# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full 'Dalton Trans.' _journal_coden_cambridge 0222 _publ_contact_author ; Martin Nieger Laboratory of Inorganic Chemistry Department of Chemistry Universitity of Helsinki P.O. Box 55 FIN-00014 University of Helsinki Finland ; _publ_contact_author_phone ++358-9-19150192 _publ_contact_author_fax ++358-9-19150198 _publ_contact_author_email martin.nieger@helsinki.fi _publ_requested_coeditor_name ? _publ_contact_letter ; enclosed you will find the necessary data for our publication in J. Chem. Soc., Dalton Trans. It's a new cif-file for CCDC 875800-875802 ; #============================================================================== # 3. TITLE AND AUTHOR LIST _publ_section_title ; Hydrogen activation by 2-boryl-N,N-dialkylaniniles: a revision of Piers' ansa-aminoborane ; loop_ _publ_author_name _publ_author_address K.Chernichenko ; Laboratory of Inorganic Chemistry Department of Chemistry Universitity of Helsinki P.O. Box 55 FIN-00014 University of Helsinki Finland ; M.Nieger ; Laboratory of Inorganic Chemistry Department of Chemistry Universitity of Helsinki P.O. Box 55 FIN-00014 University of Helsinki Finland ; M.Leskel/"a ; Laboratory of Inorganic Chemistry Department of Chemistry Universitity of Helsinki P.O. Box 55 FIN-00014 University of Helsinki Finland ; T.Repo ; Laboratory of Inorganic Chemistry Department of Chemistry Universitity of Helsinki P.O. Box 55 FIN-00014 University of Helsinki Finland ; _publ_contact_author_name 'Martin Nieger' #============================================================================== data_les083_CCDC-875800 _database_code_depnum_ccdc_archive 'CCDC 875800' #TrackingRef '- dalton.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1-(2-(bis(perfluorophenyl)boryl)phenyl)-2,2,6,6-tetramethylpiperidin ; _chemical_name_common ;1-(2-(bis(perfluorophenyl)boryl)phenyl)-2,2,6,6- tetramethylpiperidin ; _chemical_melting_point ? _chemical_formula_moiety 'C27 H22 B F10 N' _chemical_formula_sum 'C27 H22 B F10 N' _chemical_formula_weight 561.27 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' F F 0.0171 0.0103 '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 7.8910(5) _cell_length_b 17.3435(15) _cell_length_c 17.8672(15) _cell_angle_alpha 90.00 _cell_angle_beta 101.330(7) _cell_angle_gamma 90.00 _cell_volume 2397.6(3) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 80 _cell_measurement_theta_min 2.5 _cell_measurement_theta_max 25.0 _exptl_crystal_description blocks _exptl_crystal_colour orange _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.555 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1144 _exptl_absorpt_coefficient_mu 0.144 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9080 _exptl_absorpt_correction_T_max 0.9925 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2008)' _exptl_special_details ; dx = 35 mm 180 sec./deg., 2 deg., 3 sets, 204 frames, 4708 refl. postref. ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius KappaCCD' _diffrn_measurement_method 'rotation in phi and omega, 2 deg.' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 25679 _diffrn_reflns_av_R_equivalents 0.0616 _diffrn_reflns_av_sigmaI/netI 0.0665 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 3.15 _diffrn_reflns_theta_max 27.48 _reflns_number_total 5411 _reflns_number_gt 3279 _reflns_threshold_expression >2sigma(I) _computing_data_collection Collect _computing_cell_refinement EVALCCD _computing_data_reduction EVALCCD _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics XP _computing_publication_material '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. ; _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^)+(0.0360P)^2^+2.2200P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5411 _refine_ls_number_parameters 352 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1153 _refine_ls_R_factor_gt 0.0579 _refine_ls_wR_factor_ref 0.1205 _refine_ls_wR_factor_gt 0.1015 _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 B1 B 0.8246(3) 0.29974(17) 0.57107(17) 0.0209(6) Uani 1 1 d . . . C1 C 0.9045(3) 0.27423(14) 0.65263(14) 0.0202(5) Uani 1 1 d . . . C2 C 1.0388(3) 0.32123(15) 0.69101(15) 0.0234(6) Uani 1 1 d . . . H2 H 1.0598 0.3692 0.6688 0.028 Uiso 1 1 calc R . . C3 C 1.1405(3) 0.30041(15) 0.75924(14) 0.0244(6) Uani 1 1 d . . . H3 H 1.2345 0.3320 0.7825 0.029 Uiso 1 1 calc R . . C4 C 1.1047(3) 0.23329(16) 0.79341(15) 0.0260(6) Uani 1 1 d . . . H4 H 1.1738 0.2183 0.8409 0.031 Uiso 1 1 calc R . . C5 C 0.9689(3) 0.18733(15) 0.75927(14) 0.0229(6) Uani 1 1 d . . . H5 H 0.9432 0.1420 0.7848 0.028 Uiso 1 1 calc R . . C6 C 0.8691(3) 0.20542(14) 0.68869(14) 0.0193(5) Uani 1 1 d . . . N7 N 0.7275(2) 0.15805(12) 0.65256(11) 0.0198(5) Uani 1 1 d . . . C8 C 0.7668(3) 0.07432(15) 0.64325(15) 0.0235(6) Uani 1 1 d . . . C9 C 0.6126(3) 0.04023(16) 0.58801(16) 0.0310(7) Uani 1 1 d . . . H9A H 0.6033 0.0653 0.5376 0.037 Uiso 1 1 calc R . . H9B H 0.6332 -0.0155 0.5815 0.037 Uiso 1 1 calc R . . C10 C 0.4449(4) 0.05031(17) 0.61475(18) 0.0372(7) Uani 1 1 d . . . H10A H 0.4514 0.0250 0.6649 0.045 Uiso 1 1 calc R . . H10B H 0.3492 0.0265 0.5778 0.045 Uiso 1 1 calc R . . C11 C 0.4129(3) 0.13534(16) 0.62142(17) 0.0326(7) Uani 1 1 d . . . H11A H 0.3041 0.1426 0.6403 0.039 Uiso 1 1 calc R . . H11B H 0.3969 0.1588 0.5700 0.039 Uiso 1 1 calc R . . C12 C 0.5585(3) 0.17801(16) 0.67469(15) 0.0253(6) Uani 1 1 d . . . C13 C 0.5526(4) 0.16108(18) 0.75825(16) 0.0340(7) Uani 1 1 d . . . H13A H 0.5749 0.1061 0.7687 0.051 Uiso 1 1 calc R . . H13B H 0.4383 0.1744 0.7680 0.051 Uiso 1 1 calc R . . H13C H 0.6410 0.1918 0.7915 0.051 Uiso 1 1 calc R . . C14 C 0.5235(3) 0.26355(15) 0.66226(17) 0.0293(6) Uani 1 1 d . . . H14A H 0.5251 0.2767 0.6091 0.044 Uiso 1 1 calc R . . H14B H 0.6129 0.2931 0.6962 0.044 Uiso 1 1 calc R . . H14C H 0.4100 0.2760 0.6735 0.044 Uiso 1 1 calc R . . C15 C 0.8054(4) 0.02292(16) 0.71415(16) 0.0317(7) Uani 1 1 d . . . H15A H 0.9037 0.0441 0.7505 0.048 Uiso 1 1 calc R . . H15B H 0.8335 -0.0292 0.6994 0.048 Uiso 1 1 calc R . . H15C H 0.7038 0.0210 0.7380 0.048 Uiso 1 1 calc R . . C16 C 0.9228(3) 0.06931(15) 0.60506(17) 0.0298(6) Uani 1 1 d . . . H16A H 0.9029 0.1014 0.5590 0.045 Uiso 1 1 calc R . . H16B H 0.9401 0.0156 0.5911 0.045 Uiso 1 1 calc R . . H16C H 1.0259 0.0877 0.6405 0.045 Uiso 1 1 calc R . . C17 C 0.7862(3) 0.38743(14) 0.55063(14) 0.0222(6) Uani 1 1 d . . . C18 C 0.7353(3) 0.44059(16) 0.60005(15) 0.0282(6) Uani 1 1 d . . . F18 F 0.7113(2) 0.41868(9) 0.66845(9) 0.0415(4) Uani 1 1 d . . . C19 C 0.7033(4) 0.51657(16) 0.58244(17) 0.0332(7) Uani 1 1 d . . . F19 F 0.6522(3) 0.56405(10) 0.63211(11) 0.0539(5) Uani 1 1 d . . . C20 C 0.7242(4) 0.54411(16) 0.51336(18) 0.0334(7) Uani 1 1 d . . . F20 F 0.6945(2) 0.61782(9) 0.49584(11) 0.0501(5) Uani 1 1 d . . . C21 C 0.7762(4) 0.49504(16) 0.46273(16) 0.0299(6) Uani 1 1 d . . . F21 F 0.7997(3) 0.52126(10) 0.39551(10) 0.0497(5) Uani 1 1 d . . . C22 C 0.8054(3) 0.41906(15) 0.48198(15) 0.0252(6) Uani 1 1 d . . . F22 F 0.8617(2) 0.37597(9) 0.42959(9) 0.0388(4) Uani 1 1 d . . . C23 C 0.8140(3) 0.24212(14) 0.50256(14) 0.0211(5) Uani 1 1 d . . . C24 C 0.9670(3) 0.21458(14) 0.48630(14) 0.0216(6) Uani 1 1 d . . . F24 F 1.11668(18) 0.23904(9) 0.52888(8) 0.0295(4) Uani 1 1 d . . . C25 C 0.9750(3) 0.16401(15) 0.42904(15) 0.0237(6) Uani 1 1 d . . . F25 F 1.12759(19) 0.13718(9) 0.41837(8) 0.0313(4) Uani 1 1 d . . . C26 C 0.8251(3) 0.13943(15) 0.38316(14) 0.0250(6) Uani 1 1 d . . . F26 F 0.8286(2) 0.09025(9) 0.32665(9) 0.0360(4) Uani 1 1 d . . . C27 C 0.6696(3) 0.16662(16) 0.39607(15) 0.0267(6) Uani 1 1 d . . . F27 F 0.5231(2) 0.14300(10) 0.35124(9) 0.0399(4) Uani 1 1 d . . . C28 C 0.6669(3) 0.21750(15) 0.45413(15) 0.0227(6) Uani 1 1 d . . . F28 F 0.51192(18) 