# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Delia Haynes' _publ_contact_author_email DHAYNES@SUN.AC.ZA _publ_section_title ; Packing motifs in organic ammonium carboxylate salts: extension of the ring-stacking and ring-laddering concepts ; loop_ _publ_author_name 'Delia Haynes' 'Jocelyn Bruce' 'Klaus Koch' 'James A Odendal' # Attachment 'C000922A.CIF' data_1 _database_code_depnum_ccdc_archive 'CCDC 762137' #TrackingRef 'C000922A.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'ammonium benzoate' _chemical_melting_point ? _chemical_formula_moiety 'C7 H5 O2 1- , H4 N 1+' _chemical_formula_sum 'C7 H9 N O2' _chemical_formula_weight 139.15 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 orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' _cell_length_a 6.9446(19) _cell_length_b 7.0471(19) _cell_length_c 30.246(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1480.2(7) _cell_formula_units_Z 8 _cell_measurement_temperature 99(2) _cell_measurement_reflns_used 5184 _cell_measurement_theta_min 2.694 _cell_measurement_theta_max 27.043 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.249 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 592 _exptl_absorpt_coefficient_mu 0.092 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9720 _exptl_absorpt_correction_T_max 0.9991 _exptl_absorpt_process_details '(SADABS; Bruker, 2002)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 99(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 APEX CCD area-detector' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% . _diffrn_reflns_number 14990 _diffrn_reflns_av_R_equivalents 0.0515 _diffrn_reflns_av_sigmaI/netI 0.0217 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -38 _diffrn_reflns_limit_l_max 38 _diffrn_reflns_theta_min 1.35 _diffrn_reflns_theta_max 27.00 _reflns_number_total 1611 _reflns_number_gt 1294 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX II, Bruker 2007' _computing_cell_refinement 'APEX II, Bruker 2007' _computing_data_reduction 'APEX II, Bruker 2007' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. Ammonium hydrogen atoms were located in the difference map. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1012P)^2^+0.0268P] 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 1611 _refine_ls_number_parameters 107 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0518 _refine_ls_R_factor_gt 0.0404 _refine_ls_wR_factor_ref 0.1485 _refine_ls_wR_factor_gt 0.1291 _refine_ls_goodness_of_fit_ref 1.089 _refine_ls_restrained_S_all 1.089 _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 0.00080(18) 0.2390(2) 0.53733(4) 0.0494(4) Uani 1 1 d . . . H1N H -0.018(3) 0.260(2) 0.5055(7) 0.073(5) Uiso 1 1 d . . . H2N H 0.129(3) 0.241(3) 0.5425(6) 0.078(6) Uiso 1 1 d . . . H3N H -0.047(3) 0.115(3) 0.5454(6) 0.088(6) Uiso 1 1 d . . . H4N H -0.052(3) 0.332(3) 0.5502(7) 0.099(8) Uiso 1 1 d . . . O1 O 0.13691(13) 0.11324(14) 0.43355(3) 0.0522(3) Uani 1 1 d . . . O2 O -0.09492(15) 0.31930(17) 0.44955(3) 0.0610(4) Uani 1 1 d . . . C1 C 0.01853(16) 0.23845(19) 0.42277(4) 0.0403(3) Uani 1 1 d . . . C2 C 0.01055(15) 0.30078(15) 0.37520(4) 0.0362(3) Uani 1 1 d . . . C3 C -0.12171(18) 0.43487(19) 0.36134(4) 0.0473(4) Uani 1 1 d . . . H3 H -0.2089 0.4886 0.3820 0.057 Uiso 1 1 calc R . . C4 C -0.1280(2) 0.4916(2) 0.31739(5) 0.0559(4) Uani 1 1 d . . . H4 H -0.2188 0.5842 0.3081 0.067 Uiso 1 1 calc R . . C5 C -0.0022(2) 0.4132(2) 0.28730(5) 0.0540(4) Uani 1 1 d . . . H5 H -0.0069 0.4512 0.2572 0.065 Uiso 1 1 calc R . . C6 C 0.1299(2) 0.2803(2) 0.30075(5) 0.0514(4) Uani 1 1 d . . . H6 H 0.2169 0.2273 0.2799 0.062 Uiso 1 1 calc R . . C7 C 0.13685(18) 0.22333(17) 0.34444(4) 0.0432(3) Uani 1 1 d . . . H7 H 0.2283 0.1309 0.3535 0.052 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0493(8) 0.0537(8) 0.0452(7) 0.0020(5) 0.0002(5) 0.0054(5) O1 0.0506(6) 0.0508(6) 0.0551(6) 0.0147(4) -0.0075(4) 0.0000(4) O2 0.0510(6) 0.0876(8) 0.0446(6) 0.0033(5) 0.0053(4) 0.0088(5) C1 0.0336(6) 0.0446(7) 0.0428(7) 0.0023(5) -0.0025(5) -0.0068(5) C2 0.0335(6) 0.0340(6) 0.0412(7) -0.0005(4) -0.0022(4) -0.0039(4) C3 0.0446(7) 0.0483(7) 0.0490(8) -0.0012(5) -0.0013(5) 0.0086(5) C4 0.0604(9) 0.0513(8) 0.0559(8) 0.0079(6) -0.0114(6) 0.0108(6) C5 0.0670(10) 0.0543(8) 0.0406(7) 0.0064(6) -0.0066(6) -0.0086(7) C6 0.0572(8) 0.0526(8) 0.0445(8) -0.0038(6) 0.0070(6) -0.0019(6) C7 0.0437(7) 0.0397(7) 0.0463(7) -0.0005(5) 0.0015(5) 0.0039(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.2493(16) . ? O2 C1 1.2654(17) . ? C1 C2 1.5052(17) . ? C2 C3 1.3829(17) . ? C2 C7 1.3903(17) . ? C3 C4 1.389(2) . ? C4 C5 1.377(2) . ? C5 C6 1.373(2) . ? C6 C7 1.382(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 O2 124.10(12) . . ? O1 C1 C2 118.68(11) . . ? O2 C1 C2 117.22(11) . . ? C3 C2 C7 118.97(11) . . ? C3 C2 C1 120.91(11) . . ? C7 C2 C1 120.12(11) . . ? C2 C3 C4 120.53(12) . . ? C5 C4 C3 119.80(13) . . ? C6 C5 C4 120.12(13) . . ? C5 C6 C7 120.34(13) . . ? C6 C7 C2 120.24(12) . . ? 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 N1 H1N O2 0.98(2) 1.82(2) 2.7949(18) 169.4(18) . N1 H4N O1 0.85(2) 2.25(2) 2.8717(17) 131(2) 3_456 N1 H2N O2 0.90(2) 1.98(2) 2.8651(18) 166.3(18) 3_556 N1 H3N O1 0.97(2) 1.84(2) 2.8020(18) 174.4(18) 5_556 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.211 _refine_diff_density_min -0.239 _refine_diff_density_rms 0.058 #END data_2 _database_code_depnum_ccdc_archive 'CCDC 762138' #TrackingRef 'C000922A.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common 'propylammonium diphenylacetate' _chemical_melting_point ? _chemical_formula_moiety 'C14 H11 O2 - , C3 H10 N +' _chemical_formula_sum 'C17 H21 N O2' _chemical_formula_weight 271.35 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 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 14.529(12) _cell_length_b 5.882(5) _cell_length_c 17.727(15) _cell_angle_alpha 90.00 _cell_angle_beta 101.346(12) _cell_angle_gamma 90.00 _cell_volume 1485(2) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2073 _cell_measurement_theta_min 2.3435 _cell_measurement_theta_max 27.859 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.214 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 584 _exptl_absorpt_coefficient_mu 0.079 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9883 _exptl_absorpt_correction_T_max 0.9984 _exptl_absorpt_process_details '(SADABS; Bruker, 2002)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX CCD area-detector' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% . _diffrn_reflns_number 8644 _diffrn_reflns_av_R_equivalents 0.0306 _diffrn_reflns_av_sigmaI/netI 0.0408 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.34 _diffrn_reflns_theta_max 28.09 _reflns_number_total 3351 _reflns_number_gt 2509 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX II, Bruker 2007' _computing_cell_refinement 'APEX II, Bruker 2007' _computing_data_reduction 'APEX II, Bruker 2007' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. Ammonium hydrogen atoms were located in the difference map. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0423P)^2^+0.3413P] 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 3351 _refine_ls_number_parameters 194 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0634 _refine_ls_R_factor_gt 0.0426 _refine_ls_wR_factor_ref 0.1057 _refine_ls_wR_factor_gt 0.0939 _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_restrained_S_all 1.037 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.08523(6) 0.15925(16) 0.20965(5) 0.0215(2) Uani 1 1 d . . . N1 N 0.03035(9) 0.7137(2) 0.18157(7) 0.0210(3) Uani 1 1 d . . . C1 C 0.16753(9) 0.2392(2) 0.21549(7) 0.0186(3) Uani 1 1 d . . . O2 O 0.18576(7) 0.44553(16) 0.21231(6) 0.0257(2) Uani 1 1 d . . . C2 C 0.24824(9) 0.0648(2) 0.23109(7) 0.0176(3) Uani 1 1 d . . . H2 H 0.2215 -0.0840 0.2100 0.021 Uiso 1 1 calc R . . C3 C 0.33173(9) 0.1147(2) 0.19358(7) 0.0182(3) Uani 1 1 d . . . C4 C 0.38135(9) 0.3191(2) 0.20225(8) 0.0212(3) Uani 1 1 d . . . H4 H 0.3604 0.4407 0.2299 0.025 Uiso 1 1 calc R . . C5 C 0.46112(10) 0.3467(3) 0.17081(8) 0.0249(3) Uani 1 1 d . . . H5 H 0.4952 0.4854 0.1783 0.030 Uiso 1 1 calc R . . C6 C 0.49110(10) 0.1731(3) 0.12867(8) 0.0260(3) Uani 1 1 d . . . H6 H 0.5455 0.1925 0.1071 0.031 Uiso 1 1 calc R . . C7 C 0.44128(10) -0.0292(3) 0.11817(8) 0.0252(3) Uani 1 1 d . . . H7 H 0.4609 -0.1482 0.0887 0.030 Uiso 1 1 calc R . . C8 C 0.36260(10) -0.0578(2) 0.15076(8) 0.0214(3) Uani 1 1 d . . . H8 H 0.3292 -0.1975 0.1437 0.026 Uiso 1 1 calc R . . C9 C 0.27510(9) 0.0372(2) 0.31852(8) 0.0184(3) Uani 1 1 d . . . C10 C 0.32236(10) 0.2064(2) 0.36525(8) 0.0239(3) Uani 1 1 d . . . H10 H 0.3394 0.3426 0.3427 0.029 Uiso 1 1 calc R . . C11 C 0.34503(10) 0.1794(3) 0.44426(8) 0.0264(3) Uani 1 1 d . . . H11 H 0.3778 0.2965 0.4754 0.032 Uiso 1 1 calc R . . C12 C 0.32025(10) -0.0169(3) 0.47815(8) 0.0275(3) Uani 1 1 d . . . H12 H 0.3360 -0.0352 0.5324 0.033 Uiso 1 1 calc R . . C13 C 0.27237(11) -0.1865(3) 0.43255(9) 0.0297(4) Uani 1 1 d . . . H13 H 0.2546 -0.3214 0.4555 0.036 Uiso 1 1 calc R . . C14 C 0.25031(10) -0.1596(2) 0.35306(8) 0.0249(3) Uani 1 1 d . . . H14 H 0.2179 -0.2773 0.3220 0.030 Uiso 1 1 calc R . . C15 C -0.01162(10) 0.6777(3) 0.09913(8) 0.0252(3) Uani 1 1 d . . . H15A H -0.0346 0.5193 0.0917 0.030 Uiso 1 1 calc R . . H15B H 0.0374 0.6993 0.0681 0.030 Uiso 1 1 calc R . . C16 C -0.09181(10) 0.8386(3) 0.07081(8) 0.0265(3) Uani 1 1 d . . . H16A H -0.0708 0.9969 0.0828 0.032 Uiso 1 1 calc R . . H16B H -0.1439 0.8064 0.0979 0.032 Uiso 1 1 calc R . . C17 C -0.12683(11) 0.8140(3) -0.01550(9) 0.0346(4) Uani 1 1 d . . . H17A H -0.0754 0.8461 -0.0423 0.052 Uiso 1 1 calc R . . H17B H -0.1782 0.9215 -0.0326 0.052 Uiso 1 1 calc R . . H17C H -0.1494 0.6585 -0.0272 0.052 Uiso 1 1 calc R . . H1N H 0.0844(13) 0.610(3) 0.1969(10) 0.045(5) Uiso 1 1 d . . . H2N H -0.0130(12) 0.693(3) 0.2159(9) 0.033(4) Uiso 1 1 d . . . H3N H 0.0535(12) 0.864(3) 0.1893(9) 0.039(5) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0154(5) 0.0232(5) 0.0263(5) -0.0015(4) 0.0051(4) 0.0001(4) N1 0.0183(6) 0.0192(6) 0.0263(6) 0.0014(5) 0.0063(5) 0.0010(5) C1 0.0178(7) 0.0218(7) 0.0153(6) -0.0015(5) 0.0008(5) 0.0017(6) O2 0.0195(5) 0.0178(5) 0.0387(6) -0.0020(4) 0.0028(4) 0.0004(4) C2 0.0165(7) 0.0155(7) 0.0205(7) -0.0019(5) 0.0027(5) -0.0006(5) C3 0.0142(6) 0.0225(7) 0.0170(6) 0.0034(5) 0.0006(5) 0.0028(5) C4 0.0200(7) 