# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2001 # CCDC Number: 440/224 data_global _audit_creation_method SHELXL-97 _publ_contact_author_name 'Dr. Thomas Steiner' _publ_contact_author_address ; Institut f\"ur Chemie - Kristallographie Freie Universit\"at Berlin Takustra\sse 6 D-14195 Berlin Germany ; _publ_contact_author_email steiner@chemie.fu-berlin.de _publ_contact_letter ; This file contains in one stream CIFs of three crystal structures which are part of a manuscript submitted to New J. Chem. on June 16, 2000 ; _publ_requested_journal 'New Journal of Chemistry' _publ_section_title ; Making very short O-H...Ph hydrogen bonds: the example of tetraphenylborate salts ; loop_ _publ_author_name _publ_author_address 'Steiner, Thomas' ; Institut f\"ur Chemie - Kristallographie Freie Universit\"at Berlin Takustr. 6 D-14195 Berlin Germany ; 'Schreurs, Antoine M. M.' ; Bijvoet Center for Biomolecular Research Department of Crystal and Structural Chemistry Utrecht University Padualaan 8 3584 CH Utrecht The Netherlands ; 'Lutz, Martin' ; Bijvoet Center for Biomolecular Research Department of Crystal and Structural Chemistry Utrecht University Padualaan 8 3584 CH Utrecht The Netherlands ; 'Kroon, Jan' ; Bijvoet Center for Biomolecular Research Department of Crystal and Structural Chemistry Utrecht University Padualaan 8 3584 CH Utrecht The Netherlands ; data_(I) _audit_creation_method SHELXL-97 _chemical_name_systematic ; choline tetraphenylborate ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C29 H34 B N O' _chemical_formula_weight 423.38 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' 'B' 'B' 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21 /c' 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 9.743(2) _cell_length_b 13.474(7) _cell_length_c 18.902(11) _cell_angle_alpha 90.00 _cell_angle_beta 107.08(3) _cell_angle_gamma 90.00 _cell_volume 2372.0(19) _cell_formula_units_Z 4 _cell_measurement_temperature 125(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.186 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 912 _exptl_absorpt_coefficient_mu 0.070 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; twinned crystal, reflection data collected for both lattice orientation, twin refinement with SHELXL-97 ; _diffrn_ambient_temperature 125(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 'Nonius Kappa CCD' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 44261 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0742 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.89 _diffrn_reflns_theta_max 25.00 _reflns_number_total 44261 _reflns_number_gt 28347 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _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^)+(0.0489P)^2^+5.4720P] 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 44261 _refine_ls_number_parameters 294 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1526 _refine_ls_R_factor_gt 0.0871 _refine_ls_wR_factor_ref 0.2231 _refine_ls_wR_factor_gt 0.1811 _refine_ls_goodness_of_fit_ref 1.144 _refine_ls_restrained_S_all 1.144 _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 O O 0.22763(15) 0.43157(9) 0.45942(8) 0.0407(4) Uani 1 1 d . . . H1O H 0.231(3) 0.4815(19) 0.4277(15) 0.126(11) Uiso 1 1 d . . . N N 0.17471(14) 0.21749(8) 0.40237(7) 0.0198(3) Uani 1 1 d . . . C1 C 0.0893(2) 0.39307(11) 0.42377(10) 0.0321(5) Uani 1 1 d . . . H1A H 0.0648 0.4055 0.3699 0.038 Uiso 1 1 calc R . . H1B H 0.0171 0.4271 0.4427 0.038 Uiso 1 1 calc R . . C2 C 0.08584(19) 0.28268(10) 0.43788(10) 0.0265(4) Uani 1 1 d . . . H2A H -0.0152 0.2602 0.4201 0.032 Uiso 1 1 calc R . . H2B H 0.1193 0.2717 0.4920 0.032 Uiso 1 1 calc R . . C3 C 0.33148(18) 0.23127(13) 0.43789(11) 0.0397(5) Uani 1 1 d . . . H3A H 0.3543 0.2179 0.4911 0.060 Uiso 1 1 calc R . . H3B H 0.3583 0.2997 0.4303 0.060 Uiso 1 1 calc R . . H3C H 0.3851 0.1853 0.4157 0.060 Uiso 1 1 calc R . . C4 C 0.1410(2) 0.23744(12) 0.32137(9) 0.0335(5) Uani 1 1 d . . . H4A H 0.0380 0.2281 0.2976 0.050 Uiso 1 1 calc R . . H4B H 0.1953 0.1914 0.2996 0.050 Uiso 1 1 calc R . . H4C H 0.1677 0.3058 0.3137 0.050 Uiso 1 1 calc R . . C5 C 0.1354(2) 0.11194(10) 0.41409(11) 0.0399(5) Uani 1 1 d . . . H5A H 0.0326 0.1018 0.3902 0.060 Uiso 1 1 calc R . . H5B H 0.1575 0.0987 0.4672 0.060 Uiso 1 1 calc R . . H5C H 0.1906 0.0666 0.3924 0.060 Uiso 1 1 calc R . . B B 0.8201(2) 0.25524(13) 0.08768(10) 0.0171(4) Uani 1 1 d . . . C11 C 0.99548(16) 0.25472(11) 0.11148(8) 0.0172(4) Uani 1 1 d . . . C12 C 1.07565(18) 0.16659(11) 0.11654(9) 0.0206(4) Uani 1 1 d . . . H12 H 1.0256 0.1052 0.1083 0.025 Uiso 1 1 calc R . . C13 C 1.22361(18) 0.16501(12) 0.13288(9) 0.0255(4) Uani 1 1 d . . . H13 H 1.2724 0.1033 0.1364 0.031 Uiso 1 1 calc R . . C14 C 1.30109(17) 0.25250(13) 0.14404(9) 0.0262(4) Uani 1 1 d . . . H14 H 1.4028 0.2518 0.1556 0.031 Uiso 1 1 calc R . . C15 C 1.22669(18) 0.34105(12) 0.13798(9) 0.0253(4) Uani 1 1 d . . . H15 H 1.2777 0.4021 0.1448 0.030 Uiso 1 1 calc R . . C16 C 1.07899(18) 0.34166(11) 0.12218(9) 0.0207(4) Uani 1 1 d . . . H16 H 1.0315 0.4039 0.1184 0.025 Uiso 1 1 calc R . . C21 C 0.75602(17) 0.35116(10) 0.12306(9) 0.0161(4) Uani 1 1 d . . . C22 C 0.62296(17) 0.39391(10) 0.08662(9) 0.0195(4) Uani 1 1 d . . . H22 H 0.5733 0.3714 0.0382 0.023 Uiso 1 1 calc R . . C23 C 0.56019(18) 0.46805(11) 0.11828(10) 