# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2012 data_global _journal_coden_Cambridge 222 loop_ _publ_author_name 'Tamm, Matthias' 'Schlosser, Janin' 'Theuergarten, Eileen' 'Schluns, Danny' 'Freytag, Matthias' 'Daniliuc, Constantin' 'Jones, P.' _publ_contact_author_name 'Tamm, Matthias' _publ_contact_author_email m.tamm@tu-bs.de _publ_section_title ; Fixation of carbon dioxide and related small molecules by a bifunctional frustrated pyrazolylborane Lewis pair ; # Attachment '- eileen16.cif' data_eileen16 _database_code_depnum_ccdc_archive 'CCDC 869097' #TrackingRef '- eileen16.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H19 B F10 N2 O2' _chemical_formula_weight 568.22 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' 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 '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 15.3482(4) _cell_length_b 14.1117(4) _cell_length_c 23.0099(6) _cell_angle_alpha 90.00 _cell_angle_beta 108.656(4) _cell_angle_gamma 90.00 _cell_volume 4721.8(2) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 24200 _cell_measurement_theta_min 2.3940 _cell_measurement_theta_max 29.3580 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.599 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2304 _exptl_absorpt_coefficient_mu 0.155 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.95635 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Diffraction Xcalibur, Eos' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 16.1419 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 95441 _diffrn_reflns_av_R_equivalents 0.0475 _diffrn_reflns_av_sigmaI/netI 0.0181 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 2.40 _diffrn_reflns_theta_max 26.37 _reflns_number_total 4817 _reflns_number_gt 4135 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker XP' _computing_publication_material SHELXL-97 _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^)+(0.0289P)^2^+5.9223P] 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 4817 _refine_ls_number_parameters 358 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0406 _refine_ls_R_factor_gt 0.0322 _refine_ls_wR_factor_ref 0.0740 _refine_ls_wR_factor_gt 0.0703 _refine_ls_goodness_of_fit_ref 1.011 _refine_ls_restrained_S_all 1.011 _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 B B 0.26348(11) 0.45084(11) 0.59758(7) 0.0137(3) Uani 1 1 d . . . N1 N 0.28480(8) 0.52989(8) 0.64979(5) 0.0125(2) Uani 1 1 d . . . N2 N 0.24616(8) 0.49961(8) 0.69275(5) 0.0124(2) Uani 1 1 d . . . O1 O 0.22603(7) 0.37586(7) 0.62973(4) 0.0146(2) Uani 1 1 d . . . O2 O 0.18523(7) 0.35814(7) 0.71470(4) 0.0174(2) Uani 1 1 d . . . F1 F 0.32565(6) 0.46183(6) 0.48437(4) 0.02090(19) Uani 1 1 d . . . F2 F 0.48419(6) 0.39766(7) 0.47796(4) 0.0255(2) Uani 1 1 d . . . F3 F 0.60962(6) 0.31770(6) 0.57724(4) 0.0258(2) Uani 1 1 d . . . F4 F 0.57027(6) 0.29959(7) 0.68399(4) 0.0266(2) Uani 1 1 d . . . F5 F 0.41118(6) 0.36539(6) 0.69242(4) 0.0223(2) Uani 1 1 d . . . F6 F 0.19346(6) 0.32832(6) 0.49469(4) 0.02088(19) Uani 1 1 d . . . F7 F 0.05538(6) 0.36178(6) 0.39104(4) 0.0231(2) Uani 1 1 d . . . F8 F -0.03386(6) 0.53066(7) 0.37376(4) 0.0240(2) Uani 1 1 d . . . F9 F 0.01096(6) 0.66289(6) 0.46485(4) 0.02126(19) Uani 1 1 d . . . F10 F 0.14132(6) 0.62742(6) 0.57037(4) 0.01874(18) Uani 1 1 d . . . C1 C 0.32018(9) 0.61629(10) 0.66659(6) 0.0131(3) Uani 1 1 d . . . C2 C 0.30151(9) 0.64109(10) 0.72065(6) 0.0138(3) Uani 1 1 d . . . H2 H 0.3178 0.6992 0.7422 0.017 Uiso 1 1 calc R . . C3 C 0.25579(9) 0.56708(10) 0.73697(6) 0.0128(3) Uani 1 1 d . . . C4 C 0.37652(10) 0.67265(10) 0.63509(6) 0.0153(3) Uani 1 1 d . . . C5 C 0.47350(10) 0.62871(11) 0.65239(7) 0.0212(3) Uani 1 1 d . . . H5A H 0.4997 0.6244 0.6971 0.032 Uiso 1 1 calc R . . H5B H 0.5130 0.6686 0.6365 0.032 Uiso 1 1 calc R . . H5C H 0.4695 0.5652 0.6345 0.032 Uiso 1 1 calc R . . C6 C 0.33304(10) 0.67418(11) 0.56515(6) 0.0189(3) Uani 1 1 d . . . H6A H 0.3233 0.6090 0.5497 0.028 Uiso 1 1 calc R . . H6B H 0.3741 0.7071 0.5469 0.028 Uiso 1 1 calc R . . H6C H 0.2739 0.7073 0.5542 0.028 Uiso 1 1 calc R . . C7 C 0.38516(12) 0.77499(11) 0.65878(8) 0.0262(4) Uani 1 1 d . . . H7A H 0.3238 0.8030 0.6493 0.039 Uiso 1 1 calc R . . H7B H 0.4216 0.8120 0.6389 0.039 Uiso 1 1 calc R . . H7C H 0.4156 0.7753 0.7033 0.039 Uiso 1 1 calc R . . C8 C 0.22303(9) 0.55784(10) 0.79230(6) 0.0150(3) Uani 1 1 d . . . C9 C 0.11962(10) 0.53520(11) 0.77199(7) 0.0195(3) Uani 1 1 d . . . H9A H 0.0856 0.5847 0.7440 0.029 Uiso 1 1 calc R . . H9B H 0.0989 0.5327 0.8081 0.029 Uiso 1 1 calc R . . H9C H 0.1085 0.4738 0.7510 0.029 Uiso 1 1 calc R . . C10 C 0.27960(10) 0.48143(11) 0.83533(6) 0.0202(3) Uani 1 1 d . . . H10A H 0.2727 0.4210 0.8133 0.030 Uiso 1 1 calc R . . H10B H 0.2577 0.4745 0.8707 0.030 Uiso 1 1 calc R . . H10C H 0.3446 0.4999 0.8495 0.030 Uiso 1 1 calc R . . C11 C 0.23872(11) 0.65301(11) 0.82631(7) 0.0206(3) Uani 1 1 d . . . H11A H 0.3043 0.6687 0.8394 0.031 Uiso 1 1 calc R . . H11B H 0.2181 0.6484 0.8623 0.031 Uiso 1 1 calc R . . H11C H 0.2038 0.7027 0.7989 0.031 Uiso 1 1 calc R . . C12 C 0.21508(9) 0.40284(9) 0.68127(6) 0.0134(3) Uani 1 1 d . . . C13 C 0.35847(9) 0.41391(9) 0.58847(6) 0.0142(3) Uani 1 1 d . . . C14 C 0.38248(10) 0.42041(10) 0.53517(6) 0.0156(3) Uani 1 1 d . . . C15 C 0.46499(10) 0.38817(10) 0.53070(7) 0.0176(3) Uani 1 1 d . . . C16 C 0.52873(10) 0.34761(10) 0.58080(7) 0.0185(3) Uani 1 1 d . . . C17 C 0.50878(10) 0.33922(10) 0.63504(7) 0.0183(3) Uani 1 1 d . . . C18 C 0.42557(10) 0.37241(10) 0.63758(6) 0.0161(3) Uani 1 1 d . . . C19 C 0.17967(9) 0.47902(10) 0.53585(6) 0.0133(3) Uani 1 1 d . . . C20 C 0.15108(10) 0.41313(10) 0.48860(6) 0.0151(3) Uani 1 1 d . . . C21 C 0.08063(10) 0.42862(10) 0.43464(6) 0.0163(3) Uani 1 1 d . . . C22 C 0.03473(9) 0.51421(11) 0.42596(6) 0.0168(3) Uani 1 1 d . . . C23 C 0.05789(9) 0.58095(10) 