0.24361(9) 0.46348(9) 0.0336(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 B1 0.0174(14) 0.0216(15) 0.0251(16) 0.0019(12) 0.0078(11) -0.0030(12) C1 0.0207(13) 0.0196(13) 0.0214(13) -0.0024(11) 0.0066(10) 0.0015(10) C2 0.0265(14) 0.0183(13) 0.0273(15) -0.0024(11) 0.0103(11) -0.0010(11) C3 0.0231(13) 0.0256(15) 0.0239(14) -0.0088(12) 0.0030(11) -0.0022(11) C4 0.0269(14) 0.0295(16) 0.0197(14) -0.0032(12) 0.0002(11) 0.0066(12) C5 0.0285(14) 0.0201(14) 0.0208(14) 0.0038(11) 0.0062(10) 0.0040(11) C6 0.0186(12) 0.0187(13) 0.0223(14) -0.0033(11) 0.0083(10) -0.0002(10) N7 0.0184(11) 0.0175(11) 0.0240(12) 0.0002(9) 0.0054(8) -0.0004(8) C8 0.0239(13) 0.0200(14) 0.0268(15) 0.0036(11) 0.0053(11) -0.0016(11) C9 0.0353(16) 0.0227(15) 0.0336(17) -0.0005(12) 0.0029(12) -0.0070(12) C10 0.0271(15) 0.0347(17) 0.0474(19) -0.0009(14) 0.0014(13) -0.0100(13) C11 0.0212(14) 0.0350(17) 0.0406(17) 0.0048(14) 0.0035(12) -0.0018(12) C12 0.0182(13) 0.0280(15) 0.0315(15) 0.0037(12) 0.0094(11) 0.0014(11) C13 0.0355(16) 0.0354(17) 0.0355(17) 0.0064(13) 0.0180(13) 0.0054(13) C14 0.0234(14) 0.0277(15) 0.0395(17) 0.0054(13) 0.0130(12) 0.0051(11) C15 0.0384(16) 0.0205(15) 0.0364(17) 0.0051(12) 0.0080(13) -0.0001(12) C16 0.0337(15) 0.0174(14) 0.0417(17) -0.0010(12) 0.0156(13) 0.0011(12) C17 0.0232(13) 0.0198(13) 0.0233(14) -0.0002(11) 0.0035(10) 0.0002(11) C18 0.0346(15) 0.0245(15) 0.0269(15) 0.0036(12) 0.0097(12) 0.0006(12) F18 0.0717(12) 0.0267(9) 0.0333(10) 0.0021(8) 0.0278(8) 0.0062(8) C19 0.0402(17) 0.0228(15) 0.0395(18) -0.0064(13) 0.0150(13) 0.0028(12) F19 0.0861(14) 0.0251(10) 0.0599(13) -0.0048(9) 0.0376(11) 0.0113(9) C20 0.0369(17) 0.0162(14) 0.0460(19) 0.0050(13) 0.0060(14) 0.0042(12) F20 0.0708(13) 0.0200(9) 0.0611(13) 0.0113(9) 0.0169(10) 0.0092(9) C21 0.0381(16) 0.0240(15) 0.0269(15) 0.0070(12) 0.0049(12) -0.0038(12) F21 0.0863(14) 0.0306(10) 0.0338(10) 0.0122(8) 0.0156(9) -0.0042(9) C22 0.0317(14) 0.0216(14) 0.0225(14) -0.0038(11) 0.0059(11) -0.0018(11) F22 0.0686(12) 0.0240(9) 0.0287(9) 0.0016(7) 0.0217(8) 0.0000(8) C23 0.0267(14) 0.0169(13) 0.0191(13) 0.0045(10) 0.0029(10) 0.0036(10) C24 0.0231(13) 0.0196(14) 0.0207(14) 0.0035(11) 0.0009(10) -0.0004(10) F24 0.0221(8) 0.0345(9) 0.0305(9) -0.0066(7) 0.0016(6) 0.0006(6) C25 0.0277(14) 0.0217(14) 0.0226(14) 0.0055(11) 0.0069(11) 0.0075(11) F25 0.0346(9) 0.0312(9) 0.0300(9) 0.0001(7) 0.0112(7) 0.0108(7) C26 0.0391(16) 0.0184(14) 0.0171(14) -0.0005(11) 0.0042(11) 0.0018(11) F26 0.0531(10) 0.0283(9) 0.0255(9) -0.0082(7) 0.0046(7) 0.0033(7) C27 0.0295(15) 0.0229(14) 0.0229(14) 0.0025(11) -0.0062(11) -0.0039(11) F27 0.0341(9) 0.0425(11) 0.0363(10) -0.0084(8) -0.0094(7) -0.0043(8) C28 0.0221(13) 0.0209(14) 0.0248(14) 0.0037(11) 0.0036(10) 0.0020(11) F28 0.0224(8) 0.0396(10) 0.0376(9) -0.0047(8) 0.0031(7) 0.0043(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 B1 C1 1.535(4) . ? B1 C23 1.570(4) . ? B1 C17 1.579(4) . ? C1 C2 1.404(3) . ? C1 C6 1.410(3) . ? C2 C3 1.370(4) . ? C2 H2 0.9500 . ? C3 C4 1.370(4) . ? C3 H3 0.9500 . ? C4 C5 1.378(4) . ? C4 H4 0.9500 . ? C5 C6 1.385(3) . ? C5 H5 0.9500 . ? C6 N7 1.434(3) . ? N7 C8 1.501(3) . ? N7 C12 1.504(3) . ? C8 C16 1.523(4) . ? C8 C9 1.527(4) . ? C8 C15 1.530(4) . ? C9 C10 1.503(4) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C11 1.505(4) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.531(4) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C14 1.517(4) . ? C12 C13 1.531(4) . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 C22 1.379(4) . ? C17 C18 1.389(4) . ? C18 F18 1.329(3) . ? C18 C19 1.367(4) . ? C19 F19 1.330(3) . ? C19 C20 1.364(4) . ? C20 F20 1.326(3) . ? C20 C21 1.363(4) . ? C21 F21 1.331(3) . ? C21 C22 1.370(4) . ? C22 F22 1.340(3) . ? C23 C28 1.372(3) . ? C23 C24 1.381(4) . ? C24 F24 1.342(3) . ? C24 C25 1.358(4) . ? C25 F25 1.339(3) . ? C25 C26 1.368(4) . ? C26 F26 1.326(3) . ? C26 C27 1.376(4) . ? C27 F27 1.335(3) . ? C27 C28 1.365(4) . ? C28 F28 1.345(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 C1 B1 C23 120.4(2) . . ? C1 B1 C17 121.4(2) . . ? C23 B1 C17 117.0(2) . . ? C2 C1 C6 117.8(2) . . ? C2 C1 B1 115.2(2) . . ? C6 C1 B1 126.6(2) . . ? C3 C2 C1 122.4(2) . . ? C3 C2 H2 118.8 . . ? C1 C2 H2 118.8 . . ? C4 C3 C2 119.0(2) . . ? C4 C3 H3 120.5 . . ? C2 C3 H3 120.5 . . ? C3 C4 C5 120.3(2) . . ? C3 C4 H4 119.8 . . ? C5 C4 H4 119.8 . . ? C4 C5 C6 121.7(2) . . ? C4 C5 H5 119.1 . . ? C6 C5 H5 119.1 . . ? C5 C6 C1 118.6(2) . . ? C5 C6 N7 122.2(2) . . ? C1 C6 N7 119.1(2) . . ? C6 N7 C8 116.40(19) . . ? C6 N7 C12 113.73(19) . . ? C8 N7 C12 117.71(19) . . ? N7 C8 C16 107.9(2) . . ? N7 C8 C9 106.9(2) . . ? C16 C8 C9 107.5(2) . . ? N7 C8 C15 118.9(2) . . ? C16 C8 C15 106.9(2) . . ? C9 C8 C15 108.3(2) . . ? C10 C9 C8 112.9(2) . . ? C10 C9 H9A 109.0 . . ? C8 C9 H9A 109.0 . . ? C10 C9 H9B 109.0 . . ? C8 C9 H9B 109.0 . . ? H9A C9 H9B 107.8 . . ? C9 C10 C11 108.1(2) . . ? C9 C10 H10A 110.1 . . ? C11 C10 H10A 110.1 . . ? C9 C10 H10B 110.1 . . ? C11 C10 H10B 110.1 . . ? H10A C10 H10B 108.4 . . ? C10 C11 C12 114.0(2) . . ? C10 C11 H11A 108.8 . . ? C12 C11 H11A 108.8 . . ? C10 C11 H11B 108.8 . . ? C12 C11 H11B 108.8 . . ? H11A C11 H11B 107.7 . . ? N7 C12 C14 109.4(2) . . ? N7 C12 C11 108.7(2) . . ? C14 C12 C11 106.8(2) . . ? N7 C12 C13 114.2(2) . . ? C14 C12 C13 106.9(2) . . ? C11 C12 C13 110.5(2) . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C12 C14 H14A 109.5 . . ? C12 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C12 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C8 C15 H15A 109.5 . . ? C8 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C8 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C8 C16 H16A 109.5 . . ? C8 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C8 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C22 C17 C18 113.4(2) . . ? C22 C17 B1 122.6(2) . . ? C18 C17 B1 123.9(2) . . ? F18 C18 C19 115.7(2) . . ? F18 C18 C17 120.4(2) . . ? C19 C18 C17 123.8(3) . . ? F19 C19 C20 119.6(3) . . ? F19 C19 C18 120.7(3) . . ? C20 C19 C18 119.8(3) . . ? F20 C20 C21 120.5(3) . . ? F20 C20 C19 120.3(3) . . ? C21 C20 C19 119.2(3) . . ? F21 C21 C20 119.9(2) . . ? F21 C21 C22 120.6(3) . . ? C20 C21 C22 119.5(3) . . ? F22 C22 C21 115.0(2) . . ? F22 C22 C17 120.6(2) . . ? C21 C22 C17 124.3(2) . . ? C28 C23 C24 115.2(2) . . ? C28 C23 B1 126.8(2) . . ? C24 C23 B1 118.0(2) . . ? F24 C24 C25 117.7(2) . . ? F24 C24 C23 118.7(2) . . ? C25 C24 C23 123.6(2) . . ? F25 C25 C24 120.5(2) . . ? F25 C25 C26 120.1(2) . . ? C24 C25 C26 119.3(2) . . ? F26 C26 C25 120.8(2) . . ? F26 C26 C27 120.0(2) . . ? C25 C26 C27 119.1(2) . . ? F27 C27 C28 120.9(2) . . ? F27 C27 C26 119.3(2) . . ? C28 C27 C26 119.8(2) . . ? F28 C28 C27 117.5(2) . . ? F28 C28 C23 119.6(2) . . ? C27 C28 C23 122.9(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C23 B1 C1 C2 125.6(2) . . . . ? C17 B1 C1 C2 -41.8(3) . . . . ? C23 B1 C1 C6 -47.3(4) . . . . ? C17 B1 C1 C6 145.3(2) . . . . ? C6 C1 C2 C3 3.6(4) . . . . ? B1 C1 C2 C3 -169.9(2) . . . . ? C1 C2 C3 C4 -3.5(4) . . . . ? C2 C3 C4 C5 0.4(4) . . . . ? C3 C4 C5 C6 2.5(4) . . . . ? C4 C5 C6 C1 -2.3(4) . . . . ? C4 C5 C6 N7 180.0(2) . . . . ? C2 C1 C6 C5 -0.7(3) . . . . ? B1 C1 C6 C5 172.1(2) . . . . ? C2 C1 C6 N7 177.1(2) . . . . ? B1 C1 C6 N7 -10.2(4) . . . . ? C5 C6 N7 C8 -53.7(3) . . . . ? C1 C6 N7 C8 128.6(2) . . . . ? C5 C6 N7 C12 88.0(3) . . . . ? C1 C6 N7 C12 -89.6(3) . . . . ? C6 N7 C8 C16 -51.6(3) . . . . ? C12 N7 C8 C16 168.2(2) . . . . ? C6 N7 C8 C9 -166.9(2) . . . . ? C12 N7 C8 C9 52.9(3) . . . . ? C6 N7 C8 C15 70.3(3) . . . . ? C12 N7 C8 C15 -69.9(3) . . . . ? N7 C8 C9 C10 -57.4(3) . . . . ? C16 C8 C9 C10 -173.0(2) . . . . ? C15 C8 C9 C10 71.8(3) . . . . ? C8 C9 C10 C11 60.8(3) . . . . ? C9 C10 C11 C12 -57.0(3) . . . . ? C6 N7 C12 C14 52.6(3) . . . . ? C8 