0.0230(4) Uani 1 1 d . . . H23 H 0.4698 0.4950 0.0914 0.028 Uiso 1 1 calc R . . C24 C 0.6294(2) 0.50234(11) 0.18872(10) 0.0240(4) Uani 1 1 d . . . H24 H 0.5863 0.5517 0.2111 0.029 Uiso 1 1 calc R . . C25 C 0.76154(19) 0.46389(11) 0.22580(10) 0.0236(4) Uani 1 1 d . . . H25 H 0.8117 0.4884 0.2735 0.028 Uiso 1 1 calc R . . C26 C 0.82250(18) 0.38897(11) 0.19367(9) 0.0207(4) Uani 1 1 d . . . H26 H 0.9130 0.3626 0.2210 0.025 Uiso 1 1 calc R . . C31 C 0.75448(17) 0.15744(10) 0.12028(9) 0.0161(4) Uani 1 1 d . . . C32 C 0.83059(18) 0.10498(11) 0.18384(9) 0.0201(4) Uani 1 1 d . . . H32 H 0.9270 0.1238 0.2080 0.024 Uiso 1 1 calc R . . C33 C 0.77099(19) 0.02603(11) 0.21332(9) 0.0231(4) Uani 1 1 d . . . H33 H 0.8269 -0.0073 0.2565 0.028 Uiso 1 1 calc R . . C34 C 0.6327(2) -0.00290(11) 0.18001(10) 0.0247(4) Uani 1 1 d . . . H34 H 0.5920 -0.0564 0.1998 0.030 Uiso 1 1 calc R . . C35 C 0.55237(18) 0.04625(11) 0.11730(10) 0.0232(4) Uani 1 1 d . . . H35 H 0.4562 0.0265 0.0936 0.028 Uiso 1 1 calc R . . C36 C 0.61294(17) 0.12507(11) 0.08876(9) 0.0203(4) Uani 1 1 d . . . H36 H 0.5554 0.1583 0.0460 0.024 Uiso 1 1 calc R . . C41 C 0.76760(16) 0.25864(11) -0.00360(8) 0.0171(4) Uani 1 1 d . . . C42 C 0.73237(18) 0.17454(11) -0.04886(9) 0.0223(4) Uani 1 1 d . . . H42 H 0.7330 0.1117 -0.0259 0.027 Uiso 1 1 calc R . . C43 C 0.69655(18) 0.17828(13) -0.12568(10) 0.0276(4) Uani 1 1 d . . . H43 H 0.6716 0.1191 -0.1538 0.033 Uiso 1 1 calc R . . C44 C 0.69718(18) 0.26768(13) -0.16115(10) 0.0305(4) Uani 1 1 d . . . H44 H 0.6738 0.2707 -0.2136 0.037 Uiso 1 1 calc R . . C45 C 0.73270(18) 0.35299(12) -0.11866(10) 0.0270(4) Uani 1 1 d . . . H45 H 0.7336 0.4152 -0.1421 0.032 Uiso 1 1 calc R . . C46 C 0.76674(17) 0.34802(11) -0.04254(9) 0.0219(4) Uani 1 1 d . . . H46 H 0.7908 0.4078 -0.0150 0.026 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 O 0.0556(10) 0.0298(8) 0.0388(9) -0.0018(7) 0.0170(8) -0.0179(7) N 0.0215(8) 0.0156(7) 0.0224(8) -0.0015(6) 0.0065(7) 0.0015(6) C1 0.0384(12) 0.0165(9) 0.0440(13) -0.0010(8) 0.0162(11) -0.0011(8) C2 0.0299(11) 0.0191(8) 0.0356(11) -0.0033(8) 0.0179(10) 0.0005(8) C3 0.0203(10) 0.0496(12) 0.0435(12) -0.0124(10) 0.0006(9) 0.0070(9) C4 0.0486(12) 0.0323(11) 0.0178(10) 0.0002(9) 0.0070(9) 0.0089(10) C5 0.0599(14) 0.0088(8) 0.0622(15) 0.0011(9) 0.0353(13) 0.0001(9) B 0.0212(10) 0.0107(8) 0.0214(10) -0.0034(9) 0.0096(8) -0.0018(9) C11 0.0255(9) 0.0151(8) 0.0131(8) 0.0012(8) 0.0087(7) 0.0023(8) C12 0.0256(11) 0.0157(9) 0.0233(11) 0.0019(8) 0.0114(9) 0.0001(8) C13 0.0260(11) 0.0245(10) 0.0300(11) 0.0088(8) 0.0145(9) 0.0112(8) C14 0.0170(9) 0.0396(11) 0.0231(9) 0.0002(9) 0.0075(8) 0.0005(10) C15 0.0234(11) 0.0267(10) 0.0271(11) -0.0080(8) 0.0096(9) -0.0078(8) C16 0.0251(11) 0.0139(8) 0.0255(11) -0.0028(8) 0.0110(9) 0.0014(8) C21 0.0186(9) 0.0104(8) 0.0213(10) 0.0029(7) 0.0090(8) -0.0030(7) C22 0.0201(10) 0.0152(8) 0.0232(10) -0.0035(7) 0.0066(9) -0.0022(7) C23 0.0178(10) 0.0201(9) 0.0331(12) 0.0025(8) 0.0106(9) 0.0003(8) C24 0.0295(11) 0.0147(8) 0.0352(12) -0.0015(8) 0.0212(10) 0.0017(8) C25 0.0334(12) 0.0191(9) 0.0209(10) -0.0028(8) 0.0118(9) -0.0026(8) C26 0.0268(11) 0.0168(9) 0.0198(10) 0.0044(8) 0.0090(9) 0.0038(8) C31 0.0194(10) 0.0121(8) 0.0189(10) -0.0042(8) 0.0087(8) 0.0029(8) C32 0.0209(10) 0.0214(9) 0.0190(10) -0.0042(8) 0.0074(9) -0.0011(8) C33 0.0306(12) 0.0199(9) 0.0212(11) 0.0027(8) 0.0114(9) 0.0017(8) C34 0.0289(11) 0.0190(8) 0.0325(12) 0.0015(8) 0.0189(10) -0.0016(9) C35 0.0174(10) 0.0228(9) 0.0322(12) -0.0019(9) 0.0114(9) 0.0003(8) C36 0.0191(10) 0.0175(9) 0.0249(10) 0.0042(8) 0.0076(9) 0.0065(8) C41 0.0147(8) 0.0142(8) 0.0237(9) -0.0004(8) 0.0080(7) 0.0029(7) C42 0.0266(10) 0.0174(9) 0.0257(11) 0.0007(8) 0.0119(9) -0.0032(8) C43 0.0275(11) 0.0308(10) 0.0268(12) -0.0084(9) 0.0114(9) -0.0098(8) C44 0.0263(11) 0.0459(13) 0.0211(10) 0.0041(9) 0.0095(8) 0.0044(9) C45 0.0333(11) 0.0231(10) 0.0286(11) 0.0064(9) 0.0154(10) 0.0086(8) C46 0.0286(11) 0.0147(9) 0.0250(11) -0.0013(8) 0.0121(9) 0.0019(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 O C1 1.416(2) . ? O H1O 0.91(3) . ? N C3 1.489(2) . ? N C4 1.493(2) . ? N C5 1.5060(19) . ? N C2 1.5209(18) . ? C1 C2 1.513(2) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3 H3C 0.9800 . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? B C11 1.634(2) . ? B C41 1.650(3) . ? B C21 1.659(2) . ? B C31 1.660(2) . ? C11 C16 1.407(2) . ? C11 C12 1.409(2) . ? C12 C13 1.383(2) . ? C12 H12 0.9500 . ? C13 C14 1.382(2) . ? C13 H13 0.9500 . ? C14 C15 1.383(2) . ? C14 H14 0.9500 . ? C15 C16 1.381(2) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C21 C26 1.397(2) . ? C21 C22 1.401(2) . ? C22 C23 1.395(2) . ? C22 H22 0.9500 . ? C23 C24 1.383(2) . ? C23 H23 0.9500 . ? C24 C25 1.374(2) . ? C24 H24 0.9500 . ? C25 C26 1.397(2) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? C31 C36 1.402(2) . ? C31 C32 1.404(2) . ? C32 C33 1.403(2) . ? C32 H32 0.9500 . ? C33 C34 1.366(2) . ? C33 H33 0.9500 . ? C34 C35 1.382(2) . ? C34 H34 0.9500 . ? C35 C36 1.398(2) . ? C35 H35 0.9500 . ? C36 H36 0.9500 . ? C41 C42 1.401(2) . ? C41 C46 1.410(2) . ? C42 C43 1.391(2) . ? C42 H42 0.9500 . ? C43 C44 1.379(2) . ? C43 H43 0.9500 . ? C44 C45 1.387(2) . ? C44 H44 0.9500 . ? C45 C46 1.380(2) . ? C45 H45 0.9500 . ? C46 H46 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O H1O 100.0(17) . . ? C3 N C4 