108.7 . . ? C3 C2 C1 109.3(3) . . ? C3 C2 H2A 109.8 . . ? C1 C2 H2A 109.8 . . ? C3 C2 H2B 109.8 . . ? C1 C2 H2B 109.8 . . ? H2A C2 H2B 108.3 . . ? C2 C3 C4 108.6(3) . . ? C2 C3 H3B 110.0 . . ? C4 C3 H3B 110.0 . . ? C2 C3 H3A 110.0 . . ? C4 C3 H3A 110.0 . . ? H3B C3 H3A 108.3 . . ? 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 O3A C3A C2A C7A 178.8(2) . . . . ? C4A C3A C2A C7A -2.3(4) . . . . ? O3A C3A C2A C1A -2.6(4) . . . . ? C4A C3A C2A C1A 176.3(2) . . . . ? O1A C1A C2A C3A -172.9(2) . . . . ? O2A C1A C2A C3A 5.2(4) . . . . ? O1A C1A C2A C7A 5.8(4) . . . . ? O2A C1A C2A C7A -176.1(2) . . . . ? O3A C3A C4A C5A 179.4(3) . . . . ? C2A C3A C4A C5A 0.5(4) . . . . ? C3A C2A C7A C6A 2.4(4) . . . . ? C1A C2A C7A C6A -176.3(3) . . . . ? C2A C7A C6A C5A -0.5(5) . . . . ? C3A C4A C5A C6A 1.4(5) . . . . ? C7A C6A C5A C4A -1.4(5) . . . . ? C1 N1 C5 C6 62.4(3) . . . . ? C4 N1 C5 C6 -176.0(2) . . . . ? O1 C6 C5 N1 62.9(3) . . . . ? C5 N1 C4 C3 -123.4(3) . . . . ? C1 N1 C4 C3 1.9(3) . . . . ? C5 N1 C1 C2 135.3(3) . . . . ? C4 N1 C1 C2 9.9(4) . . . . ? N1 C1 C2 C3 -18.8(5) . . . . ? C1 C2 C3 C4 20.5(5) . . . . ? N1 C4 C3 C2 -13.5(4) . . . . ? _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 28.34 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 0.456 _refine_diff_density_min -0.492 _refine_diff_density_rms 0.058 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 _geom_hbond_publ_flag N1 H1N O1A 0.90(4) 1.81(4) 2.697(3) 169(4) 2_655 y O1 H1O O2A 0.80(4) 1.94(4) 2.739(3) 176(3) 2_655 y O3A* H3AO O2A 0.96(4) 1.60(4) 2.520(3) 159(3) ? y C1 H1B O1 0.99 2.46 3.431(3) 167 2_745 y C6 H6A O3A 0.99 2.51 3.391(4) 148 4_654 y loop_ _geom_extra_tableA_col_1 _geom_extra_tableA_col_2 _geom_extra_tableA_col_3 _geom_extra_tableA_col_4 _geom_extra_tableA_col_5 _geom_extra_tableA_col_6 X--H CgJ H..Cg X-H..Cg X..Cg 'Symmetry position of CgJ' C4--H4B Cg1 2.69 162 3.640(3) 1-X,-Y,1-Z _geom_extra_table_head_A ; Geometrical parameters (\%A, \%) of selected inter-ring C-H...\p interactions. The CgJ refer to the Ring Centre-of-Gravity ; _geom_table_footnote_A ; Notes: Cg1 is the centroid of ring C2A/C3A/C4A/C5A/C6A/C7A. ; loop_ _geom_extra_tableB_col_1 _geom_extra_tableB_col_2 _geom_extra_tableB_col_3 _geom_extra_tableB_col_4 _geom_extra_tableB_col_5 CgI CgJ Cg...Cg \a 'Symmetry position of CgJ' Cg1 Cg1 5.686(2) 82 1-X,-1/2+Y,3/2-Z Cg1 Cg1 5.686(2) 82 1-X,1/2+Y,3/2-Z _geom_extra_table_head_B ; Geometrical parameters (\%A, \%) of selected inter-ring \p---\p interactions. \a is the dihedral angle between planes I and J, CgI is the centroid of plane I and CgJ the centroid of plane J. ; _geom_table_footnote_B ; Notes: Cg1 is the centroid of ring C2A/C3A/C4A/C5A/C6A/C7A. ;