N7 C12 C14 -166.2(2) . . . . ? C6 N7 C12 C11 168.9(2) . . . . ? C8 N7 C12 C11 -49.9(3) . . . . ? C6 N7 C12 C13 -67.2(3) . . . . ? C8 N7 C12 C13 74.1(3) . . . . ? C10 C11 C12 N7 50.7(3) . . . . ? C10 C11 C12 C14 168.6(2) . . . . ? C10 C11 C12 C13 -75.4(3) . . . . ? C1 B1 C17 C22 144.1(2) . . . . ? C23 B1 C17 C22 -23.7(3) . . . . ? C1 B1 C17 C18 -33.9(4) . . . . ? C23 B1 C17 C18 158.3(2) . . . . ? C22 C17 C18 F18 179.9(2) . . . . ? B1 C17 C18 F18 -1.9(4) . . . . ? C22 C17 C18 C19 1.4(4) . . . . ? B1 C17 C18 C19 179.5(3) . . . . ? F18 C18 C19 F19 0.3(4) . . . . ? C17 C18 C19 F19 178.9(3) . . . . ? F18 C18 C19 C20 -179.9(2) . . . . ? C17 C18 C19 C20 -1.3(4) . . . . ? F19 C19 C20 F20 0.2(4) . . . . ? C18 C19 C20 F20 -179.6(3) . . . . ? F19 C19 C20 C21 -179.9(3) . . . . ? C18 C19 C20 C21 0.3(4) . . . . ? F20 C20 C21 F21 0.9(4) . . . . ? C19 C20 C21 F21 -179.0(2) . . . . ? F20 C20 C21 C22 -179.7(3) . . . . ? C19 C20 C21 C22 0.4(4) . . . . ? F21 C21 C22 F22 1.6(4) . . . . ? C20 C21 C22 F22 -177.8(2) . . . . ? F21 C21 C22 C17 179.2(2) . . . . ? C20 C21 C22 C17 -0.2(4) . . . . ? C18 C17 C22 F22 176.9(2) . . . . ? B1 C17 C22 F22 -1.3(4) . . . . ? C18 C17 C22 C21 -0.6(4) . . . . ? B1 C17 C22 C21 -178.8(3) . . . . ? C1 B1 C23 C28 119.9(3) . . . . ? C17 B1 C23 C28 -72.2(3) . . . . ? C1 B1 C23 C24 -62.6(3) . . . . ? C17 B1 C23 C24 105.3(3) . . . . ? C28 C23 C24 F24 176.8(2) . . . . ? B1 C23 C24 F24 -0.9(3) . . . . ? C28 C23 C24 C25 -2.9(4) . . . . ? B1 C23 C24 C25 179.4(2) . . . . ? F24 C24 C25 F25 3.1(4) . . . . ? C23 C24 C25 F25 -177.2(2) . . . . ? F24 C24 C25 C26 -178.3(2) . . . . ? C23 C24 C25 C26 1.4(4) . . . . ? F25 C25 C26 F26 -1.5(4) . . . . ? C24 C25 C26 F26 179.8(2) . . . . ? F25 C25 C26 C27 178.8(2) . . . . ? C24 C25 C26 C27 0.1(4) . . . . ? F26 C26 C27 F27 0.0(4) . . . . ? C25 C26 C27 F27 179.8(2) . . . . ? F26 C26 C27 C28 -179.7(2) . . . . ? C25 C26 C27 C28 0.0(4) . . . . ? F27 C27 C28 F28 -1.0(4) . . . . ? C26 C27 C28 F28 178.7(2) . . . . ? F27 C27 C28 C23 178.6(2) . . . . ? C26 C27 C28 C23 -1.6(4) . . . . ? C24 C23 C28 F28 -177.4(2) . . . . ? B1 C23 C28 F28 0.1(4) . . . . ? C24 C23 C28 C27 2.9(4) . . . . ? B1 C23 C28 C27 -179.5(2) . . . . ? _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 0.292 _refine_diff_density_min -0.271 _refine_diff_density_rms 0.059 #============================================================================== data_les084_CCDC-875801 _database_code_depnum_ccdc_archive 'CCDC 875801' #TrackingRef '- dalton.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; bis(perfluorophenyl)(2-(2,2,6,6-tetramethylpiperidin-1-ium-1yl)phenyl)- hydrobarate ; _chemical_name_common ; bis(perfluorophenyl)(2-(2,2,6,6-tetramethylpiperidin-1-ium- 1yl)phenyl)-hydrobarate ; _chemical_melting_point ? _chemical_formula_moiety 'C27 H24 B F10 N, 0.5(C6 D6)' _chemical_formula_sum 'C30 H24 B D3 F10 N' _chemical_formula_weight 605.35 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' D D 0.0000 0.0000 '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' F F 0.0171 0.0103 '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 10.944(1) _cell_length_b 11.974(1) _cell_length_c 12.513(1) _cell_angle_alpha 117.39(1) _cell_angle_beta 98.29(1) _cell_angle_gamma 106.57(1) _cell_volume 1320.4(2) _cell_formula_units_Z 2 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 173 _cell_measurement_theta_min 2.5 _cell_measurement_theta_max 25.0 _exptl_crystal_description blocks _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.523 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 618 _exptl_absorpt_coefficient_mu 0.137 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; dx = 35 mm, 120 sec./deg., 2 deg., 6 sets, 288 frames, 7255 refl. postref. ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonis KappaCCD' _diffrn_measurement_method 'rotation in phi and omega, 2 deg.' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 20736 _diffrn_reflns_av_R_equivalents 0.0317 _diffrn_reflns_av_sigmaI/netI 0.0325 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.25 _diffrn_reflns_theta_max 27.48 _reflns_number_total 6029 _reflns_number_gt 4637 _reflns_threshold_expression >2sigma(I) _computing_data_collection Collect _computing_cell_refinement EVALCCD _computing_data_reduction EVALCCd _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics XP _computing_publication_material '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. ; _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^)+(0.0480P)^2^+0.7147P] 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 6029 _refine_ls_number_parameters 385 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0635 _refine_ls_R_factor_gt 0.0436 _refine_ls_wR_factor_ref 0.1117 _refine_ls_wR_factor_gt 0.1008 _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_restrained_S_all 1.030 _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 B1 B 0.29467(17) 0.57139(18) 0.78501(17) 0.0183(3) Uani 1 1 d . . . H1 H 0.3503(18) 0.5209(18) 0.7219(17) 0.022 Uiso 1 1 d . . . C1 C 0.40023(15) 0.68498(15) 0.92700(14) 0.0173(3) Uani 1 1 d . . . C2 C 0.35944(16) 0.73129(16) 1.03444(15) 0.0196(3) Uani 1 1 d . . . H2 H 0.2659 0.6967 1.0234 0.023 Uiso 1 1 calc R . . C3 C 0.44803(17) 0.82447(17) 1.15535(15) 0.0221(3) Uani 1 1 d . . . H3 H 0.4155 0.8516 1.2258 0.027 Uiso 1 1 calc R . . C4 C 0.58397(17) 0.87872(18) 1.17469(16) 0.0261(4) Uani 1 1 d . . . H4 H 0.6455 0.9445 1.2582 0.031 Uiso 1 1 calc R . . C5 C 0.62953(16) 0.83710(17) 1.07284(16) 0.0240(3) Uani 1 1 d . . . H5 H 0.7230 0.8741 1.0847 0.029 Uiso 1 1 calc R . . C6 C 0.53855(15) 0.74083(16) 0.95246(14) 0.0180(3) Uani 1 1 d . . . N7 N 0.58867(13) 0.68774(13) 0.84392(12) 0.0169(3) Uani 1 1 d . . . H7 H 0.5117(19) 0.6248(19) 0.7808(18) 0.020 Uiso 1 1 d . . . C8 C 0.66830(16) 0.60020(17) 0.84892(16) 0.0213(3) Uani 1 1 d . . . C9 C 0.81724(16) 0.69045(19) 0.91399(18) 0.0274(4) Uani 1 1 d . . . H9A H 0.8333 0.7516 1.0057 0.033 Uiso 1 1 calc R . . H9B H 0.8674 0.6315 0.9059 0.033 Uiso 1 1 calc R . . C10 C 0.87242(17) 0.7769(2) 0.86133(19) 0.0311(4) Uani 1 1 d . . . H10A H 0.8631 0.7168 0.7711 0.037 Uiso 1 1 calc R . . H10B H 0.9694 0.8343 0.9092 0.037 Uiso 1 1 calc R . . C11 C 0.79790(17) 0.86811(18) 0.87114(18) 0.0284(4) Uani 1 1 d . . . H11A H 0.8356 0.9231 0.8350 0.034 Uiso 1 1 calc R . . H11B H 0.8140 0.9327 0.9622 0.034 Uiso 1 1 calc R . . C12 C 0.64736(17) 0.79093(17) 0.80362(16) 0.0227(3) Uani 1 1 d . . . C13 C 0.57771(19) 0.88926(19) 0.83691(19) 0.0303(4) Uani 1 1 d . . . H13A H 0.4805 0.8375 0.7929 0.045 Uiso 1 1 calc R . . H13B H 0.6126 0.9540 0.8104 0.045 Uiso 1 1 calc R . . H13C H 0.5949 0.9400 0.9290 0.045 Uiso 1 1 calc R . . C14 C 0.6130(2) 0.7117(2) 0.65985(17) 0.0317(4) Uani 1 1 d . . . H14A H 0.5150 0.6628 0.6199 0.048 Uiso 1 1 calc R . . H14B H 0.6551 0.6455 0.6345 0.048 Uiso 1 1 calc R . . H14C H 0.6468 0.7758 0.6324 0.048 Uiso 1 1 calc R . . C15 C 0.61660(18) 0.53445(19) 0.92037(18) 0.0279(4) Uani 1 1 d . . . H15A H 0.5203 0.4758 0.8767 0.042 Uiso 1 1 calc R . . H15B H 0.6300 0.6061 1.0071 0.042 Uiso 1 1 calc R . . H15C H 0.6659 0.4788 0.9237 0.042 Uiso 1 1 calc R . . C16 C 0.63861(18) 0.48567(18) 0.71402(17) 0.0289(4) Uani 1 1 d . . . H16A H 0.5414 0.4299 0.6754 0.043 Uiso 1 1 calc R . . H16B H 0.6861 0.4279 0.7151 0.043 Uiso 1 1 calc R . . H16C H 0.6691 0.5250 0.6643 0.043 Uiso 1 1 calc R . . C17 C 0.18254(16) 0.44503(17) 0.78000(15) 0.0215(3) Uani 1 1 d . . . C18 C 0.07095(16) 0.45127(18) 0.81650(16) 0.0246(4) Uani 1 1 d . . . F18 F 0.05124(9) 0.56771(11) 0.86125(9) 0.0285(2) Uani 1 1 d . . . C19 C -0.02551(18) 0.3447(2) 0.80986(18) 0.0337(4) Uani 1 1 d . . . F19 F -0.13187(11) 0.35910(15) 0.84632(12) 0.0485(3) Uani 1 1 d . . . C20 C -0.01368(19) 0.2224(2) 0.7640(2) 0.0396(5) Uani 1 1 d . . . F20 