109.11(13) . . ? C3 N C5 108.84(13) . . ? C4 N C5 109.40(13) . . ? C3 N C2 111.76(13) . . ? C4 N C2 111.50(13) . . ? C5 N C2 106.15(12) . . ? O C1 C2 110.09(14) . . ? O C1 H1A 109.6 . . ? C2 C1 H1A 109.6 . . ? O C1 H1B 109.6 . . ? C2 C1 H1B 109.6 . . ? H1A C1 H1B 108.2 . . ? C1 C2 N 116.41(13) . . ? C1 C2 H2A 108.2 . . ? N C2 H2A 108.2 . . ? C1 C2 H2B 108.2 . . ? N C2 H2B 108.2 . . ? H2A C2 H2B 107.3 . . ? N C3 H3A 109.5 . . ? N C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? N C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? N C4 H4A 109.5 . . ? N C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? N C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? N C5 H5A 109.5 . . ? N C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? N C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C11 B C41 105.42(12) . . ? C11 B C21 112.29(13) . . ? C41 B C21 111.23(14) . . ? C11 B C31 112.33(13) . . ? C41 B C31 112.04(13) . . ? C21 B C31 103.72(11) . . ? C16 C11 C12 113.98(14) . . ? C16 C11 B 123.36(13) . . ? C12 C11 B 122.43(14) . . ? C13 C12 C11 123.29(15) . . ? C13 C12 H12 118.4 . . ? C11 C12 H12 118.4 . . ? C14 C13 C12 120.51(15) . . ? C14 C13 H13 119.7 . . ? C12 C13 H13 119.7 . . ? C13 C14 C15 118.27(15) . . ? C13 C14 H14 120.9 . . ? C15 C14 H14 120.9 . . ? C16 C15 C14 120.69(15) . . ? C16 C15 H15 119.7 . . ? C14 C15 H15 119.7 . . ? C15 C16 C11 123.24(15) . . ? C15 C16 H16 118.4 . . ? C11 C16 H16 118.4 . . ? C26 C21 C22 114.96(14) . . ? C26 C21 B 123.04(15) . . ? C22 C21 B 121.72(15) . . ? C23 C22 C21 122.87(16) . . ? C23 C22 H22 118.6 . . ? C21 C22 H22 118.6 . . ? C24 C23 C22 120.06(17) . . ? C24 C23 H23 120.0 . . ? C22 C23 H23 120.0 . . ? C25 C24 C23 118.97(15) . . ? C25 C24 H24 120.5 . . ? C23 C24 H24 120.5 . . ? C24 C25 C26 120.32(17) . . ? C24 C25 H25 119.8 . . ? C26 C25 H25 119.8 . . ? C21 C26 C25 122.80(17) . . ? C21 C26 H26 118.6 . . ? C25 C26 H26 118.6 . . ? C36 C31 C32 114.44(14) . . ? C36 C31 B 121.83(15) . . ? C32 C31 B 123.59(15) . . ? C33 C32 C31 123.06(16) . . ? C33 C32 H32 118.5 . . ? C31 C32 H32 118.5 . . ? C34 C33 C32 120.03(17) . . ? C34 C33 H33 120.0 . . ? C32 C33 H33 120.0 . . ? C33 C34 C35 119.47(15) . . ? C33 C34 H34 120.3 . . ? C35 C34 H34 120.3 . . ? C34 C35 C36 119.87(16) . . ? C34 C35 H35 120.1 . . ? C36 C35 H35 120.1 . . ? C35 C36 C31 123.14(16) . . ? C35 C36 H36 118.4 . . ? C31 C36 H36 118.4 . . ? C42 C41 C46 114.16(15) . . ? C42 C41 B 124.16(14) . . ? C46 C41 B 121.47(14) . . ? C43 C42 C41 123.35(15) . . ? C43 C42 H42 118.3 . . ? C41 C42 H42 118.3 . . ? C44 C43 C42 120.23(16) . . ? C44 C43 H43 119.9 . . ? C42 C43 H43 119.9 . . ? C43 C44 C45 118.58(16) . . ? C43 C44 H44 120.7 . . ? C45 C44 H44 120.7 . . ? C46 C45 C44 120.42(16) . . ? C46 C45 H45 119.8 . . ? C44 C45 H45 119.8 . . ? C45 C46 C41 123.26(15) . . ? C45 C46 H46 118.4 . . ? C41 C46 H46 118.4 . . ? 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 O H1O C31 0.91(3) 2.56(3) 3.423(2) 160(2) 2_655 O H1O C32 0.91(3) 2.61(3) 3.494(2) 164(2) 2_655 O H1O C33 0.91(3) 2.73(3) 3.508(3) 145(2) 2_655 O H1O C34 0.91(3) 2.74(3) 3.418(3) 132(2) 2_655 O H1O C35 0.91(3) 2.64(3) 3.303(2) 130(2) 2_655 O H1O C36 0.91(3) 2.53(3) 3.297(2) 142(2) 2_655 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.346 _refine_diff_density_min -0.376 _refine_diff_density_rms 0.070 #===END data_(II) _audit_creation_method SHELXL-97 _chemical_name_systematic ; triethanolammonium tetraphenylborate dihydrate ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H40 B N O5' _chemical_formula_weight 505.44 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'B' 'B' 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.2759(6) _cell_length_b 11.6163(4) _cell_length_c 13.0526(6) _cell_angle_alpha 69.066(3) _cell_angle_beta 70.612(2) _cell_angle_gamma 61.747(3) _cell_volume 1378.77(11) _cell_formula_units_Z 2 _cell_measurement_temperature 125(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.217 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 544 _exptl_absorpt_coefficient_mu 0.081 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 125(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 'Nonius Kappa CCD' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13145 _diffrn_reflns_av_R_equivalents 0.0320 _diffrn_reflns_av_sigmaI/netI 0.0305 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.70 _diffrn_reflns_theta_max 27.50 _reflns_number_total 6323 _reflns_number_gt 5125 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _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^)+(0.0400P)^2^+1.1930P] 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 6323 _refine_ls_number_parameters 398 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0692 _refine_ls_R_factor_gt 0.0509 _refine_ls_wR_factor_ref 0.1246 _refine_ls_wR_factor_gt 0.1121 _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_restrained_S_all 1.054 _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 B B 0.25691(17) 0.26280(17) 0.24486(14) 0.0141(3) Uani 1 1 d . . . C11 C 0.30484(15) 0.10042(15) 0.30334(12) 0.0151(3) Uani 1 1 d . . . C21 C 0.25697(17) 0.02158(16) 0.28003(13) 0.0189(3) Uani 1 1 d . . . H21 H 0.1916 0.0651 0.2330 0.019(5) Uiso 1 1 calc R . . C31 C 0.30164(17) -0.11721(17) 0.32314(14) 0.0209(3) Uani 1 1 d . . . H31 H 0.2678 -0.1664 0.3043 0.031(5) Uiso 1 1 calc R . . C41 C 0.39556(18) -0.18382(17) 0.39365(14) 0.0224(3) Uani 1 1 d . . . H41 H 0.4263 -0.2784 0.4233 0.022(5) Uiso 1 1 calc R . . C51 C 0.44393(17) -0.11029(17) 0.42024(14) 0.0208(3) Uani 1 1 d . . . H51 H 0.5076 -0.1544 0.4689 0.028(5) Uiso 1 1 calc R . . C61 C 0.39891(16) 0.02862(16) 0.37541(13) 0.0171(3) Uani 1 1 d . . . H61 H 0.4336 0.0768 0.3946 0.014(4) Uiso 1 1 calc R . . C12 C 0.29188(16) 0.33298(15) 0.31479(12) 0.0147(3) Uani 1 1 d . . . C22 C 0.42303(17) 0.33151(16) 0.29418(13) 0.0183(3) Uani 1 1 d . . . H22 H 0.4925 0.2894 0.2380 0.018(5) Uiso 1 1 calc R . . C32 C 0.45582(17) 0.38903(17) 0.35243(14) 0.0205(3) Uani 1 1 d . . . H32 H 0.5457 0.3863 0.3350 0.030(5) Uiso 1 1 calc R . . C42 C 0.35748(18) 0.45011(16) 0.43575(14) 0.0211(3) Uani 1 1 d . . . H42 H 0.3788 0.4906 0.4750 0.023(5) Uiso 1 1 calc R . . C52 C 0.22745(18) 0.45107(16) 0.46090(14) 0.0210(3) Uani 1 1 d . . . H52 H 0.1596 0.4907 0.5189 0.025(5) Uiso 1 1 calc R . . C62 C 0.19610(16) 0.39379(16) 0.40093(13) 0.0177(3) Uani 1 1 d . . . H62 H 0.1062 0.3962 0.4193 0.027(5) Uiso 1 1 calc R . . C13 C 0.34019(15) 0.28602(15) 0.11344(12) 0.0145(3) Uani 1 1 d . . . C23 C 0.35146(16) 0.40960(16) 0.05493(13) 0.0175(3) Uani 1 1 d . . . H23 H 0.3118 0.4794 0.0931 0.022(5) Uiso 1 1 calc R . . C33 C 0.41836(17) 0.43386(17) -0.05667(13) 0.0201(3) Uani 1 1 d . . . H33 H 0.4223 0.5193 -0.0932 0.022(5) Uiso 1 1 calc R . . C43 C 0.47925(17) 0.33329(17) -0.11443(13) 0.0202(3) Uani 1 1 d . . . H43 H 0.5260 0.3487 -0.1901 0.030(5) Uiso 1 1 calc R . . C53 C 0.47064(17) 0.20981(17) -0.05967(14) 0.0206(3) Uani 1 1 d . . . H53 H 0.5119 0.1400 -0.0980 0.024(5) Uiso 1 1 calc R . . C63 C 0.40156(16) 0.18776(16) 0.05165(13) 0.0181(3) Uani 1 1 d . . . H63 H 0.3959 0.1029 0.0869 0.020(5) Uiso 1 1 calc R . . C14 C 0.08999(15) 0.33312(15) 0.24857(13) 0.0149(3) Uani 1 1 d . . . C24 C 0.02710(16) 0.44319(16) 0.16507(13) 0.0178(3) Uani 1 1 d . . . H24 H 0.0834 0.4775 0.1016 0.026(5) Uiso 1 1 calc R . . C34 C -0.11519(17) 0.50395(17) 0.17210(15) 0.0216(3) Uani 1 1 d . . . H34 H -0.1534 0.5768 0.1132 0.027(5) Uiso 1 1 calc R . . C44 C -0.20070(17) 0.45837(17) 0.26455(15) 0.0235(4) Uani 1 1 d . . . H44 H -0.2975 0.5006 0.2702 0.028(5) Uiso 1 1 calc R . . C54 C -0.14294(17) 0.34995(17) 0.34895(14) 0.0209(3) Uani 1 1 d . . . H54 H -0.2003 0.3173 0.4126 0.026(5) Uiso 1 1 calc R . . C64 C -0.00109(16) 0.28919(16) 0.34012(13) 0.0184(3) Uani 1 1 d . . . H64 H 0.0361 0.2147 0.3985 0.023(5) Uiso 1 1 calc R . . N N 0.12006(14) 0.14654(14) 0.71827(13) 0.0206(3) Uani 1 1 d . . . H10 H 0.096(2) 0.100(2) 0.7847(18) 0.024(5) Uiso 1 1 d . . . O1 O 0.20545(16) 0.08503(18) 0.92022(12) 0.0385(4) Uani 1 1 d . . . H1 H 0.225(3) 0.001(3) 0.945(2) 0.052(8) Uiso 1 1 d . . . O2 O 0.17555(14) -0.13125(14) 0.78588(11) 0.0305(3) Uani 1 1 d . . . H2 H 0.110(3) -0.159(3) 0.823(2) 0.046(7) Uiso 1 1 d . . . O3 O -0.12708(14) 0.16220(14) 0.84876(12) 0.0345(3) Uani 1 1 d . . . H3 H -0.142(3) 0.183(3) 0.921(2) 0.059(8) Uiso 1 1 d . . . C15 C 0.1949(2) 0.2157(2) 0.73311(16) 0.0295(4) Uani 1 1 d . . . H15A H 0.2507 0.2432 0.6601 0.037(6) Uiso 1 1 calc R . . H15B H 0.1273 0.2979 0.7591 0.045(7) Uiso 1 1 calc R . . C25 C 0.2866(2) 0.1255(2) 0.81598(16) 0.0343(5) Uani 1 1 d . . . H25A H 0.3579 0.0453 0.7886 0.041(6) Uiso 1 1 calc R . . H25B H 0.3330 0.1740 0.8257 0.050(7) Uiso 1 1 calc R . . C35 C 0.20842(18) 0.05121(18) 0.64306(15) 0.0244(4) Uani 1 1 d . . . H35A H 0.3054 0.0128 0.6504 0.031(5) Uiso 1 1 calc R . . H35B H 0.2028 0.1007 0.5642 0.031(6) Uiso 1 1 calc R . . C45 C 0.1611(2) -0.06121(19) 0.67411(15) 0.0273(4) Uani 1 1 d . . . H45A H 0.0640 -0.0237 0.6676 0.033(6) Uiso 1 1 calc R . . H45B H 0.2178 -0.1228 0.6236 0.031(5) Uiso 1 1 calc R . . C55 C -0.01146(19) 0.24809(19) 0.67868(16) 0.0299(4) Uani 1 1 d . . . H55A H -0.0381 0.2092 0.6381 0.044(7) Uiso 1 1 calc R . . H55B H 0.0019 0.3293 0.6269 0.041(6) Uiso 1 1 calc R . . C65 C -0.12317(19) 0.28574(19) 0.77923(16) 0.0303(4) Uani 1 1 d . . . H65A H -0.1005 0.3300 0.8180 0.036(6) Uiso 1 1 calc R . . H65B H -0.2126 0.3474 0.7566 0.038(6) Uiso 1 1 calc R . . OW1 O 0.00500(17) 0.22727(17) 0.07497(14) 0.0396(4) Uani 1 1 d . . . H1W1 H 0.074(3) 0.188(3) 0.029(2) 0.050(8) Uiso 1 1 d . . . H2W1 H 0.023(3) 0.278(3) 0.090(3) 0.078(11) Uiso 1 1 d . . . OW2 O 0.69828(15) 0.18664(16) 0.04981(12) 0.0356(3) Uani 1 1 d . . . H1W2 H 0.728(4) 0.186(4) 0.115(3) 0.101(12) Uiso 1 1 d . . . H2W2 H 0.602(4) 0.245(4) 0.050(3) 0.116(14) 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 B 0.0131(8) 0.0142(8) 0.0147(8) -0.0045(6) -0.0016(6) -0.0053(6) C11 0.0139(7) 0.0164(7) 0.0137(7) -0.0051(6) 0.0024(5) -0.0074(6) C21 0.0181(8) 0.0205(8) 0.0193(8) -0.0044(6) -0.0034(6) -0.0091(6) C31 0.0219(8) 0.0211(8) 0.0237(8) -0.0077(7) 0.0004(6) -0.0132(7) C41 0.0234(8) 0.0159(8) 0.0224(8) -0.0020(6) 0.0003(7) -0.0084(7) C51 0.0193(8) 0.0202(8) 0.0192(8) -0.0027(6) -0.0034(6) -0.0068(7) C61 0.0169(7) 0.0192(8) 0.0164(7) -0.0057(6) 0.0001(6) -0.0094(6) C12 0.0175(7) 0.0124(7) 0.0134(7) -0.0006(5) -0.0036(6) -0.0070(6) C22 0.0184(8) 0.0200(8) 0.0163(7) -0.0034(6) -0.0026(6) -0.0088(6) C32 0.0208(8) 0.0221(8) 0.0221(8) 0.0005(6) -0.0077(6) -0.0134(7) C42 0.0304(9) 0.0165(8) 0.0230(8) -0.0026(6) -0.0119(7) -0.0118(7) C52 0.0244(9) 0.0186(8) 0.0193(8) -0.0075(6) -0.0042(6) -0.0059(7) C62 0.0169(8) 0.0178(7) 