0.0212(7) 0.0214(7) 0.0007(6) 0.0016(6) 0.0009(6) C5 0.0191(7) 0.0279(8) 0.0260(7) 0.0061(6) 0.0006(6) -0.0043(6) C6 0.0168(7) 0.0375(9) 0.0243(7) 0.0080(6) 0.0057(6) 0.0024(6) C7 0.0237(7) 0.0297(8) 0.0227(7) 0.0016(6) 0.0060(6) 0.0095(6) C8 0.0201(7) 0.0211(7) 0.0222(7) 0.0015(6) 0.0022(6) 0.0016(6) C9 0.0129(6) 0.0215(7) 0.0211(7) -0.0002(6) 0.0041(5) 0.0037(5) C10 0.0231(7) 0.0235(8) 0.0251(7) 0.0014(6) 0.0050(6) -0.0035(6) C11 0.0241(8) 0.0288(8) 0.0256(7) -0.0048(6) 0.0025(6) -0.0034(6) C12 0.0254(8) 0.0364(9) 0.0204(7) 0.0024(6) 0.0035(6) 0.0050(7) C13 0.0355(9) 0.0269(8) 0.0278(8) 0.0066(6) 0.0087(7) -0.0010(7) C14 0.0258(8) 0.0217(7) 0.0267(7) -0.0019(6) 0.0042(6) -0.0023(6) C15 0.0247(8) 0.0248(8) 0.0263(7) -0.0023(6) 0.0057(6) 0.0010(6) C16 0.0213(7) 0.0329(9) 0.0258(7) 0.0011(6) 0.0056(6) 0.0020(6) C17 0.0283(8) 0.0478(11) 0.0274(8) 0.0000(7) 0.0051(7) 0.0032(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.2701(18) . ? N1 C15 1.484(2) . ? C1 O2 1.2456(19) . ? C1 C2 1.542(2) . ? C2 C3 1.522(2) . ? C2 C9 1.531(2) . ? C3 C8 1.393(2) . ? C3 C4 1.395(2) . ? C4 C5 1.391(2) . ? C5 C6 1.385(2) . ? C6 C7 1.386(2) . ? C7 C8 1.389(2) . ? C9 C10 1.387(2) . ? C9 C14 1.390(2) . ? C10 C11 1.383(2) . ? C11 C12 1.381(2) . ? C12 C13 1.383(2) . ? C13 C14 1.391(2) . ? C15 C16 1.508(2) . ? C16 C17 1.521(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 C1 O1 124.21(13) . . ? O2 C1 C2 119.70(13) . . ? O1 C1 C2 116.03(13) . . ? C3 C2 C9 113.35(11) . . ? C3 C2 C1 115.88(12) . . ? C9 C2 C1 106.60(10) . . ? C8 C3 C4 118.23(13) . . ? C8 C3 C2 117.84(13) . . ? C4 C3 C2 123.87(12) . . ? C5 C4 C3 120.66(13) . . ? C6 C5 C4 120.35(14) . . ? C5 C6 C7 119.61(14) . . ? C6 C7 C8 119.92(14) . . ? C7 C8 C3 121.21(14) . . ? C10 C9 C14 118.37(14) . . ? C10 C9 C2 121.77(12) . . ? C14 C9 C2 119.85(12) . . ? C11 C10 C9 120.91(14) . . ? C12 C11 C10 120.38(14) . . ? C11 C12 C13 119.54(14) . . ? C12 C13 C14 119.94(14) . . ? C9 C14 C13 120.87(14) . . ? N1 C15 C16 112.29(12) . . ? C15 C16 C17 111.02(12) . . ? 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 N1 H1N O2 0.99(2) 1.74(2) 2.720(2) 171.3(16) . N1 H3N O1 0.944(19) 1.82(2) 2.756(3) 172.8(16) 1_565 N1 H2N O1 0.967(17) 1.850(17) 2.813(2) 173.8(14) 2 _diffrn_measured_fraction_theta_max 0.925 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.285 _refine_diff_density_min -0.223 _refine_diff_density_rms 0.043 #END data_3 _database_code_depnum_ccdc_archive 'CCDC 762139' #TrackingRef 'C000922A.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'cyclohexylammonium acetate' _chemical_melting_point ? _chemical_formula_moiety 'C6 H14 N 1+ , C2 H3 O2 1-' _chemical_formula_sum 'C8 H17 N O2' _chemical_formula_weight 159.23 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 I2/a loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y, -z' 'x+1/2, y+1/2, z+1/2' '-x+1, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y, z' '-x+1/2, -y+1/2, -z+1/2' 'x, -y+1/2, z+1/2' _cell_length_a 16.064(3) _cell_length_b 6.4139(13) _cell_length_c 17.668(4) _cell_angle_alpha 90.00 _cell_angle_beta 91.84(3) _cell_angle_gamma 90.00 _cell_volume 1819.4(6) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3468 _cell_measurement_theta_min 2.3065 _cell_measurement_theta_max 27.803 _exptl_crystal_description rhombic _exptl_crystal_colour colourless _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.163 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 704 _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9918 _exptl_absorpt_correction_T_max 0.9975 _exptl_absorpt_process_details '(SADABS; Bruker, 2002)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX CCD area-detector' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% . _diffrn_reflns_number 5258 _diffrn_reflns_av_R_equivalents 0.0148 _diffrn_reflns_av_sigmaI/netI 0.0166 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.31 _diffrn_reflns_theta_max 28.05 _reflns_number_total 2036 _reflns_number_gt 1876 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX II, Bruker 2007' _computing_cell_refinement 'APEX II, Bruker 2007' _computing_data_reduction 'APEX II, Bruker 2007' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. Ammonium hydrogen atoms were located in the difference map. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0499P)^2^+0.9977P] 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 2036 _refine_ls_number_parameters 112 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0372 _refine_ls_R_factor_gt 0.0345 _refine_ls_wR_factor_ref 0.0956 _refine_ls_wR_factor_gt 0.0928 _refine_ls_goodness_of_fit_ref 1.074 _refine_ls_restrained_S_all 1.074 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.59216(4) 0.74807(11) 0.22035(4) 0.01989(18) Uani 1 1 d . . . O2 O 0.65568(5) 1.03702(11) 0.18126(4) 0.02301(19) Uani 1 1 d . . . C1 C 0.64893(5) 0.84373(15) 0.18581(5) 0.0159(2) Uani 1 1 d . . . C2 C 0.71304(6) 0.70951(17) 0.14742(6) 0.0240(2) Uani 1 1 d . . . H2A H 0.7001 0.5620 0.1554 0.036 Uiso 0.50 1 calc PR . . H2B H 0.7686 0.7403 0.1691 0.036 Uiso 0.50 1 calc PR . . H2C H 0.7118 0.7397 0.0930 0.036 Uiso 0.50 1 calc PR . . H2D H 0.7536 0.7993 0.1230 0.036 Uiso 0.50 1 calc PR . . H2E H 0.6851 0.6210 0.1092 0.036 Uiso 0.50 1 calc PR . . H2F H 0.7419 0.6216 0.1853 0.036 Uiso 0.50 1 calc PR . . N1 N 0.57597(5) 0.33482(13) 0.26529(4) 0.01645(19) Uani 1 1 d . . . H1N H 0.5191(9) 0.317(2) 0.2678(7) 0.025(3) Uiso 1 1 d . . . H2N H 0.5991(8) 0.232(2) 0.2343(8) 0.028(3) Uiso 1 1 d . . . H3N H 0.5868(8) 0.466(2) 0.2470(8) 0.030(3) Uiso 1 1 d . . . C3 C 0.61304(6) 0.31396(15) 0.34386(5) 0.0164(2) Uani 1 1 d . . . H3 H 0.6748 0.3312 0.3417 0.020 Uiso 1 1 calc R . . C4 C 0.57895(6) 0.48286(15) 0.39507(5) 0.0181(2) Uani 1 1 d . . . H4A H 0.5175 0.4725 0.3957 0.022 Uiso 1 1 calc R . . H4B H 0.5935 0.6220 0.3751 0.022 Uiso 1 1 calc R . . C5 C 0.61548(6) 0.45841(16) 0.47575(5) 0.0211(2) Uani 1 1 d . . . H5A H 0.6762 0.4854 0.4757 0.025 Uiso 1 1 calc R . . H5B H 0.5900 0.5632 0.5090 0.025 Uiso 1 1 calc R . . C6 C 0.60025(7) 0.24030(16) 0.50748(5) 0.0226(2) Uani 1 1 d . . . H6A H 0.6287 0.2270 0.5578 0.027 Uiso 1 1 calc R . . H6B H 0.5398 0.2198 0.5140 0.027 Uiso 1 1 calc R . . C7 C 0.63264(7) 0.07284(16) 0.45444(6) 0.0233(2) Uani 1 1 d . . . H7A H 0.6187 -0.0667 0.4744 0.028 Uiso 1 1 calc R . . H7B H 0.6940 0.0832 0.4526 0.028 Uiso 1 1 calc R . . C8 C 0.59452(6) 0.09730(15) 0.37454(5) 0.0189(2) Uani 1 1 d . . . H8A H 0.6179 -0.0097 0.3408 0.023 Uiso 1 1 calc R . . H8B H 0.5335 0.0762 0.3756 0.023 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0177(3) 0.0172(4) 0.0250(4) 0.0015(3) 0.0041(3) 0.0003(2) O2 0.0303(4) 0.0152(4) 0.0240(4) -0.0001(3) 0.0082(3) 0.0001(3) C1 0.0164(4) 0.0171(5) 0.0142(4) -0.0010(3) -0.0011(3) 0.0013(3) C2 0.0221(5) 0.0216(5) 0.0287(5) -0.0034(4) 0.0069(4) 0.0031(4) N1 0.0170(4) 0.0145(4) 0.0180(4) 0.0003(3) 0.0027(3) 0.0000(3) C3 0.0154(4) 0.0160(5) 0.0179(4) -0.0011(3) 0.0011(3) 0.0002(3) C4 0.0203(4) 0.0134(4) 0.0208(5) -0.0013(3) 0.0033(4) 0.0003(3) C5 0.0238(5) 0.0189(5) 0.0206(5) -0.0046(4) 0.0009(4) -0.0003(4) C6 0.0283(5) 0.0207(5) 0.0186(4) -0.0006(4) -0.0001(4) 0.0032(4) C7 0.0299(5) 0.0183(5) 0.0215(5) -0.0003(4) -0.0030(4) 0.0059(4) C8 0.0231(5) 0.0144(5) 0.0190(5) -0.0010(3) -0.0004(4) 0.0026(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.2712(12) . ? O2 C1 1.2473(12) . ? C1 C2 1.5188(13) . ? N1 C3 1.4987(12) . ? C3 C4 1.5244(13) . ? C3 C8 1.5244(13) . ? C4 C5 1.5321(14) . ? C5 C6 1.5297(14) . ? C6 C7 1.5277(14) . ? C7 C8 1.5288(14) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 C1 O1 125.16(9) . . ? O2 C1 C2 118.23(9) . . ? O1 C1 C2 116.61(9) . . ? N1 C3 C4 110.29(8) . . ? N1 C3 C8 109.54(7) . . ? C4 C3 C8 111.03(8) . . ? C3 C4 C5 110.21(8) . . ? C6 C5 C4 111.93(8) . . ? C7 C6 C5 110.89(8) . . ? C6 C7 C8 111.10(8) . . ? C3 C8 C7 110.18(8) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H3N O1 0.920(15) 1.872(16) 2.7815(12) 169.4(12) . N1 H1N O1 0.923(14) 1.860(14) 2.7771(12) 172.2(12) 4_545 N1 H2N O2 0.940(14) 1.824(14) 2.7593(12) 173.0(12) 1_545 _diffrn_measured_fraction_theta_max 0.921 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.315 _refine_diff_density_min -0.186 _refine_diff_density_rms 0.040 #END data_4 _database_code_depnum_ccdc_archive 'CCDC 762140' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common 'cyclohexylammonium benzoate' _chemical_melting_point ? _chemical_formula_moiety 'C6 H14 N +, C7 H5 O2 -' _chemical_formula_sum 'C13 H19 N O2' _chemical_formula_weight 221.29 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 orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 6.4832(7) _cell_length_b 21.423(2) _cell_length_c 45.021(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 6252.9(12) _cell_formula_units_Z 20 _cell_measurement_temperature 101(2) _cell_measurement_reflns_used 9942 _cell_measurement_theta_min 2.3335 _cell_measurement_theta_max 20.334 _exptl_crystal_description block _exptl_crystal_colour brown _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.175 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2400 _exptl_absorpt_coefficient_mu 0.079 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9891 _exptl_absorpt_correction_T_max 0.9976 _exptl_absorpt_process_details '(SADABS; Bruker, 2002)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 101(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 APEX CCD area-detector' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% . _diffrn_reflns_number 34151 _diffrn_reflns_av_R_equivalents 0.0311 _diffrn_reflns_av_sigmaI/netI 0.1771 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -55 _diffrn_reflns_limit_l_max 52 _diffrn_reflns_theta_min 0.90 _diffrn_reflns_theta_max 26.00 _reflns_number_total 6924 _reflns_number_gt 6568 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX II, Bruker 2007' _computing_cell_refinement 'APEX II, Bruker 2007' _computing_data_reduction 'APEX II, Bruker 2007' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. Ammonium hydrogen atoms were located in the difference map. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0000P)^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 6924 _refine_ls_number_parameters 781 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0400 _refine_ls_R_factor_gt 0.0373 _refine_ls_wR_factor_ref 0.1390 _refine_ls_wR_factor_gt 0.1307 _refine_ls_goodness_of_fit_ref 0.848 _refine_ls_restrained_S_all 0.848 _refine_ls_shift/su_max 0.009 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O11 O 0.5042(2) 0.13634(7) 0.12511(3) 0.0243(3) Uani 1 1 d . . . C11 C 0.3125(3) 0.12988(8) 0.12667(4) 0.0184(4) Uani 1 1 d . . . O12 O 0.1836(2) 0.16453(7) 0.11341(3) 0.0255(3) Uani 1 1 d . . . C12 C 0.2312(3) 0.07830(8) 0.14627(4) 0.0184(4) Uani 1 1 d . . . C13 C 0.0254(3) 0.07551(9) 0.15453(4) 0.0229(4) Uani 1 1 d . . . H13 H -0.0706 0.1045 0.1466 0.027 Uiso 1 1 calc R . . C14 C -0.0406(4) 0.02991(9) 0.17460(4) 0.0257(5) Uani 1 1 d . . . H14 H -0.1812 0.0285 0.1805 0.031 Uiso 1 1 calc R . . C15 C 0.0978(4) -0.01314(9) 0.18590(4) 0.0266(5) Uani 1 1 d . . . H15 H 0.0531 -0.0436 0.1998 0.032 Uiso 1 1 calc R . . C16 C 0.3033(4) -0.01150(10) 0.17674(5) 0.0309(5) Uani 1 1 d . . . H16 H 0.3979 -0.0418 0.1840 0.037 Uiso 1 1 calc R . . C17 C 0.3694(3) 0.03379(9) 0.15727(4) 0.0258(5) Uani 1 1 d . . . H17 H 0.5098 0.0348 0.1513 0.031 Uiso 1 1 calc R . . N21 N 0.7917(3) 0.19054(8) 0.09035(4) 0.0203(4) Uani 1 1 d . . . C21 C 0.7829(3) 0.16242(9) 0.05992(4) 0.0194(4) Uani 1 1 d . . . H21 H 0.7908 0.1160 0.0619 0.023 Uiso 1 1 calc R . . C22 C 0.5767(3) 0.17923(10) 0.04527(5) 0.0264(5) Uani 1 1 d . . . H22A H 0.4616 0.1625 0.0573 0.032 Uiso 1 1 calc R . . H22B H 0.5621 0.2252 0.0443 0.032 Uiso 1 1 calc R . . C23 C 0.5668(4) 0.15185(11) 0.01397(5) 0.0319(5) Uani 1 1 d . . . H23A H 0.5668 0.1057 0.0152 0.038 Uiso 1 1 calc R . . H23B H 0.4368 0.1650 0.0043 0.038 Uiso 1 1 calc R . . C24 C 0.7499(4) 0.17339(11) -0.00474(5) 0.0312(5) Uani 1 1 d . . . H24A H 0.7434 0.1533 -0.0245 0.037 Uiso 1 1 calc R . . H24B H 0.7421 0.2191 -0.0076 0.037 Uiso 1 1 calc R . . C25 C 0.9533(4) 0.15697(10) 0.01007(5) 0.0279(5) Uani 1 1 d . . . H25A H 1.0687 0.1734 -0.0020 0.033 Uiso 1 1 calc R . . H25B H 0.9676 0.1110 0.0111 0.033 Uiso 1 1 calc R . . C26 C 0.9653(3) 0.18438(9) 0.04153(4) 0.0233(4) Uani 1 1 d . . . H26A H 1.0953 0.1710 0.0511 0.028 Uiso 1 1 calc R . . H26B H 0.9651 0.2305 0.0404 0.028 Uiso 1 1 calc R . . O31 O 0.9871(2) 0.34528(7) 0.07114(3) 0.0258(3) Uani 1 1 d . . . C31 C 0.7961(3) 0.35269(8) 0.07267(4) 0.0182(4) Uani 1 1 d . . . O32 O 0.6740(2) 0.31473(6) 0.08504(3) 0.0246(3) Uani 1 1 d . . . C32 C 0.7072(3) 0.41012(8) 0.05833(4) 0.0188(4) Uani 1 1 d . . . C33 C 0.8362(4) 0.44847(9) 0.04175(4) 0.0249(5) Uani 1 1 d . . . H33 H 0.9766 0.4371 0.0390 0.030 Uiso 1 1 calc R . . C34 C 0.7627(4) 0.50295(10) 0.02914(5) 0.0318(5) Uani 1 1 d . . . H34 H 0.8521 0.5288 0.0178 0.038 Uiso 1 1 calc R . . C35 C 0.5573(4) 0.51969(10) 0.03311(5) 0.0327(5) Uani 1 1 d . . . H35 H 0.5062 0.5569 0.0243 0.039 Uiso 1 1 calc R . . C36 C 0.4276(4) 0.48253(9) 0.04971(5) 0.0282(5) Uani 1 1 d . . . H36 H 0.2880 0.4946 0.0527 0.034 Uiso 1 1 calc R . . C37 C 0.5014(3) 0.42717(9) 0.06219(4) 0.0228(4) Uani 1 1 d . . . H37 H 0.4114 0.4011 0.0733 0.027 Uiso 1 1 calc R . . N41 N 0.2778(3) 0.28982(8) 0.10560(4) 0.0200(4) Uani 1 1 d . . . C41 C 0.2548(3) 0.32051(9) 0.13529(4) 0.0204(4) Uani 1 1 d . . . H41 H 0.2600 0.3668 0.1324 0.024 Uiso 1 1 calc R . . C42 C 0.4305(3) 0.30160(10) 0.15568(5) 0.0251(5) Uani 1 1 d . . . H42A H 0.5634 0.3149 0.1469 0.030 Uiso 1 1 calc R . . H42B H 0.4329 0.2556 0.1578 0.030 Uiso 1 1 calc R . . C43 C 0.4038(4) 0.33173(10) 0.18628(5) 0.0279(5) Uani 1 1 d . . . H43A H 0.5162 0.3176 0.1996 0.033 Uiso 1 1 calc R . . H43B H 0.4139 0.3777 0.1843 0.033 Uiso 1 1 calc R . . C44 C 0.1975(4) 0.31487(10) 0.19993(5) 0.0294(5) Uani 1 1 d . . . H44A H 0.1816 0.3366 0.2192 0.035 Uiso 1 1 calc R . . H44B H 0.1919 0.2694 0.2036 0.035 Uiso 1 1 calc R . . C45 C 0.0230(4) 0.33354(13) 0.17924(5) 0.0378(6) Uani 1 1 d . . . H45A H 0.0216 0.3795 0.1771 0.045 Uiso 1 1 calc R . . H45B H -0.1102 0.3207 0.1881 0.045 Uiso 1 1 calc R . . C46 C 0.0458(4) 0.30356(12) 0.14865(5) 0.0326(5) Uani 1 1 d . . . H46A H -0.0660 0.3184 0.1354 0.039 Uiso 1 1 calc R . . H46B H 0.0342 0.2576 0.1505 0.039 Uiso 1 1 calc R . . O51 O 0.5965(2) 0.65967(7) 0.16853(3) 0.0258(3) Uani 1 1 d . . . C51 C 0.7875(3) 0.65167(8) 0.16926(4) 0.0188(4) Uani 1 1 d . . . O52 O 0.9135(2) 0.68634(6) 0.18284(3) 0.0247(3) Uani 1 1 d . . . C52 C 0.8717(3) 0.59627(8) 0.15252(4) 0.0177(4) Uani 1 1 d . . . C53 C 0.7392(3) 0.56340(9) 0.13385(4) 0.0226(4) Uani 1 1 d . . . H53 H 0.5995 0.5761 0.1319 0.027 Uiso 1 1 calc R . . C54 C 0.8110(4) 0.51176(10) 0.11788(5) 0.0304(5) Uani 1 1 d . . . H54 H 0.7210 0.4900 0.1048 0.036 Uiso 1 1 calc R . . C55 C 1.0128(4) 0.49263(10) 0.12114(5) 0.0318(5) Uani 1 1 d . . . H55 H 1.0611 0.4574 0.1104 0.038 Uiso 1 1 calc R . . C56 C 1.1461(4) 0.52423(9) 0.13991(5) 0.0273(5) Uani 1 1 d . . . H56 H 1.2847 0.5106 0.1421 0.033 Uiso 1 1 calc R . . C57 C 1.0746(3) 0.57650(9) 0.15559(4) 0.0218(4) Uani 1 1 d . . . H57 H 1.1656 0.5985 0.1684 0.026 Uiso 1 1 calc R . . N61 N 0.3085(3) 0.71081(8) 0.20444(4) 0.0195(4) Uani 1 1 d . . . C61 C 0.3105(3) 0.67432(8) 0.23290(4) 0.0191(4) Uani 1 1 d . . . H61 H 0.2801 0.6297 0.2281 0.023 Uiso 1 1 calc R . . C62 C 0.1431(4) 0.69777(10) 0.25379(4) 0.0244(4) Uani 1 1 d . . . H62A H 0.0064 0.6932 0.2442 0.029 Uiso 1 1 calc R . . H62B H 0.1655 0.7426 0.2581 0.029 Uiso 1 1 calc R . . C63 C 0.1480(4) 0.66033(10) 0.28277(5) 0.0279(5) Uani 1 1 d . . . H63A H 0.0438 0.6773 0.2967 0.033 Uiso 1 1 calc R . . H63B H 0.1120 0.6163 0.2786 0.033 Uiso 1 1 calc R . . C64 C 0.3596(4) 0.66319(10) 0.29713(5) 0.0305(5) Uani 1 1 d . . . H64A H 0.3601 0.6371 0.3153 0.037 Uiso 1 1 calc R . . H64B H 0.3898 0.7067 0.3031 0.037 Uiso 1 1 calc R . . C65 C 0.5275(4) 0.64023(11) 0.27595(5) 0.0335(5) Uani 1 1 d . . . H65A H 0.5054 0.5954 0.2716 0.040 Uiso 1 1 calc R . . H65B H 0.6640 0.6447 0.2856 0.040 Uiso 1 1 calc R . . C66 C 0.5247(4) 0.67739(11) 0.24696(5) 0.0284(5) Uani 1 1 d . . . H66A H 0.5616 0.7214 0.2510 0.034 Uiso 1 1 calc R . . H66B H 0.6280 0.6600 0.2330 0.034 Uiso 1 1 calc R . . O71 O 0.4169(2) 0.83367(6) 0.21758(3) 0.0254(3) Uani 1 1 d . . . C71 C 0.2879(3) 0.86485(8) 0.23242(4) 0.0195(4) Uani 1 1 d . . . O72 O 0.0978(2) 0.85535(6) 0.23219(3) 0.0234(3) Uani 1 1 d . . . C72 C 0.3653(3) 0.91696(9) 0.25184(4) 0.0190(4) Uani 1 1 d . . . C73 C 0.5688(3) 0.93707(9) 0.25125(5) 0.0239(4) Uani 1 1 d . . . H73 H 0.6643 0.9181 0.2381 0.029 Uiso 1 1 calc R . . C74 C 0.6337(4) 0.98538(9) 0.27006(5) 0.0289(5) Uani 1 1 d . . . H74 H 0.7729 0.9992 0.2696 0.035 Uiso 1 1 calc R . . C75 C 0.4946(4) 1.01279(9) 0.28936(5) 0.0297(5) Uani 1 1 d . . . H75 H 0.5384 1.0456 0.3021 0.036 Uiso 1 1 calc R . . C76 C 0.2927(4) 0.99275(10) 0.29023(5) 0.0321(5) Uani 1 1 d . . . H76 H 0.1983 1.0113 0.3037 0.038 Uiso 1 1 calc R . . C77 C 0.2273(4) 0.94555(9) 0.27142(5) 0.0263(5) Uani 1 1 d . . . H77 H 0.0873 0.9325 0.2718 0.032 Uiso 1 1 calc R . . N81 N 0.8073(3) 0.80858(8) 0.19504(4) 0.0210(4) Uani 1 1 d . . . C81 C 0.8094(3) 0.84333(9) 0.16619(4) 0.0208(4) Uani 1 1 d . . . H81 H 0.7858 0.8886 0.1705 0.025 Uiso 1 1 calc R . . C82 C 1.0193(4) 0.83673(10) 0.15153(5) 0.0263(5) Uani 1 1 d . . . H82A H 1.1270 0.8540 0.1648 0.032 Uiso 1 1 calc R . . H82B H 1.0499 0.7920 0.1482 0.032 Uiso 1 1 calc R . . C83 C 1.0229(4) 0.87126(11) 0.12195(5) 0.0327(5) Uani 1 1 d . . . H83A H 1.1576 0.8646 0.1121 0.039 Uiso 1 1 calc R . . H83B H 1.0062 0.9166 0.1255 0.039 Uiso 1 1 calc R . . C84 C 0.8500(4) 0.84810(11) 0.10175(5) 0.0323(5) Uani 1 1 d . . . H84A H 0.8516 0.8722 0.0830 0.039 Uiso 1 1 calc R . . H84B H 0.8739 0.8036 0.0968 0.039 Uiso 1 1 calc R . . C85 C 0.6398(4) 0.85502(11) 0.11656(5) 0.0292(5) Uani 1 1 d . . . H85A H 0.5317 0.8380 0.1033 0.035 Uiso 1 1 calc R . . H85B H 0.6102 0.8998 0.1199 0.035 Uiso 1 1 calc R . . C86 C 0.6345(3) 0.82048(10) 0.14625(5) 0.0258(5) Uani 1 1 d . . . H86A H 0.5004 0.8279 0.1562 0.031 Uiso 1 1 calc R . . H86B H 0.6491 0.7751 0.1428 0.031 Uiso 1 1 calc R . . O91 O 0.2896(2) 0.82601(6) 0.01178(3) 0.0230(3) Uani 1 1 d . . . C91 C 0.1688(3) 0.86483(8) 0.02396(4) 0.0175(4) Uani 1 1 d . . . O92 O -0.0247(2) 0.86044(7) 0.02365(3) 0.0262(3) Uani 1 1 d . . . C92 C 0.2604(3) 0.91914(9) 0.04046(4) 0.0191(4) Uani 1 1 d . . . C93 C 0.4678(3) 0.92076(9) 0.04776(5) 0.0245(4) Uani 1 1 d . . . H93 H 0.5563 0.8877 0.0419 0.029 Uiso 1 1 calc R . . C94 C 0.5463(4) 0.97129(10) 0.06382(5) 0.0298(5) Uani 1 1 d . . . H94 H 0.6887 0.9724 0.0688 0.036 Uiso 1 1 calc R . . C95 C 0.4194(4) 1.01959(10) 0.07251(5) 0.0290(5) Uani 1 1 d . . . H95 H 0.4735 1.0535 0.0837 0.035 Uiso 1 1 calc R . . C96 C 0.2127(4) 1.01839(10) 0.06482(5) 0.0331(5) Uani 1 1 d . . . H96 H 0.1251 1.0519 0.0705 0.040 Uiso 1 1 calc R . . C97 C 0.1329(3) 0.96837(9) 0.04888(5) 0.0277(5) Uani 1 1 d . . . H97 H -0.0092 0.9678 0.0437 0.033 Uiso 1 1 calc R . . N101 N 0.1891(3) 0.69999(8) 0.00881(4) 0.0187(3) Uani 1 1 d . . . C101 C 0.2150(3) 0.67583(9) 0.03985(4) 0.0195(4) Uani 1 1 d . . . H101 H 0.2103 0.6292 0.0392 0.023 Uiso 1 1 calc R . . C102 C 0.4244(3) 0.69566(10) 0.05185(5) 0.0244(4) Uani 1 1 d . . . H10A H 0.4355 0.7417 0.0514 0.029 Uiso 1 1 calc R . . H10B H 0.5350 0.6782 0.0391 0.029 Uiso 1 1 calc R . . C103 C 0.4515(4) 0.67239(12) 0.08371(5) 0.0317(5) Uani 1 1 d . . . H10C H 0.4529 0.6262 0.0838 0.038 Uiso 1 1 calc R . . H10D H 0.5856 0.6871 0.0916 0.038 Uiso 1 1 calc R . . C104 C 0.2778(4) 0.69579(10) 0.10375(4) 0.0280(5) Uani 1 1 d . . . H10E H 0.2837 0.7419 0.1051 0.034 Uiso 1 1 calc R . . H10F H 0.2957 0.6786 0.1240 0.034 Uiso 1 1 calc R . . C105 C 0.0683(4) 0.67586(11) 0.09138(5) 0.0284(5) Uani 1 1 d . . . H10G H -0.0428 0.6931 0.1040 0.034 Uiso 1 1 calc R . . H10H H 0.0577 0.6298 0.0919 0.034 Uiso 1 1 calc R . . C106 C 0.0392(3) 0.69878(10) 0.05939(4) 0.0238(4) Uani 1 1 d . . . H10I H -0.0937 0.6832 0.0515 0.029 Uiso 1 1 calc R . . H10J H 0.0352 0.7450 0.0591 0.029 Uiso 1 1 calc R . . H21N H 0.677(5) 0.1763(12) 0.1015(6) 0.033(7) Uiso 1 1 d . . . H22N H 0.907(4) 0.1803(10) 0.0983(5) 0.016(5) Uiso 1 1 d . . . H23N H 0.765(5) 0.2320(13) 0.0888(6) 0.040(7) Uiso 1 1 d . . . H41N H 0.410(4) 0.3028(11) 0.0973(6) 0.028(6) Uiso 1 1 d . . . H42N H 0.266(5) 0.2481(13) 0.1062(6) 0.048(8) Uiso 1 1 d . . . H43N H 0.169(4) 0.3047(11) 0.0930(6) 0.029(7) Uiso 1 1 d . . . H61N H 0.414(4) 0.6963(11) 0.1914(5) 0.025(6) Uiso 1 1 d . . . H62N H 0.329(4) 0.7493(11) 0.2075(5) 0.027(7) Uiso 1 1 d . . . H63N H 0.181(5) 0.6992(14) 0.1931(7) 0.057(9) Uiso 1 1 d . . . H81N H 0.830(4) 0.7651(10) 0.1898(5) 0.020(6) Uiso 1 1 d . . . H82N H 0.702(4) 0.8145(11) 0.2036(5) 0.019(6) Uiso 1 1 d . . . H83N H 0.916(4) 