0.47175(7) 0.0156(3) Uani 1 1 d . . . C24 C 0.12781(9) 0.56146(10) 0.52594(6) 0.0142(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 B 0.0168(8) 0.0126(7) 0.0122(7) 0.0001(6) 0.0055(6) -0.0010(6) N1 0.0142(5) 0.0144(6) 0.0110(5) 0.0019(4) 0.0069(4) 0.0002(5) N2 0.0138(6) 0.0148(6) 0.0103(5) 0.0014(4) 0.0064(4) -0.0003(5) O1 0.0194(5) 0.0127(5) 0.0132(5) -0.0003(4) 0.0076(4) -0.0005(4) O2 0.0223(5) 0.0156(5) 0.0178(5) 0.0028(4) 0.0111(4) -0.0013(4) F1 0.0225(4) 0.0286(5) 0.0129(4) 0.0052(4) 0.0075(3) 0.0053(4) F2 0.0286(5) 0.0327(5) 0.0220(5) -0.0020(4) 0.0176(4) 0.0024(4) F3 0.0183(4) 0.0256(5) 0.0357(5) -0.0060(4) 0.0118(4) 0.0054(4) F4 0.0208(5) 0.0308(5) 0.0239(5) 0.0050(4) 0.0009(4) 0.0087(4) F5 0.0229(5) 0.0316(5) 0.0127(4) 0.0045(4) 0.0064(3) 0.0033(4) F6 0.0251(5) 0.0150(4) 0.0216(4) -0.0029(3) 0.0063(4) 0.0037(3) F7 0.0261(5) 0.0257(5) 0.0166(4) -0.0075(4) 0.0058(4) -0.0064(4) F8 0.0175(4) 0.0352(5) 0.0156(4) 0.0046(4) 0.0001(3) 0.0002(4) F9 0.0175(4) 0.0181(4) 0.0276(5) 0.0064(4) 0.0064(4) 0.0048(3) F10 0.0195(4) 0.0152(4) 0.0209(4) -0.0049(3) 0.0056(3) 0.0016(3) C1 0.0122(6) 0.0137(7) 0.0129(6) 0.0006(5) 0.0036(5) 0.0012(5) C2 0.0142(7) 0.0149(7) 0.0128(6) -0.0017(5) 0.0051(5) -0.0007(5) C3 0.0115(6) 0.0150(7) 0.0113(6) -0.0005(5) 0.0029(5) 0.0026(5) C4 0.0174(7) 0.0163(7) 0.0150(7) -0.0002(5) 0.0089(6) -0.0030(6) C5 0.0158(7) 0.0296(8) 0.0191(7) 0.0016(6) 0.0069(6) -0.0030(6) C6 0.0200(7) 0.0218(8) 0.0164(7) 0.0047(6) 0.0078(6) -0.0020(6) C7 0.0386(9) 0.0185(8) 0.0300(9) -0.0037(7) 0.0228(8) -0.0086(7) C8 0.0169(7) 0.0183(7) 0.0124(6) -0.0001(5) 0.0084(5) -0.0007(6) C9 0.0170(7) 0.0246(8) 0.0201(7) -0.0031(6) 0.0104(6) -0.0020(6) C10 0.0227(8) 0.0242(8) 0.0130(7) 0.0018(6) 0.0049(6) -0.0014(6) C11 0.0245(8) 0.0226(8) 0.0191(7) -0.0055(6) 0.0133(6) -0.0050(6) C12 0.0131(6) 0.0127(6) 0.0141(7) 0.0009(5) 0.0039(5) 0.0022(5) C13 0.0178(7) 0.0114(6) 0.0140(7) -0.0018(5) 0.0060(5) -0.0007(5) C14 0.0188(7) 0.0147(7) 0.0129(7) -0.0003(5) 0.0047(5) 0.0011(6) C15 0.0224(7) 0.0172(7) 0.0170(7) -0.0037(6) 0.0116(6) -0.0020(6) C16 0.0161(7) 0.0139(7) 0.0273(8) -0.0055(6) 0.0096(6) 0.0009(6) C17 0.0164(7) 0.0154(7) 0.0193(7) -0.0002(6) 0.0006(6) 0.0014(6) C18 0.0200(7) 0.0155(7) 0.0141(7) -0.0006(5) 0.0072(6) -0.0011(6) C19 0.0142(6) 0.0152(7) 0.0126(6) 0.0010(5) 0.0073(5) -0.0018(5) C20 0.0172(7) 0.0138(7) 0.0163(7) 0.0012(5) 0.0082(6) 0.0004(5) C21 0.0188(7) 0.0198(7) 0.0124(6) -0.0045(6) 0.0078(6) -0.0065(6) C22 0.0118(7) 0.0266(8) 0.0118(7) 0.0045(6) 0.0034(5) -0.0029(6) C23 0.0132(6) 0.0150(7) 0.0211(7) 0.0057(6) 0.0089(6) 0.0004(5) C24 0.0154(7) 0.0149(7) 0.0143(7) -0.0011(5) 0.0075(5) -0.0030(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag B O1 1.5063(18) . ? B N1 1.5946(18) . ? B C13 1.624(2) . ? B C19 1.631(2) . ? N1 C1 1.3404(18) . ? N1 N2 1.3735(15) . ? N2 C3 1.3667(17) . ? N2 C12 1.4428(17) . ? O1 C12 1.3067(16) . ? O2 C12 1.1936(16) . ? F1 C14 1.3478(16) . ? F2 C15 1.3439(16) . ? F3 C16 1.3384(16) . ? F4 C17 1.3387(16) . ? F5 C18 1.3525(16) . ? F6 C20 1.3479(16) . ? F7 C21 1.3407(16) . ? F8 C22 1.3400(16) . ? F9 C23 1.3445(16) . ? F10 C24 1.3487(16) . ? C1 C2 1.4070(19) . ? C1 C4 1.5188(18) . ? C2 C3 1.3759(19) . ? C3 C8 1.5167(18) . ? C4 C6 1.5325(19) . ? C4 C7 1.534(2) . ? C4 C5 1.543(2) . ? C8 C10 1.532(2) . ? C8 C11 1.534(2) . ? C8 C9 1.5378(19) . ? C13 C18 1.391(2) . ? C13 C14 1.3920(19) . ? C14 C15 1.380(2) . ? C15 C16 1.376(2) . ? C16 C17 1.382(2) . ? C17 C18 1.379(2) . ? C19 C24 1.3867(19) . ? C19 C20 1.3907(19) . ? C20 C21 1.378(2) . ? C21 C22 1.380(2) . ? C22 C23 1.373(2) . ? C23 C24 1.3878(19) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 B N1 98.05(10) . . ? O1 B C13 109.71(11) . . ? N1 B C13 110.21(11) . . ? O1 B C19 106.28(11) . . ? N1 B C19 113.57(11) . . ? C13 B C19 117.15(11) . . ? C1 N1 N2 107.68(11) . . ? C1 N1 B 145.10(11) . . ? N2 N1 B 107.02(10) . . ? C3 N2 N1 110.51(11) . . ? C3 N2 C12 138.28(11) . . ? N1 N2 C12 110.88(10) . . ? C12 O1 B 114.90(11) . . ? N1 C1 C2 107.64(12) . . ? N1 C1 C4 125.36(12) . . ? C2 C1 C4 126.85(12) . . ? C3 C2 C1 108.57(12) . . ? N2 C3 C2 105.59(11) . . ? N2 C3 C8 125.39(12) . . ? C2 C3 C8 129.01(12) . . ? C1 C4 C6 112.67(11) . . ? C1 C4 C7 108.72(11) . . ? C6 C4 C7 108.60(12) . . ? C1 C4 C5 108.42(11) . . ? C6 C4 C5 109.69(11) . . ? C7 C4 C5 108.67(12) . . ? C3 C8 C10 109.36(11) . . ? C3 C8 C11 108.22(11) . . ? C10 C8 C11 108.82(12) . . ? C3 C8 C9 110.48(11) . . ? C10 C8 C9 111.51(12) . . ? C11 C8 C9 108.37(11) . . ? O2 C12 O1 128.19(13) . . ? O2 C12 N2 123.70(12) . . ? O1 C12 N2 108.11(11) . . ? C18 C13 C14 114.06(12) . . ? C18 C13 B 119.48(12) . . ? C14 C13 B 126.46(12) . . ? F1 C14 C15 115.66(12) . . ? F1 C14 C13 120.83(12) . . ? C15 C14 C13 123.48(13) . . ? F2 C15 C16 119.70(13) . . ? F2 C15 C14 120.39(13) . . ? C16 C15 C14 119.89(13) . . ? F3 C16 C15 120.33(13) . . ? F3 C16 C17 120.41(13) . . ? C15 C16 C17 119.26(13) . . ? F4 C17 C18 121.29(13) . . ? F4 C17 C16 119.70(13) . . ? C18 C17 C16 119.01(13) . . ? F5 C18 C17 116.40(12) . . ? F5 C18 C13 119.28(12) . . ? C17 C18 C13 124.30(13) . . ? C24 C19 C20 114.29(12) . . ? C24 C19 B 126.80(12) . . ? C20 C19 B 118.78(12) . . ? F6 C20 C21 116.61(12) . . ? F6 C20 C19 119.42(12) . . ? C21 C20 C19 123.97(13) . . ? F7 C21 C20 121.22(13) . . ? F7 C21 C22 119.69(13) . . ? C20 C21 C22 119.09(13) . . ? F8 C22 C23 120.37(13) . . ? F8 C22 C21 119.97(13) . . ? C23 C22 C21 119.63(13) . . ? F9 C23 C22 120.13(13) . . ? F9 C23 C24 120.50(13) . . ? C22 C23 C24 119.32(13) . . ? F10 C24 C19 120.89(12) . . ? F10 C24 C23 115.57(12) . . ? C19 C24 C23 123.52(13) . . ? 