0.0192(8) -0.0053(6) -0.0026(6) -0.0076(6) C13 0.0119(7) 0.0171(7) 0.0156(7) -0.0041(6) -0.0037(6) -0.0059(6) C23 0.0181(8) 0.0184(8) 0.0172(7) -0.0070(6) -0.0021(6) -0.0073(6) C33 0.0213(8) 0.0210(8) 0.0179(8) -0.0010(6) -0.0034(6) -0.0113(7) C43 0.0175(8) 0.0278(9) 0.0139(7) -0.0050(6) -0.0016(6) -0.0090(7) C53 0.0206(8) 0.0234(8) 0.0189(8) -0.0113(6) -0.0022(6) -0.0065(7) C63 0.0203(8) 0.0166(7) 0.0186(8) -0.0043(6) -0.0035(6) -0.0084(6) C14 0.0147(7) 0.0154(7) 0.0175(7) -0.0083(6) -0.0015(6) -0.0064(6) C24 0.0180(8) 0.0170(7) 0.0208(8) -0.0068(6) -0.0027(6) -0.0080(6) C34 0.0204(8) 0.0186(8) 0.0279(9) -0.0071(7) -0.0108(7) -0.0046(7) C44 0.0148(8) 0.0248(9) 0.0361(10) -0.0151(7) -0.0048(7) -0.0065(7) C54 0.0182(8) 0.0256(8) 0.0253(8) -0.0132(7) 0.0019(6) -0.0128(7) C64 0.0189(8) 0.0208(8) 0.0184(8) -0.0073(6) -0.0026(6) -0.0092(7) N 0.0194(7) 0.0214(7) 0.0225(7) -0.0085(6) -0.0001(6) -0.0099(6) O1 0.0401(8) 0.0482(10) 0.0265(7) -0.0161(7) 0.0010(6) -0.0173(7) O2 0.0317(7) 0.0346(7) 0.0317(7) -0.0053(6) -0.0077(6) -0.0194(6) O3 0.0322(7) 0.0315(7) 0.0309(7) -0.0053(6) 0.0040(6) -0.0142(6) C15 0.0298(10) 0.0324(10) 0.0352(10) -0.0142(8) 0.0014(8) -0.0203(8) C25 0.0307(10) 0.0527(13) 0.0307(10) -0.0179(9) 0.0004(8) -0.0243(10) C35 0.0214(9) 0.0305(9) 0.0232(9) -0.0136(7) 0.0026(7) -0.0114(7) C45 0.0296(9) 0.0326(10) 0.0273(9) -0.0151(8) -0.0009(7) -0.0158(8) C55 0.0229(9) 0.0297(10) 0.0301(10) -0.0046(8) -0.0034(7) -0.0082(8) C65 0.0225(9) 0.0241(9) 0.0354(10) -0.0065(8) 0.0007(8) -0.0070(7) OW1 0.0466(9) 0.0422(9) 0.0405(9) -0.0238(7) 0.0085(7) -0.0275(8) OW2 0.0225(7) 0.0504(9) 0.0275(7) -0.0115(6) -0.0049(6) -0.0083(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 B C11 1.647(2) . ? B C14 1.651(2) . ? B C12 1.652(2) . ? B C13 1.654(2) . ? C11 C61 1.403(2) . ? C11 C21 1.414(2) . ? C21 C31 1.393(2) . ? C31 C41 1.389(2) . ? C41 C51 1.388(2) . ? C51 C61 1.397(2) . ? C12 C62 1.403(2) . ? C12 C22 1.405(2) . ? C22 C32 1.395(2) . ? C32 C42 1.386(2) . ? C42 C52 1.388(2) . ? C52 C62 1.400(2) . ? C13 C63 1.404(2) . ? C13 C23 1.409(2) . ? C23 C33 1.396(2) . ? C33 C43 1.390(2) . ? C43 C53 1.390(2) . ? C53 C63 1.398(2) . ? C14 C24 1.409(2) . ? C14 C64 1.410(2) . ? C24 C34 1.399(2) . ? C34 C44 1.386(2) . ? C44 C54 1.390(3) . ? C54 C64 1.392(2) . ? N C15 1.502(2) . ? N C35 1.505(2) . ? N C55 1.508(2) . ? O1 C25 1.426(2) . ? O2 C45 1.415(2) . ? O3 C65 1.410(2) . ? C15 C25 1.498(3) . ? C35 C45 1.514(2) . ? C55 C65 1.514(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 C11 B C14 109.55(12) . . ? C11 B C12 109.33(12) . . ? C14 B C12 109.04(12) . . ? C11 B C13 109.74(12) . . ? C14 B C13 109.61(12) . . ? C12 B C13 109.55(12) . . ? C61 C11 C21 114.87(14) . . ? C61 C11 B 123.63(13) . . ? C21 C11 B 121.45(14) . . ? C31 C21 C11 122.78(15) . . ? C41 C31 C21 120.15(15) . . ? C51 C41 C31 119.12(15) . . ? C41 C51 C61 119.92(15) . . ? C51 C61 C11 123.15(15) . . ? C62 C12 C22 115.05(14) . . ? C62 C12 B 123.20(13) . . ? C22 C12 B 121.71(13) . . ? C32 C22 C12 122.98(15) . . ? C42 C32 C22 120.13(15) . . ? C32 C42 C52 118.91(15) . . ? C42 C52 C62 120.14(15) . . ? C52 C62 C12 122.76(15) . . ? C63 C13 C23 115.28(14) . . ? C63 C13 B 123.52(13) . . ? C23 C13 B 121.20(13) . . ? C33 C23 C13 122.82(15) . . ? C43 C33 C23 120.09(15) . . ? C53 C43 C33 118.89(15) . . ? C43 C53 C63 120.31(15) . . ? C53 C63 C13 122.60(15) . . ? C24 C14 C64 115.08(14) . . ? C24 C14 B 123.59(13) . . ? C64 C14 B 121.27(14) . . ? C34 C24 C14 122.47(15) . . ? C44 C34 C24 120.33(16) . . ? C34 C44 C54 119.09(15) . . ? C44 C54 C64 119.98(15) . . ? C54 C64 C14 123.04(15) . . ? C15 N C35 112.68(13) . . ? C15 N C55 110.78(14) . . ? C35 N C55 111.71(14) . . ? C25 C15 N 111.46(16) . . ? O1 C25 C15 108.80(16) . . ? N C35 C45 110.18(14) . . ? O2 C45 C35 107.29(14) . . ? N C55 C65 108.85(15) . . ? O3 C65 C55 104.54(15) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N H10 O1 0.88(2) 2.39(2) 2.841(2) 112.3(16) . N H10 O2 0.88(2) 2.39(2) 2.829(2) 111.5(16) . N H10 O3 0.88(2) 2.21(2) 2.700(2) 115.4(16) . O1 H1 OW2 0.85(3) 1.91(3) 2.729(2) 161(3) 2_656 O2 H2 OW1 0.88(3) 1.77(3) 2.633(2) 167(2) 2_556 O3 H3 OW2 0.99(3) 2.01(3) 2.723(2) 127(2) 1_456 OW1 H1W1 O1 0.84(3) 1.95(3) 2.782(2) 168(3) 1_554 OW1 H2W1 C14 0.81(4) 2.77(4) 3.480(2) 147(3) . OW1 H2W1 C24 0.81(4) 2.46(4) 3.260(2) 167(3) . OW1 H2W1 C34 0.81(4) 2.73(4) 3.379(2) 138(3) . OW1 H2W1 C44 0.81(4) 3.24(3) 3.708(2) 119(3) . OW1 H2W1 C54 0.81(4) 3.45(3) 3.877(2) 116(3) . OW1 H2W1 C64 0.81(4) 3.22(3) 3.751(2) 125(3) . OW2 H1W2 O2 1.01(4) 1.72(4) 2.685(2) 159(3) 2_656 OW2 H2W2 C13 0.97(4) 2.64(4) 3.517(2) 151(3) . OW2 H2W2 C23 0.97(4) 2.55(4) 3.517(2) 177(3) . OW2 H2W2 C33 0.97(4) 2.54(4) 3.409(2) 148(3) . OW2 H2W2 C43 0.97(4) 2.58(4) 3.243(2) 126(3) . OW2 H2W2 C53 0.97(4) 2.62(4) 3.195(2) 119(3) . OW2 H2W2 C63 0.97(4) 2.64(4) 3.332(2) 129(3) . _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.375 _refine_diff_density_min -0.251 _refine_diff_density_rms 0.049 #===END data_(III) _audit_creation_method SHELXL-97 _chemical_name_systematic ; 6-ammonium-n-hexanoic acid tetraphenylborate monohydrate ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H36 B N O3' _chemical_formula_weight 469.41 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'B' 'B' 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2 / c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 