0.8212(11) 0.2076(6) 0.031(7) Uiso 1 1 d . . . H102 H 0.298(5) 0.6841(11) -0.0032(6) 0.032(7) Uiso 1 1 d . . . H103 H 0.214(5) 0.7412(14) 0.0099(6) 0.045(8) Uiso 1 1 d . . . H104 H 0.073(4) 0.6872(10) 0.0030(5) 0.015(6) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O11 0.0205(8) 0.0264(7) 0.0261(8) 0.0043(5) 0.0013(6) -0.0017(6) C11 0.0241(11) 0.0175(9) 0.0137(8) -0.0029(7) 0.0011(7) -0.0016(8) O12 0.0227(8) 0.0255(7) 0.0283(7) 0.0078(6) -0.0047(6) -0.0004(6) C12 0.0215(10) 0.0173(8) 0.0164(9) -0.0007(7) -0.0018(7) -0.0009(8) C13 0.0226(11) 0.0211(9) 0.0248(10) 0.0005(7) -0.0028(8) 0.0040(8) C14 0.0255(11) 0.0239(10) 0.0276(10) 0.0024(8) 0.0017(9) -0.0016(9) C15 0.0328(13) 0.0233(10) 0.0238(10) 0.0048(8) -0.0011(9) -0.0038(9) C16 0.0329(13) 0.0243(11) 0.0356(12) 0.0092(8) -0.0059(10) 0.0023(10) C17 0.0224(11) 0.0255(10) 0.0295(11) 0.0041(8) -0.0034(9) 0.0029(8) N21 0.0174(9) 0.0225(9) 0.0209(8) 0.0040(6) -0.0003(7) 0.0005(7) C21 0.0193(10) 0.0198(9) 0.0190(9) -0.0023(7) -0.0021(8) 0.0015(8) C22 0.0198(11) 0.0331(11) 0.0261(11) -0.0021(8) -0.0039(9) 0.0021(9) C23 0.0245(12) 0.0413(12) 0.0298(11) -0.0091(9) -0.0072(9) 0.0016(10) C24 0.0295(13) 0.0403(12) 0.0237(10) -0.0051(9) -0.0057(9) 0.0067(10) C25 0.0243(12) 0.0354(12) 0.0240(10) -0.0048(8) -0.0009(9) 0.0033(10) C26 0.0188(11) 0.0283(10) 0.0227(10) -0.0010(8) -0.0006(8) 0.0009(9) O31 0.0194(8) 0.0306(8) 0.0275(8) 0.0082(6) 0.0008(6) 0.0032(6) C31 0.0197(11) 0.0204(9) 0.0145(8) -0.0018(7) -0.0010(7) 0.0013(8) O32 0.0223(8) 0.0228(7) 0.0286(7) 0.0044(6) 0.0050(6) 0.0002(6) C32 0.0219(11) 0.0171(9) 0.0174(9) -0.0022(7) -0.0022(8) 0.0014(8) C33 0.0240(11) 0.0267(10) 0.0238(10) 0.0024(8) 0.0010(8) 0.0024(9) C34 0.0340(13) 0.0285(11) 0.0329(12) 0.0109(9) 0.0079(10) 0.0022(10) C35 0.0394(14) 0.0273(10) 0.0315(11) 0.0053(9) -0.0016(10) 0.0079(10) C36 0.0282(12) 0.0223(10) 0.0341(11) 0.0043(8) -0.0039(9) 0.0022(9) C37 0.0233(11) 0.0215(9) 0.0235(10) -0.0006(7) -0.0005(8) -0.0002(8) N41 0.0192(9) 0.0206(8) 0.0202(8) 0.0020(6) 0.0005(7) 0.0013(7) C41 0.0209(11) 0.0202(9) 0.0200(9) -0.0007(7) 0.0025(8) 0.0021(8) C42 0.0177(11) 0.0317(11) 0.0258(10) -0.0033(8) -0.0014(9) 0.0004(9) C43 0.0250(12) 0.0316(11) 0.0270(11) -0.0048(9) -0.0013(9) -0.0049(9) C44 0.0300(13) 0.0349(11) 0.0233(10) -0.0042(8) 0.0051(9) -0.0060(10) C45 0.0255(13) 0.0612(16) 0.0267(12) -0.0059(11) 0.0060(10) 0.0038(11) C46 0.0188(12) 0.0525(14) 0.0263(11) -0.0045(10) 0.0019(9) 0.0009(10) O51 0.0188(8) 0.0328(8) 0.0257(7) -0.0079(6) -0.0001(6) 0.0027(6) C51 0.0228(11) 0.0183(9) 0.0153(9) 0.0025(7) -0.0011(7) 0.0018(8) O52 0.0233(8) 0.0240(7) 0.0266(7) -0.0071(6) -0.0046(6) 0.0004(6) C52 0.0201(11) 0.0148(9) 0.0181(9) 0.0044(7) 0.0019(8) 0.0011(7) C53 0.0209(11) 0.0242(10) 0.0227(10) -0.0014(7) -0.0006(8) -0.0005(8) C54 0.0375(14) 0.0275(11) 0.0261(11) -0.0083(8) -0.0058(10) -0.0002(10) C55 0.0388(14) 0.0232(10) 0.0334(11) -0.0073(9) 0.0000(11) 0.0061(10) C56 0.0262(12) 0.0263(11) 0.0295(11) -0.0018(8) 0.0003(9) 0.0051(9) C57 0.0207(11) 0.0215(9) 0.0233(10) -0.0008(7) -0.0027(8) -0.0010(8) N61 0.0202(9) 0.0179(8) 0.0205(8) -0.0030(6) 0.0017(7) -0.0001(7) C61 0.0197(11) 0.0181(9) 0.0197(9) -0.0011(7) -0.0027(8) -0.0004(8) C62 0.0231(11) 0.0263(10) 0.0238(10) 0.0033(8) 0.0035(8) 0.0012(8) C63 0.0293(12) 0.0297(11) 0.0246(10) 0.0057(8) 0.0039(9) 0.0016(9) C64 0.0345(14) 0.0336(12) 0.0233(10) 0.0034(8) -0.0078(9) -0.0066(10) C65 0.0277(13) 0.0415(12) 0.0312(12) 0.0034(10) -0.0089(10) 0.0018(10) C66 0.0189(12) 0.0376(12) 0.0288(11) 0.0017(9) -0.0027(9) -0.0013(9) O71 0.0250(8) 0.0261(7) 0.0251(7) -0.0083(6) 0.0064(6) 0.0006(6) C71 0.0236(11) 0.0184(9) 0.0165(9) 0.0037(7) -0.0001(8) -0.0017(8) O72 0.0204(8) 0.0261(7) 0.0237(7) -0.0042(5) -0.0001(6) -0.0020(6) C72 0.0215(11) 0.0173(9) 0.0182(9) 0.0004(7) -0.0024(8) 0.0004(8) C73 0.0229(11) 0.0219(10) 0.0270(10) -0.0017(7) 0.0021(9) 0.0002(9) C74 0.0281(12) 0.0234(10) 0.0354(12) -0.0009(8) -0.0091(9) -0.0050(9) C75 0.0414(14) 0.0207(10) 0.0272(11) -0.0061(8) -0.0063(10) -0.0041(9) C76 0.0363(14) 0.0298(11) 0.0301(11) -0.0092(9) 0.0041(10) -0.0004(10) C77 0.0253(11) 0.0283(10) 0.0254(10) -0.0073(8) -0.0002(9) -0.0015(9) N81 0.0206(10) 0.0221(9) 0.0203(8) -0.0043(6) 0.0007(8) 0.0000(7) C81 0.0224(11) 0.0220(9) 0.0179(9) -0.0014(7) -0.0004(8) 0.0011(8) C82 0.0211(11) 0.0308(11) 0.0269(11) 0.0005(8) 0.0028(9) 0.0016(9) C83 0.0266(13) 0.0393(12) 0.0322(12) 0.0041(9) 0.0102(10) 0.0025(10) C84 0.0365(14) 0.0389(12) 0.0217(10) 0.0037(9) 0.0047(10) 0.0073(10) C85 0.0239(12) 0.0364(12) 0.0272(11) 0.0020(9) -0.0027(9) 0.0005(9) C86 0.0232(11) 0.0317(11) 0.0225(10) -0.0007(8) -0.0024(8) -0.0021(9) O91 0.0207(8) 0.0219(7) 0.0264(7) -0.0051(5) 0.0012(6) -0.0014(6) C91 0.0183(10) 0.0204(9) 0.0139(8) -0.0005(7) 0.0011(7) 0.0008(8) O92 0.0202(8) 0.0310(7) 0.0272(8) -0.0079(6) -0.0018(6) -0.0017(6) C92 0.0213(11) 0.0194(9) 0.0167(9) 0.0002(7) 0.0008(7) 0.0002(8) C93 0.0212(11) 0.0244(9) 0.0279(10) -0.0066(8) -0.0012(9) 0.0036(9) C94 0.0239(12) 0.0344(11) 0.0312(11) -0.0094(9) -0.0023(9) -0.0046(10) C95 0.0328(13) 0.0247(10) 0.0296(11) -0.0058(8) 0.0055(9) -0.0098(9) C96 0.0382(14) 0.0228(10) 0.0383(12) -0.0097(9) 0.0034(10) 0.0034(10) C97 0.0230(11) 0.0286(11) 0.0314(11) -0.0053(8) -0.0004(9) 0.0024(9) N101 0.0183(10) 0.0187(8) 0.0192(8) -0.0008(6) -0.0015(7) -0.0002(7) C101 0.0200(10) 0.0211(9) 0.0175(9) 0.0002(7) -0.0029(8) 0.0020(8) C102 0.0159(10) 0.0343(11) 0.0231(10) 0.0010(8) 0.0004(8) -0.0008(9) C103 0.0246(12) 0.0449(13) 0.0257(11) 0.0032(9) -0.0065(9) 0.0007(10) C104 0.0318(13) 0.0351(11) 0.0171(9) 0.0049(8) -0.0005(9) -0.0036(10) C105 0.0271(12) 0.0357(11) 0.0223(10) 0.0049(8) 0.0014(9) 0.0006(10) C106 0.0199(11) 0.0307(10) 0.0209(10) 0.0011(8) 0.0008(8) 0.0013(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O11 C11 1.253(3) . ? C11 O12 1.267(2) . ? C11 C12 1.509(3) . ? C12 C13 1.387(3) . ? C12 C17 1.399(3) . ? C13 C14 1.398(3) . ? C14 C15 1.384(3) . ? C15 C16 1.395(3) . ? C16 C17 1.376(3) . ? N21 C21 1.498(2) . ? C21 C26 1.518(3) . ? C21 C22 1.533(3) . ? C22 C23 1.528(3) . ? C23 C24 1.527(3) . ? C24 C25 1.519(3) . ? C25 C26 1.535(3) . ? O31 C31 1.250(3) . ? C31 O32 1.264(2) . ? C31 C32 1.504(3) . ? C32 C33 1.390(3) . ? C32 C37 1.394(3) . ? C33 C34 1.383(3) . ? C34 C35 1.391(3) . ? C35 C36 1.378(3) . ? C36 C37 1.397(3) . ? N41 C41 1.497(2) . ? C41 C42 1.518(3) . ? C41 C46 1.526(3) . ? C42 C43 1.531(3) . ? C43 C44 1.515(3) . ? C44 C45 1.519(3) . ? C45 C46 1.527(3) . ? O51 C51 1.251(3) . ? C51 O52 1.262(2) . ? C51 C52 1.508(3) . ? C52 C57 1.389(3) . ? C52 C53 1.393(3) . ? C53 C54 1.399(3) . ? C54 C55 1.379(3) . ? C55 C56 1.385(3) . ? C56 C57 1.403(3) . ? N61 C61 1.501(2) . ? C61 C62 1.521(3) . ? C61 C66 1.528(3) . ? C62 C63 1.532(3) . ? C63 C64 1.518(3) . ? C64 C65 1.528(3) . ? C65 C66 1.529(3) . ? O71 C71 1.262(2) . ? C71 O72 1.249(3) . ? C71 C72 1.504(3) . ? C72 C73 1.388(3) . ? C72 C77 1.397(3) . ? C73 C74 1.402(3) . ? C74 C75 1.383(3) . ? C75 C76 1.378(4) . ? C76 C77 1.385(3) . ? N81 C81 1.497(2) . ? C81 C82 1.519(3) . ? C81 C86 1.527(3) . ? C82 C83 1.524(3) . ? C83 C84 1.526(3) . ? C84 C85 1.525(3) . ? C85 C86 1.528(3) . ? O91 C91 1.267(2) . ? C91 O92 1.258(3) . ? C91 C92 1.503(3) . ? C92 C93 1.385(3) . ? C92 C97 1.393(3) . ? C93 C94 1.398(3) . ? C94 C95 1.379(3) . ? C95 C96 1.384(4) . ? C96 C97 1.390(3) . ? N101 C101 1.500(2) . ? C101 C106 1.521(3) . ? C101 C102 1.522(3) . ? C102 C103 1.529(3) . ? C103 C104 1.528(3) . ? C104 C105 1.529(3) . ? C105 C106 1.533(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O11 C11 O12 124.28(18) . . ? O11 C11 C12 117.37(18) . . ? O12 C11 C12 118.34(18) . . ? C13 C12 C17 119.46(19) . . ? C13 C12 C11 121.62(18) . . ? C17 C12 C11 118.87(18) . . ? C12 C13 C14 119.89(19) . . ? C15 C14 C13 120.3(2) . . ? C14 C15 C16 119.60(19) . . ? C17 C16 C15 120.2(2) . . ? C16 C17 C12 120.4(2) . . ? N21 C21 C26 110.14(16) . . ? N21 C21 C22 109.42(17) . . ? C26 C21 C22 111.82(16) . . ? C23 C22 C21 110.07(18) . . ? C24 C23 C22 111.11(18) . . ? C25 C24 C23 111.27(18) . . ? C24 C25 C26 111.13(18) . . ? C21 C26 C25 110.19(17) . . ? O31 C31 O32 124.23(18) . . ? O31 C31 C32 117.37(18) . . ? O32 C31 C32 118.39(18) . . ? C33 C32 C37 119.21(18) . . ? C33 C32 C31 118.89(18) . . ? C37 C32 C31 121.85(18) . . ? C34 C33 C32 120.8(2) . . ? C33 C34 C35 119.7(2) . . ? C36 C35 C34 120.3(2) . . ? C35 C36 C37 119.9(2) . . ? C32 C37 C36 120.0(2) . . ? N41 C41 C42 110.37(17) . . ? N41 C41 C46 109.62(17) . . ? C42 C41 C46 111.36(16) . . ? C41 C42 C43 110.29(18) . . ? C44 C43 C42 111.36(18) . . ? C43 C44 C45 110.22(18) . . ? C44 C45 C46 111.7(2) . . ? C45 C46 C41 109.95(19) . . ? O51 C51 O52 124.96(18) . . ? O51 C51 C52 116.95(18) . . ? O52 C51 C52 118.09(18) . . ? C57 C52 C53 119.33(18) . . ? C57 C52 C51 122.20(18) . . ? C53 C52 C51 118.46(19) . . ? C52 C53 C54 120.3(2) . . ? C55 C54 C53 119.7(2) . . ? C54 C55 C56 120.8(2) . . ? C55 C56 C57 119.4(2) . . ? C52 C57 C56 120.40(19) . . ? N61 C61 C62 110.47(16) . . ? N61 C61 C66 109.81(17) . . ? C62 C61 C66 112.22(16) . . ? C61 C62 C63 109.81(17) . . ? C64 C63 C62 111.11(18) . . ? C63 C64 C65 111.41(17) . . ? C64 C65 C66 110.91(19) . . ? C61 C66 C65 110.00(18) . . ? O72 C71 O71 124.29(18) . . ? O72 C71 C72 117.05(18) . . ? O71 C71 C72 118.66(19) . . ? C73 C72 C77 118.98(18) . . ? C73 C72 C71 122.43(18) . . ? C77 C72 C71 118.59(19) . . ? C72 C73 C74 120.2(2) . . ? C75 C74 C73 119.8(2) . . ? C76 C75 C74 120.3(2) . . ? C75 C76 C77 120.0(2) . . ? C76 C77 C72 120.7(2) . . ? N81 C81 C82 109.82(17) . . ? N81 C81 C86 110.11(17) . . ? C82 C81 C86 112.34(16) . . ? C83 C82 C81 110.39(18) . . ? C82 C83 C84 110.61(19) . . ? C85 C84 C83 111.34(17) . . ? C84 C85 C86 110.84(18) . . ? C81 C86 C85 110.02(17) . . ? O92 C91 O91 124.22(18) . . ? O92 C91 C92 117.23(17) . . ? O91 C91 C92 118.53(18) . . ? C93 C92 C97 119.53(19) . . ? C93 C92 C91 121.37(18) . . ? C97 C92 C91 119.10(18) . . ? C92 C93 C94 119.73(19) . . ? C95 C94 C93 120.7(2) . . ? C94 C95 C96 119.5(2) . . ? C95 C96 C97 120.3(2) . . ? C96 C97 C92 120.2(2) . . ? N101 C101 C106 110.09(16) . . ? N101 C101 C102 109.53(17) . . ? C106 C101 C102 111.89(16) . . ? C101 C102 C103 110.17(18) . . ? C104 C103 C102 111.24(18) . . ? C103 C104 C105 110.38(17) . . ? C104 C105 C106 111.21(18) . . ? C101 C106 C105 110.34(17) . . ? 