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 O1 B N1 C1 176.56(17) . . . . ? C13 B N1 C1 62.0(2) . . . . ? C19 B N1 C1 -71.7(2) . . . . ? O1 B N1 N2 -9.65(13) . . . . ? C13 B N1 N2 -124.18(11) . . . . ? C19 B N1 N2 102.10(12) . . . . ? C1 N1 N2 C3 0.66(14) . . . . ? B N1 N2 C3 -175.61(11) . . . . ? C1 N1 N2 C12 -173.96(11) . . . . ? B N1 N2 C12 9.77(14) . . . . ? N1 B O1 C12 6.90(14) . . . . ? C13 B O1 C12 121.82(12) . . . . ? C19 B O1 C12 -110.62(12) . . . . ? N2 N1 C1 C2 -1.16(14) . . . . ? B N1 C1 C2 172.61(17) . . . . ? N2 N1 C1 C4 174.49(12) . . . . ? B N1 C1 C4 -11.7(3) . . . . ? N1 C1 C2 C3 1.27(16) . . . . ? C4 C1 C2 C3 -174.30(13) . . . . ? N1 N2 C3 C2 0.13(15) . . . . ? C12 N2 C3 C2 172.56(14) . . . . ? N1 N2 C3 C8 -178.90(12) . . . . ? C12 N2 C3 C8 -6.5(2) . . . . ? C1 C2 C3 N2 -0.84(15) . . . . ? C1 C2 C3 C8 178.14(13) . . . . ? N1 C1 C4 C6 47.00(18) . . . . ? C2 C1 C4 C6 -138.18(14) . . . . ? N1 C1 C4 C7 167.43(13) . . . . ? C2 C1 C4 C7 -17.75(19) . . . . ? N1 C1 C4 C5 -74.59(16) . . . . ? C2 C1 C4 C5 100.23(16) . . . . ? N2 C3 C8 C10 67.27(17) . . . . ? C2 C3 C8 C10 -111.53(16) . . . . ? N2 C3 C8 C11 -174.33(13) . . . . ? C2 C3 C8 C11 6.9(2) . . . . ? N2 C3 C8 C9 -55.83(18) . . . . ? C2 C3 C8 C9 125.37(15) . . . . ? B O1 C12 O2 178.47(14) . . . . ? B O1 C12 N2 -1.70(15) . . . . ? C3 N2 C12 O2 1.9(2) . . . . ? N1 N2 C12 O2 174.32(12) . . . . ? C3 N2 C12 O1 -177.94(14) . . . . ? N1 N2 C12 O1 -5.52(14) . . . . ? O1 B C13 C18 -46.81(17) . . . . ? N1 B C13 C18 60.07(16) . . . . ? C19 B C13 C18 -168.03(12) . . . . ? O1 B C13 C14 134.28(14) . . . . ? N1 B C13 C14 -118.83(14) . . . . ? C19 B C13 C14 13.1(2) . . . . ? C18 C13 C14 F1 -177.80(12) . . . . ? B C13 C14 F1 1.2(2) . . . . ? C18 C13 C14 C15 0.5(2) . . . . ? B C13 C14 C15 179.43(13) . . . . ? F1 C14 C15 F2 -0.9(2) . . . . ? C13 C14 C15 F2 -179.25(13) . . . . ? F1 C14 C15 C16 177.93(12) . . . . ? C13 C14 C15 C16 -0.4(2) . . . . ? F2 C15 C16 F3 0.0(2) . . . . ? C14 C15 C16 F3 -178.78(13) . . . . ? F2 C15 C16 C17 179.22(13) . . . . ? C14 C15 C16 C17 0.4(2) . . . . ? F3 C16 C17 F4 -1.0(2) . . . . ? C15 C16 C17 F4 179.80(13) . . . . ? F3 C16 C17 C18 178.73(13) . . . . ? C15 C16 C17 C18 -0.4(2) . . . . ? F4 C17 C18 F5 2.0(2) . . . . ? C16 C17 C18 F5 -177.72(13) . . . . ? F4 C17 C18 C13 -179.70(13) . . . . ? C16 C17 C18 C13 0.5(2) . . . . ? C14 C13 C18 F5 177.67(12) . . . . ? B C13 C18 F5 -1.36(19) . . . . ? C14 C13 C18 C17 -0.5(2) . . . . ? B C13 C18 C17 -179.57(13) . . . . ? O1 B C19 C24 106.10(15) . . . . ? N1 B C19 C24 -0.56(19) . . . . ? C13 B C19 C24 -130.90(14) . . . . ? O1 B C19 C20 -69.46(15) . . . . ? N1 B C19 C20 -176.12(11) . . . . ? C13 B C19 C20 53.53(17) . . . . ? C24 C19 C20 F6 -176.56(12) . . . . ? B C19 C20 F6 -0.46(19) . . . . ? C24 C19 C20 C21 3.3(2) . . . . ? B C19 C20 C21 179.42(13) . . . . ? F6 C20 C21 F7 0.78(19) . . . . ? C19 C20 C21 F7 -179.10(12) . . . . ? F6 C20 C21 C22 179.92(12) . . . . ? C19 C20 C21 C22 0.0(2) . . . . ? F7 C21 C22 F8 -0.95(19) . . . . ? C20 C21 C22 F8 179.89(12) . . . . ? F7 C21 C22 C23 177.08(12) . . . . ? C20 C21 C22 C23 -2.1(2) . . . . ? F8 C22 C23 F9 0.92(19) . . . . ? C21 C22 C23 F9 -177.10(12) . . . . ? F8 C22 C23 C24 178.57(12) . . . . ? C21 C22 C23 C24 0.6(2) . . . . ? C20 C19 C24 F10 173.06(12) . . . . ? B C19 C24 F10 -2.7(2) . . . . ? C20 C19 C24 C23 -4.93(19) . . . . ? B C19 C24 C23 179.34(13) . . . . ? F9 C23 C24 F10 2.74(18) . . . . ? C22 C23 C24 F10 -174.90(12) . . . . ? F9 C23 C24 C19 -179.17(12) . . . . ? C22 C23 C24 C19 3.2(2) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.297 _refine_diff_density_min -0.223 _refine_diff_density_rms 0.042 # # end of cif data for "eileen16" # Attachment '- eileen20.cif' data_eileen20 _database_code_depnum_ccdc_archive 'CCDC 869098' #TrackingRef '- eileen20.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H28 B F10 N3 O' _chemical_formula_weight 623.34 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' 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/n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 10.9606(4) _cell_length_b 19.1668(6) _cell_length_c 14.3458(4) _cell_angle_alpha 90.00 _cell_angle_beta 102.930(4) _cell_angle_gamma 90.00 _cell_volume 2937.34(16) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 20700 _cell_measurement_theta_min 2.1208 _cell_measurement_theta_max 29.2868 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.410 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1280 _exptl_absorpt_coefficient_mu 0.130 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.93091 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Diffraction Xcalibur, Eos' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 16.1419 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 106116 _diffrn_reflns_av_R_equivalents 0.0554 _diffrn_reflns_av_sigmaI/netI 0.0298 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.18 _diffrn_reflns_theta_max 27.88 _reflns_number_total 7000 _reflns_number_gt 5364 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker XP' _computing_publication_material SHELXL-97 _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^)+(0.0380P)^2^+1.2877P] 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 7000 _refine_ls_number_parameters 397 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0632 _refine_ls_R_factor_gt 0.0426 _refine_ls_wR_factor_ref 0.0983 _refine_ls_wR_factor_gt 0.0909 _refine_ls_goodness_of_fit_ref 1.028 _refine_ls_restrained_S_all 1.028 _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 B B 0.66663(16) 0.12335(8) 0.81276(12) 0.0186(3) Uani 1 1 d . . . N1 N 0.63254(11) 0.20289(6) 0.78736(8) 0.0183(3) Uani 1 1 d . . . N2 N 0.61276(11) 0.23496(6) 0.86838(8) 0.0178(2) Uani 1 1 d . . . N3 N 0.60235(12) 0.20266(6) 1.02450(9) 0.0217(3) Uani 1 1 d . . . O O 0.64530(10) 0.12299(5) 0.91201(7) 0.0204(2) Uani 1 1 d . . . F1 F 0.70244(8) 0.01062(5) 0.67013(7) 0.0298(2) Uani 1 1 d . . . F2 F 0.52136(10) -0.06854(5) 0.57051(8) 0.0431(3) Uani 1 1 d . . . F3 F 0.28070(10) -0.05221(6) 0.58754(8) 0.0458(3) Uani 1 1 d . . . F4 F 0.22483(8) 0.04582(5) 0.70783(7) 