33.832(16) _cell_length_b 10.11(2) _cell_length_c 17.45(4) _cell_angle_alpha 90.00 _cell_angle_beta 117.750(5) _cell_angle_gamma 90.00 _cell_volume 5283(16) _cell_formula_units_Z 8 _cell_measurement_temperature 125(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description rod _exptl_crystal_colour colorless _exptl_crystal_size_max 0.62 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.180 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2016 _exptl_absorpt_coefficient_mu 0.074 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 125(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 'Nonius Kappa CCD' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 27080 _diffrn_reflns_av_R_equivalents 0.0824 _diffrn_reflns_av_sigmaI/netI 0.0500 _diffrn_reflns_limit_h_min -38 _diffrn_reflns_limit_h_max 43 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.36 _diffrn_reflns_theta_max 27.50 _reflns_number_total 5947 _reflns_number_gt 4582 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _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^)+(0.0532P)^2^+6.7074P] 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 5947 _refine_ls_number_parameters 370 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0812 _refine_ls_R_factor_gt 0.0553 _refine_ls_wR_factor_ref 0.1408 _refine_ls_wR_factor_gt 0.1250 _refine_ls_goodness_of_fit_ref 1.104 _refine_ls_restrained_S_all 1.104 _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 0.24717(4) 0.58216(14) 0.03242(8) 0.0232(3) Uani 1 1 d . . . H1 H 0.2398(8) 0.666(3) 0.0351(16) 0.043(7) Uiso 1 1 d . . . O2 O 0.27785(4) 0.67217(13) -0.04426(8) 0.0244(3) Uani 1 1 d . . . C1 C 0.26788(6) 0.57417(18) -0.01535(11) 0.0184(4) Uani 1 1 d . . . C2 C 0.27708(6) 0.43516(18) -0.03247(12) 0.0215(4) Uani 1 1 d . . . H2A H 0.2493 0.3966 -0.0787 0.031(6) Uiso 1 1 calc R . . H2B H 0.2859 0.3817 0.0206 0.034(6) Uiso 1 1 calc R . . C3 C 0.31367(6) 0.42683(18) -0.05965(11) 0.0201(4) Uani 1 1 d . . . H3A H 0.3068 0.4891 -0.1081 0.016(5) Uiso 1 1 calc R . . H3B H 0.3142 0.3364 -0.0809 0.017(5) Uiso 1 1 calc R . . C4 C 0.35983(6) 0.45963(18) 0.01469(11) 0.0213(4) Uani 1 1 d . . . H4A H 0.3574 0.5401 0.0446 0.019(5) Uiso 1 1 calc R . . H4B H 0.3695 0.3862 0.0571 0.027(5) Uiso 1 1 calc R . . C5 C 0.39548(6) 0.48229(19) -0.01452(12) 0.0241(4) Uani 1 1 d . . . H5A H 0.4233 0.5124 0.0359 0.037(6) Uiso 1 1 calc R . . H5B H 0.4020 0.3970 -0.0341 0.031(6) Uiso 1 1 calc R . . C6 C 0.38246(6) 0.5826(2) -0.08679(12) 0.0250(4) Uani 1 1 d . . . H6A H 0.4088 0.6033 -0.0951 0.025(5) Uiso 1 1 calc R . . H6B H 0.3592 0.5441 -0.1414 0.027(5) Uiso 1 1 calc R . . N N 0.36522(6) 0.70677(18) -0.06713(13) 0.0277(4) Uani 1 1 d . . . H1N H 0.3382(9) 0.695(2) -0.0686(15) 0.035(6) Uiso 1 1 d . . . H2N H 0.3627(8) 0.771(3) -0.1036(17) 0.043(7) Uiso 1 1 d . . . H3N H 0.3828(8) 0.741(2) -0.0139(18) 0.036(6) Uiso 1 1 d . . . O10 O 0.41983(7) 0.79257(18) 0.09945(11) 0.0436(4) Uani 1 1 d . . . H10 H 0.4230(10) 0.877(3) 0.1043(19) 0.060(9) Uiso 1 1 d . . . H20 H 0.4134(14) 0.766(4) 0.138(3) 0.104(14) Uiso 1 1 d . . . B B 0.11278(6) 0.58305(18) 0.26070(11) 0.0131(4) Uani 1 1 d . . . C11 C 0.15887(5) 0.64416(16) 0.26388(10) 0.0141(3) Uani 1 1 d . . . C21 C 0.17389(6) 0.77097(17) 0.29862(11) 0.0170(3) Uani 1 1 d . . . H21 H 0.1583 0.8169 0.3238 0.023(5) Uiso 1 1 calc R . . C31 C 0.21051(6) 0.83186(18) 0.29762(11) 0.0216(4) Uani 1 1 d . . . H31 H 0.2196 0.9172 0.3224 0.032(6) Uiso 1 1 calc R . . C41 C 0.23378(6) 0.76828(19) 0.26042(12) 0.0231(4) Uani 1 1 d . . . H41 H 0.2586 0.8098 0.2590 0.029(6) Uiso 1 1 calc R . . C51 C 0.22022(6) 0.64354(19) 0.22557(11) 0.0216(4) Uani 1 1 d . . . H51 H 0.2360 0.5986 0.2004 0.027(5) Uiso 1 1 calc R . . C61 C 0.18338(6) 0.58306(17) 0.22722(10) 0.0170(3) Uani 1 1 d . . . H61 H 0.1746 0.4975 0.2026 0.024(5) Uiso 1 1 calc R . . C12 C 0.10853(6) 0.42190(16) 0.24579(10) 0.0161(3) Uani 1 1 d . . . C22 C 0.06728(6) 0.35836(18) 0.20163(11) 0.0219(4) Uani 1 1 d . . . H22 H 0.0411 0.4110 0.1731 0.032(6) Uiso 1 1 calc R . . C32 C 0.06280(7) 0.22116(19) 0.19764(12) 0.0292(4) Uani 1 1 d . . . H32 H 0.0341 0.1822 0.1671 0.032(6) Uiso 1 1 calc R . . C42 C 0.10026(8) 0.14150(19) 0.23825(13) 0.0318(5) Uani 1 1 d . . . H42 H 0.0975 0.0479 0.2355 0.036(6) Uiso 1 1 calc R . . C52 C 0.14183(7) 0.20024(19) 0.28291(13) 0.0285(4) Uani 1 1 d . . . H52 H 0.1678 0.1469 0.3108 0.034(6) Uiso 1 1 calc R . . C62 C 0.14556(6) 0.33755(18) 0.28690(11) 0.0217(4) Uani 1 1 d . . . H62 H 0.1743 0.3758 0.3188 0.026(5) Uiso 1 1 calc R . . C13 C 0.07205(5) 0.66550(16) 0.18250(10) 0.0141(3) Uani 1 1 d . . . C23 C 0.05340(6) 0.78186(16) 0.19615(11) 0.0177(4) Uani 1 1 d . . . H23 H 0.0629 0.8108 0.2539 0.025(5) Uiso 1 1 calc R . . C33 C 0.02155(6) 0.85632(17) 0.12844(12) 0.0205(4) Uani 1 1 d . . . H33 H 0.0095 0.9335 0.1407 0.026(5) Uiso 1 1 calc R . . C43 C 0.00726(6) 0.81825(18) 0.04296(12) 0.0209(4) Uani 1 1 d . . . H43 H -0.0142 0.8693 -0.0034 0.039(6) Uiso 1 1 calc R . . C53 C 0.02496(6) 0.70452(18) 0.02671(11) 0.0205(4) Uani 1 1 d . . . H53 H 0.0157 0.6774 -0.0313 0.039(6) Uiso 1 1 calc R . . C63 C 0.05633(6) 0.62971(17) 0.09519(11) 0.0173(3) Uani 1 1 d . . . H63 H 0.0676 0.5513 0.0823 0.014(5) Uiso 1 1 calc R . . C14 C 0.11295(6) 0.60102(16) 0.35447(10) 0.0144(3) Uani 1 1 d . . . C24 C 0.15245(6) 0.59410(17) 0.43278(11) 