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 N21 H21N O11 0.95(3) 1.77(3) 2.697(2) 167(2) . N21 H23N O32 0.91(3) 1.87(3) 2.778(2) 173(3) . N21 H22N O12 0.85(3) 1.95(3) 2.801(2) 173(2) 1_655 N41 H42N O12 0.90(3) 1.90(3) 2.775(2) 166(3) . N41 H41N O32 0.97(3) 1.82(3) 2.782(2) 170(2) . N41 H43N O31 0.96(3) 1.76(3) 2.715(2) 170(2) 1_455 N61 H61N O51 0.95(3) 1.75(3) 2.702(2) 172(2) . N61 H62N O71 0.85(2) 1.95(2) 2.788(2) 171(2) . N61 H63N O52 1.00(3) 1.82(3) 2.789(2) 163(3) 1_455 N81 H82N O71 0.79(3) 2.00(3) 2.779(3) 169(2) . N81 H81N O52 0.97(2) 1.80(2) 2.763(2) 171(2) . N81 H83N O72 0.94(3) 1.78(3) 2.711(2) 171(2) 1_655 N101 H103 O91 0.90(3) 1.88(3) 2.780(2) 175(3) . N101 H104 O91 0.84(3) 1.97(3) 2.807(2) 169(2) 3_465 N101 H102 O92 0.95(3) 1.75(3) 2.694(2) 168(2) 3_565 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.207 _refine_diff_density_min -0.157 _refine_diff_density_rms 0.032 #END data_5 _database_code_depnum_ccdc_archive 'CCDC 762141' #TrackingRef 'C000922A.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'anilinium benoate benzoic acid' _chemical_melting_point ? _chemical_formula_moiety 'C7 H6 O2 , C6 H8 N +, C7 H5 O2 -' _chemical_formula_sum 'C20 H19 N O4' _chemical_formula_weight 337.36 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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 6.5265(4) _cell_length_b 18.4160(11) _cell_length_c 14.9966(9) _cell_angle_alpha 90.00 _cell_angle_beta 93.5180(10) _cell_angle_gamma 90.00 _cell_volume 1799.08(19) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 4356 _cell_measurement_theta_min 2.597 _cell_measurement_theta_max 27.396 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.03 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.246 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 712 _exptl_absorpt_coefficient_mu 0.087 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9871 _exptl_absorpt_correction_T_max 0.9983 _exptl_absorpt_process_details '(SADABS; Bruker, 2002)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX CCD area-detector' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% . _diffrn_reflns_number 10470 _diffrn_reflns_av_R_equivalents 0.0222 _diffrn_reflns_av_sigmaI/netI 0.3779 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.75 _diffrn_reflns_theta_max 28.22 _reflns_number_total 4025 _reflns_number_gt 2751 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX II, Bruker 2007' _computing_cell_refinement 'APEX II, Bruker 2007' _computing_data_reduction 'APEX II, Bruker 2007' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. Ammonium and carboxylic acid hydrogen atoms were located in the difference map. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0001P)^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 4025 _refine_ls_number_parameters 242 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0659 _refine_ls_R_factor_gt 0.0491 _refine_ls_wR_factor_ref 0.3052 _refine_ls_wR_factor_gt 0.2081 _refine_ls_goodness_of_fit_ref 0.715 _refine_ls_restrained_S_all 0.715 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.5201(2) 0.05587(7) 0.85746(10) 0.0652(5) Uani 1 1 d . . . O2 O 0.81889(19) 0.00224(7) 0.88507(8) 0.0568(4) Uani 1 1 d . . . C3 C 0.6954(3) 0.03686(8) 0.83450(11) 0.0473(4) Uani 1 1 d . . . C4 C 0.7542(2) 0.05514(8) 0.74138(11) 0.0500(4) Uani 1 1 d . . . C5 C 0.6094(4) 0.08573(11) 0.68100(14) 0.0707(6) Uani 1 1 d . . . H5 H 0.4761 0.0971 0.6990 0.085 Uiso 1 1 calc R . . C6 C 0.6605(5) 0.09966(15) 0.59368(17) 0.0908(8) Uani 1 1 d . . . H6 H 0.5617 0.1204 0.5521 0.109 Uiso 1 1 calc R . . C7 C 0.8529(5) 0.08345(13) 0.56776(15) 0.0851(8) Uani 1 1 d . . . H7 H 0.8864 0.0927 0.5081 0.102 Uiso 1 1 calc R . . C8 C 0.9972(4) 0.05401(13) 0.62726(16) 0.0767(7) Uani 1 1 d . . . H8 H 1.1304 0.0430 0.6090 0.092 Uiso 1 1 calc R . . C9 C 0.9479(3) 0.04032(10) 0.71455(13) 0.0616(5) Uani 1 1 d . . . H9 H 1.0488 0.0206 0.7561 0.074 Uiso 1 1 calc R . . O4 O 0.3406(3) 0.18294(8) 0.84763(12) 0.0804(6) Uani 1 1 d . . . H4 H 0.399(6) 0.137(2) 0.851(2) 0.110(10) Uiso 1 1 d . . . O3 O 0.1139(2) 0.12630(6) 0.92706(12) 0.0728(5) Uani 1 1 d . . . C10 C 0.1675(3) 0.17999(9) 0.88901(12) 0.0569(5) Uani 1 1 d . . . C11 C 0.0471(3) 0.24847(9) 0.88222(12) 0.0574(5) Uani 1 1 d . . . C12 C -0.1484(4) 0.24787(12) 0.91060(18) 0.0749(6) Uani 1 1 d . . . H12 H -0.2034 0.2045 0.9339 0.090 Uiso 1 1 calc R . . C13 C -0.2660(5) 0.31071(15) 0.9053(2) 0.0968(9) Uani 1 1 d . . . H13 H -0.4018 0.3102 0.9248 0.116 Uiso 1 1 calc R . . C14 C -0.1875(5) 0.37348(13) 0.8722(2) 0.0961(9) Uani 1 1 d . . . H14 H -0.2692 0.4162 0.8684 0.115 Uiso 1 1 calc R . . C15 C 0.0119(5) 0.37470(11) 0.84401(18) 0.0879(8) Uani 1 1 d . . . H15 H 0.0669 0.4182 0.8213 0.105 Uiso 1 1 calc R . . C16 C 0.1288(4) 0.31227(10) 0.84933(15) 0.0710(6) Uani 1 1 d . . . H16 H 0.2652 0.3128 0.8306 0.085 Uiso 1 1 calc R . . N1 N 0.2281(2) -0.03044(7) 0.93408(10) 0.0491(4) Uani 1 1 d . . . H1N H 0.325(3) 0.0008(10) 0.9138(11) 0.041(4) Uiso 1 1 d . . . H2N H 0.222(4) -0.0238(13) 0.9980(19) 0.074(6) Uiso 1 1 d . . . H3N H 0.104(4) -0.0200(13) 0.9091(16) 0.067(6) Uiso 1 1 d . . . C17 C 0.2614(3) -0.10620(8) 0.90859(10) 0.0494(4) Uani 1 1 d . . . C18 C 0.4544(3) -0.13536(10) 0.92203(14) 0.0613(5) Uani 1 1 d . . . H18 H 0.5653 -0.1069 0.9467 0.074 Uiso 1 1 calc R . . C19 C 0.4839(4) -0.20743(11) 0.89873(17) 0.0746(6) Uani 1 1 d . . . H19 H 0.6160 -0.2288 0.9078 0.090 Uiso 1 1 calc R . . C20 C 0.3221(5) -0.24804(11) 0.86242(18) 0.0805(7) Uani 1 1 d . . . H20 H 0.3437 -0.2972 0.8463 0.097 Uiso 1 1 calc R . . C21 C 0.1291(4) -0.21790(12) 0.84935(18) 0.0790(6) Uani 1 1 d . . . H21 H 0.0181 -0.2463 0.8247 0.095 Uiso 1 1 calc R . . C22 C 0.0975(3) -0.14617(10) 0.87225(14) 0.0626(5) Uani 1 1 d . . . H22 H -0.0346 -0.1248 0.8632 0.075 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0585(9) 0.0618(7) 0.0777(9) 0.0165(6) 0.0229(7) 0.0179(6) O2 0.0537(8) 0.0605(7) 0.0562(7) 0.0083(5) 0.0033(6) 0.0099(5) C3 0.0481(9) 0.0391(8) 0.0552(9) 0.0000(6) 0.0066(7) 0.0024(6) C4 0.0559(10) 0.0405(7) 0.0538(9) -0.0009(6) 0.0034(7) -0.0047(6) C5 0.0741(13) 0.0724(12) 0.0654(12) 0.0097(9) 0.0016(9) 0.0109(10) C6 0.111(2) 0.0924(16) 0.0674(14) 0.0222(12) -0.0052(13) 0.0068(14) C7 0.118(2) 0.0807(15) 0.0575(12) 0.0062(10) 0.0162(13) -0.0222(13) C8 0.0806(14) 0.0827(13) 0.0694(13) -0.0092(10) 0.0256(11) -0.0228(11) C9 0.0588(11) 0.0678(11) 0.0590(11) -0.0034(8) 0.0092(8) -0.0084(8) O4 0.0803(11) 0.0628(9) 0.1010(13) 0.0238(7) 0.0292(9) 0.0246(7) O3 0.0731(10) 0.0503(8) 0.0966(11) 0.0106(6) 0.0180(8) 0.0104(6) C10 0.0628(11) 0.0497(9) 0.0578(10) 0.0042(7) 0.0005(8) 0.0090(7) C11 0.0679(12) 0.0489(9) 0.0549(10) -0.0007(6) 0.0000(8) 0.0126(7) C12 0.0726(13) 0.0653(11) 0.0872(14) 0.0097(10) 0.0086(10) 0.0179(10) C13 0.0845(17) 0.0935(18) 0.113(2) 0.0096(15) 0.0124(15) 0.0387(14) C14 0.118(2) 0.0735(15) 0.0969(17) 0.0133(12) 0.0076(15) 0.0514(15) C15 0.124(2) 0.0551(11) 0.0860(16) 0.0117(10) 0.0144(14) 0.0235(12) C16 0.0870(15) 0.0536(10) 0.0733(13) 0.0088(8) 0.0132(11) 0.0124(9) N1 0.0476(8) 0.0491(8) 0.0511(8) 0.0021(5) 0.0061(6) 0.0077(5) C17 0.0543(10) 0.0474(8) 0.0469(9) 0.0012(6) 0.0067(7) 0.0066(6) C18 0.0565(10) 0.0593(10) 0.0682(11) -0.0020(7) 0.0059(8) 0.0107(7) C19 0.0776(14) 0.0645(11) 0.0825(14) 0.0022(10) 0.0108(11) 0.0270(10) C20 0.1077(18) 0.0499(10) 0.0842(15) -0.0070(9) 0.0083(13) 0.0150(11) C21 0.0875(16) 0.0610(12) 0.0878(15) -0.0110(10) -0.0003(11) -0.0065(10) C22 0.0623(11) 0.0564(10) 0.0690(12) -0.0040(8) 0.0023(8) 0.0023(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C3 1.264(2) . ? O2 C3 1.247(2) . ? C3 C4 1.509(2) . ? C4 C9 1.378(2) . ? C4 C5 1.387(3) . ? C5 C6 1.395(3) . ? C6 C7 1.370(4) . ? C7 C8 1.369(4) . ? C8 C9 1.390(3) . ? O4 C10 1.323(2) . ? O3 C10 1.204(2) . ? C10 C11 1.486(2) . ? C11 C12 1.370(3) . ? C11 C16 1.393(3) . ? C12 C13 1.388(3) . ? C13 C14 1.370(4) . ? C14 C15 1.393(4) . ? C15 C16 1.380(3) . ? N1 C17 1.466(2) . ? C17 C18 1.373(2) . ? C17 C22 1.383(3) . ? C18 C19 1.389(3) . ? C19 C20 1.379(4) . ? C20 C21 1.380(4) . ? C21 C22 1.383(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 C3 O1 122.52(14) . . ? O2 C3 C4 119.05(13) . . ? O1 C3 C4 118.41(15) . . ? C9 C4 C5 119.36(17) . . ? C9 C4 C3 121.06(16) . . ? C5 C4 C3 119.56(15) . . ? C4 C5 C6 119.7(2) . . ? C7 C6 C5 120.2(2) . . ? C8 C7 C6 120.5(2) . . ? C7 C8 C9 119.8(2) . . ? C4 C9 C8 120.6(2) . . ? O3 C10 O4 122.49(16) . . ? O3 C10 C11 124.17(17) . . ? O4 C10 C11 113.34(15) . . ? C12 C11 C16 120.08(18) . . ? C12 C11 C10 118.06(17) . . ? C16 C11 C10 121.85(18) . . ? C11 C12 C13 119.8(2) . . ? C14 C13 C12 120.4(3) . . ? C13 C14 C15 120.0(2) . . ? C16 C15 C14 119.5(2) . . ? C15 C16 C11 120.0(2) . . ? C18 C17 C22 122.03(16) . . ? C18 C17 N1 118.91(16) . . ? C22 C17 N1 119.06(15) . . ? C17 C18 C19 118.5(2) . . ? C20 C19 C18 120.2(2) . . ? C19 C20 C21 120.56(18) . . ? C20 C21 C22 119.8(2) . . ? C17 C22 C21 118.86(18) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1N O1 0.921(18) 1.869(19) 2.7837(19) 171.6(16) . N1 H3N O2 0.89(3) 1.92(3) 2.792(2) 166(2) 1_455 N1 H2N O2 0.97(3) 1.83(3) 2.7966(18) 172(2) 3_657 N1 H3N O3 0.89(3) 2.71(2) 2.9813(18) 99.1(17) . O4 H4 O1 0.92(4) 1.70(4) 2.6171(19) 177(3) . _diffrn_measured_fraction_theta_max 0.907 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.167 _refine_diff_density_min -0.142 _refine_diff_density_rms 0.023 #END data_6 _database_code_depnum_ccdc_archive 'CCDC 762142' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common 'benzylammonium formate' _chemical_melting_point ? _chemical_formula_moiety 'C7 H10 N + , C H O2 -' _chemical_formula_sum 'C8 H11 N O2' _chemical_formula_weight 153.18 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' _cell_length_a 8.5689(15) _cell_length_b 11.0491(19) _cell_length_c 17.529(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1659.6(5) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5997 _cell_measurement_theta_min 2.324 _cell_measurement_theta_max 27.987 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.226 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 656 _exptl_absorpt_coefficient_mu 0.088 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9791 _exptl_absorpt_correction_T_max 0.9982 _exptl_absorpt_process_details '(SADABS; Bruker, 2002)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX CCD area-detector' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% . _diffrn_reflns_number 8626 _diffrn_reflns_av_R_equivalents 0.0208 _diffrn_reflns_av_sigmaI/netI 0.0155 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.32 _diffrn_reflns_theta_max 25.99 _reflns_number_total 1634 _reflns_number_gt 1508 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX II, Bruker 2007' _computing_cell_refinement 'APEX II, Bruker 2007' _computing_data_reduction 'APEX II, Bruker 2007' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. Ammonium hydrogen atoms were located in the difference map. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0487P)^2^+0.3574P] 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 1634 _refine_ls_number_parameters 116 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0318 _refine_ls_R_factor_gt 0.0294 _refine_ls_wR_factor_ref 0.0830 _refine_ls_wR_factor_gt 0.0807 _refine_ls_goodness_of_fit_ref 1.040 _refine_ls_restrained_S_all 1.040 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.17225(8) 0.39531(6) 0.32288(4) 0.0272(2) Uani 1 1 d . . . N1 N 0.13979(10) 0.14598(7) 0.33014(4) 0.0200(2) Uani 1 1 d . . . C1 C 0.07664(11) 0.45337(9) 0.28388(5) 0.0216(2) Uani 1 1 d . . . H1 H 0.0055(14) 0.4051(10) 0.2492(7) 0.025(3) Uiso 1 1 d . . . H1N H 0.0857(15) 0.1254(11) 0.2844(7) 0.034(3) Uiso 1 1 d . . . H3N H 0.1456(15) 0.2328(12) 0.3335(7) 0.033(3) Uiso 1 1 d . . . H2N H 0.2378(16) 0.1121(12) 0.3248(7) 0.033(3) Uiso 1 1 d . . . O2 O 0.06088(8) 0.56656(6) 0.28334(4) 0.02460(19) Uani 1 1 d . . . C2 C 0.05444(11) 0.09022(9) 0.39555(5) 0.0232(2) Uani 1 1 d . . . H2A H 0.0493 0.0016 0.3877 0.028 Uiso 1 1 calc R . . H2B H -0.0539 0.1214 0.3961 0.028 Uiso 1 1 calc R . . C3 C 0.12875(11) 0.11518(8) 0.47185(5) 0.0207(2) Uani 1 1 d . . . C4 C 0.25325(11) 0.04463(9) 0.49713(5) 0.0222(2) Uani 1 1 d . . . H4 H 0.2950 -0.0166 0.4650 0.027 Uiso 1 1 calc R . . C5 C 0.31651(11) 0.06335(9) 0.56897(6) 0.0251(2) Uani 1 1 d . . . H5 H 0.4014 0.0150 0.5859 0.030 Uiso 1 1 calc R . . C6 C 0.25574(12) 0.15295(9) 0.61634(5) 0.0258(2) Uani 1 1 d . . . H6 H 0.2991 0.1657 0.6656 0.031 Uiso 1 1 calc R . . C7 C 0.13186(13) 0.22346(9) 0.59152(6) 0.0285(2) Uani 1 1 d . . . H7 H 0.0901 0.2845 0.6238 0.034 Uiso 1 1 calc R . . C8 C 0.06893(12) 0.20473(9) 0.51953(6) 0.0262(2) Uani 1 1 d . . . H8 H -0.0157 0.2534 0.5026 0.031 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0322(4) 0.0211(4) 0.0282(4) 0.0017(3) -0.0027(3) -0.0006(3) N1 0.0217(4) 0.0189(4) 0.0194(4) 0.0006(3) -0.0007(3) -0.0004(3) C1 0.0234(5) 0.0240(5) 0.0173(4) -0.0015(3) 0.0030(4) -0.0040(4) O2 0.0277(4) 0.0220(4) 0.0240(4) -0.0002(3) -0.0021(3) 0.0013(3) C2 0.0236(5) 0.0244(5) 0.0218(5) 0.0027(4) -0.0007(4) -0.0044(4) C3 0.0226(5) 0.0198(5) 0.0199(5) 0.0032(3) 0.0013(4) -0.0049(4) C4 0.0220(5) 0.0208(4) 0.0237(5) -0.0001(4) 0.0028(4) -0.0014(4) C5 0.0221(5) 0.0268(5) 0.0263(5) 0.0040(4) -0.0015(4) -0.0014(4) C6 0.0305(5) 0.0279(5) 0.0189(4) 0.0011(4) -0.0009(4) -0.0075(4) C7 0.0380(6) 0.0219(5) 0.0255(5) -0.0030(4) 0.0051(4) -0.0004(4) C8 0.0303(5) 0.0213(5) 0.0269(5) 0.0031(4) 0.0001(4) 0.0040(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.2450(12) . ? N1 C2 1.4931(12) . ? C1 O2 1.2580(12) . ? C2 C3 1.5067(13) . ? C3 C8 1.3931(14) . ? C3 C4 1.3936(14) . ? C4 C5 1.3864(14) . ? C5 C6 1.3931(15) . ? C6 C7 1.3867(15) . ? C7 C8 1.3878(15) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 O2 125.95(9) . . ? N1 C2 C3 113.52(8) . . ? C8 C3 C4 119.22(9) . . ? C8 C3 C2 120.47(9) . . ? C4 C3 C2 120.23(9) . . ? C5 C4 C3 120.31(9) . . ? C4 C5 C6 120.08(9) . . ? C7 C6 C5 119.89(9) . . ? C6 C7 C8 119.93(9) . . ? C7 C8 C3 120.56(9) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H3N O1 0.962(13) 1.820(13) 2.7718(12) 169.6(11) . N1 H1N O2 0.954(13) 1.846(14) 2.7719(11) 162.8(11) 4_545 N1 H2N O2 0.924(14) 1.938(14) 2.8323(11) 162.1(11) 7_655 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.99 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.241 _refine_diff_density_min -0.151 _refine_diff_density_rms 0.033 #END data_7 _database_code_depnum_ccdc_archive 'CCDC 762143' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common 'benzylammonium acetate' _chemical_melting_point ? _chemical_formula_moiety 'C7 H10 N + , C2 H3 O2 -' _chemical_formula_sum 'C9 H13 N O2' _chemical_formula_weight 167.20 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 12.7338(8) _cell_length_b 7.9987(5) _cell_length_c 17.5766(11) _cell_angle_alpha 90.00 _cell_angle_beta 93.0730(10) _cell_angle_gamma 90.00 _cell_volume 1787.67(19) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 4604 _cell_measurement_theta_min 2.799 _cell_measurement_theta_max 27.99 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.13 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.243 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 720 _exptl_absorpt_coefficient_mu 0.088 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9887 _exptl_absorpt_correction_T_max 0.9982 _exptl_absorpt_process_details '(SADABS; Bruker, 2002)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX CCD area-detector' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% . _diffrn_reflns_number 10553 _diffrn_reflns_av_R_equivalents 0.0237 _diffrn_reflns_av_sigmaI/netI 0.0287 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.93 _diffrn_reflns_theta_max 28.19 _reflns_number_total 4023 _reflns_number_gt 3227 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX II, Bruker 2007' _computing_cell_refinement 'APEX II, Bruker 2007' _computing_data_reduction 'APEX II, Bruker 2007' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. Ammonium hydrogen atoms were located in the difference map. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0545P)^2^+0.1235P] 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 4023 _refine_ls_number_parameters 242 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0462 _refine_ls_R_factor_gt 0.0363 _refine_ls_wR_factor_ref 0.1025 _refine_ls_wR_factor_gt 0.0966 _refine_ls_goodness_of_fit_ref 1.075 _refine_ls_restrained_S_all 1.075 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.58016(6) 0.65701(10) 0.40140(4) 0.02133(19) Uani 1 1 d . . . N1 N 0.45573(8) 0.67611(13) 0.56165(6) 0.0196(2) Uani 1 1 d . . . C1 C 0.50416(9) 0.75042(14) 0.37815(6) 0.0193(2) Uani 1 1 d . . . H1N H 0.4575(10) 0.562(2) 0.5679(7) 0.029(4) Uiso 1 1 d . . . H6N H 0.7849(11) 0.7770(19) 0.3195(8) 0.030(4) Uiso 1 1 d . . . H5N H 0.7491(10) 0.6197(18) 0.2724(8) 0.030(4) Uiso 1 1 d . . . H2N H 0.4409(11) 0.6992(18) 0.5084(9) 0.037(4) Uiso 1 1 d . . . H3N H 0.3962(11) 0.7154(19) 0.5899(8) 0.036(4) Uiso 1 1 d . . . H4N H 0.7090(12) 0.6486(18) 0.3499(8) 0.037(4) Uiso 1 1 d . . . O2 O 0.42249(6) 0.77147(12) 0.41345(4) 0.0304(2) Uani 1 1 d . . . N2 N 0.76774(8) 0.65986(13) 0.32071(6) 0.0212(2) Uani 1 1 d . . . C2 C 0.51471(9) 0.84185(16) 0.30333(6) 0.0247(3) Uani 1 1 d . . . H2A H 0.4466 0.8898 0.2864 0.037 Uiso 1 1 calc R . . H2B H 0.5376 0.7632 0.2648 0.037 Uiso 1 1 calc R . . H2C H 0.5667 0.9316 0.3104 0.037 Uiso 1 1 calc R . . O3 O 0.79492(7) 0.72415(10) 0.14559(4) 0.0248(2) Uani 1 1 d . . . C3 C 0.74924(8) 0.58837(14) 0.12993(6) 0.0186(2) Uani 1 1 d . . . O4 O 0.70090(7) 0.50573(10) 0.17872(4) 0.0257(2) Uani 1 1 d . . . C4 C 0.75355(10) 0.51824(16) 0.04996(6) 0.0261(3) Uani 1 1 d . . . H4A H 0.7146 0.4126 0.0465 0.039 Uiso 0.50 1 calc PR . . H4B H 0.8270 0.4986 0.0384 0.039 Uiso 0.50 1 calc PR . . H4C H 0.7218 0.5983 0.0133 0.039 Uiso 0.50 1 calc PR . . H4D H 0.7943 0.5937 0.0190 0.039 Uiso 0.50 1 calc PR . . H4E H 0.6820 0.5077 0.0271 0.039 Uiso 0.50 1 calc PR . . H4F H 0.7871 0.4080 0.0522 0.039 Uiso 0.50 1 calc PR . . C5 C 0.55528(9) 0.75978(15) 0.58707(6) 0.0222(3) Uani 1 1 d . . . H5A H 0.5472 0.8817 0.5790 0.027 Uiso 1 1 calc R . . H5B H 0.6118 0.7205 0.5549 0.027 Uiso 1 1 calc R . . C6 C 0.58868(9) 0.72879(14) 0.66975(6) 0.0208(2) Uani 1 1 d . . . C7 C 0.53161(9) 0.63231(15) 0.71861(6) 0.0226(3) Uani 1 1 d . . . H7 H 0.4667 0.5838 0.7009 0.027 Uiso 1 1 calc R . . C8 C 0.56937(11) 0.60666(16) 0.79347(7) 0.0282(3) Uani 1 1 d . . . H8 H 0.5304 0.5398 0.8266 0.034 Uiso 1 1 calc R . . C9 C 0.66346(11) 0.67803(17) 0.82001(7) 0.0328(3) Uani 1 1 d . . . H9 H 0.6894 0.6592 0.8710 0.039 Uiso 1 1 calc R . . C10 C 0.71960(10) 0.77716(18) 0.77177(7) 0.0325(3) Uani 1 1 d . . . H10 H 0.7836 0.8278 0.7899 0.039 Uiso 1 1 calc R . . C11 C 0.68250(9) 0.80231(16) 0.69726(7) 0.0267(3) Uani 1 1 d . . . H11 H 0.7213 0.8703 0.6645 0.032 Uiso 1 1 calc R . . C12 C 0.85916(9) 0.56399(15) 0.35539(6) 0.0211(2) Uani 1 1 d . . . H12A H 0.9234 0.5932 0.3290 0.025 Uiso 1 1 calc R . . H12B H 0.8463 0.4427 0.3486 0.025 Uiso 1 1 calc R . . C13 C 0.87569(8) 0.60266(14) 0.43910(6) 0.0193(2) Uani 1 1 d . . . C14 C 0.80805(9) 0.53385(15) 0.49061(6) 0.0228(3) Uani 1 1 d . . . H14 H 0.7535 0.4603 0.4728 0.027 Uiso 1 1 calc R . . C15 C 0.81981(10) 0.57202(16) 0.56752(6) 0.0272(3) Uani 1 1 d . . . H15 H 0.7732 0.5252 0.6022 0.033 Uiso 1 1 calc R . . C16 C 0.89947(10) 0.67845(17) 0.59377(7) 0.0295(3) Uani 1 1 d . . . H16 H 0.9070 0.7057 0.6464 0.035 Uiso 1 1 calc R . . C17 C 0.96816(10) 0.74527(16) 0.54347(7) 0.0279(3) Uani 1 1 d . . . H17 H 1.0235 0.8169 0.5617 0.034 Uiso 1 1 calc R . . C18 C 0.95606(9) 0.70749(15) 0.46632(7) 0.0231(3) Uani 1 1 d . . . H18 H 1.0032 0.7538 0.4319 0.028 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0232(4) 0.0207(4) 0.0199(4) 0.0009(3) -0.0006(3) 0.0029(3) N1 0.0208(5) 0.0208(5) 0.0172(5) 0.0006(4) 0.0011(4) 0.0027(4) C1 0.0222(6) 0.0196(6) 0.0158(5) -0.0023(4) -0.0022(4) 0.0001(4) O2 0.0245(5) 0.0470(6) 0.0197(4) 0.0052(4) 0.0026(3) 0.0097(4) N2 0.0242(5) 0.0240(6) 0.0155(5) -0.0013(4) 0.0011(4) 0.0039(4) C2 0.0269(6) 0.0269(7) 0.0201(6) 0.0027(5) -0.0005(5) 0.0024(5) O3 0.0284(5) 0.0237(5) 0.0229(4) -0.0032(3) 0.0055(3) -0.0063(4) C3 0.0172(5) 0.0207(6) 0.0179(5) 0.0008(4) 0.0006(4) 0.0016(4) O4 0.0323(5) 0.0249(5) 0.0205(4) -0.0001(3) 0.0076(3) -0.0057(4) C4 0.0306(7) 0.0280(7) 0.0198(6) -0.0024(5) 0.0030(5) -0.0071(5) C5 0.0231(6) 0.0234(6) 0.0203(6) 0.0014(4) 0.0023(4) -0.0015(5) C6 0.0213(6) 0.0204(6) 0.0207(6) -0.0036(4) 0.0019(4) 0.0041(4) C7 0.0263(6) 0.0206(6) 0.0206(6) -0.0028(4) -0.0002(5) 0.0005(5) C8 0.0408(7) 0.0239(6) 0.0198(6) -0.0010(5) 0.0015(5) 0.0053(5) C9 0.0378(7) 0.0393(8) 0.0203(6) -0.0097(5) -0.0073(5) 0.0147(6) C10 0.0222(6) 0.0442(8) 0.0307(7) -0.0172(6) -0.0030(5) 0.0055(6) C11 0.0222(6) 0.0308(7) 0.0276(6) -0.0089(5) 0.0048(5) 0.0004(5) C12 0.0226(6) 0.0216(6) 0.0193(6) -0.0009(4) 0.0029(4) 