0.0343(2) Uani 1 1 d . . . F5 F 0.40382(8) 0.12882(5) 0.80576(6) 0.0282(2) Uani 1 1 d . . . F6 F 0.77250(8) -0.01056(4) 0.86613(7) 0.0282(2) Uani 1 1 d . . . F7 F 1.01340(9) -0.04566(5) 0.90860(7) 0.0313(2) Uani 1 1 d . . . F8 F 1.19278(8) 0.05092(5) 0.89901(7) 0.0341(2) Uani 1 1 d . . . F9 F 1.12315(9) 0.18246(5) 0.83798(7) 0.0365(2) Uani 1 1 d . . . F10 F 0.88422(8) 0.21949(5) 0.79722(7) 0.0307(2) Uani 1 1 d . . . C1 C 0.61459(13) 0.25026(7) 0.71705(10) 0.0192(3) Uani 1 1 d . . . C2 C 0.58340(14) 0.31313(8) 0.75494(10) 0.0204(3) Uani 1 1 d . . . H2 H 0.5660 0.3558 0.7209 0.025 Uiso 1 1 calc R . . C3 C 0.58191(13) 0.30325(7) 0.84957(10) 0.0183(3) Uani 1 1 d . . . C4 C 0.62044(15) 0.23804(8) 0.61387(11) 0.0240(3) Uani 1 1 d . . . C5 C 0.7021(2) 0.17708(9) 0.59890(13) 0.0389(4) Uani 1 1 d . . . H5A H 0.7893 0.1868 0.6305 0.058 Uiso 1 1 calc R . . H5B H 0.6957 0.1703 0.5303 0.058 Uiso 1 1 calc R . . H5C H 0.6740 0.1348 0.6262 0.058 Uiso 1 1 calc R . . C6 C 0.48755(19) 0.22503(17) 0.55752(15) 0.0737(9) Uani 1 1 d . . . H6A H 0.4540 0.1833 0.5824 0.111 Uiso 1 1 calc R . . H6B H 0.4879 0.2180 0.4899 0.111 Uiso 1 1 calc R . . H6C H 0.4351 0.2654 0.5639 0.111 Uiso 1 1 calc R . . C7 C 0.6746(3) 0.30336(11) 0.57806(16) 0.0647(8) Uani 1 1 d . . . H7A H 0.6158 0.3422 0.5755 0.097 Uiso 1 1 calc R . . H7B H 0.6887 0.2948 0.5139 0.097 Uiso 1 1 calc R . . H7C H 0.7543 0.3152 0.6217 0.097 Uiso 1 1 calc R . . C8 C 0.55203(14) 0.35674(7) 0.91959(11) 0.0218(3) Uani 1 1 d . . . C9 C 0.52617(16) 0.42702(8) 0.86703(12) 0.0283(3) Uani 1 1 d . . . H9A H 0.6006 0.4416 0.8450 0.042 Uiso 1 1 calc R . . H9B H 0.5059 0.4623 0.9107 0.042 Uiso 1 1 calc R . . H9C H 0.4555 0.4219 0.8119 0.042 Uiso 1 1 calc R . . C10 C 0.43457(15) 0.33509(9) 0.95390(12) 0.0285(4) Uani 1 1 d . . . H10A H 0.3640 0.3303 0.8987 0.043 Uiso 1 1 calc R . . H10B H 0.4150 0.3708 0.9972 0.043 Uiso 1 1 calc R . . H10C H 0.4497 0.2904 0.9877 0.043 Uiso 1 1 calc R . . C11 C 0.66464(16) 0.36587(9) 1.00402(12) 0.0305(4) Uani 1 1 d . . . H11A H 0.6817 0.3217 1.0390 0.046 Uiso 1 1 calc R . . H11B H 0.6460 0.4021 1.0470 0.046 Uiso 1 1 calc R . . H11C H 0.7382 0.3796 0.9801 0.046 Uiso 1 1 calc R . . C12 C 0.61973(13) 0.18470(7) 0.94473(10) 0.0188(3) Uani 1 1 d . . . C13 C 0.60623(15) 0.15034(8) 1.10173(11) 0.0261(3) Uani 1 1 d . . . C14 C 0.50741(17) 0.09417(10) 1.07023(13) 0.0365(4) Uani 1 1 d . . . H14A H 0.4258 0.1162 1.0461 0.055 Uiso 1 1 calc R . . H14B H 0.5034 0.0642 1.1248 0.055 Uiso 1 1 calc R . . H14C H 0.5295 0.0659 1.0195 0.055 Uiso 1 1 calc R . . C15 C 0.73617(17) 0.11833(10) 1.13086(13) 0.0382(4) Uani 1 1 d . . . H15A H 0.7548 0.0926 1.0767 0.057 Uiso 1 1 calc R . . H15B H 0.7392 0.0864 1.1846 0.057 Uiso 1 1 calc R . . H15C H 0.7983 0.1554 1.1500 0.057 Uiso 1 1 calc R . . C16 C 0.5783(2) 0.19152(11) 1.18518(13) 0.0507(6) Uani 1 1 d . . . H16A H 0.6411 0.2284 1.2036 0.076 Uiso 1 1 calc R . . H16B H 0.5809 0.1602 1.2396 0.076 Uiso 1 1 calc R . . H16C H 0.4949 0.2125 1.1661 0.076 Uiso 1 1 calc R . . C17 C 0.56331(14) 0.07273(7) 0.74585(10) 0.0196(3) Uani 1 1 d . . . C18 C 0.58587(14) 0.02137(8) 0.68378(11) 0.0231(3) Uani 1 1 d . . . C19 C 0.49333(16) -0.02060(8) 0.63075(11) 0.0285(4) Uani 1 1 d . . . C20 C 0.37164(16) -0.01219(9) 0.63897(12) 0.0296(4) Uani 1 1 d . . . C21 C 0.34360(15) 0.03766(8) 0.69956(11) 0.0255(3) Uani 1 1 d . . . C22 C 0.43841(14) 0.07908(8) 0.75035(10) 0.0213(3) Uani 1 1 d . . . C23 C 0.81447(14) 0.10526(7) 0.82460(10) 0.0196(3) Uani 1 1 d . . . C24 C 0.85624(14) 0.03880(8) 0.85526(10) 0.0211(3) Uani 1 1 d . . . C25 C 0.98022(15) 0.01947(8) 0.87825(11) 0.0231(3) Uani 1 1 d . . . C26 C 1.07160(14) 0.06790(9) 0.87291(11) 0.0248(3) Uani 1 1 d . . . C27 C 1.03590(14) 0.13436(8) 0.84319(11) 0.0249(3) Uani 1 1 d . . . C28 C 0.91013(14) 0.15179(8) 0.82109(11) 0.0223(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 B 0.0211(8) 0.0161(7) 0.0199(8) -0.0009(6) 0.0072(6) 0.0000(6) N1 0.0208(6) 0.0174(6) 0.0181(6) -0.0036(5) 0.0074(5) 0.0008(5) N2 0.0187(6) 0.0177(6) 0.0178(6) -0.0030(5) 0.0058(5) 0.0018(5) N3 0.0237(7) 0.0225(6) 0.0197(6) -0.0001(5) 0.0067(5) 0.0041(5) O 0.0259(6) 0.0164(5) 0.0211(5) -0.0011(4) 0.0098(4) 0.0026(4) F1 0.0271(5) 0.0299(5) 0.0346(5) -0.0114(4) 0.0118(4) 0.0015(4) F2 0.0511(7) 0.0362(6) 0.0425(6) -0.0227(5) 0.0114(5) -0.0081(5) F3 0.0404(6) 0.0514(7) 0.0423(6) -0.0137(5) 0.0025(5) -0.0246(5) F4 0.0203(5) 0.0522(6) 0.0304(5) 0.0069(5) 0.0055(4) -0.0068(4) F5 0.0233(5) 0.0319(5) 0.0316(5) -0.0048(4) 0.0108(4) 0.0042(4) F6 0.0263(5) 0.0193(4) 0.0395(5) 0.0032(4) 0.0087(4) -0.0009(4) F7 0.0313(5) 0.0255(5) 0.0361(5) 0.0051(4) 0.0055(4) 0.0094(4) F8 0.0192(5) 0.0479(6) 0.0342(5) 0.0059(5) 0.0038(4) 0.0063(4) F9 0.0225(5) 0.0430(6) 0.0423(6) 0.0115(5) 0.0037(4) -0.0091(4) F10 0.0266(5) 0.0214(5) 0.0427(6) 0.0066(4) 0.0051(4) -0.0033(4) C1 0.0164(7) 0.0193(7) 0.0217(7) 0.0002(6) 0.0040(6) -0.0006(6) C2 0.0199(7) 0.0186(7) 0.0228(7) 0.0011(6) 0.0049(6) 0.0009(6) C3 0.0131(7) 0.0172(7) 0.0241(7) -0.0023(6) 0.0032(6) 0.0004(5) C4 0.0280(8) 0.0250(8) 0.0194(7) -0.0004(6) 0.0066(6) 0.0030(6) C5 0.0590(13) 0.0364(10) 0.0279(9) 0.0039(7) 0.0239(9) 0.0148(9) C6 0.0322(12) 0.155(3) 0.0303(11) -0.0361(14) -0.0013(9) 0.0171(14) C7 0.136(2) 0.0335(11) 0.0397(12) 0.0035(9) 0.0523(14) -0.0054(13) C8 0.0225(8) 0.0182(7) 0.0252(8) -0.0049(6) 0.0064(6) 0.0033(6) C9 0.0306(9) 0.0197(7) 0.0350(9) -0.0037(7) 0.0087(7) 0.0036(7) C10 0.0269(9) 0.0273(8) 0.0345(9) 0.0014(7) 0.0139(7) 0.0084(7) C11 0.0316(9) 0.0280(8) 0.0290(9) -0.0097(7) 0.0005(7) 0.0016(7) C12 0.0164(7) 0.0174(7) 0.0222(7) 0.0000(6) 0.0036(6) 0.0014(5) C13 0.0330(9) 0.0267(8) 0.0202(7) 0.0028(6) 0.0098(6) 0.0050(7) C14 0.0377(10) 0.0386(10) 0.0364(10) 0.0071(8) 0.0153(8) -0.0046(8) C15 0.0345(10) 0.0447(11) 0.0332(10) 0.0153(8) 0.0031(8) 0.0053(8) C16 0.0895(17) 0.0416(11) 0.0284(10) 0.0018(8) 0.0293(10) 