0.0175(3) Uani 1 1 d . . . H24 H 0.1800 0.5882 0.4310 0.019(5) Uiso 1 1 calc R . . C34 C 0.15311(6) 0.59550(18) 0.51332(11) 0.0223(4) Uani 1 1 d . . . H34 H 0.1807 0.5885 0.5648 0.027(5) Uiso 1 1 calc R . . C44 C 0.11353(7) 0.60714(18) 0.51817(12) 0.0241(4) Uani 1 1 d . . . H44 H 0.1138 0.6112 0.5728 0.032(6) Uiso 1 1 calc R . . C54 C 0.07362(6) 0.61271(18) 0.44220(12) 0.0234(4) Uani 1 1 d . . . H54 H 0.0462 0.6192 0.4446 0.034(6) Uiso 1 1 calc R . . C64 C 0.07343(6) 0.60887(17) 0.36195(11) 0.0191(4) Uani 1 1 d . . . H64 H 0.0456 0.6117 0.3107 0.021(5) 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 0.0252(7) 0.0235(7) 0.0271(7) 0.0025(6) 0.0174(6) 0.0006(6) O2 0.0279(7) 0.0222(7) 0.0295(7) 0.0052(5) 0.0187(6) 0.0019(5) C1 0.0121(8) 0.0251(9) 0.0153(8) 0.0012(7) 0.0040(6) -0.0014(7) C2 0.0174(8) 0.0235(9) 0.0232(9) -0.0005(7) 0.0090(7) -0.0031(7) C3 0.0190(9) 0.0199(9) 0.0203(8) 0.0008(7) 0.0084(7) 0.0002(7) C4 0.0180(9) 0.0225(9) 0.0204(8) 0.0053(7) 0.0063(7) 0.0003(7) C5 0.0152(9) 0.0251(10) 0.0301(10) 0.0029(8) 0.0088(8) 0.0020(7) C6 0.0183(9) 0.0339(11) 0.0260(9) 0.0008(8) 0.0131(8) -0.0020(8) N 0.0241(9) 0.0286(9) 0.0318(10) 0.0120(8) 0.0142(8) 0.0017(7) O10 0.0746(13) 0.0285(9) 0.0404(9) -0.0070(7) 0.0374(9) -0.0048(8) B 0.0130(8) 0.0126(8) 0.0125(8) -0.0009(7) 0.0050(7) 0.0001(7) C11 0.0123(8) 0.0177(8) 0.0094(7) 0.0008(6) 0.0026(6) 0.0012(6) C21 0.0172(8) 0.0197(9) 0.0149(8) 0.0009(7) 0.0082(7) 0.0018(7) C31 0.0218(9) 0.0227(9) 0.0181(8) -0.0003(7) 0.0073(7) -0.0055(7) C41 0.0140(8) 0.0327(10) 0.0236(9) 0.0040(8) 0.0095(7) -0.0022(7) C51 0.0173(8) 0.0303(10) 0.0198(8) 0.0020(8) 0.0108(7) 0.0041(7) C61 0.0160(8) 0.0194(9) 0.0141(8) -0.0001(7) 0.0057(6) 0.0023(7) C12 0.0214(9) 0.0145(8) 0.0134(7) -0.0002(6) 0.0089(7) -0.0003(7) C22 0.0236(9) 0.0201(9) 0.0158(8) 0.0020(7) 0.0038(7) -0.0011(7) C32 0.0333(11) 0.0232(10) 0.0207(9) -0.0022(8) 0.0039(8) -0.0090(8) C42 0.0494(13) 0.0149(9) 0.0266(10) -0.0010(8) 0.0140(9) -0.0015(9) C52 0.0351(11) 0.0209(9) 0.0257(10) 0.0043(8) 0.0109(9) 0.0099(8) C62 0.0217(9) 0.0216(9) 0.0190(9) 0.0008(7) 0.0072(7) 0.0022(7) C13 0.0109(7) 0.0154(8) 0.0159(8) 0.0003(6) 0.0061(6) -0.0030(6) C23 0.0158(8) 0.0166(8) 0.0184(8) -0.0002(7) 0.0060(7) -0.0015(7) C33 0.0165(8) 0.0158(8) 0.0283(9) 0.0018(7) 0.0098(7) 0.0019(7) C43 0.0132(8) 0.0218(9) 0.0236(9) 0.0089(7) 0.0052(7) 0.0019(7) C53 0.0153(8) 0.0279(10) 0.0155(8) 0.0012(7) 0.0048(7) -0.0014(7) C63 0.0144(8) 0.0195(9) 0.0175(8) 0.0003(7) 0.0069(7) 0.0008(7) C14 0.0163(8) 0.0105(7) 0.0166(8) 0.0004(6) 0.0078(7) -0.0002(6) C24 0.0159(8) 0.0203(9) 0.0175(8) 0.0017(7) 0.0088(7) 0.0004(7) C34 0.0262(9) 0.0249(9) 0.0144(8) 0.0017(7) 0.0083(7) -0.0021(8) C44 0.0376(11) 0.0216(9) 0.0200(9) 0.0000(7) 0.0192(8) -0.0023(8) C54 0.0266(10) 0.0236(9) 0.0303(10) 0.0056(8) 0.0218(8) 0.0048(8) C64 0.0176(8) 0.0193(9) 0.0210(9) 0.0030(7) 0.0094(7) 0.0024(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 1.317(3) . ? O1 H1 0.89(3) . ? O2 C1 1.228(3) . ? C1 C2 1.500(4) . ? C2 C3 1.520(3) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.531(3) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.529(3) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.515(4) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 N 1.491(3) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? N H1N 0.91(3) . ? N H2N 0.89(3) . ? N H3N 0.91(3) . ? O10 H10 0.86(3) . ? O10 H20 0.83(4) . ? B C14 1.643(4) . ? B C13 1.645(3) . ? B C12 1.646(4) . ? B C11 1.654(3) . ? C11 C61 1.404(3) . ? C11 C21 1.408(3) . ? C21 C31 1.391(3) . ? C21 H21 0.9500 . ? C31 C41 1.389(3) . ? C31 H31 0.9500 . ? C41 C51 1.383(4) . ? C41 H41 0.9500 . ? C51 C61 1.401(3) . ? C51 H51 0.9500 . ? C61 H61 0.9500 . ? C12 C22 1.398(3) . ? C12 C62 1.405(3) . ? C22 C32 1.394(4) . ? C22 H22 0.9500 . ? C32 C42 1.386(3) . ? C32 H32 0.9500 . ? C42 C52 1.385(3) . ? C42 H42 0.9500 . ? C52 C62 1.393(4) . ? C52 H52 0.9500 . ? C62 H62 0.9500 . ? C13 C23 1.407(3) . ? C13 C63 1.407(4) . ? C23 C33 1.392(3) . ? C23 H23 0.9500 . ? C33 C43 1.391(4) . ? C33 H33 0.9500 . ? C43 C53 1.386(3) . ? C43 H43 0.9500 . ? C53 C63 1.395(3) . ? C53 H53 0.9500 . ? C63 H63 0.9500 . ? C14 C24 1.399(3) . ? C14 C64 1.405(2) . ? C24 C34 1.395(4) . ? C24 H24 0.9500 . ? C34 C44 1.385(3) . ? C34 H34 0.9500 . ? C44 C54 1.384(3) . ? C44 H44 0.9500 . ? C54 C64 1.398(4) . ? C54 H54 0.9500 . ? C64 H64 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O1 H1 109.5(16) . . ? O2 C1 O1 122.60(18) . . ? O2 C1 C2 123.53(19) . . ? O1 C1 C2 113.85(15) . . ? C1 C2 C3 112.88(15) . . ? C1 C2 H2A 109.0 . . ? C3 C2 H2A 109.0 . . ? C1 C2 H2B 109.0 . . ? C3 C2 H2B 109.0 . . ? H2A C2 H2B 107.8 . . ? C2 C3 C4 112.4(2) . . ? C2 C3 H3A 109.1 . . ? C4 C3 H3A 109.1 . . ? C2 C3 H3B 109.1 . . ? C4 C3 H3B 109.1 . . ? H3A C3 H3B 107.9 . . ? C5 C4 C3 113.7(2) . . ? C5 C4 H4A 108.8 . . ? C3 C4 H4A 108.8 . . ? C5 C4 H4B 108.8 . . ? C3 C4 H4B 108.8 . . ? H4A C4 H4B 107.7 . . ? C6 C5 C4 114.14(16) . . ? C6 C5 H5A 108.7 . . ? C4 C5 H5A 108.7 . . ? C6 C5 H5B 108.7 . . ? C4 C5 H5B 108.7 . . ? H5A C5 H5B 107.6 . . ? N C6 C5 111.5(2) . . ? N C6 H6A 109.3 . . ? C5 C6 H6A 109.3 . . ? N C6 H6B 109.3 . . ? C5 C6 H6B 109.3 . . ? H6A C6 H6B 108.0 . . ? C6 N H1N 112.4(15) . . ? C6 N H2N 111.8(16) . . ? H1N N H2N 108(2) . . ? C6 N H3N 114.8(15) . . ? H1N N H3N 104(2) . . ? H2N N H3N 104(2) . . ? H10 