0.0042(5) C13 0.0199(6) 0.0200(6) 0.0182(5) 0.0004(4) 0.0015(4) 0.0066(4) C14 0.0205(6) 0.0243(6) 0.0238(6) 0.0033(5) 0.0027(4) 0.0034(5) C15 0.0263(6) 0.0343(7) 0.0215(6) 0.0076(5) 0.0064(5) 0.0108(5) C16 0.0302(7) 0.0409(8) 0.0169(6) -0.0021(5) -0.0025(5) 0.0144(6) C17 0.0237(6) 0.0318(7) 0.0276(6) -0.0050(5) -0.0054(5) 0.0054(5) C18 0.0204(6) 0.0246(6) 0.0244(6) 0.0018(5) 0.0027(4) 0.0037(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.2726(13) . ? N1 C5 1.4812(15) . ? C1 O2 1.2506(14) . ? C1 C2 1.5170(15) . ? N2 C12 1.4963(14) . ? O3 C3 1.2556(14) . ? C3 O4 1.2680(13) . ? C3 C4 1.5171(15) . ? C5 C6 1.5126(15) . ? C6 C7 1.3886(16) . ? C6 C11 1.3945(16) . ? C7 C8 1.3916(16) . ? C8 C9 1.3853(19) . ? C9 C10 1.387(2) . ? C10 C11 1.3829(18) . ? C12 C13 1.5072(15) . ? C13 C18 1.3880(16) . ? C13 C14 1.3958(15) . ? C14 C15 1.3861(16) . ? C15 C16 1.3844(19) . ? C16 C17 1.3839(18) . ? C17 C18 1.3899(16) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 C1 O1 123.92(10) . . ? O2 C1 C2 118.68(10) . . ? O1 C1 C2 117.40(10) . . ? O3 C3 O4 122.60(10) . . ? O3 C3 C4 118.92(10) . . ? O4 C3 C4 118.48(10) . . ? N1 C5 C6 114.07(10) . . ? C7 C6 C11 119.14(10) . . ? C7 C6 C5 123.77(10) . . ? C11 C6 C5 117.10(11) . . ? C6 C7 C8 120.07(11) . . ? C9 C8 C7 120.42(12) . . ? C8 C9 C10 119.64(11) . . ? C11 C10 C9 120.07(12) . . ? C10 C11 C6 120.65(12) . . ? N2 C12 C13 110.94(9) . . ? C18 C13 C14 118.94(10) . . ? C18 C13 C12 121.48(10) . . ? C14 C13 C12 119.58(10) . . ? C15 C14 C13 120.51(11) . . ? C16 C15 C14 119.96(11) . . ? C17 C16 C15 120.10(11) . . ? C16 C17 C18 119.90(12) . . ? C13 C18 C17 120.58(11) . . ? 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 N1 H2N O2 0.962(15) 1.770(15) 2.7254(13) 171.3(13) . N1 H1N O1 0.922(15) 1.900(15) 2.7861(13) 160.6(12) 3_666 N1 H3N O3 0.979(15) 1.730(16) 2.7074(13) 175.6(13) 4_576 N2 H4N O1 0.934(16) 1.917(16) 2.8425(13) 170.7(13) . N2 H5N O4 0.927(14) 1.952(15) 2.8715(13) 171.2(13) . N2 H6N O4 0.963(15) 1.838(15) 2.7951(14) 172.1(13) 2_655 _diffrn_measured_fraction_theta_max 0.915 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.295 _refine_diff_density_min -0.226 _refine_diff_density_rms 0.039 #END data_8 _database_code_depnum_ccdc_archive 'CCDC 762144' #TrackingRef 'C000922A.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'benzylammonium proprionate hydrate' _chemical_melting_point ? _chemical_formula_moiety 'C7 H10 N + , C3 H5 O2 -, H2 O' _chemical_formula_sum 'C10 H17 N O3' _chemical_formula_weight 199.25 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/c 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 12.0457(3) _cell_length_b 5.88960(10) _cell_length_c 15.8690(4) _cell_angle_alpha 90.00 _cell_angle_beta 102.0770(10) _cell_angle_gamma 90.00 _cell_volume 1100.90(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3179 _cell_measurement_theta_min 2.625 _cell_measurement_theta_max 27.924 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.202 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 432 _exptl_absorpt_coefficient_mu 0.088 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9810 _exptl_absorpt_correction_T_max 0.9982 _exptl_absorpt_process_details '(SADABS; Bruker, 2002)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX CCD area-detector' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% . _diffrn_reflns_number 4281 _diffrn_reflns_av_R_equivalents 0.0634 _diffrn_reflns_av_sigmaI/netI 0.0352 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.73 _diffrn_reflns_theta_max 25.00 _reflns_number_total 1709 _reflns_number_gt 1550 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX II, Bruker 2007' _computing_cell_refinement 'APEX II, Bruker 2007' _computing_data_reduction 'APEX II, Bruker 2007' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. Ammonium hydrogen atoms were located in the difference map. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0693P)^2^+0.1930P] 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 1709 _refine_ls_number_parameters 148 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0409 _refine_ls_R_factor_gt 0.0381 _refine_ls_wR_factor_ref 0.1072 _refine_ls_wR_factor_gt 0.1039 _refine_ls_goodness_of_fit_ref 1.028 _refine_ls_restrained_S_all 1.028 _refine_ls_shift/su_max 0.007 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.10554(8) 0.32017(15) 0.43156(5) 0.0252(3) Uani 1 1 d . . . O2 O 0.10601(8) 0.04668(15) 0.33553(5) 0.0206(3) Uani 1 1 d . . . C1 C 0.11621(10) 0.1151(2) 0.41241(8) 0.0185(3) Uani 1 1 d . . . C2 C 0.14582(12) -0.0575(2) 0.48410(8) 0.0235(3) Uani 1 1 d . . . H2B H 0.0988 -0.1950 0.4684 0.028 Uiso 1 1 calc R . . H2A H 0.1276 0.0061 0.5374 0.028 Uiso 1 1 calc R . . C3 C 0.27053(13) -0.1233(3) 0.50146(9) 0.0328(4) Uani 1 1 d . . . H3B H 0.2877 -0.1959 0.4501 0.049 Uiso 1 1 calc R . . H3A H 0.2869 -0.2294 0.5501 0.049 Uiso 1 1 calc R . . H3C H 0.3174 0.0131 0.5154 0.049 Uiso 1 1 calc R . . N1 N 0.09842(11) 0.5991(2) 0.28581(7) 0.0196(3) Uani 1 1 d . . . H3N H 0.1103(13) 0.753(3) 0.3073(10) 0.034(4) Uiso 1 1 d . . . H1N H 0.1043(13) 0.495(3) 0.3317(11) 0.033(4) Uiso 1 1 d . . . H2N H 0.0268(15) 0.591(3) 0.2534(11) 0.029(4) Uiso 1 1 d . . . C4 C 0.18218(11) 0.5423(2) 0.23103(8) 0.0223(3) Uani 1 1 d . . . H4B H 0.1691 0.3850 0.2092 0.027 Uiso 1 1 calc R . . H4A H 0.1711 0.6460 0.1808 0.027 Uiso 1 1 calc R . . C5 C 0.30141(11) 0.5644(2) 0.28212(8) 0.0205(3) Uani 1 1 d . . . C6 C 0.35014(12) 0.3903(2) 0.33728(8) 0.0227(3) Uani 1 1 d . . . H6 H 0.3084 0.2554 0.3415 0.027 Uiso 1 1 calc R . . C7 C 0.45925(12) 0.4136(2) 0.38598(9) 0.0270(4) Uani 1 1 d . . . H7 H 0.4918 0.2952 0.4239 0.032 Uiso 1 1 calc R . . C8 C 0.52122(12) 0.6092(3) 0.37966(9) 0.0286(4) Uani 1 1 d . . . H8 H 0.5961 0.6246 0.4131 0.034 Uiso 1 1 calc R . . C9 C 0.47370(12) 0.7823(2) 0.32441(9) 0.0282(4) Uani 1 1 d . . . H9 H 0.5163 0.9158 0.3197 0.034 Uiso 1 1 calc R . . C10 C 0.36405(12) 0.7605(2) 0.27607(8) 0.0240(3) Uani 1 1 d . . . H10 H 0.3315 0.8798 0.2387 0.029 Uiso 1 1 calc R . . O1W O -0.11236(10) 0.54458(19) 0.39447(6) 0.0311(3) Uani 1 1 d . . . H1W H -0.1257(18) 0.590(4) 0.4439(15) 0.064(6) Uiso 1 1 d . . . H2W H -0.0431(18) 0.461(4) 0.4103(12) 0.057(6) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0339(6) 0.0207(5) 0.0222(5) -0.0003(4) 0.0089(4) 0.0027(4) O2 0.0218(5) 0.0225(5) 0.0162(5) -0.0011(3) 0.0012(4) -0.0001(4) C1 0.0135(7) 0.0227(7) 0.0197(6) -0.0007(5) 0.0042(5) -0.0012(5) C2 0.0272(8) 0.0246(8) 0.0192(6) 0.0025(5) 0.0062(6) 0.0022(6) C3 0.0293(9) 0.0363(9) 0.0298(8) 0.0071(6) -0.0009(7) 0.0057(7) N1 0.0195(7) 0.0198(7) 0.0180(6) -0.0003(4) 0.0009(5) 0.0002(5) C4 0.0265(8) 0.0244(8) 0.0163(6) -0.0014(5) 0.0050(6) -0.0004(6) C5 0.0231(8) 0.0231(7) 0.0168(6) -0.0032(5) 0.0072(6) 0.0013(5) C6 0.0231(8) 0.0233(8) 0.0233(7) -0.0002(5) 0.0082(6) -0.0007(6) C7 0.0264(8) 0.0284(8) 0.0261(7) 0.0022(5) 0.0054(6) 0.0062(6) C8 0.0193(8) 0.0358(9) 0.0301(7) -0.0067(6) 0.0037(6) -0.0004(6) C9 0.0280(9) 0.0263(8) 0.0328(7) -0.0056(6) 0.0121(7) -0.0063(6) C10 0.0289(8) 0.0220(8) 0.0235(7) 0.0001(5) 0.0106(6) 0.0009(6) O1W 0.0389(7) 0.0325(6) 0.0213(5) -0.0009(4) 0.0048(5) 0.0030(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.2583(16) . ? O2 C1 1.2662(15) . ? C1 C2 1.5117(17) . ? C2 C3 1.520(2) . ? N1 C4 1.5009(16) . ? C4 C5 1.4999(19) . ? C5 C10 1.3938(19) . ? C5 C6 1.3953(19) . ? C6 C7 1.385(2) . ? C7 C8 1.388(2) . ? C8 C9 1.388(2) . ? C9 C10 1.388(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 O2 122.96(12) . . ? O1 C1 C2 118.92(11) . . ? O2 C1 C2 118.10(11) . . ? C1 C2 C3 112.12(11) . . ? C5 C4 N1 110.56(10) . . ? C10 C5 C6 119.30(13) . . ? C10 C5 C4 120.37(12) . . ? C6 C5 C4 120.33(12) . . ? C7 C6 C5 120.18(13) . . ? C6 C7 C8 120.26(13) . . ? C7 C8 C9 119.90(13) . . ? C10 C9 C8 120.03(13) . . ? C9 C10 C5 120.33(13) . . ? 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 N1 H1N O1 0.943(17) 1.887(17) 2.8234(14) 171.6(14) . N1 H3N O2 0.970(18) 1.789(18) 2.7479(14) 169.3(14) 1_565 N1 H2N O2 0.908(18) 1.917(19) 2.8076(16) 166.2(14) 2 O1W H2W O1 0.96(2) 1.94(2) 2.8873(15) 172.1(18) . O1W H1W O1 0.87(2) 2.01(2) 2.8580(13) 163(2) 3_566 _diffrn_measured_fraction_theta_max 0.886 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.886 _refine_diff_density_max 0.142 _refine_diff_density_min -0.209 _refine_diff_density_rms 0.043 #END data_9 _database_code_depnum_ccdc_archive 'CCDC 762145' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common 'phenylethylammonium diphenylacetate diphenylacetic acid' _chemical_melting_point ? _chemical_formula_moiety 'C14 H12 O2 , C14 H11 O2 - , C8 H12 N +' _chemical_formula_sum 'C36 H35 N O4' _chemical_formula_weight 545.65 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/c 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 28.1285(3) _cell_length_b 10.83670(10) _cell_length_c 9.71540(10) _cell_angle_alpha 90.00 _cell_angle_beta 97.1000(10) _cell_angle_gamma 90.00 _cell_volume 2938.74(5) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5924 _cell_measurement_theta_min 2.828 _cell_measurement_theta_max 29.8975 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.233 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1160 _exptl_absorpt_coefficient_mu 0.080 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9765 _exptl_absorpt_correction_T_max 0.9765 _exptl_absorpt_process_details '(SADABS; Bruker, 2002)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX CCD area-detector' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% . _diffrn_reflns_number 25477 _diffrn_reflns_av_R_equivalents 0.0335 _diffrn_reflns_av_sigmaI/netI 0.0275 _diffrn_reflns_limit_h_min -34 _diffrn_reflns_limit_h_max 34 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 0.73 _diffrn_reflns_theta_max 26.00 _reflns_number_total 5757 _reflns_number_gt 4450 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX II, Bruker 2007' _computing_cell_refinement 'APEX II, Bruker 2007' _computing_data_reduction 'APEX II, Bruker 2007' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0419P)^2^+0.7381P] 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 5757 _refine_ls_number_parameters 386 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0527 _refine_ls_R_factor_gt 0.0375 _refine_ls_wR_factor_ref 0.0982 _refine_ls_wR_factor_gt 0.0889 _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_restrained_S_all 1.029 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.21552(3) 