0.0115(11) C17 0.0223(8) 0.0162(7) 0.0209(7) 0.0008(5) 0.0061(6) -0.0013(6) C18 0.0233(8) 0.0218(7) 0.0253(8) -0.0008(6) 0.0080(6) -0.0002(6) C19 0.0381(10) 0.0227(8) 0.0247(8) -0.0071(6) 0.0075(7) -0.0054(7) C20 0.0296(9) 0.0306(8) 0.0256(8) -0.0001(7) 0.0002(7) -0.0136(7) C21 0.0216(8) 0.0320(8) 0.0227(8) 0.0071(6) 0.0047(6) -0.0041(7) C22 0.0239(8) 0.0216(7) 0.0196(7) 0.0020(6) 0.0071(6) -0.0002(6) C23 0.0216(8) 0.0200(7) 0.0182(7) -0.0026(5) 0.0068(6) 0.0001(6) C24 0.0233(8) 0.0205(7) 0.0207(7) -0.0025(6) 0.0074(6) -0.0029(6) C25 0.0273(8) 0.0223(7) 0.0196(7) 0.0004(6) 0.0050(6) 0.0059(6) C26 0.0194(8) 0.0359(9) 0.0190(7) -0.0009(6) 0.0043(6) 0.0035(7) C27 0.0208(8) 0.0311(8) 0.0229(8) 0.0010(6) 0.0052(6) -0.0066(6) C28 0.0248(8) 0.0200(7) 0.0219(7) 0.0009(6) 0.0050(6) -0.0006(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 B O 1.4937(19) . ? B N1 1.5924(19) . ? B C23 1.628(2) . ? B C17 1.631(2) . ? N1 C1 1.3386(18) . ? N1 N2 1.3742(16) . ? N2 C3 1.3637(18) . ? N2 C12 1.4478(18) . ? N3 C12 1.2499(19) . ? N3 C13 1.4878(19) . ? O C12 1.3254(17) . ? F1 C18 1.3510(17) . ? F2 C19 1.3432(18) . ? F3 C20 1.3405(18) . ? F4 C21 1.3424(18) . ? F5 C22 1.3489(17) . ? F6 C24 1.3512(17) . ? F7 C25 1.3451(17) . ? F8 C26 1.3371(18) . ? F9 C27 1.3424(17) . ? F10 C28 1.3558(17) . ? C1 C2 1.396(2) . ? C1 C4 1.514(2) . ? C2 C3 1.374(2) . ? C3 C8 1.5213(19) . ? C4 C5 1.516(2) . ? C4 C6 1.520(3) . ? C4 C7 1.523(2) . ? C8 C11 1.534(2) . ? C8 C10 1.535(2) . ? C8 C9 1.539(2) . ? C13 C15 1.521(2) . ? C13 C16 1.521(2) . ? C13 C14 1.522(2) . ? C17 C18 1.386(2) . ? C17 C22 1.390(2) . ? C18 C19 1.382(2) . ? C19 C20 1.375(2) . ? C20 C21 1.372(2) . ? C21 C22 1.379(2) . ? C23 C28 1.386(2) . ? C23 C24 1.391(2) . ? C24 C25 1.375(2) . ? C25 C26 1.380(2) . ? C26 C27 1.372(2) . ? C27 C28 1.384(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O B N1 98.26(11) . . ? O B C23 105.31(12) . . ? N1 B C23 113.88(12) . . ? O B C17 108.80(12) . . ? N1 B C17 109.79(12) . . ? C23 B C17 118.59(12) . . ? C1 N1 N2 108.03(11) . . ? C1 N1 B 144.02(12) . . ? N2 N1 B 107.95(11) . . ? C3 N2 N1 109.95(11) . . ? C3 N2 C12 139.21(12) . . ? N1 N2 C12 110.53(11) . . ? C12 N3 C13 120.75(13) . . ? C12 O B 115.10(11) . . ? N1 C1 C2 107.44(12) . . ? N1 C1 C4 126.90(13) . . ? C2 C1 C4 125.60(13) . . ? C3 C2 C1 108.90(13) . . ? N2 C3 C2 105.68(12) . . ? N2 C3 C8 126.64(13) . . ? C2 C3 C8 127.68(13) . . ? C1 C4 C5 114.41(13) . . ? C1 C4 C6 107.47(13) . . ? C5 C4 C6 108.90(16) . . ? C1 C4 C7 107.91(13) . . ? C5 C4 C7 107.37(15) . . ? C6 C4 C7 110.79(19) . . ? C3 C8 C11 110.14(12) . . ? C3 C8 C10 110.46(12) . . ? C11 C8 C10 111.24(13) . . ? C3 C8 C9 108.04(12) . . ? C11 C8 C9 108.34(13) . . ? C10 C8 C9 108.54(12) . . ? N3 C12 O 131.12(14) . . ? N3 C12 N2 121.09(13) . . ? O C12 N2 107.78(11) . . ? N3 C13 C15 110.21(13) . . ? N3 C13 C16 105.02(13) . . ? C15 C13 C16 109.51(16) . . ? N3 C13 C14 110.84(13) . . ? C15 C13 C14 110.89(14) . . ? C16 C13 C14 110.21(15) . . ? C18 C17 C22 114.27(13) . . ? C18 C17 B 126.90(13) . . ? C22 C17 B 118.82(13) . . ? F1 C18 C19 115.65(13) . . ? F1 C18 C17 120.79(13) . . ? C19 C18 C17 123.55(15) . . ? F2 C19 C20 120.09(14) . . ? F2 C19 C18 120.47(15) . . ? C20 C19 C18 119.43(14) . . ? F3 C20 C21 120.18(15) . . ? F3 C20 C19 120.14(15) . . ? C21 C20 C19 119.69(14) . . ? F4 C21 C20 119.75(14) . . ? F4 C21 C22 121.14(14) . . ? C20 C21 C22 119.10(15) . . ? F5 C22 C21 116.12(13) . . ? F5 C22 C17 119.92(13) . . ? C21 C22 C17 123.96(14) . . ? C28 C23 C24 113.73(13) . . ? C28 C23 B 127.05(13) . . ? C24 C23 B 118.51(13) . . ? F6 C24 C25 116.35(13) . . ? F6 C24 C23 119.57(13) . . ? C25 C24 C23 124.06(14) . . ? F7 C25 C24 120.57(14) . . ? F7 C25 C26 119.68(14) . . ? C24 C25 C26 119.72(14) . . ? F8 C26 C27 120.61(14) . . ? F8 C26 C25 120.57(14) . . ? C27 C26 C25 118.79(14) . . ? F9 C27 C26 119.84(14) . . ? F9 C27 C28 120.46(14) . . ? C26 C27 C28 119.68(14) . . ? F10 C28 C27 115.49(13) . . ? F10 C28 C23 120.50(13) . . ? C27 C28 C23 123.99(14) . . ? 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 O B N1 C1 -173.09(18) . . . . ? C23 B N1 C1 76.1(2) . . . . ? C17 B N1 C1 -59.6(2) . . . . ? O B N1 N2 5.94(14) . . . . ? C23 B N1 N2 -104.92(13) . . . . ? C17 B N1 N2 119.41(12) . . . . ? C1 N1 N2 C3 0.03(15) . . . . ? B N1 N2 C3 -179.37(11) . . . . ? C1 N1 N2 C12 174.82(11) . . . . ? B N1 N2 C12 -4.58(15) . . . . ? N1 B O C12 -5.76(15) . . . . ? C23 B O C12 111.87(13) . . . . ? C17 B O C12 -120.01(13) . . . . ? N2 N1 C1 C2 0.18(16) . . . . ? B N1 C1 C2 179.21(18) . . . . ? N2 N1 C1 C4 -177.10(13) . . . . ? B N1 C1 C4 1.9(3) . . . . ? N1 C1 C2 C3 -0.33(17) . . . . ? C4 C1 C2 C3 177.00(14) . . . . ? N1 N2 C3 C2 -0.23(15) . . . . ? C12 N2 C3 C2 -172.75(16) . . . . ? N1 N2 C3 C8 179.65(13) . . . . ? C12 N2 C3 C8 7.1(3) . . . . ? C1 C2 C3 N2 0.35(16) . . . . ? C1 C2 C3 C8 -179.54(14) . . . . ? N1 C1 C4 C5 -25.7(2) . . . . ? C2 C1 C4 C5 157.48(15) . . . . ? N1 C1 C4 C6 95.4(2) . . . . ? C2 C1 C4 C6 -81.5(2) . . . . ? N1 C1 C4 C7 -145.13(18) . . . . ? C2 C1 C4 C7 38.1(2) . . . . ? N2 C3 C8 C11 60.39(19) . . . . ? C2 C3 C8 C11 -119.74(16) . . . . ? N2 C3 C8 C10 -62.87(19) . . . . ? C2 C3 C8 C10 116.99(16) . . . . ? N2 C3 C8 C9 178.54(14) . . . . ? C2 C3 C8 C9 -1.6(2) . . . . ? C13 N3 C12 O -1.3(2) . . . . ? C13 N3 C12 N2 178.31(13) . . . . ? B O C12 N3 -176.79(16) . . . . ? B O C12 N2 3.51(16) . . . . ? C3 N2 C12 N3 -6.3(3) . . . . ? N1 N2 C12 N3 -178.77(13) . . . . ? C3 N2 C12 O 173.44(16) . . . . ? N1 N2 C12 O 0.96(15) . . . . ? C12 N3 C13 C15 63.38(19) . . . . ? C12 N3 C13 C16 -178.76(16) . . . . ? C12 N3 C13 C14 -59.77(19) . . . . ? O B C17 C18 -131.75(15) . . . . ? N1 B C17 C18 121.76(15) . . . . ? C23 B C17 C18 -11.5(2) . . . . ? O B C17 C22 47.06(17) . . . . ? N1 B C17 C22 -59.42(17) . . . . ? C23 B C17 C22 167.27(13) . . . . ? C22 C17 C18 F1 178.16(13) . . . . ? B C17 C18 F1 -3.0(2) . . . . ? C22 C17 C18 C19 -0.3(2) . . . . ? B C17 C18 C19 178.56(15) . . . . ? F1 C18 C19 F2 0.2(2) . . . . ? C17 C18 C19 F2 178.73(14) . . . . ? F1 C18 C19 C20 -178.79(14) . . . . ? C17 C18 C19 C20 -0.3(2) . . . . ? F2 C19 C20 F3 0.6(2) . . . . ? C18 C19 C20 F3 179.58(14) . . . . ? F2 C19 C20 C21 -178.98(15) . . . . ? C18 C19 C20 C21 0.0(2) . . . . ? F3 C20 C21 F4 0.6(2) . . . . ? C19 C20 C21 F4 -179.85(14) . . . . ? F3 C20 C21 C22 -178.78(14) . . . . ? C19 C20 C21 C22 0.8(2) . . . . ? F4 C21 C22 F5 -1.8(2) . . . . ? C20 C21 C22 F5 177.51(13) . . . . ? F4 C21 C22 C17 179.21(13) . . . . ? C20 C21 C22 C17 -1.4(2) . . . . ? C18 C17 C22 F5 -177.75(13) . . . . ? B C17 C22 F5 3.3(2) . . . . ? C18 C17 C22 C21 1.2(2) . . . . ? B C17 C22 C21 -177.80(14) . . . . ? O B C23 C28 -101.97(16) . . . . ? N1 B C23 C28 4.5(2) . . . . ? C17 B C23 C28 136.05(15) . . . . ? O B C23 C24 67.75(16) . . . . ? N1 B C23 C24 174.25(12) . . . . ? C17 B C23 C24 -54.23(18) . . . . ? C28 C23 C24 F6 176.90(12) . . . . ? B C23 C24 F6 5.9(2) . . . . ? C28 C23 C24 C25 -1.4(2) . . . . ? B C23 C24 C25 -172.44(14) . . . . ? F6 C24 C25 F7 0.8(2) . . . . ? C23 C24 C25 F7 179.13(13) . . . . ? F6 C24 C25 C26 -177.24(13) . . . . ? C23 C24 C25 C26 1.1(2) . . . . ? F7 C25 C26 F8 -1.0(2) . . . . ? C24 C25 C26 F8 177.04(13) . . . . ? F7 C25 C26 C27 -179.01(13) . . . . ? C24 C25 C26 C27 -1.0(2) . . . . ? F8 C26 C27 F9 1.6(2) . . . . ? C25 C26 C27 F9 179.60(14) . . . . ? F8 C26 C27 C28 -176.76(13) . . . . ? C25 C26 C27 C28 1.2(2) . . . . ? F9 C27 C28 F10 -1.7(2) . . . . ? C26 C27 C28 F10 176.69(13) . . . . ? F9 C27 C28 C23 179.95(14) . . . . ? C26 C27 C28 C23 -1.7(2) . . . . ? C24 C23 C28 F10 -176.63(13) . . . . ? B C23 C28 F10 -6.5(2) . . . . ? C24 C23 C28 C27 1.7(2) . . . . ? B C23 C28 C27 171.82(14) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.88 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.321 _refine_diff_density_min -0.300 _refine_diff_density_rms 0.044 # # end of cif data for "eileen20" # Attachment '- eileen21.cif' data_eileen21 _database_code_depnum_ccdc_archive 'CCDC 869099' #TrackingRef '- eileen21.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H22 B F10 N3 S' _chemical_formula_weight 597.33 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 '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 10.1128(2) _cell_length_b 12.5196(2) _cell_length_c 20.7678(4) _cell_angle_alpha 90.00 _cell_angle_beta 97.885(2) _cell_angle_gamma 90.00 _cell_volume 2604.51(8) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 27255 _cell_measurement_theta_min 3.5274 _cell_measurement_theta_max 75.6250 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.11 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.523 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1216 _exptl_absorpt_coefficient_mu 1.962 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.64326 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_source 'Nova (Cu) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'Oxford Diffraction Xcalibur, Atlas, Nova' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 10.3543 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 41673 _diffrn_reflns_av_R_equivalents 0.0289 _diffrn_reflns_av_sigmaI/netI 0.0137 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 4.13 _diffrn_reflns_theta_max 74.49 _reflns_number_total 5324 _reflns_number_gt 4908 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker XP' _computing_publication_material SHELXL-97 _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^)+(0.0388P)^2^+0.9580P] 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 5324 _refine_ls_number_parameters 368 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0315 _refine_ls_R_factor_gt 0.0289 _refine_ls_wR_factor_ref 0.0784 _refine_ls_wR_factor_gt 0.0763 _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_restrained_S_all 1.037 _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 S S 0.63415(3) 0.34626(3) 0.653933(16) 0.02935(9) Uani 1 1 d . . . B B 0.27414(13) 0.23288(11) 0.57422(6) 0.0205(3) Uani 1 1 d . . . N1 N 0.29742(9) 0.18833(8) 0.64633(5) 0.0205(2) Uani 1 1 d . . . N2 N 0.42018(9) 0.22255(8) 0.67748(5) 0.0198(2) Uani 1 1 d . . . N3 N 0.40420(9) 0.30016(8) 0.58011(5) 0.0206(2) Uani 1 1 d . . . F1 F 0.24389(7) 0.42801(6) 0.64351(4) 0.03220(18) Uani 1 1 d . . . F2 F 0.03313(8) 0.55777(6) 0.63279(5) 0.0398(2) Uani 1 1 d . . . F3 F -0.19417(8) 0.50636(7) 0.55379(5) 0.0422(2) Uani 1 1 d . . . F4 F -0.20354(8) 0.32444(7) 0.48148(4) 0.0402(2) Uani 1 1 d . . . F5 F 0.00427(7) 0.19618(6) 0.48816(4) 0.03179(17) Uani 1 1 d . . . F6 F 0.21024(8) 0.26352(6) 0.43239(4) 0.03135(17) Uani 1 1 d . . . F7 F 0.23968(8) 0.12226(8) 0.34039(4) 0.0435(2) Uani 1 1 d . . . F8 F 0.33404(9) -0.07733(8) 0.37196(5) 0.0516(3) Uani 1 1 d . . . F9 F 0.39467(8) -0.13305(6) 0.49962(5) 0.0435(2) Uani 1 1 d . . . F10 F 0.37541(7) 0.00841(6) 0.59240(4) 0.03044(17) Uani 1 1 d . . . C1 C 0.24016(12) 0.12841(10) 0.68859(6) 0.0229(2) Uani 1 1 d . . . C2 C 0.32793(12) 0.12488(10) 0.74659(6) 0.0248(2) Uani 1 1 d . . . H2 H 0.3128 0.0873 0.7846 0.030 Uiso 1 1 calc R . . C3 C 0.43992(12) 0.18446(10) 0.74009(6) 0.0219(2) Uani 1 1 d . . . C4 C 0.10183(12) 0.07879(11) 0.67730(6) 0.0275(3) Uani 1 1 d . . . C5 C -0.00065(13) 0.16629(13) 0.68712(7) 0.0360(3) Uani 1 1 d . . . H5A H 0.0223 0.1984 0.7302 0.054 Uiso 1 1 calc R . . H5B H -0.0900 0.1347 0.6836 0.054 Uiso 1 1 calc R . . H5C H 0.0006 0.2214 0.6537 0.054 Uiso 1 1 calc R . . C6 C 0.06961(13) 0.02786(12) 0.61007(7) 0.0315(3) Uani 1 1 d . . . H6A H 0.0764 0.0820 0.5766 0.047 Uiso 1 1 calc R . . H6B H -0.0213 -0.0010 0.6049 0.047 Uiso 1 1 calc R . . H6C H 0.1331 -0.0300 0.6056 0.047 Uiso 1 1 calc R . . C7 C 0.09393(14) -0.00933(13) 0.72839(7) 0.0373(3) Uani 1 1 d . . . H7A H 0.1622 -0.0635 0.7244 0.056 Uiso 1 1 calc R . . H7B H 0.0054 -0.0426 0.7213 0.056 Uiso 1 1 calc R . . H7C H 0.1092 0.0220 0.7720 0.056 Uiso 1 1 calc R . . C8 C 0.55653(12) 0.20297(11) 0.79347(6) 0.0261(3) Uani 1 1 d . . . C9 C 0.57010(14) 0.32186(12) 0.81127(7) 0.0365(3) Uani 1 1 d . . . H9A H 0.5858 0.3630 0.7729 0.055 Uiso 1 1 calc R . . H9B H 0.6453 0.3317 0.8459 0.055 Uiso 1 1 calc R . . H9C H 0.4878 0.3467 0.8264 0.055 Uiso 1 1 calc R . . C10 C 0.68683(13) 0.15747(12) 0.77478(6) 0.0302(3) Uani 1 1 d . . . H10A H 0.6754 0.0811 0.7651 0.045 Uiso 1 1 calc R . . H10B H 0.7589 0.1673 0.8110 0.045 Uiso 1 1 calc R . . H10C H 0.7094 0.1949 0.7363 0.045 Uiso 1 1 calc R . . C11 C 0.52661(15) 0.14261(15) 0.85446(7) 0.0408(4) Uani 1 1 d . . . H11A H 0.4435 0.1697 0.8677 0.061 Uiso 1 1 calc R . . H11B H 0.6001 0.1535 0.8898 0.061 Uiso 1 1 calc R . . H11C H 0.5172 0.0662 0.8447 0.061 Uiso 1 1 calc R . . C12 C 0.48576(11) 0.29061(9) 0.63571(6) 0.0206(2) Uani 1 1 d . . . C13 C 0.44410(12) 0.36659(10) 0.52884(6) 0.0261(3) Uani 1 1 d . . . H13A H 0.4648 0.4387 0.5457 0.039 Uiso 1 1 calc R . . H13B H 0.3711 0.3702 0.4926 0.039 Uiso 1 1 calc R . . H13C H 0.5233 0.3358 0.5136 0.039 Uiso 1 1 calc R . . C14 C 0.13935(11) 0.30678(10) 0.56457(6) 0.0222(2) Uani 1 1 d . . . C15 C 0.13628(12) 0.40008(10) 0.60097(6) 0.0246(2) Uani 1 1 d . . . C16 C 0.02745(13) 0.46767(10) 0.59777(7) 0.0289(3) Uani 1 1 d . . . C17 C -0.08821(13) 0.44186(11) 0.55766(7) 0.0302(3) Uani 1 1 d . . . C18 C -0.09218(12) 0.35026(11) 0.52103(7) 0.0290(3) Uani 1 1 d . . . C19 C 0.01975(12) 0.28527(10) 0.52484(6) 0.0253(2) Uani 1 1 d . . . C20 C 0.28485(11) 0.14242(10) 0.51805(6) 0.0224(2) Uani 1 1 d . . . C21 C 0.25603(12) 0.16608(10) 0.45202(6) 0.0258(3) Uani 1 1 d . . . C22 C 0.27148(12) 0.09406(12) 0.40300(6) 0.0316(3) Uani 1 1 d . . . C23 C 0.31774(13) -0.00693(12) 0.41875(7) 0.0352(3) Uani 1 1 d . . . C24 C 0.34835(12) -0.03497(11) 0.48312(8) 0.0318(3) Uani 1 1 d . . . C25 C 0.33438(12) 0.04015(10) 0.53069(6) 0.0253(2) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S 0.02136(15) 0.03332(17) 0.03189(17) 0.00527(12) -0.00170(12) -0.00739(12) B 0.0187(6) 0.0214(6) 0.0209(6) 0.0005(5) 0.0015(5) 0.0005(5) N1 0.0154(4) 0.0234(5) 0.0223(5) -0.0001(4) 0.0008(4) -0.0008(4) N2 0.0160(4) 0.0218(5) 0.0210(5) -0.0006(4) 0.0008(4) -0.0012(4) N3 0.0175(4) 0.0217(5) 0.0225(5) -0.0010(4) 0.0023(4) 0.0005(4) F1 0.0259(4) 0.0328(4) 0.0367(4) -0.0129(3) -0.0003(3) 0.0014(3) F2 0.0378(4) 0.0263(4) 0.0578(5) -0.0077(4) 0.0157(4) 0.0052(3) F3 0.0268(4) 0.0347(4) 0.0666(6) 0.0158(4) 0.0116(4) 0.0137(3) F4 0.0206(4) 0.0513(5) 0.0454(5) 0.0079(4) -0.0077(3) 0.0026(3) F5 0.0243(4) 0.0354(4) 0.0334(4) -0.0073(3) -0.0042(3) -0.0007(3) F6 0.0346(4) 0.0339(4) 0.0246(4) 0.0031(3) 0.0005(3) 0.0018(3) F7 0.0338(4) 0.0718(6) 0.0244(4) -0.0137(4) 0.0024(3) -0.0066(4) F8 0.0350(5) 0.0591(6) 0.0613(6) -0.0425(5) 0.0086(4) -0.0040(4) F9 0.0312(4) 0.0227(4) 0.0781(7) -0.0120(4) 0.0126(4) 0.0011(3) F10 0.0288(4) 0.0246(4) 0.0384(4) 0.0065(3) 0.0061(3) 0.0051(3) C1 0.0194(6) 0.0254(6) 0.0243(6) 0.0004(5) 0.0047(4) 0.0000(4) C2 0.0235(6) 0.0299(6) 0.0214(6) 0.0018(5) 0.0045(4) -0.0015(5) C3 0.0213(5) 0.0252(6) 0.0192(5) -0.0018(4) 0.0028(4) 0.0017(4) C4 0.0189(6) 0.0347(7) 0.0291(6) 0.0032(5) 0.0043(5) -0.0038(5) C5 0.0214(6) 0.0477(8) 0.0406(8) -0.0003(6) 0.0095(5) 0.0007(6) C6 0.0212(6) 0.0394(7) 0.0336(7) -0.0012(6) 0.0029(5) -0.0087(5) C7 0.0275(7) 0.0473(8) 0.0372(7) 0.0102(6) 0.0051(5) -0.0118(6) C8 0.0234(6) 0.0353(7) 0.0190(5) -0.0021(5) 0.0003(4) -0.0028(5) C9 0.0315(7) 0.0430(8) 0.0357(7) -0.0181(6) 0.0074(6) -0.0067(6) C10 0.0246(6) 0.0367(7) 0.0278(6) 0.0027(5) -0.0014(5) 0.0045(5) C11 0.0345(7) 0.0659(11) 0.0203(6) 0.0048(6) -0.0017(5) -0.0113(7) C12 0.0198(5) 0.0192(5) 0.0230(5) 0.0004(4) 0.0036(4) 0.0019(4) C13 0.0252(6) 0.0266(6) 0.0263(6) 0.0055(5) 0.0024(5) -0.0015(5) C14 0.0197(5) 0.0235(6) 0.0231(6) 0.0018(4) 0.0024(4) 0.0018(4) C15 0.0215(6) 0.0250(6) 0.0274(6) 0.0002(5) 0.0035(4) 0.0005(5) C16 0.0295(6) 0.0223(6) 0.0367(7) 0.0019(5) 0.0114(5) 0.0028(5) C17 0.0223(6) 0.0279(6) 0.0417(7) 0.0134(5) 0.0096(5) 0.0088(5) C18 0.0191(6) 0.0338(7) 0.0327(7) 0.0103(5) -0.0008(5) 0.0015(5) C19 0.0232(6) 0.0270(6) 0.0252(6) 0.0019(5) 0.0011(5) 0.0007(5) C20 0.0174(5) 0.0240(6) 0.0261(6) -0.0027(5) 0.0039(4) -0.0022(4) C21 0.0211(6) 0.0290(6) 0.0271(6) -0.0030(5) 0.0028(5) -0.0022(5) C22 0.0215(6) 0.0463(8) 0.0273(6) -0.0118(6) 0.0037(5) -0.0069(5) C23 0.0207(6) 0.0411(8) 0.0448(8) -0.0255(6) 0.0078(5) -0.0066(5) C24 0.0194(6) 0.0238(6) 0.0531(8) -0.0113(6) 0.0082(5) -0.0023(5) C25 0.0182(5) 0.0246(6) 0.0334(6) -0.0017(5) 0.0054(5) -0.0019(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S C12 1.6507(12) . ? B N3 1.5525(16) . ? B N1 1.5851(16) . ? B C14 1.6369(17) . ? B C20 1.6400(17) . ? N1 C1 1.3445(15) . ? N1 N2 1.3868(13) . ? N2 C3 1.3735(15) . ? N2 C12 1.4410(15) . ? N3 C12 1.3289(15) . ? N3 C13 1.4513(15) . ? F1 C15 1.3503(14) . ? F2 C16 1.3391(16) . ? F3 C17 1.3353(14) . ? F4 C18 1.3393(15) . ? F5 C19 1.3477(15) . ? F6 C21 1.3480(15) . ? F7 C22 1.3431(16) . ? F8 C23 1.3387(15) . ? F9 C24 1.3418(16) . ? F10 C25 1.3514(15) . ? C1 C2 1.3956(17) . ? C1 C4 1.5192(16) . ? C2 C3 1.3781(17) . ? C3 C8 1.5215(16) . ? C4 C6 1.5288(18) . ? C4 C7 1.5404(19) . ? C4 C5 1.5407(19) . ? C8 C10 1.5336(18) . ? C8 C9 1.5352(19) . ? C8 C11 1.5402(18) . ? C14 C19 1.3936(17) . ? C14 C15 1.3940(17) . ? C15 C16 1.3826(17) . ? C16 C17 1.378(2) . ? C17 C18 1.374(2) . ? C18 C19 1.3875(18) . ? C20 C25 1.3868(18) . ? C20 C21 1.3940(18) . ? C21 C22 1.3847(18) . ? C22 C23 1.372(2) . ? C23 C24 1.376(2) . ? C24 C25 1.3853(18) . ? 