F -0.10587(13) 0.11731(15) 0.75786(15) 0.0620(4) Uani 1 1 d . . . C21 C 0.0943(2) 0.20937(19) 0.7257(2) 0.0370(5) Uani 1 1 d . . . F21 F 0.10679(13) 0.08976(12) 0.67912(14) 0.0573(4) Uani 1 1 d . . . C22 C 0.18906(17) 0.31943(18) 0.73446(17) 0.0279(4) Uani 1 1 d . . . F22 F 0.29188(11) 0.29744(11) 0.69413(11) 0.0384(3) Uani 1 1 d . . . C23 C 0.22345(15) 0.63328(16) 0.71403(15) 0.0184(3) Uani 1 1 d . . . C24 C 0.19327(15) 0.57355(17) 0.58446(15) 0.0209(3) Uani 1 1 d . . . F24 F 0.21774(10) 0.46209(10) 0.51623(9) 0.0282(2) Uani 1 1 d . . . C25 C 0.13711(16) 0.61862(18) 0.51553(15) 0.0236(3) Uani 1 1 d . . . F25 F 0.11219(11) 0.55521(12) 0.38997(9) 0.0346(3) Uani 1 1 d . . . C26 C 0.10519(16) 0.72860(18) 0.57617(16) 0.0237(4) Uani 1 1 d . . . F26 F 0.04999(11) 0.77414(11) 0.51136(10) 0.0333(3) Uani 1 1 d . . . C27 C 0.13104(15) 0.79129(16) 0.70425(16) 0.0214(3) Uani 1 1 d . . . F27 F 0.09835(10) 0.89779(10) 0.76438(9) 0.0275(2) Uani 1 1 d . . . C28 C 0.18952(15) 0.74401(16) 0.76979(15) 0.0201(3) Uani 1 1 d . . . F28 F 0.21280(10) 0.81376(10) 0.89536(9) 0.0255(2) Uani 1 1 d . . . C1B C 0.4251(3) 0.0719(3) 0.4981(2) 0.0556(7) Uani 1 1 d . . . D1B D 0.3728(3) 0.1229(3) 0.4974(2) 0.067 Uiso 1 1 d R . . C2B C 0.5558(3) 0.1195(2) 0.5056(2) 0.0518(6) Uani 1 1 d . . . D2B D 0.5950(3) 0.2033(2) 0.5090(2) 0.062 Uiso 1 1 d R . . C3B C 0.6313(2) 0.0477(3) 0.5082(2) 0.0508(6) Uani 1 1 d . . . D3B D 0.7235(2) 0.0817(3) 0.5145(2) 0.061 Uiso 1 1 d R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 B1 0.0172(8) 0.0215(8) 0.0191(8) 0.0107(7) 0.0080(7) 0.0106(7) C1 0.0200(7) 0.0185(7) 0.0191(7) 0.0116(6) 0.0083(6) 0.0112(6) C2 0.0201(7) 0.0236(8) 0.0226(8) 0.0147(7) 0.0097(6) 0.0129(6) C3 0.0289(9) 0.0268(8) 0.0200(8) 0.0139(7) 0.0135(7) 0.0177(7) C4 0.0270(9) 0.0267(9) 0.0167(8) 0.0065(7) 0.0043(7) 0.0105(7) C5 0.0191(8) 0.0259(8) 0.0227(8) 0.0097(7) 0.0068(6) 0.0089(7) C6 0.0211(8) 0.0203(7) 0.0183(7) 0.0114(6) 0.0100(6) 0.0117(6) N7 0.0161(6) 0.0185(6) 0.0176(6) 0.0093(5) 0.0069(5) 0.0085(5) C8 0.0215(8) 0.0230(8) 0.0275(9) 0.0151(7) 0.0120(7) 0.0143(7) C9 0.0201(8) 0.0335(9) 0.0331(10) 0.0180(8) 0.0104(7) 0.0151(7) C10 0.0195(8) 0.0361(10) 0.0375(10) 0.0189(8) 0.0130(7) 0.0100(7) C11 0.0260(9) 0.0259(9) 0.0339(10) 0.0174(8) 0.0135(7) 0.0066(7) C12 0.0255(8) 0.0222(8) 0.0265(9) 0.0160(7) 0.0113(7) 0.0102(7) C13 0.0353(10) 0.0260(9) 0.0389(10) 0.0213(8) 0.0141(8) 0.0161(8) C14 0.0390(10) 0.0384(10) 0.0282(9) 0.0227(8) 0.0158(8) 0.0177(8) C15 0.0297(9) 0.0309(9) 0.0371(10) 0.0244(8) 0.0149(8) 0.0169(7) C16 0.0313(9) 0.0262(9) 0.0342(10) 0.0144(8) 0.0178(8) 0.0170(7) C17 0.0183(7) 0.0254(8) 0.0199(8) 0.0130(7) 0.0018(6) 0.0078(6) C18 0.0223(8) 0.0308(9) 0.0213(8) 0.0159(7) 0.0036(7) 0.0093(7) F18 0.0223(5) 0.0377(6) 0.0293(5) 0.0171(5) 0.0128(4) 0.0158(4) C19 0.0226(9) 0.0496(12) 0.0335(10) 0.0299(9) 0.0067(7) 0.0079(8) F19 0.0271(6) 0.0731(9) 0.0541(8) 0.0435(7) 0.0198(6) 0.0108(6) C20 0.0295(10) 0.0411(11) 0.0452(12) 0.0340(10) -0.0028(9) -0.0018(8) F20 0.0408(7) 0.0585(9) 0.0861(10) 0.0582(8) 0.0009(7) -0.0062(6) C21 0.0334(10) 0.0275(9) 0.0457(12) 0.0240(9) -0.0050(9) 0.0068(8) F21 0.0488(8) 0.0264(6) 0.0832(10) 0.0306(7) -0.0068(7) 0.0085(5) C22 0.0220(8) 0.0267(9) 0.0325(9) 0.0161(8) 0.0008(7) 0.0098(7) F22 0.0307(6) 0.0270(5) 0.0524(7) 0.0154(5) 0.0087(5) 0.0170(5) C23 0.0137(7) 0.0223(8) 0.0206(8) 0.0125(6) 0.0064(6) 0.0065(6) C24 0.0175(7) 0.0238(8) 0.0223(8) 0.0115(7) 0.0088(6) 0.0096(6) F24 0.0317(5) 0.0347(6) 0.0185(5) 0.0097(4) 0.0104(4) 0.0202(5) C25 0.0192(8) 0.0335(9) 0.0179(8) 0.0147(7) 0.0064(6) 0.0085(7) F25 0.0368(6) 0.0546(7) 0.0192(5) 0.0205(5) 0.0109(4) 0.0242(5) C26 0.0184(8) 0.0309(9) 0.0276(9) 0.0213(8) 0.0050(7) 0.0084(7) F26 0.0351(6) 0.0434(6) 0.0340(6) 0.0290(5) 0.0076(5) 0.0188(5) C27 0.0178(7) 0.0191(8) 0.0283(9) 0.0130(7) 0.0072(7) 0.0078(6) F27 0.0294(5) 0.0238(5) 0.0322(5) 0.0154(4) 0.0074(4) 0.0143(4) C28 0.0180(7) 0.0232(8) 0.0178(8) 0.0105(6) 0.0055(6) 0.0074(6) F28 0.0332(5) 0.0271(5) 0.0173(5) 0.0093(4) 0.0069(4) 0.0184(4) C1B 0.091(2) 0.0765(18) 0.0464(14) 0.0447(14) 0.0431(14) 0.0627(16) C2B 0.0884(19) 0.0273(10) 0.0347(12) 0.0147(9) 0.0283(12) 0.0153(11) C3B 0.0423(12) 0.0753(17) 0.0250(10) 0.0247(11) 0.0117(9) 0.0135(12) _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 B1 C1 1.622(2) . ? B1 C17 1.622(2) . ? B1 C23 1.637(2) . ? B1 H1 1.127(18) . ? C1 C6 1.388(2) . ? C1 C2 1.394(2) . ? C2 C3 1.371(2) . ? C2 H2 0.9500 . ? C3 C4 1.376(2) . ? C3 H3 0.9500 . ? C4 C5 1.364(2) . ? C4 H4 0.9500 . ? C5 C6 1.380(2) . ? C5 H5 0.9500 . ? C6 N7 1.4727(19) . ? N7 C12 1.552(2) . ? N7 C8 1.5582(19) . ? N7 H7 0.894(19) . ? C8 C15 1.509(2) . ? C8 C9 1.513(2) . ? C8 C16 1.514(2) . ? C9 C10 1.502(3) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C11 1.512(3) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.515(2) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C13 1.514(2) . ? C12 C14 1.520(2) . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 C22 1.370(2) . ? C17 C18 1.374(2) . ? C18 F18 1.339(2) . ? C18 C19 1.363(3) . ? C19 F19 1.337(2) . ? C19 C20 1.359(3) . ? C20 F20 1.331(2) . ? C20 C21 1.360(3) . ? C21 F21 1.333(2) . ? C21 C22 1.371(3) . ? C22 F22 1.342(2) . ? C23 C28 1.374(2) . ? C23 C24 1.376(2) . ? C24 F24 1.3428(18) . ? C24 C25 1.370(2) . ? C25 F25 1.3342(19) . ? C25 C26 1.361(2) . ? C26 F26 1.3317(18) . ? C26 C27 1.361(2) . ? C27 F27 1.3324(18) . ? C27 C28 1.373(2) . ? C28 F28 1.3368(18) . ? C1B D1B 0.9500 . ? C1B C3B 1.347(4) 2_656 ? C1B C2B 1.352(4) . ? C2B D2B 0.9500 . ? C2B C3B 1.359(4) . ? C3B D3B 0.9500 . ? C3B C1B 1.347(4) 2_656 ? 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 B1 C17 112.62(13) . . ? C1 B1 C23 114.82(13) . . ? C17 B1 C23 110.89(12) . . ? C1 B1 H1 109.0(9) . . ? C17 B1 H1 103.7(9) . . ? C23 B1 H1 104.9(9) . . ? C6 C1 C2 114.38(14) . . ? C6 C1 B1 123.11(13) . . ? C2 C1 B1 122.47(14) . . ? C3 C2 C1 123.03(15) . . ? C3 C2 H2 118.5 . . ? C1 C2 H2 118.5 . . ? C2 C3 C4 120.06(15) . . ? C2 C3 H3 120.0 . . ? C4 C3 H3 120.0 . . ? C5 C4 C3 119.37(15) . . ? C5 C4 H4 120.3 . . ? C3 C4 H4 120.3 . . ? C4 C5 C6 119.40(15) . . ? C4 C5 H5 120.3 . . ? C6 C5 H5 120.3 . . ? C5 C6 C1 123.71(14) . . ? C5 C6 N7 119.34(14) . . ? C1 C6 N7 116.88(13) . . ? C6 N7 C12 114.98(12) . . ? C6 N7 C8 113.38(12) . . ? C12 N7 C8 117.15(12) . . ? C6 N7 H7 101.0(12) . . ? C12 N7 H7 104.7(12) . . ? C8 N7 H7 102.8(12) . . ? C15 C8 C9 110.45(14) . . ? C15 C8 C16 107.38(14) . . ? C9 C8 C16 112.06(14) . . ? C15 C8 N7 108.88(12) . . ? C9 C8 N7 109.88(13) . . ? C16 C8 N7 108.10(13) . . ? C10 C9 C8 113.95(14) . . ? C10 C9 H9A 108.8 . . ? C8 C9 H9A 108.8 . . ? C10 C9 H9B 108.8 . . ? C8 C9 H9B 108.8 . . ? H9A C9 H9B 107.7 . . ? C9 C10 C11 110.46(14) . . ? C9 C10 H10A 109.6 . . ? C11 C10 H10A 109.6 . . ? C9 C10 H10B 109.6 . . ? C11 C10 H10B 109.6 . . ? H10A C10 H10B 108.1 . . ? C10 C11 C12 114.11(15) . . ? C10 C11 H11A 108.7 . . ? C12 C11 H11A 108.7 . . ? C10 C11 H11B 108.7 . . ? C12 C11 H11B 108.7 . . ? H11A C11 H11B 107.6 . . ? C13 C12 C11 110.65(14) . . ? C13 C12 C14 107.14(14) . . ? C11 C12 C14 112.06(15) . . ? C13 C12 N7 108.63(13) . . ? C11 C12 N7 109.90(13) . . ? C14 C12 N7 108.34(13) . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C12 C14 H14A 109.5 . . ? C12 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C12 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C8 C15 H15A 109.5 . . ? C8 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C8 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C8 C16 H16A 109.5 . . ? C8 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C8 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C22 C17 C18 113.65(16) . . ? C22 C17 B1 122.32(15) . . ? C18 C17 B1 124.00(15) . . ? F18 C18 C19 115.73(16) . . ? F18 C18 C17 119.81(15) . . ? C19 C18 C17 124.46(17) . . ? F19 C19 C20 120.04(17) . . ? F19 C19 C18 120.62(19) . . ? C20 C19 C18 119.33(18) . . ? F20 C20 C19 120.4(2) . . ? F20 C20 C21 120.5(2) . . ? C19 C20 C21 119.08(17) . . ? F21 C21 C20 119.95(18) . . ? F21 C21 C22 120.44(19) . . ? C20 C21 C22 119.61(18) . . ? F22 C22 C17 120.45(16) . . ? F22 C22 C21 115.68(16) . . ? C17 C22 C21 123.87(18) . . ? C28 C23 C24 113.14(14) . . ? C28 C23 B1 127.21(14) . . ? C24 C23 B1 119.64(14) . . ? F24 C24 C25 115.20(14) . . ? F24 C24 C23 120.03(14) . . ? C25 C24 C23 124.76(15) . . ? F25 C25 C26 119.81(15) . . ? F25 C25 C24 120.85(15) . . ? C26 C25 C24 119.33(15) . . ? F26 C26 C25 120.56(15) . . ? F26 C26 C27 120.68(15) . . ? C25 C26 C27 118.76(15) . . ? F27 C27 C26 119.30(14) . . ? F27 C27 C28 120.79(15) . . ? C26 C27 C28 119.91(15) . . ? F28 C28 C27 115.38(14) . . ? F28 C28 C23 120.54(14) . . ? C27 C28 C23 124.08(15) . . ? D1B C1B C3B 119.93(16) . 2_656 ? D1B C1B C2B 119.93(15) . . ? C3B C1B C2B 120.1(2) 2_656 . ? D2B C2B C1B 119.95(15) . . ? D2B C2B C3B 119.95(15) . . ? C1B C2B C3B 120.1(2) . . ? D3B C3B C1B 120.12(16) . 2_656 ? D3B C3B C2B 120.12(15) . . ? C1B C3B C2B 119.8(2) 2_656 . ? 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 C17 B1 C1 C6 134.39(15) . . . . ? C23 B1 C1 C6 -97.41(17) . . . . ? C17 B1 C1 C2 -43.42(19) . . . . ? C23 B1 C1 C2 84.78(18) . . . . ? C6 C1 C2 C3 0.2(2) . . . . ? B1 C1 C2 C3 178.16(14) . . . . ? C1 C2 C3 C4 1.2(2) . . . . ? C2 C3 C4 C5 -1.1(2) . . . . ? C3 C4 C5 C6 -0.4(3) . . . . ? C4 C5 C6 C1 1.9(3) . . . . ? C4 C5 C6 N7 -175.10(15) . . . . ? C2 C1 C6 C5 -1.7(2) . . . . ? B1 C1 C6 C5 -179.72(15) . . . . ? C2 C1 C6 N7 175.32(13) . . . . ? B1 C1 C6 N7 -2.7(2) . . . . ? C5 C6 N7 C12 -71.76(18) . . . . ? C1 C6 N7 C12 111.04(15) . . . . ? C5 C6 N7 C8 66.81(18) . . . . ? C1 C6 N7 C8 -110.39(15) . . . . ? C6 N7 C8 C15 28.24(18) . . . . ? C12 N7 C8 C15 165.87(14) . . . . ? C6 N7 C8 C9 -92.83(16) . . . . ? C12 N7 C8 C9 44.79(18) . . . . ? C6 N7 C8 C16 144.60(13) . . . . ? C12 N7 C8 C16 -77.78(17) . . . . ? C15 C8 C9 C10 -170.96(15) . . . . ? C16 C8 C9 C10 69.36(19) . . . . ? N7 C8 C9 C10 -50.83(19) . . . . ? C8 C9 C10 C11 58.2(2) . . . . ? C9 C10 C11 C12 -57.9(2) . . . . ? C10 C11 C12 C13 170.14(15) . . . . ? C10 C11 C12 C14 -70.35(19) . . . . ? C10 C11 C12 N7 50.18(19) . . . . ? C6 N7 C12 C13 -28.70(18) . . . . ? C8 N7 C12 C13 -165.66(14) . . . . ? C6 N7 C12 C11 92.48(16) . . . . ? C8 N7 C12 C11 -44.47(18) . . . . ? C6 N7 C12 C14 -144.78(14) . . . . ? C8 N7 C12 C14 78.27(17) . . . . ? C1 B1 C17 C22 -102.95(17) . . . . ? C23 B1 C17 C22 126.82(16) . . . . ? C1 B1 C17 C18 79.16(19) . . . . ? C23 B1 C17 C18 -51.1(2) . . . . ? C22 C17 C18 F18 -179.12(14) . . . . ? B1 C17 C18 F18 -1.1(2) . . . . ? C22 C17 C18 C19 0.3(2) . . . . ? B1 C17 C18 C19 178.39(15) . . . . ? F18 C18 C19 F19 0.1(2) . . . . ? C17 C18 C19 F19 -179.35(16) . . . . ? F18 C18 C19 C20 179.21(15) . . . . ? C17 C18 C19 C20 -0.3(3) . . . . ? F19 C19 C20 F20 -1.6(3) . . . . ? C18 C19 C20 F20 179.30(16) . . . . ? F19 C19 C20 C21 179.06(17) . . . . ? C18 C19 C20 C21 0.0(3) . . . . ? F20 C20 C21 F21 1.5(3) . . . . ? C19 C20 C21 F21 -179.22(17) . . . . ? F20 C20 C21 C22 -179.11(17) . . . . ? C19 C20 C21 C22 0.2(3) . . . . ? C18 C17 C22 F22 179.43(15) . . . . ? B1 C17 C22 F22 1.3(2) . . . . ? C18 C17 C22 C21 -0.1(3) . . . . ? B1 C17 C22 C21 -178.22(16) . . . . ? F21 C21 C22 F22 -0.3(3) . . . . ? C20 C21 C22 F22 -179.72(16) . . . . ? F21 C21 C22 C17 179.30(16) . . . . ? C20 C21 C22 C17 -0.1(3) . . . . ? C1 B1 C23 C28 -33.3(2) . . . . ? C17 B1 C23 C28 95.74(19) . . . . ? C1 B1 C23 C24 145.71(15) . . . . ? C17 B1 C23 C24 -85.22(18) . . . . ? C28 C23 C24 F24 -178.44(13) . . . . ? B1 C23 C24 F24 2.4(2) . . . . ? C28 C23 C24 C25 1.0(2) . . . . ? B1 C23 C24 C25 -178.18(15) . . . . ? F24 C24 C25 F25 -1.2(2) . . . . ? C23 C24 C25 F25 179.39(15) . . . . ? F24 C24 C25 C26 178.12(14) . . . . ? C23 C24 C25 C26 -1.3(3) . . . . ? F25 C25 C26 F26 -0.4(2) . . . . ? C24 C25 C26 F26 -179.71(14) . . . . ? F25 C25 C26 C27 179.73(15) . . . . ? C24 C25 C26 C27 0.4(2) . . . . ? F26 C26 C27 F27 1.2(2) . . . . ? C25 C26 C27 F27 -179.00(14) . . . . ? F26 C26 C27 C28 -179.20(14) . . . . ? C25 C26 C27 C28 0.6(2) . . . . ? F27 C27 C28 F28 -1.4(2) . . . . ? C26 C27 C28 F28 178.95(14) . . . . ? F27 C27 C28 C23 178.64(14) . . . . ? C26 C27 C28 C23 -1.0(2) . . . . ? C24 C23 C28 F28 -179.76(14) . . . . ? B1 C23 C28 F28 -0.7(2) . . . . ? C24 C23 C28 C27 0.2(2) . . . . ? B1 C23 C28 C27 179.28(15) . . . . ? D1B C1B C2B D2B -0.78(16) . . . . ? C3B C1B C2B D2B 179.22(15) 2_656 . . . ? D1B C1B C2B C3B 179.22(15) . . . . ? C3B C1B C2B C3B -0.8(4) 2_656 . . . ? D2B C2B C3B D3B 0.78(15) . . . . ? C1B C2B C3B D3B -179.22(16) . . . . ? D2B C2B C3B C1B -179.22(15) . . . 2_656 ? C1B C2B C3B C1B 0.8(4) . . . 2_656 ? 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 N7 H7 H1 0.894(19) 1.65(3) 2.490(18) 154.0(19) . C2 H2 F18 0.95 2.39 3.1824(19) 141.1 . C2 H2 F19 0.95 2.53 3.259(2) 133.9 2_567 C5 H5 F27 0.95 2.45 3.163(2) 131.9 2_677 C9 H9B F18 0.99 2.40 3.3008(19) 151.2 1_655 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.320 _refine_diff_density_min -0.230 _refine_diff_density_rms 0.049 # start Validation Reply Form _vrf_PLAT412_les084_CCDC-875801 ; PROBLEM: Short Intra XH3 .. XHn H14B .. H16C .. 1.69 Ang. RESPONSE: that's the methyl-hydrogen atoms from methyl groups bonded to the piperidine substituent ; _vrf_PLAT414_les084_CCDC-875801 ; PROBLEM: Short Intra D-H..H-X H1 .. H7 .. 1.66 Ang. RESPONSE: this is an intramolecular hydrogen-hydrogen bond ; # end Validation Reply Form #============================================================================== data_les086_CCDC-875802 _database_code_depnum_ccdc_archive 'CCDC 875802' #TrackingRef '- dalton.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 7,7-dimethyl-8,8-bis(perfluorophenyl)-7-aza-8-borabicyclo[4.2.0]octa- 1,3,5-trien-7-ium-8-uide ; _chemical_name_common ; 7,7-dimethyl-8,8-bis(perfluorophenyl)-7-aza-8- borabicyclo(4.2.0)octa-1,3,5-trien-7-ium-8-uide ; _chemical_melting_point ? _chemical_formula_moiety 'C20 H10 B F10 N' _chemical_formula_sum 'C20 H10 B F10 N' _chemical_formula_weight 465.10 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' F F 0.0171 0.0103 '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 9.8216(4) _cell_length_b 35.0210(15) _cell_length_c 11.1291(4) _cell_angle_alpha 90.00 _cell_angle_beta 107.047(2) _cell_angle_gamma 90.00 _cell_volume 3659.8(3) _cell_formula_units_Z 8 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 4015 _cell_measurement_theta_min 1 _cell_measurement_theta_max 27.5 _exptl_crystal_description blocks _exptl_crystal_colour colourless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.688 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1856 _exptl_absorpt_coefficient_mu 0.170 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; dx = 50 mm, 40 sec./deg., 1 deg., 4 sets, 304 frames ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius APEXII' _diffrn_measurement_method 'rotation in phi and omega, 1 deg.' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18746 _diffrn_reflns_av_R_equivalents 0.0309 _diffrn_reflns_av_sigmaI/netI 0.0367 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -45 _diffrn_reflns_limit_k_max 41 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.00 _diffrn_reflns_theta_max 27.48 _reflns_number_total 8151 _reflns_number_gt 6761 _reflns_threshold_expression >2sigma(I) _computing_data_collection Collect _computing_cell_refinement DENZO-SMN _computing_data_reduction DENZO-SMN _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics XP _computing_publication_material '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. ; _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^)+(0.0201P)^2^+3.3060P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 8151 _refine_ls_number_parameters 581 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0644 _refine_ls_R_factor_gt 0.0506 _refine_ls_wR_factor_ref 0.1107 _refine_ls_wR_factor_gt 0.1023 _refine_ls_goodness_of_fit_ref 1.107 _refine_ls_restrained_S_all 1.107 _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 B1 B 0.8605(2) 0.41154(6) 0.6593(2) 0.0252(4) Uani 1 1 d . . . C1 C 0.8879(2) 0.41032(6) 0.80964(18) 0.0260(4) Uani 1 1 d . . . C2 C 0.8626(2) 0.39311(6) 0.91390(19) 0.0306(4) Uani 1 1 d . . . H2 H 0.7961 0.3728 0.9045 0.037 Uiso 1 1 calc R . . C3 C 0.9382(2) 0.40670(7) 1.0327(2) 0.0363(5) Uani 1 1 d . . . H3 H 0.9236 0.3951 1.1051 0.044 Uiso 1 1 calc R . . C4 C 1.0343(3) 0.43674(7) 1.0477(2) 0.0407(6) Uani 1 1 d . . . H4 H 1.0843 0.4450 1.1301 0.049 Uiso 1 1 calc R . . C5 C 1.0589(3) 0.45491(7) 0.9455(2) 0.0373(5) Uani 1 1 d . . . H5 H 1.1235 0.4756 0.9539 0.045 Uiso 1 1 calc R . . C6 C 0.9819(2) 0.44042(6) 0.83029(18) 0.0281(4) Uani 1 1 d . . . N7 N 0.97548(19) 0.45145(5) 0.70074(16) 0.0287(4) Uani 1 1 d . . . C8 C 0.9177(3) 0.49097(6) 0.6740(2) 0.0410(5) Uani 1 1 d . . . H8A H 0.8218 0.4920 0.6839 0.062 Uiso 1 1 calc R . . H8B H 0.9133 0.4980 0.5878 0.062 Uiso 1 1 calc R . . H8C H 0.9799 0.5089 0.7329 0.062 Uiso 1 1 calc R . . C9 C 1.1176(2) 0.44952(7) 0.6786(2) 0.0371(5) Uani 1 1 d . . . H9A H 1.1802 0.4690 0.7295 0.056 Uiso 1 1 calc R . . H9B H 1.1069 0.4541 0.5895 0.056 Uiso 1 1 calc R . . H9C H 1.1591 0.4242 0.7024 0.056 Uiso 1 1 calc R . . C10 C 0.6986(2) 0.41945(6) 0.57187(18) 0.0283(4) Uani 1 1 d . . . C11 C 0.5927(2) 0.39623(6) 0.59308(18) 0.0292(4) Uani 1 1 d . . . F11 F 0.62861(13) 0.36919(4) 0.68414(11) 0.0363(3) Uani 1 1 d . . . C12 C 0.4503(2) 0.39836(7) 0.5264(2) 0.0348(5) Uani 1 1 d . . . F12 F 0.35396(14) 0.37539(4) 0.55360(13) 0.0467(4) Uani 1 1 d . . . C13 C 0.4073(2) 0.42478(8) 0.4317(2) 0.0437(6) Uani 1 1 d . . . F13 F 0.26817(16) 0.42796(5) 0.36622(16) 0.0659(5) Uani 1 1 d . . . C14 C 0.5067(3) 0.44783(8) 0.4041(2) 0.0463(6) Uani 1 1 d . . . F14 F 0.46551(19) 0.47328(5) 0.30966(16) 0.0743(6) Uani 1 1 d . . . C15 C 0.6484(2) 0.44464(7) 0.4722(2) 0.0361(5) Uani 1 1 d . . . F15 F 0.73878(15) 0.46803(4) 0.43616(13) 0.0480(4) Uani 1 1 d . . . C16 C 0.9369(2) 0.37841(6) 0.59988(18) 0.0255(4) Uani 1 1 d . . . C17 C 0.9728(2) 0.34281(6) 0.65469(19) 0.0278(4) Uani 1 1 d . . . F17 F 0.94469(15) 0.33391(3) 0.76345(12) 0.0387(3) Uani 1 1 d . . . C18 C 1.0365(2) 0.31400(6) 0.6048(2) 0.0334(5) Uani 1 1 d . . . F18 F 1.07113(16) 0.28065(4) 0.66476(14) 0.0458(3) Uani 1 1 d . . . C19 C 1.0658(2) 0.32032(7) 0.4925(2) 0.0334(5) Uani 1 1 d . . . F19 F 1.12629(15) 0.29264(4) 0.44224(14) 0.0468(4) Uani 1 1 d . . . C20 C 1.0322(2) 0.35509(7) 0.43285(19) 0.0323(5) Uani 1 1 d . . . F20 F 1.06182(15) 0.36132(4) 0.32430(12) 0.0452(3) Uani 1 1 d . . . C21 C 0.9696(2) 0.38282(6) 0.48691(19) 0.0290(4) Uani 1 1 d . . . F21 F 0.94137(14) 0.41668(4) 0.42539(11) 0.0383(3) Uani 1 1 d . . . B1' B 0.5185(2) 0.16093(7) 0.5627(2) 0.0285(5) Uani 1 1 d . . . C1' C 0.5477(2) 0.17205(6) 0.7086(2) 0.0299(4) Uani 1 1 d . . . C2' C 0.6410(3) 0.17635(6) 0.8288(2) 0.0357(5) Uani 1 1 d . . . H2' H 0.7399 0.1713 0.8454 0.043 Uiso 1 1 calc R . . C3' C 0.5854(3) 0.18824(7) 0.9245(2) 0.0408(5) Uani 1 1 d . . . H3' H 0.6479 0.1913 1.0071 0.049 Uiso 1 1 calc R . . C4' C 0.4409(3) 0.19568(7) 0.9024(2) 0.0426(6) Uani 1 1 d . . . H4' H 0.4067 0.2034 0.9701 0.051 Uiso 1 1 calc R . . C5' C 0.3462(3) 0.19195(7) 0.7831(2) 0.0407(5) Uani 1 1 d . . . H5' H 0.2473 0.1971 0.7655 0.049 Uiso 1 1 calc R . . C6' C 0.4066(2) 0.18016(6) 0.6918(2) 0.0308(4) Uani 1 1 d . . . N7' N 0.34499(18) 0.17362(5) 0.55578(17) 0.0306(4) Uani 1 1 d . . . C8' C 0.2828(2) 0.20978(6) 0.4919(2) 0.0394(5) Uani 1 1 d . . . H8'1 H 0.2128 0.2198 0.5311 0.059 Uiso 1 1 calc R . . H8'2 H 0.2359 0.2047 0.4027 0.059 Uiso 1 1 calc R . . H8'3 H 0.3587 0.2286 0.4999 0.059 Uiso 1 1 calc R . . C9' C 0.2343(2) 0.14305(7) 0.5285(3) 0.0430(6) Uani 1 1 d . . . H9'1 H 0.2744 0.1198 0.5741 0.065 Uiso 1 1 calc R . . H9'2 H 0.2030 0.1378 0.4381 0.065 Uiso 1 1 calc R . . H9'3 H 0.1527 0.1515 0.5555 0.065 Uiso 1 1 calc R . . C10' C 0.5339(2) 0.11587(6) 0.53013(19) 0.0272(4) Uani 1 1 d . . . C11' C 0.4744(2) 0.10065(6) 0.4111(2) 0.0301(4) Uani 1 1 d . . . F11' F 0.38462(14) 0.12215(4) 0.32109(12) 0.0400(3) Uani 1 1 d . . . C12' C 0.5015(2) 0.06422(6) 0.3759(2) 0.0322(5) Uani 1 1 d . . . F12' F 0.44312(15) 0.05161(4) 0.25768(12) 0.0429(3) Uani 1 1 d . . . C13' C 0.5924(2) 0.04102(6) 0.4630(2) 0.0331(5) Uani 1 1 d . . . F13' F 0.62243(15) 0.00551(4) 0.43167(13) 0.0441(3) Uani 1 1 d . . . C14' C 0.6526(2) 0.05426(6) 0.5830(2) 0.0348(5) Uani 1 1 d . . . F14' F 0.74238(17) 0.03171(4) 0.66802(13) 0.0490(4) Uani 1 1 d . . . C15' C 0.6228(2) 0.09086(6) 0.6140(2) 0.0313(4) Uani 1 1 d . . . F15' F 0.69059(15) 0.10182(4) 0.73229(12) 0.0442(3) Uani 1 1 d . . . C16' C 0.5952(2) 0.18694(6) 0.4796(2) 0.0284(4) Uani 1 1 d . . . C17' C 0.5413(2) 0.20144(6) 0.3588(2) 0.0345(5) Uani 1 1 d . . . F17' F 0.40284(15) 0.19684(4) 0.29356(13) 0.0457(3) Uani 1 1 d . . . C18' C 0.6217(3) 0.22126(6) 0.2960(2) 0.0427(6) Uani 1 1 d . . . F18' F 0.5615(2) 0.23474(4) 0.17969(15) 0.0614(5) Uani 1 1 d . . . C19' C 0.7635(3) 0.22679(7) 0.3526(3) 0.0477(7) Uani 1 1 d . . . F19' F 0.8438(2) 0.24582(5) 0.2928(2) 0.0737(6) Uani 1 1 d . . . C20' C 0.8244(3) 0.21247(7) 0.4702(3) 0.0452(6) Uani 1 1 d . . . F20' F 0.96518(16) 0.21591(5) 0.52630(19) 0.0674(5) Uani 1 1 d . . . C21' C 0.7407(2) 0.19296(6) 0.5309(2) 0.0332(5) Uani 1 1 d . . . F21' F 0.80967(13) 0.17778(4) 0.64428(13) 0.0427(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 B1 0.0279(11) 0.0206(10) 0.0264(10) 0.0025(8) 0.0072(9) -0.0030(9) C1 0.0263(10) 0.0250(10) 0.0257(9) 0.0018(8) 0.0061(8) 0.0049(8) C2 0.0298(10) 0.0339(11) 0.0291(10) 0.0041(8) 0.0103(8) 0.0088(9) C3 0.0395(12) 0.0439(13) 0.0269(10) 0.0049(9) 0.0118(9) 0.0171(10) C4 0.0459(13) 0.0419(13) 0.0284(11) -0.0091(10) 0.0016(9) 0.0132(11) C5 0.0409(12) 0.0294(11) 0.0360(11) -0.0080(9) 0.0027(9) 0.0017(10) C6 0.0310(10) 0.0243(10) 0.0274(10) -0.0020(8) 0.0060(8) 0.0030(8) N7 0.0338(9) 0.0218(8) 0.0294(8) 0.0012(7) 0.0077(7) -0.0018(7) C8 0.0535(15) 0.0216(11) 0.0447(13) 0.0030(9) 0.0094(11) 0.0007(10) C9 0.0351(12) 0.0320(12) 0.0442(12) -0.0057(10) 0.0116(10) -0.0126(9) C10 0.0317(10) 0.0272(10) 0.0248(9) -0.0012(8) 0.0065(8) 0.0011(8) C11 0.0327(11) 0.0280(10) 0.0257(10) -0.0006(8) 0.0068(8) 0.0007(8) F11 0.0346(7) 0.0362(7) 0.0351(7) 0.0081(5) 0.0056(5) -0.0062(5) C12 0.0290(11) 0.0359(12) 0.0365(11) -0.0048(9) 0.0051(9) -0.0041(9) F12 0.0313(7) 0.0550(9) 0.0506(8) -0.0034(7) 0.0069(6) -0.0116(6) C13 0.0290(11) 0.0473(15) 0.0431(13) 0.0009(11) -0.0079(10) 0.0040(10) F13 0.0355(8) 0.0692(12) 0.0730(11) 0.0099(9) -0.0153(7) 0.0029(8) C14 0.0465(14) 0.0431(14) 0.0381(12) 0.0140(11) -0.0052(10) 0.0038(11) F14 0.0614(11) 0.0740(12) 0.0654(11) 0.0400(10) -0.0159(8) 0.0011(9) C15 0.0378(12) 0.0341(12) 0.0337(11) 0.0075(9) 0.0063(9) -0.0016(10) F15 0.0474(8) 0.0495(9) 0.0418(7) 0.0215(7) 0.0048(6) -0.0062(7) C16 0.0235(9) 0.0253(10) 0.0266(9) -0.0013(8) 0.0059(7) -0.0037(8) C17 0.0295(10) 0.0254(10) 0.0306(10) -0.0029(8) 0.0122(8) -0.0052(8) F17 0.0587(8) 0.0259(6) 0.0404(7) 0.0058(5) 0.0282(6) 0.0035(6) C18 0.0343(11) 0.0251(10) 0.0424(12) -0.0037(9) 0.0139(9) -0.0031(9) F18 0.0609(9) 0.0235(7) 0.0607(9) 0.0038(6) 0.0300(7) 0.0059(6) C19 0.0276(10) 0.0355(12) 0.0401(12) -0.0123(10) 0.0145(9) -0.0029(9) F19 0.0477(8) 0.0439(8) 0.0584(9) -0.0128(7) 0.0304(7) 0.0024(7) C20 0.0269(10) 0.0449(13) 0.0265(10) -0.0050(9) 0.0098(8) -0.0069(9) F20 0.0466(8) 0.0619(10) 0.0326(7) -0.0025(6) 