0.20175(8) 0.20702(9) 0.0249(2) Uani 1 1 d . . . O2 O 0.17557(3) 0.33120(9) 0.32754(9) 0.0267(2) Uani 1 1 d . . . C1 C 0.17678(4) 0.25149(11) 0.23772(13) 0.0187(3) Uani 1 1 d . . . C2 C 0.13096(4) 0.20855(11) 0.14815(12) 0.0188(3) Uani 1 1 d . . . H2 H 0.1348 0.2320 0.0506 0.023 Uiso 1 1 calc R . . C3 C 0.12493(4) 0.06874(11) 0.14846(13) 0.0191(3) Uani 1 1 d . . . C4 C 0.13804(4) -0.00196(12) 0.26675(14) 0.0226(3) Uani 1 1 d . . . H4 H 0.1533 0.0364 0.3485 0.027 Uiso 1 1 calc R . . C5 C 0.12903(5) -0.12795(13) 0.26643(15) 0.0280(3) Uani 1 1 d . . . H5 H 0.1380 -0.1752 0.3479 0.034 Uiso 1 1 calc R . . C6 C 0.10700(5) -0.18508(12) 0.14765(16) 0.0291(3) Uani 1 1 d . . . H6 H 0.1007 -0.2712 0.1478 0.035 Uiso 1 1 calc R . . C7 C 0.09428(5) -0.11607(12) 0.02875(15) 0.0278(3) Uani 1 1 d . . . H7 H 0.0793 -0.1549 -0.0530 0.033 Uiso 1 1 calc R . . C8 C 0.10349(4) 0.01016(12) 0.02906(14) 0.0229(3) Uani 1 1 d . . . H8 H 0.0950 0.0569 -0.0531 0.027 Uiso 1 1 calc R . . C9 C 0.08702(4) 0.27765(11) 0.18435(13) 0.0202(3) Uani 1 1 d . . . C10 C 0.05705(5) 0.22982(12) 0.27456(14) 0.0250(3) Uani 1 1 d . . . H10 H 0.0633 0.1501 0.3134 0.030 Uiso 1 1 calc R . . C11 C 0.01803(5) 0.29673(13) 0.30894(16) 0.0326(3) Uani 1 1 d . . . H11 H -0.0019 0.2630 0.3717 0.039 Uiso 1 1 calc R . . C12 C 0.00807(5) 0.41220(13) 0.25218(16) 0.0319(3) Uani 1 1 d . . . H12 H -0.0188 0.4576 0.2748 0.038 Uiso 1 1 calc R . . C13 C 0.03760(5) 0.46123(13) 0.16214(15) 0.0299(3) Uani 1 1 d . . . H13 H 0.0310 0.5406 0.1229 0.036 Uiso 1 1 calc R . . C14 C 0.07681(5) 0.39468(12) 0.12904(13) 0.0250(3) Uani 1 1 d . . . H14 H 0.0970 0.4295 0.0677 0.030 Uiso 1 1 calc R . . O4 O 0.32931(3) 0.19097(9) 0.16311(9) 0.0270(2) Uani 1 1 d . . . O3 O 0.29183(3) 0.27974(8) 0.32657(9) 0.0248(2) Uani 1 1 d . . . H3 H 0.2567(8) 0.2462(17) 0.269(2) 0.083(7) Uiso 1 1 d . . . C15 C 0.32998(4) 0.24840(11) 0.27126(13) 0.0187(3) Uani 1 1 d . . . C16 C 0.37626(4) 0.29173(11) 0.35725(12) 0.0185(3) Uani 1 1 d . . . H16 H 0.3740 0.2677 0.4556 0.022 Uiso 1 1 calc R . . C17 C 0.41962(4) 0.22523(11) 0.31366(12) 0.0191(3) Uani 1 1 d . . . C18 C 0.44772(5) 0.27408(12) 0.21914(14) 0.0246(3) Uani 1 1 d . . . H18 H 0.4408 0.3540 0.1818 0.030 Uiso 1 1 calc R . . C19 C 0.48590(5) 0.20749(13) 0.17848(16) 0.0309(3) Uani 1 1 d . . . H19 H 0.5046 0.2419 0.1130 0.037 Uiso 1 1 calc R . . C20 C 0.49678(5) 0.09184(13) 0.23264(15) 0.0305(3) Uani 1 1 d . . . H20 H 0.5231 0.0469 0.2056 0.037 Uiso 1 1 calc R . . C21 C 0.46901(5) 0.04175(13) 0.32691(14) 0.0298(3) Uani 1 1 d . . . H21 H 0.4763 -0.0379 0.3646 0.036 Uiso 1 1 calc R . . C22 C 0.43073(5) 0.10761(12) 0.36621(13) 0.0254(3) Uani 1 1 d . . . H22 H 0.4117 0.0720 0.4301 0.030 Uiso 1 1 calc R . . C23 C 0.37896(4) 0.43237(11) 0.35377(13) 0.0190(3) Uani 1 1 d . . . C24 C 0.36350(4) 0.49876(12) 0.23403(14) 0.0239(3) Uani 1 1 d . . . H24 H 0.3513 0.4560 0.1518 0.029 Uiso 1 1 calc R . . C25 C 0.36570(5) 0.62708(13) 0.23332(16) 0.0302(3) Uani 1 1 d . . . H25 H 0.3546 0.6715 0.1513 0.036 Uiso 1 1 calc R . . C26 C 0.38399(5) 0.68993(13) 0.35198(16) 0.0320(3) Uani 1 1 d . . . H26 H 0.3857 0.7775 0.3515 0.038 Uiso 1 1 calc R . . C27 C 0.39973(5) 0.62482(13) 0.47164(15) 0.0298(3) Uani 1 1 d . . . H27 H 0.4125 0.6679 0.5530 0.036 Uiso 1 1 calc R . . C28 C 0.39685(4) 0.49637(12) 0.47317(14) 0.0237(3) Uani 1 1 d . . . H28 H 0.4072 0.4524 0.5561 0.028 Uiso 1 1 calc R . . N1 N 0.24955(4) 0.43337(10) 0.50798(12) 0.0199(2) Uani 1 1 d . . . H1N H 0.2756(6) 0.3825(14) 0.5175(14) 0.029(4) Uiso 1 1 d . . . H2N H 0.2272(6) 0.4054(14) 0.4352(17) 0.037(4) Uiso 1 1 d . . . H3N H 0.2348(6) 0.4219(14) 0.5852(17) 0.037(4) Uiso 1 1 d . . . C29 C 0.26474(5) 0.56285(11) 0.49249(13) 0.0219(3) Uani 1 1 d . . . H29A H 0.2807 0.5711 0.4076 0.026 Uiso 1 1 calc R . . H29B H 0.2880 0.5866 0.5730 0.026 Uiso 1 1 calc R . . C30 C 0.22159(5) 0.64746(11) 0.48316(14) 0.0227(3) Uani 1 1 d . . . H30A H 0.2006 0.6302 0.3958 0.027 Uiso 1 1 calc R . . H30B H 0.2032 0.6293 0.5612 0.027 Uiso 1 1 calc R . . C31 C 0.23503(5) 0.78250(12) 0.48711(13) 0.0215(3) Uani 1 1 d . . . C32 C 0.26391(5) 0.83354(12) 0.39522(14) 0.0248(3) Uani 1 1 d . . . H32 H 0.2759 0.7825 0.3279 0.030 Uiso 1 1 calc R . . C33 C 0.27526(5) 0.95844(12) 0.40113(14) 0.0284(3) Uani 1 1 d . . . H33 H 0.2949 0.9923 0.3377 0.034 Uiso 1 1 calc R . . C34 C 0.25809(5) 1.03375(13) 0.49902(14) 0.0292(3) Uani 1 1 d . . . H34 H 0.2659 1.1191 0.5029 0.035 Uiso 1 1 calc R . . C35 C 0.22959(5) 0.98404(12) 0.59101(14) 0.0287(3) Uani 1 1 d . . . H35 H 0.2177 1.0353 0.6584 0.034 Uiso 1 1 calc R . . C36 C 0.21824(5) 0.85933(12) 0.58521(13) 0.0251(3) Uani 1 1 d . . . H36 H 0.1987 0.8260 0.6492 0.030 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0149(5) 0.0278(5) 0.0326(5) -0.0095(4) 0.0050(4) -0.0017(4) O2 0.0199(5) 0.0320(5) 0.0285(5) -0.0111(4) 0.0032(4) -0.0009(4) C1 0.0180(6) 0.0190(6) 0.0198(6) 0.0009(5) 0.0053(5) -0.0026(5) C2 0.0179(6) 0.0198(6) 0.0187(6) 0.0006(5) 0.0025(5) -0.0010(5) C3 0.0123(6) 0.0203(6) 0.0253(7) -0.0012(5) 0.0054(5) 0.0004(5) C4 0.0151(6) 0.0256(7) 0.0274(7) 0.0017(5) 0.0030(5) -0.0001(5) C5 0.0179(7) 0.0266(7) 0.0402(8) 0.0094(6) 0.0066(6) 0.0024(6) C6 0.0178(7) 0.0183(7) 0.0527(9) -0.0007(6) 0.0105(6) -0.0006(5) C7 0.0199(7) 0.0264(7) 0.0377(8) -0.0098(6) 0.0061(6) -0.0034(6) C8 0.0183(6) 0.0242(7) 0.0264(7) -0.0015(5) 0.0039(5) 0.0001(5) C9 0.0163(6) 0.0206(7) 0.0227(6) -0.0028(5) -0.0017(5) -0.0012(5) C10 0.0196(7) 0.0200(7) 0.0359(8) 0.0004(6) 0.0052(6) -0.0016(5) C11 0.0204(7) 0.0284(8) 0.0509(9) -0.0025(7) 0.0122(7) -0.0024(6) C12 0.0186(7) 0.0275(8) 0.0492(9) -0.0057(7) 0.0018(6) 0.0046(6) C13 0.0298(8) 0.0228(7) 0.0350(8) 0.0011(6) -0.0044(6) 0.0064(6) C14 0.0273(7) 0.0227(7) 0.0243(7) 0.0013(5) 0.0011(6) 0.0001(6) O4 0.0197(5) 0.0367(6) 0.0250(5) -0.0109(4) 0.0046(4) -0.0021(4) O3 0.0153(5) 0.0309(5) 0.0291(5) -0.0089(4) 0.0066(4) -0.0016(4) C15 0.0180(6) 0.0167(6) 0.0222(6) 0.0020(5) 0.0052(5) -0.0002(5) C16 0.0167(6) 0.0209(6) 0.0181(6) 0.0007(5) 0.0023(5) -0.0003(5) C17 0.0153(6) 0.0216(7) 0.0197(6) -0.0034(5) -0.0004(5) -0.0009(5) C18 0.0200(7) 0.0193(7) 0.0352(8) 0.0005(6) 0.0060(6) -0.0005(5) C19 0.0220(7) 0.0288(8) 0.0444(9) -0.0014(7) 0.0137(6) -0.0017(6) C20 0.0197(7) 0.0303(8) 0.0416(8) -0.0045(6) 0.0038(6) 0.0065(6) C21 0.0309(8) 0.0259(7) 0.0318(8) 0.0020(6) 0.0009(6) 0.0094(6) C22 0.0281(7) 0.0253(7) 0.0229(7) 0.0027(5) 0.0034(6) 0.0028(6) C23 0.0128(6) 0.0195(6) 0.0258(7) -0.0016(5) 0.0066(5) 0.0002(5) C24 0.0173(6) 0.0264(7) 0.0283(7) 0.0017(5) 0.0044(5) -0.0006(5) C25 0.0205(7) 0.0264(7) 0.0447(9) 0.0101(6) 0.0082(6) 0.0022(6) C26 0.0241(7) 0.0181(7) 0.0560(10) -0.0016(6) 0.0139(7) -0.0007(6) C27 0.0234(7) 0.0266(7) 0.0407(8) -0.0114(6) 0.0093(6) -0.0031(6) C28 0.0193(7) 0.0248(7) 0.0277(7) -0.0033(5) 0.0058(6) 0.0001(5) N1 0.0193(6) 0.0168(6) 0.0240(6) 0.0003(5) 0.0038(5) 0.0014(5) C29 0.0218(7) 0.0181(6) 0.0263(7) 0.0004(5) 0.0048(5) -0.0009(5) C30 0.0204(7) 0.0213(7) 0.0267(7) 0.0000(5) 0.0045(5) 0.0001(5) C31 0.0192(6) 0.0193(6) 0.0246(7) 0.0005(5) -0.0027(5) 0.0016(5) C32 0.0253(7) 0.0221(7) 0.0270(7) -0.0005(5) 0.0027(6) -0.0001(6) C33 0.0282(7) 0.0257(7) 0.0301(7) 0.0058(6) -0.0009(6) -0.0051(6) C34 0.0343(8) 0.0175(7) 0.0325(8) 0.0008(6) -0.0083(6) -0.0021(6) C35 0.0333(8) 0.0228(7) 0.0284(7) -0.0049(6) -0.0029(6) 0.0054(6) C36 0.0258(7) 0.0244(7) 0.0247(7) 0.0001(6) 0.0015(6) 0.0019(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 O1 C1 1.2834(15) . ? O2 C1 1.2313(15) . ? C1 C2 1.5356(17) . ? C2 C9 1.5229(17) . ? C2 C3 1.5246(17) . ? C3 C4 1.3924(18) . ? C3 C8 1.3927(18) . ? C4 C5 1.3886(18) . ? C5 C6 1.386(2) . ? C6 C7 1.385(2) . ? C7 C8 1.3922(18) . ? C9 C10 1.3893(18) . ? C9 C14 1.3934(18) . ? C10 C11 1.3903(19) . ? C11 C12 1.382(2) . ? C12 C13 1.385(2) . ? C13 C14 1.3882(19) . ? O4 C15 1.2194(15) . ? O3 C15 1.3032(15) . ? C15 C16 1.5309(17) . ? C16 C17 1.5212(17) . ? C16 C23 1.5265(17) . ? C17 C18 1.3884(18) . ? C17 C22 1.3942(18) . ? C18 C19 1.3911(18) . ? C19 C20 1.379(2) . ? C20 C21 1.386(2) . ? C21 C22 1.3843(19) . ? C23 C24 1.3910(18) . ? C23 C28 1.3913(18) . ? C24 C25 1.3920(19) . ? C25 C26 1.382(2) . ? C26 C27 1.385(2) . ? C27 C28 1.3945(19) . ? N1 C29 1.4798(16) . ? C29 C30 1.5149(18) . ? C30 C31 1.5107(17) . ? C31 C36 1.3914(18) . ? C31 C32 1.3936(18) . ? C32 C33 1.3902(18) . ? C33 C34 1.3846(19) . ? C34 C35 1.3816(19) . ? C35 C36 1.3882(19) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 C1 O1 123.92(12) . . ? O2 C1 C2 121.29(11) . . ? O1 C1 C2 114.73(10) . . ? C9 C2 C3 113.24(10) . . ? C9 C2 C1 111.62(10) . . ? C3 C2 C1 112.69(10) . . ? C4 C3 C8 118.68(12) . . ? C4 C3 C2 122.03(11) . . ? C8 C3 C2 119.21(11) . . ? C5 C4 C3 120.64(12) . . ? C6 C5 C4 120.23(13) . . ? C7 C6 C5 119.72(13) . . ? C6 C7 C8 119.99(13) . . ? C7 C8 C3 120.72(12) . . ? C10 C9 C14 118.07(12) . . ? C10 C9 C2 122.36(11) . . ? C14 C9 C2 119.54(11) . . ? C9 C10 C11 121.04(13) . . ? C12 C11 C10 120.23(13) . . ? C11 C12 C13 119.45(13) . . ? C12 C13 C14 120.19(13) . . ? C13 C14 C9 121.02(13) . . ? O4 C15 O3 124.23(12) . . ? O4 C15 C16 123.25(11) . . ? O3 C15 C16 112.52(10) . . ? C17 C16 C23 115.02(10) . . ? C17 C16 C15 111.08(10) . . ? C23 C16 C15 109.60(10) . . ? C18 C17 C22 118.07(12) . . ? C18 C17 C16 123.03(11) . . ? C22 C17 C16 118.84(11) . . ? C17 C18 C19 120.85(12) . . ? C20 C19 C18 120.38(13) . . ? C19 C20 C21 119.45(13) . . ? C22 C21 C20 120.10(13) . . ? C21 C22 C17 121.15(13) . . ? C24 C23 C28 118.88(12) . . ? C24 C23 C16 121.57(11) . . ? C28 C23 C16 119.54(11) . . ? C23 C24 C25 120.75(13) . . ? C26 C25 C24 120.02(13) . . ? C25 C26 C27 119.76(13) . . ? C26 C27 C28 120.30(13) . . ? C23 C28 C27 120.27(13) . . ? N1 C29 C30 109.92(11) . . ? C31 C30 C29 112.87(11) . . ? C36 C31 C32 118.39(12) . . ? C36 C31 C30 119.47(12) . . ? C32 C31 C30 122.15(11) . . ? C33 C32 C31 120.60(12) . . ? C34 C33 C32 120.29(13) . . ? C35 C34 C33 119.61(13) . . ? C34 C35 C36 120.15(13) . . ? C35 C36 C31 120.97(13) . . ? 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 N1 H2N O2 0.937(17) 1.863(17) 2.7798(14) 165.3(14) . N1 H1N O3 0.913(16) 2.258(14) 2.7947(14) 117.1(11) . O3 H3 O1 1.13(2) 1.33(2) 2.4605(13) 176.8(18) . N1 H3N O1 0.910(16) 1.910(16) 2.6939(14) 143.2(14) 4_566 N1 H1N O4 0.913(16) 2.095(16) 2.8783(15) 143.3(12) 4_566 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.225 _refine_diff_density_min -0.191 _refine_diff_density_rms 0.036