O10 H20 108(3) . . ? C14 B C13 112.53(17) . . ? C14 B C12 103.08(13) . . ? C13 B C12 113.15(15) . . ? C14 B C11 111.03(13) . . ? C13 B C11 104.54(15) . . ? C12 B C11 112.75(14) . . ? C61 C11 C21 115.17(16) . . ? C61 C11 B 124.58(16) . . ? C21 C11 B 120.02(15) . . ? C31 C21 C11 122.88(17) . . ? C31 C21 H21 118.6 . . ? C11 C21 H21 118.6 . . ? C41 C31 C21 120.18(19) . . ? C41 C31 H31 119.9 . . ? C21 C31 H31 119.9 . . ? C51 C41 C31 118.93(17) . . ? C51 C41 H41 120.5 . . ? C31 C41 H41 120.5 . . ? C41 C51 C61 120.36(17) . . ? C41 C51 H51 119.8 . . ? C61 C51 H51 119.8 . . ? C51 C61 C11 122.48(18) . . ? C51 C61 H61 118.8 . . ? C11 C61 H61 118.8 . . ? C22 C12 C62 115.24(19) . . ? C22 C12 B 122.25(16) . . ? C62 C12 B 121.93(16) . . ? C32 C22 C12 122.85(18) . . ? C32 C22 H22 118.6 . . ? C12 C22 H22 118.6 . . ? C42 C32 C22 120.1(2) . . ? C42 C32 H32 120.0 . . ? C22 C32 H32 120.0 . . ? C52 C42 C32 119.1(2) . . ? C52 C42 H42 120.5 . . ? C32 C42 H42 120.5 . . ? C42 C52 C62 120.02(19) . . ? C42 C52 H52 120.0 . . ? C62 C52 H52 120.0 . . ? C52 C62 C12 122.75(19) . . ? C52 C62 H62 118.6 . . ? C12 C62 H62 118.6 . . ? C23 C13 C63 115.16(15) . . ? C23 C13 B 123.51(18) . . ? C63 C13 B 121.07(17) . . ? C33 C23 C13 122.7(2) . . ? C33 C23 H23 118.7 . . ? C13 C23 H23 118.7 . . ? C43 C33 C23 120.4(2) . . ? C43 C33 H33 119.8 . . ? C23 C33 H33 119.8 . . ? C53 C43 C33 118.79(16) . . ? C53 C43 H43 120.6 . . ? C33 C43 H43 120.6 . . ? C43 C53 C63 120.3(2) . . ? C43 C53 H53 119.9 . . ? C63 C53 H53 119.9 . . ? C53 C63 C13 122.75(19) . . ? C53 C63 H63 118.6 . . ? C13 C63 H63 118.6 . . ? C24 C14 C64 115.45(19) . . ? C24 C14 B 121.72(18) . . ? C64 C14 B 122.43(15) . . ? C34 C24 C14 122.90(19) . . ? C34 C24 H24 118.6 . . ? C14 C24 H24 118.6 . . ? C44 C34 C24 119.99(17) . . ? C44 C34 H34 120.0 . . ? C24 C34 H34 120.0 . . ? C54 C44 C34 119.0(2) . . ? C54 C44 H44 120.5 . . ? C34 C44 H44 120.5 . . ? C44 C54 C64 120.3(2) . . ? C44 C54 H54 119.8 . . ? C64 C54 H54 119.8 . . ? C54 C64 C14 122.28(16) . . ? C54 C64 H64 118.9 . . ? C14 C64 H64 118.9 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2 C1 C2 C3 20.9(2) . . . . ? O1 C1 C2 C3 -160.36(15) . . . . ? C1 C2 C3 C4 69.69(19) . . . . ? C2 C3 C4 C5 -167.18(15) . . . . ? C3 C4 C5 C6 52.3(2) . . . . ? C4 C5 C6 N 49.3(2) . . . . ? C14 B C11 C61 137.78(16) . . . . ? C13 B C11 C61 -100.6(2) . . . . ? C12 B C11 C61 22.7(2) . . . . ? C14 B C11 C21 -47.9(2) . . . . ? C13 B C11 C21 73.7(2) . . . . ? C12 B C11 C21 -162.99(15) . . . . ? C61 C11 C21 C31 -0.5(2) . . . . ? B C11 C21 C31 -175.30(15) . . . . ? C11 C21 C31 C41 0.7(3) . . . . ? C21 C31 C41 C51 -0.7(3) . . . . ? C31 C41 C51 C61 0.5(3) . . . . ? C41 C51 C61 C11 -0.3(3) . . . . ? C21 C11 C61 C51 0.2(2) . . . . ? B C11 C61 C51 174.81(15) . . . . ? C14 B C12 C22 91.30(19) . . . . ? C13 B C12 C22 -30.5(2) . . . . ? C11 B C12 C22 -148.90(17) . . . . ? C14 B C12 C62 -79.6(2) . . . . ? C13 B C12 C62 158.63(15) . . . . ? C11 B C12 C62 40.2(2) . . . . ? C62 C12 C22 C32 -0.5(3) . . . . ? B C12 C22 C32 -171.90(16) . . . . ? C12 C22 C32 C42 -0.3(3) . . . . ? C22 C32 C42 C52 0.4(3) . . . . ? C32 C42 C52 C62 0.3(3) . . . . ? C42 C52 C62 C12 -1.1(3) . . . . ? C22 C12 C62 C52 1.2(3) . . . . ? B C12 C62 C52 172.62(16) . . . . ? C14 B C13 C23 28.2(2) . . . . ? C12 B C13 C23 144.58(16) . . . . ? C11 B C13 C23 -92.4(2) . . . . ? C14 B C13 C63 -157.86(15) . . . . ? C12 B C13 C63 -41.5(2) . . . . ? C11 B C13 C63 81.5(2) . . . . ? C63 C13 C23 C33 0.3(2) . . . . ? B C13 C23 C33 174.50(16) . . . . ? C13 C23 C33 C43 -1.0(3) . . . . ? C23 C33 C43 C53 0.7(3) . . . . ? C33 C43 C53 C63 0.3(3) . . . . ? C43 C53 C63 C13 -1.1(3) . . . . ? C23 C13 C63 C53 0.8(2) . . . . ? B C13 C63 C53 -173.62(15) . . . . ? C13 B C14 C24 -150.59(16) . . . . ? C12 B C14 C24 87.18(18) . . . . ? C11 B C14 C24 -33.8(2) . . . . ? C13 B C14 C64 37.0(2) . . . . ? C12 B C14 C64 -85.29(18) . . . . ? C11 B C14 C64 153.74(16) . . . . ? C64 C14 C24 C34 -0.3(2) . . . . ? B C14 C24 C34 -173.28(16) . . . . ? C14 C24 C34 C44 -1.5(3) . . . . ? C24 C34 C44 C54 2.2(3) . . . . ? C34 C44 C54 C64 -1.1(3) . . . . ? C44 C54 C64 C14 -0.8(3) . . . . ? C24 C14 C64 C54 1.5(2) . . . . ? B C14 C64 C54 174.38(16) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1 O2 0.89(3) 1.77(3) 2.663(5) 175(2) 7_565 N H1N O2 0.91(3) 2.28(3) 3.181(3) 169(2) . N H2N C11 0.89(3) 2.68(3) 3.481(7) 151(2) 7_565 N H2N C21 0.89(3) 3.06(3) 3.624(9) 123.3(19) 7_565 N H2N C31 0.89(3) 3.30(3) 3.646(8) 106.2(18) 7_565 N H1N C41 0.91(3) 3.11(2) 3.483(5) 106.7(16) 7_565 N H2N C51 0.89(3) 2.75(3) 3.293(4) 120.5(19) 7_565 N H2N C61 0.89(3) 2.47(3) 3.278(5) 151(2) 7_565 N H3N O10 0.91(3) 1.86(3) 2.759(6) 174(2) . O10 H10 C14 0.86(3) 2.82(3) 3.527(6) 141(2) 4 O10 H10 C24 0.86(3) 3.20(3) 3.783(6) 128(2) 4 O10 H10 C34 0.86(3) 3.29(3) 3.850(6) 126(2) 4 O10 H10 C44 0.86(3) 3.01(3) 3.667(6) 135(2) 4 O10 H10 C54 0.86(3) 2.54(3) 3.348(7) 157(3) 4 O10 H10 C64 0.86(3) 2.41(3) 3.255(7) 169(3) 4 O10 H20 C12 0.83(4) 2.93(4) 3.512(6) 129(3) 4 O10 H20 C22 0.83(4) 2.73(4) 3.357(8) 133(3) 4 O10 H20 C32 0.83(4) 2.64(5) 3.385(8) 150(4) 4 O10 H20 C42 0.83(4) 2.72(4) 3.550(7) 170(4) 4 O10 H20 C52 0.83(4) 2.88(4) 3.664(5) 158(4) 4 O10 H20 C62 0.83(4) 2.95(4) 3.622(5) 140(3) 4 _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 0.443 _refine_diff_density_min -0.289 _refine_diff_density_rms 0.061 #===END