0.0202(6) -0.0013(7) C21 0.0275(10) 0.0298(11) 0.0280(10) -0.0007(8) 0.0058(8) -0.0040(8) F21 0.0434(7) 0.0408(8) 0.0303(6) 0.0083(6) 0.0103(5) 0.0011(6) B1' 0.0213(10) 0.0261(11) 0.0388(12) 0.0022(10) 0.0102(9) 0.0019(9) C1' 0.0300(10) 0.0226(10) 0.0394(11) 0.0023(8) 0.0138(9) 0.0027(8) C2' 0.0375(12) 0.0317(11) 0.0376(12) 0.0003(9) 0.0107(9) 0.0079(9) C3' 0.0578(15) 0.0289(12) 0.0384(12) 0.0025(9) 0.0180(11) 0.0035(11) C4' 0.0539(15) 0.0329(12) 0.0511(14) -0.0015(11) 0.0313(12) 0.0012(11) C5' 0.0407(13) 0.0320(12) 0.0590(15) 0.0000(11) 0.0295(12) 0.0010(10) C6' 0.0315(11) 0.0215(10) 0.0426(12) 0.0031(9) 0.0158(9) -0.0006(8) N7' 0.0220(8) 0.0253(9) 0.0455(10) 0.0018(8) 0.0114(7) 0.0001(7) C8' 0.0288(11) 0.0294(12) 0.0590(15) 0.0083(11) 0.0115(10) 0.0083(9) C9' 0.0267(11) 0.0336(12) 0.0708(17) -0.0048(12) 0.0174(11) -0.0074(9) C10' 0.0252(10) 0.0234(10) 0.0350(10) 0.0036(8) 0.0120(8) 0.0013(8) C11' 0.0254(10) 0.0255(10) 0.0383(11) 0.0049(9) 0.0077(8) 0.0019(8) F11' 0.0402(7) 0.0334(7) 0.0395(7) 0.0017(6) 0.0011(6) 0.0081(6) C12' 0.0316(11) 0.0299(11) 0.0362(11) -0.0029(9) 0.0115(9) -0.0028(9) F12' 0.0480(8) 0.0370(7) 0.0408(7) -0.0079(6) 0.0086(6) 0.0031(6) C13' 0.0368(12) 0.0207(10) 0.0460(12) 0.0016(9) 0.0186(10) 0.0025(8) F13' 0.0543(9) 0.0239(7) 0.0558(8) -0.0026(6) 0.0189(7) 0.0071(6) C14' 0.0365(12) 0.0277(11) 0.0413(12) 0.0101(9) 0.0131(10) 0.0066(9) F14' 0.0652(10) 0.0327(7) 0.0447(8) 0.0100(6) 0.0094(7) 0.0190(7) C15' 0.0335(11) 0.0285(11) 0.0329(11) 0.0037(9) 0.0112(9) 0.0014(9) F15' 0.0573(9) 0.0339(7) 0.0345(7) 0.0022(6) 0.0029(6) 0.0137(6) C16' 0.0278(10) 0.0196(9) 0.0402(11) -0.0042(8) 0.0139(9) 0.0008(8) C17' 0.0412(12) 0.0239(10) 0.0412(12) -0.0002(9) 0.0163(10) 0.0022(9) F17' 0.0457(8) 0.0423(8) 0.0430(8) 0.0074(6) 0.0037(6) 0.0010(6) C18' 0.0676(17) 0.0233(11) 0.0481(14) 0.0017(10) 0.0342(13) 0.0039(11) F18' 0.1054(14) 0.0387(8) 0.0524(9) 0.0128(7) 0.0423(9) 0.0100(9) C19' 0.0628(17) 0.0246(11) 0.0755(18) -0.0009(12) 0.0511(15) -0.0018(11) F19' 0.0930(13) 0.0380(9) 0.1254(16) 0.0053(9) 0.0869(13) -0.0056(9) C20' 0.0326(12) 0.0308(12) 0.0821(19) -0.0172(12) 0.0323(13) -0.0069(10) F20' 0.0343(8) 0.0573(10) 0.1201(15) -0.0199(10) 0.0374(9) -0.0141(7) C21' 0.0281(11) 0.0255(10) 0.0486(13) -0.0074(9) 0.0151(9) 0.0007(8) F21' 0.0270(6) 0.0445(8) 0.0527(8) -0.0051(6) 0.0059(6) 0.0043(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 B1 C1 1.616(3) . ? B1 C16 1.624(3) . ? B1 C10 1.626(3) . ? B1 N7 1.771(3) . ? C1 C6 1.376(3) . ? C1 C2 1.393(3) . ? C2 C3 1.396(3) . ? C2 H2 0.9500 . ? C3 C4 1.391(4) . ? C3 H3 0.9500 . ? C4 C5 1.385(3) . ? C4 H4 0.9500 . ? C5 C6 1.380(3) . ? C5 H5 0.9500 . ? C6 N7 1.476(3) . ? N7 C9 1.488(3) . ? N7 C8 1.493(3) . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 C15 1.390(3) . ? C10 C11 1.393(3) . ? C11 F11 1.356(2) . ? C11 C12 1.381(3) . ? C12 F12 1.342(3) . ? C12 C13 1.372(3) . ? C13 F13 1.351(3) . ? C13 C14 1.370(4) . ? C14 F14 1.347(3) . ? C14 C15 1.380(3) . ? C15 F15 1.352(3) . ? C16 C17 1.387(3) . ? C16 C21 1.395(3) . ? C17 F17 1.355(2) . ? C17 C18 1.386(3) . ? C18 F18 1.339(3) . ? C18 C19 1.379(3) . ? C19 F19 1.342(2) . ? C19 C20 1.380(3) . ? C20 F20 1.341(2) . ? C20 C21 1.378(3) . ? C21 F21 1.357(2) . ? B1' C1' 1.611(3) . ? B1' C16' 1.632(3) . ? B1' C10' 1.636(3) . ? B1' N7' 1.741(3) . ? C1' C6' 1.373(3) . ? C1' C2' 1.391(3) . ? C2' C3' 1.395(3) . ? C2' H2' 0.9500 . ? C3' C4' 1.392(4) . ? C3' H3' 0.9500 . ? C4' C5' 1.385(4) . ? C4' H4' 0.9500 . ? C5' C6' 1.382(3) . ? C5' H5' 0.9500 . ? C6' N7' 1.474(3) . ? N7' C8' 1.492(3) . ? N7' C9' 1.493(3) . ? C8' H8'1 0.9800 . ? C8' H8'2 0.9800 . ? C8' H8'3 0.9800 . ? C9' H9'1 0.9800 . ? C9' H9'2 0.9800 . ? C9' H9'3 0.9800 . ? C10' C15' 1.387(3) . ? C10' C11' 1.388(3) . ? C11' F11' 1.353(2) . ? C11' C12' 1.383(3) . ? C12' F12' 1.346(2) . ? C12' C13' 1.375(3) . ? C13' F13' 1.347(2) . ? C13' C14' 1.372(3) . ? C14' F14' 1.345(2) . ? C14' C15' 1.381(3) . ? C15' F15' 1.345(2) . ? C16' C17' 1.388(3) . ? C16' C21' 1.391(3) . ? C17' F17' 1.350(3) . ? C17' C18' 1.385(3) . ? C18' F18' 1.341(3) . ? C18' C19' 1.363(4) . ? C19' F19' 1.348(3) . ? C19' C20' 1.365(4) . ? C20' F20' 1.346(3) . ? C20' C21' 1.387(3) . ? C21' F21' 1.353(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 C1 B1 C16 116.49(17) . . ? C1 B1 C10 117.44(17) . . ? C16 B1 C10 111.47(16) . . ? C1 B1 N7 81.44(13) . . ? C16 B1 N7 109.52(15) . . ? C10 B1 N7 117.29(16) . . ? C6 C1 C2 117.86(19) . . ? C6 C1 B1 93.01(16) . . ? C2 C1 B1 149.09(19) . . ? C1 C2 C3 117.8(2) . . ? C1 C2 H2 121.1 . . ? C3 C2 H2 121.1 . . ? C4 C3 C2 121.7(2) . . ? C4 C3 H3 119.2 . . ? C2 C3 H3 119.2 . . ? C5 C4 C3 121.6(2) . . ? C5 C4 H4 119.2 . . ? C3 C4 H4 119.2 . . ? C6 C5 C4 114.5(2) . . ? C6 C5 H5 122.8 . . ? C4 C5 H5 122.8 . . ? C1 C6 C5 126.5(2) . . ? C1 C6 N7 101.71(16) . . ? C5 C6 N7 131.8(2) . . ? C6 N7 C9 112.10(17) . . ? C6 N7 C8 109.99(16) . . ? C9 N7 C8 109.24(17) . . ? C6 N7 B1 83.65(13) . . ? C9 N7 B1 118.60(15) . . ? C8 N7 B1 120.24(16) . . ? N7 C8 H8A 109.5 . . ? N7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? N7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? N7 C9 H9A 109.5 . . ? N7 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? N7 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C15 C10 C11 113.47(19) . . ? C15 C10 B1 129.90(19) . . ? C11 C10 B1 116.51(17) . . ? F11 C11 C12 116.11(19) . . ? F11 C11 C10 119.41(18) . . ? C12 C11 C10 124.5(2) . . ? F12 C12 C13 119.9(2) . . ? F12 C12 C11 121.1(2) . . ? C13 C12 C11 119.0(2) . . ? F13 C13 C14 120.3(2) . . ? F13 C13 C12 120.3(2) . . ? C14 C13 C12 119.4(2) . . ? F14 C14 C13 119.6(2) . . ? F14 C14 C15 120.4(2) . . ? C13 C14 C15 120.0(2) . . ? F15 C15 C14 115.6(2) . . ? F15 C15 C10 120.7(2) . . ? C14 C15 C10 123.7(2) . . ? C17 C16 C21 113.56(18) . . ? C17 C16 B1 123.46(17) . . ? C21 C16 B1 122.97(18) . . ? F17 C17 C18 115.14(18) . . ? F17 C17 C16 120.50(17) . . ? C18 C17 C16 124.36(19) . . ? F18 C18 C19 120.1(2) . . ? F18 C18 C17 120.90(19) . . ? C19 C18 C17 119.0(2) . . ? F19 C19 C18 119.8(2) . . ? F19 C19 C20 120.60(19) . . ? C18 C19 C20 119.59(19) . . ? F20 C20 C21 121.4(2) . . ? F20 C20 C19 119.5(2) . . ? C21 C20 C19 119.06(19) . . ? F21 C21 C20 116.55(18) . . ? F21 C21 C16 118.98(18) . . ? C20 C21 C16 124.5(2) . . ? C1' B1' C16' 117.46(18) . . ? C1' B1' C10' 117.12(18) . . ? C16' B1' C10' 108.96(16) . . ? C1' B1' N7' 82.27(14) . . ? C16' B1' N7' 116.15(16) . . ? C10' B1' N7' 112.91(16) . . ? C6' C1' C2' 117.6(2) . . ? C6' C1' B1' 92.21(17) . . ? C2' C1' B1' 150.22(19) . . ? C1' C2' C3' 118.1(2) . . ? C1' C2' H2' 120.9 . . ? C3' C2' H2' 120.9 . . ? C4' C3' C2' 121.9(2) . . ? C4' C3' H3' 119.1 . . ? C2' C3' H3' 119.1 . . ? C5' C4' C3' 121.0(2) . . ? C5' C4' H4' 119.5 . . ? C3' C4' H4' 119.5 . . ? C6' C5' C4' 114.9(2) . . ? C6' C5' H5' 122.6 . . ? C4' C5' H5' 122.6 . . ? C1' C6' C5' 126.5(2) . . ? C1' C6' N7' 101.65(17) . . ? C5' C6' N7' 131.8(2) . . ? C6' N7' C8' 110.18(17) . . ? C6' N7' C9' 112.04(18) . . ? C8' N7' C9' 109.86(17) . . ? C6' N7' B1' 83.81(14) . . ? C8' N7' B1' 119.77(16) . . ? C9' N7' B1' 118.12(16) . . ? N7' C8' H8'1 109.5 . . ? N7' C8' H8'2 109.5 . . ? H8'1 C8' H8'2 109.5 . . ? N7' C8' H8'3 109.5 . . ? H8'1 C8' H8'3 109.5 . . ? H8'2 C8' H8'3 109.5 . . ? N7' C9' H9'1 109.5 . . ? N7' C9' H9'2 109.5 . . ? H9'1 C9' H9'2 109.5 . . ? N7' C9' H9'3 109.5 . . ? H9'1 C9' H9'3 109.5 . . ? H9'2 C9' H9'3 109.5 . . ? C15' C10' C11' 113.96(19) . . ? C15' C10' B1' 122.73(19) . . ? C11' C10' B1' 122.79(18) . . ? F11' C11' C12' 116.21(19) . . ? F11' C11' C10' 119.57(18) . . ? C12' C11' C10' 124.21(19) . . ? F12' C12' C13' 119.86(19) . . ? F12' C12' C11' 121.1(2) . . ? C13' C12' C11' 119.0(2) . . ? F13' C13' C14' 119.9(2) . . ? F13' C13' C12' 120.6(2) . . ? C14' C13' C12' 119.5(2) . . ? F14' C14' C13' 119.6(2) . . ? F14' C14' C15' 120.8(2) . . ? C13' C14' C15' 119.6(2) . . ? F15' C15' C14' 115.43(19) . . ? F15' C15' C10' 120.81(19) . . ? C14' C15' C10' 123.7(2) . . ? C17' C16' C21' 113.37(19) . . ? C17' C16' B1' 130.17(19) . . ? C21' C16' B1' 116.16(19) . . ? F17' C17' C18' 114.9(2) . . ? F17' C17' C16' 121.01(19) . . ? C18' C17' C16' 124.1(2) . . ? F18' C18' C19' 119.8(2) . . ? F18' C18' C17' 120.5(2) . . ? C19' C18' C17' 119.6(2) . . ? F19' C19' C18' 120.6(3) . . ? F19' C19' C20' 120.0(3) . . ? C18' C19' C20' 119.4(2) . . ? F20' C20' C19' 120.9(2) . . ? F20' C20' C21' 119.5(3) . . ? C19' C20' C21' 119.5(2) . . ? F21' C21' C20' 116.2(2) . . ? F21' C21' C16' 119.77(19) . . ? C20' C21' C16' 123.9(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C16 B1 C1 C6 104.53(19) . . . . ? C10 B1 C1 C6 -119.45(19) . . . . ? N7 B1 C1 C6 -3.08(14) . . . . ? C16 B1 C1 C2 -72.8(4) . . . . ? C10 B1 C1 C2 63.2(4) . . . . ? N7 B1 C1 C2 179.6(3) . . . . ? C6 C1 C2 C3 -2.2(3) . . . . ? B1 C1 C2 C3 174.7(3) . . . . ? C1 C2 C3 C4 0.9(3) . . . . ? C2 C3 C4 C5 0.6(3) . . . . ? C3 C4 C5 C6 -0.6(3) . . . . ? C2 C1 C6 C5 2.3(3) . . . . ? B1 C1 C6 C5 -176.1(2) . . . . ? C2 C1 C6 N7 -177.83(17) . . . . ? B1 C1 C6 N7 3.73(17) . . . . ? C4 C5 C6 C1 -0.9(3) . . . . ? C4 C5 C6 N7 179.4(2) . . . . ? C1 C6 N7 C9 -121.76(18) . . . . ? C5 C6 N7 C9 58.1(3) . . . . ? C1 C6 N7 C8 116.49(19) . . . . ? C5 C6 N7 C8 -63.7(3) . . . . ? C1 C6 N7 B1 -3.42(16) . . . . ? C5 C6 N7 B1 176.4(2) . . . . ? C1 B1 N7 C6 2.88(13) . . . . ? C16 B1 N7 C6 -112.28(16) . . . . ? C10 B1 N7 C6 119.41(18) . . . . ? C1 B1 N7 C9 114.63(18) . . . . ? C16 B1 N7 C9 -0.5(2) . . . . ? C10 B1 N7 C9 -128.84(19) . . . . ? C1 B1 N7 C8 -106.59(18) . . . . ? C16 B1 N7 C8 138.24(18) . . . . ? C10 B1 N7 C8 9.9(3) . . . . ? C1 B1 C10 C15 132.6(2) . . . . ? C16 B1 C10 C15 -89.3(3) . . . . ? N7 B1 C10 C15 38.0(3) . . . . ? C1 B1 C10 C11 -51.9(3) . . . . ? C16 B1 C10 C11 86.2(2) . . . . ? N7 B1 C10 C11 -146.39(17) . . . . ? C15 C10 C11 F11 177.09(18) . . . . ? B1 C10 C11 F11 0.8(3) . . . . ? C15 C10 C11 C12 -2.4(3) . . . . ? B1 C10 C11 C12 -178.7(2) . . . . ? F11 C11 C12 F12 1.6(3) . . . . ? C10 C11 C12 F12 -178.91(19) . . . . ? F11 C11 C12 C13 -179.1(2) . . . . ? C10 C11 C12 C13 0.4(3) . . . . ? F12 C12 C13 F13 0.5(4) . . . . ? C11 C12 C13 F13 -178.9(2) . . . . ? F12 C12 C13 C14 -179.4(2) . . . . ? C11 C12 C13 C14 1.2(4) . . . . ? F13 C13 C14 F14 -1.2(4) . . . . ? C12 C13 C14 F14 178.7(2) . . . . ? F13 C13 C14 C15 179.4(2) . . . . ? C12 C13 C14 C15 -0.7(4) . . . . ? F14 C14 C15 F15 -0.8(4) . . . . ? C13 C14 C15 F15 178.6(2) . . . . ? F14 C14 C15 C10 179.1(2) . . . . ? C13 C14 C15 C10 -1.5(4) . . . . ? C11 C10 C15 F15 -177.2(2) . . . . ? B1 C10 C15 F15 -1.5(4) . . . . ? C11 C10 C15 C14 3.0(3) . . . . ? B1 C10 C15 C14 178.6(2) . . . . ? C1 B1 C16 C17 26.4(3) . . . . ? C10 B1 C16 C17 -112.1(2) . . . . ? N7 B1 C16 C17 116.42(19) . . . . ? C1 B1 C16 C21 -155.18(18) . . . . ? C10 B1 C16 C21 66.3(2) . . . . ? N7 B1 C16 C21 -65.2(2) . . . . ? C21 C16 C17 F17 -178.54(18) . . . . ? B1 C16 C17 F17 0.0(3) . . . . ? C21 C16 C17 C18 0.6(3) . . . . ? B1 C16 C17 C18 179.2(2) . . . . ? F17 C17 C18 F18 -2.4(3) . . . . ? C16 C17 C18 F18 178.38(19) . . . . ? F17 C17 C18 C19 178.47(19) . . . . ? C16 C17 C18 C19 -0.7(3) . . . . ? F18 C18 C19 F19 1.4(3) . . . . ? C17 C18 C19 F19 -179.44(19) . . . . ? F18 C18 C19 C20 -178.7(2) . . . . ? C17 C18 C19 C20 0.5(3) . . . . ? F19 C19 C20 F20 -0.7(3) . . . . ? C18 C19 C20 F20 179.44(19) . . . . ? F19 C19 C20 C21 179.75(19) . . . . ? C18 C19 C20 C21 -0.2(3) . . . . ? F20 C20 C21 F21 -0.8(3) . . . . ? C19 C20 C21 F21 178.83(18) . . . . ? F20 C20 C21 C16 -179.50(18) . . . . ? C19 C20 C21 C16 0.1(3) . . . . ? C17 C16 C21 F21 -179.02(17) . . . . ? B1 C16 C21 F21 2.4(3) . . . . ? C17 C16 C21 C20 -0.3(3) . . . . ? B1 C16 C21 C20 -178.86(19) . . . . ? C16' B1' C1' C6' 117.16(19) . . . . ? C10' B1' C1' C6' -110.18(19) . . . . ? N7' B1' C1' C6' 1.65(15) . . . . ? C16' B1' C1' C2' -63.2(5) . . . . ? C10' B1' C1' C2' 69.4(4) . . . . ? N7' B1' C1' C2' -178.8(4) . . . . ? C6' C1' C2' C3' 0.6(3) . . . . ? B1' C1' C2' C3' -179.0(3) . . . . ? C1' C2' C3' C4' 0.1(3) . . . . ? C2' C3' C4' C5' -0.7(4) . . . . ? C3' C4' C5' C6' 0.6(3) . . . . ? C2' C1' C6' C5' -0.7(3) . . . . ? B1' C1' C6' C5' 179.1(2) . . . . ? C2' C1' C6' N7' 178.26(19) . . . . ? B1' C1' C6' N7' -1.97(18) . . . . ? C4' C5' C6' C1' 0.1(3) . . . . ? C4' C5' C6' N7' -178.5(2) . . . . ? C1' C6' N7' C8' -117.66(18) . . . . ? C5' C6' N7' C8' 61.2(3) . . . . ? C1' C6' N7' C9' 119.71(19) . . . . ? C5' C6' N7' C9' -61.4(3) . . . . ? C1' C6' N7' B1' 1.83(16) . . . . ? C5' C6' N7' B1' -179.3(2) . . . . ? C1' B1' N7' C6' -1.54(14) . . . . ? C16' B1' N7' C6' -118.40(19) . . . . ? C10' B1' N7' C6' 114.70(18) . . . . ? C1' B1' N7' C8' 108.2(2) . . . . ? C16' B1' N7' C8' -8.7(3) . . . . ? C10' B1' N7' C8' -135.6(2) . . . . ? C1' B1' N7' C9' -113.3(2) . . . . ? C16' B1' N7' C9' 129.9(2) . . . . ? C10' B1' N7' C9' 3.0(3) . . . . ? C1' B1' C10' C15' -27.7(3) . . . . ? C16' B1' C10' C15' 108.7(2) . . . . ? N7' B1' C10' C15' -120.7(2) . . . . ? C1' B1' C10' C11' 161.19(19) . . . . ? C16' B1' C10' C11' -62.4(2) . . . . ? N7' B1' C10' C11' 68.2(2) . . . . ? C15' C10' C11' F11' 179.34(18) . . . . ? B1' C10' C11' F11' -8.8(3) . . . . ? C15' C10' C11' C12' -1.2(3) . . . . ? B1' C10' C11' C12' 170.65(19) . . . . ? F11' C11' C12' F12' 1.3(3) . . . . ? C10' C11' C12' F12' -178.20(19) . . . . ? F11' C11' C12' C13' 179.77(19) . . . . ? C10' C11' C12' C13' 0.3(3) . . . . ? F12' C12' C13' F13' -0.8(3) . . . . ? C11' C12' C13' F13' -179.26(19) . . . . ? F12' C12' C13' C14' 179.32(19) . . . . ? C11' C12' C13' C14' 0.8(3) . . . . ? F13' C13' C14' F14' 0.6(3) . . . . ? C12' C13' C14' F14' -179.5(2) . . . . ? F13' C13' C14' C15' 179.16(19) . . . . ? C12' C13' C14' C15' -0.9(3) . . . . ? F14' C14' C15' F15' 0.9(3) . . . . ? C13' C14' C15' F15' -177.69(19) . . . . ? F14' C14' C15' C10' 178.45(19) . . . . ? C13' C14' C15' C10' -0.1(3) . . . . ? C11' C10' C15' F15' 178.57(18) . . . . ? B1' C10' C15' F15' 6.7(3) . . . . ? C11' C10' C15' C14' 1.1(3) . . . . ? B1' C10' C15' C14' -170.8(2) . . . . ? C1' B1' C16' C17' -136.8(2) . . . . ? C10' B1' C16' C17' 87.0(3) . . . . ? N7' B1' C16' C17' -41.8(3) . . . . ? C1' B1' C16' C21' 50.0(3) . . . . ? C10' B1' C16' C21' -86.2(2) . . . . ? N7' B1' C16' C21' 144.99(18) . . . . ? C21' C16' C17' F17' 177.62(18) . . . . ? B1' C16' C17' F17' 4.3(3) . . . . ? C21' C16' C17' C18' -2.3(3) . . . . ? B1' C16' C17' C18' -175.6(2) . . . . ? F17' C17' C18' F18' 0.8(3) . . . . ? C16' C17' C18' F18' -179.3(2) . . . . ? F17' C17' C18' C19' -178.7(2) . . . . ? C16' C17' C18' C19' 1.2(3) . . . . ? F18' C18' C19' F19' 0.2(3) . . . . ? C17' C18' C19' F19' 179.6(2) . . . . ? F18' C18' C19' C20' -179.0(2) . . . . ? C17' C18' C19' C20' 0.4(3) . . . . ? F19' C19' C20' F20' -2.3(3) . . . . ? C18' C19' C20' F20' 176.9(2) . . . . ? F19' C19' C20' C21' 180.0(2) . . . . ? C18' C19' C20' C21' -0.8(3) . . . . ? F20' C20' C21' F21' -1.3(3) . . . . ? C19' C20' C21' F21' 176.5(2) . . . . ? F20' C20' C21' C16' -178.2(2) . . . . ? C19' C20' C21' C16' -0.4(3) . . . . ? C17' C16' C21' F21' -174.94(18) . . . . ? B1' C16' C21' F21' -0.6(3) . . . . ? C17' C16' C21' C20' 1.9(3) . . . . ? B1' C16' C21' C20' 176.2(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C8' H8'1 F20' 0.98 2.42 3.259(3) 143.2 1_455 C9 H9A F14' 0.98 2.49 3.422(3) 159.2 2_756 _diffrn_measured_fraction_theta_max 0.970 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 0.300 _refine_diff_density_min -0.319 _refine_diff_density_rms 0.048 #============================================================================== # _eof # End of Crystallographic Information File