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 N3 B N1 95.85(8) . . ? N3 B C14 112.66(10) . . ? N1 B C14 109.13(9) . . ? N3 B C20 107.03(9) . . ? N1 B C20 114.41(10) . . ? C14 B C20 116.00(10) . . ? C1 N1 N2 107.82(9) . . ? C1 N1 B 142.33(10) . . ? N2 N1 B 109.85(9) . . ? C3 N2 N1 109.81(9) . . ? C3 N2 C12 139.13(10) . . ? N1 N2 C12 110.99(9) . . ? C12 N3 C13 119.15(10) . . ? C12 N3 B 115.96(10) . . ? C13 N3 B 124.81(9) . . ? N1 C1 C2 107.53(10) . . ? N1 C1 C4 126.68(11) . . ? C2 C1 C4 125.69(11) . . ? C3 C2 C1 109.40(11) . . ? N2 C3 C2 105.43(10) . . ? N2 C3 C8 129.37(11) . . ? C2 C3 C8 125.19(11) . . ? C1 C4 C6 112.82(10) . . ? C1 C4 C7 108.68(10) . . ? C6 C4 C7 107.80(12) . . ? C1 C4 C5 108.10(11) . . ? C6 C4 C5 110.77(11) . . ? C7 C4 C5 108.58(11) . . ? C3 C8 C10 111.46(10) . . ? C3 C8 C9 110.97(11) . . ? C10 C8 C9 111.69(11) . . ? C3 C8 C11 107.72(10) . . ? C10 C8 C11 107.37(11) . . ? C9 C8 C11 107.39(12) . . ? N3 C12 N2 107.12(10) . . ? N3 C12 S 126.69(9) . . ? N2 C12 S 126.19(9) . . ? C19 C14 C15 113.63(11) . . ? C19 C14 B 127.14(11) . . ? C15 C14 B 119.17(10) . . ? F1 C15 C16 115.96(11) . . ? F1 C15 C14 119.73(11) . . ? C16 C15 C14 124.30(12) . . ? F2 C16 C17 119.70(12) . . ? F2 C16 C15 120.99(12) . . ? C17 C16 C15 119.31(12) . . ? F3 C17 C18 120.62(12) . . ? F3 C17 C16 120.14(13) . . ? C18 C17 C16 119.23(12) . . ? F4 C18 C17 119.96(12) . . ? F4 C18 C19 120.28(13) . . ? C17 C18 C19 119.76(12) . . ? F5 C19 C18 114.99(11) . . ? F5 C19 C14 121.24(11) . . ? C18 C19 C14 123.74(12) . . ? C25 C20 C21 113.81(11) . . ? C25 C20 B 124.07(11) . . ? C21 C20 B 121.84(11) . . ? F6 C21 C22 115.82(12) . . ? F6 C21 C20 120.44(11) . . ? C22 C21 C20 123.74(13) . . ? F7 C22 C23 120.10(12) . . ? F7 C22 C21 120.29(13) . . ? C23 C22 C21 119.60(13) . . ? F8 C23 C22 120.37(14) . . ? F8 C23 C24 120.24(14) . . ? C22 C23 C24 119.39(12) . . ? F9 C24 C23 120.39(12) . . ? F9 C24 C25 120.35(13) . . ? C23 C24 C25 119.24(13) . . ? F10 C25 C24 115.38(12) . . ? F10 C25 C20 120.46(11) . . ? C24 C25 C20 124.15(13) . . ? 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 N3 B N1 C1 176.28(15) . . . . ? C14 B N1 C1 59.83(19) . . . . ? C20 B N1 C1 -72.01(19) . . . . ? N3 B N1 N2 -3.85(11) . . . . ? C14 B N1 N2 -120.31(10) . . . . ? C20 B N1 N2 107.86(11) . . . . ? C1 N1 N2 C3 -0.45(13) . . . . ? B N1 N2 C3 179.64(9) . . . . ? C1 N1 N2 C12 -178.02(9) . . . . ? B N1 N2 C12 2.07(12) . . . . ? N1 B N3 C12 4.92(12) . . . . ? C14 B N3 C12 118.49(11) . . . . ? C20 B N3 C12 -112.85(11) . . . . ? N1 B N3 C13 -178.34(10) . . . . ? C14 B N3 C13 -64.77(14) . . . . ? C20 B N3 C13 63.89(14) . . . . ? N2 N1 C1 C2 -0.15(13) . . . . ? B N1 C1 C2 179.72(14) . . . . ? N2 N1 C1 C4 176.45(11) . . . . ? B N1 C1 C4 -3.7(2) . . . . ? N1 C1 C2 C3 0.69(14) . . . . ? C4 C1 C2 C3 -175.95(12) . . . . ? N1 N2 C3 C2 0.85(13) . . . . ? C12 N2 C3 C2 177.38(13) . . . . ? N1 N2 C3 C8 -177.99(11) . . . . ? C12 N2 C3 C8 -1.5(2) . . . . ? C1 C2 C3 N2 -0.94(14) . . . . ? C1 C2 C3 C8 177.96(11) . . . . ? N1 C1 C4 C6 43.27(18) . . . . ? C2 C1 C4 C6 -140.72(13) . . . . ? N1 C1 C4 C7 162.77(13) . . . . ? C2 C1 C4 C7 -21.22(18) . . . . ? N1 C1 C4 C5 -79.56(15) . . . . ? C2 C1 C4 C5 96.44(15) . . . . ? N2 C3 C8 C10 -63.20(17) . . . . ? C2 C3 C8 C10 118.17(14) . . . . ? N2 C3 C8 C9 61.97(16) . . . . ? C2 C3 C8 C9 -116.66(14) . . . . ? N2 C3 C8 C11 179.26(13) . . . . ? C2 C3 C8 C11 0.63(18) . . . . ? C13 N3 C12 N2 178.92(10) . . . . ? B N3 C12 N2 -4.14(13) . . . . ? C13 N3 C12 S -0.90(16) . . . . ? B N3 C12 S 176.04(9) . . . . ? C3 N2 C12 N3 -175.35(13) . . . . ? N1 N2 C12 N3 1.15(13) . . . . ? C3 N2 C12 S 4.5(2) . . . . ? N1 N2 C12 S -179.02(8) . . . . ? N3 B C14 C19 141.53(12) . . . . ? N1 B C14 C19 -113.29(13) . . . . ? C20 B C14 C19 17.70(17) . . . . ? N3 B C14 C15 -41.49(15) . . . . ? N1 B C14 C15 63.68(14) . . . . ? C20 B C14 C15 -165.33(11) . . . . ? C19 C14 C15 F1 177.28(11) . . . . ? B C14 C15 F1 -0.09(17) . . . . ? C19 C14 C15 C16 -1.47(18) . . . . ? B C14 C15 C16 -178.84(11) . . . . ? F1 C15 C16 F2 3.25(18) . . . . ? C14 C15 C16 F2 -177.95(12) . . . . ? F1 C15 C16 C17 -177.05(11) . . . . ? C14 C15 C16 C17 1.7(2) . . . . ? F2 C16 C17 F3 -0.07(19) . . . . ? C15 C16 C17 F3 -179.78(11) . . . . ? F2 C16 C17 C18 178.81(12) . . . . ? C15 C16 C17 C18 -0.90(19) . . . . ? F3 C17 C18 F4 -0.67(19) . . . . ? C16 C17 C18 F4 -179.55(12) . . . . ? F3 C17 C18 C19 178.83(12) . . . . ? C16 C17 C18 C19 -0.05(19) . . . . ? F4 C18 C19 F5 -2.02(18) . . . . ? C17 C18 C19 F5 178.48(11) . . . . ? F4 C18 C19 C14 179.76(11) . . . . ? C17 C18 C19 C14 0.3(2) . . . . ? C15 C14 C19 F5 -177.66(11) . . . . ? B C14 C19 F5 -0.54(19) . . . . ? C15 C14 C19 C18 0.45(18) . . . . ? B C14 C19 C18 177.57(12) . . . . ? N3 B C20 C25 93.03(13) . . . . ? N1 B C20 C25 -11.82(16) . . . . ? C14 B C20 C25 -140.27(12) . . . . ? N3 B C20 C21 -80.67(13) . . . . ? N1 B C20 C21 174.49(10) . . . . ? C14 B C20 C21 46.04(15) . . . . ? C25 C20 C21 F6 -178.36(10) . . . . ? B C20 C21 F6 -4.07(17) . . . . ? C25 C20 C21 C22 1.66(18) . . . . ? B C20 C21 C22 175.95(11) . . . . ? F6 C21 C22 F7 -0.98(17) . . . . ? C20 C21 C22 F7 179.00(11) . . . . ? F6 C21 C22 C23 179.94(11) . . . . ? C20 C21 C22 C23 -0.08(19) . . . . ? F7 C22 C23 F8 1.33(19) . . . . ? C21 C22 C23 F8 -179.58(11) . . . . ? F7 C22 C23 C24 -179.22(11) . . . . ? C21 C22 C23 C24 -0.13(19) . . . . ? F8 C23 C24 F9 -0.06(19) . . . . ? C22 C23 C24 F9 -179.51(11) . . . . ? F8 C23 C24 C25 178.14(11) . . . . ? C22 C23 C24 C25 -1.32(19) . . . . ? F9 C24 C25 F10 2.66(17) . . . . ? C23 C24 C25 F10 -175.54(11) . . . . ? F9 C24 C25 C20 -178.63(11) . . . . ? C23 C24 C25 C20 3.18(19) . . . . ? C21 C20 C25 F10 175.43(10) . . . . ? B C20 C25 F10 1.29(17) . . . . ? C21 C20 C25 C24 -3.22(17) . . . . ? B C20 C25 C24 -177.36(11) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 74.49 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.291 _refine_diff_density_min -0.210 _refine_diff_density_rms 0.038 # # end of cif data for "eileen21" # Attachment '- eileen28.cif' data_eileen28 _database_code_depnum_ccdc_archive 'CCDC 869100' #TrackingRef '- eileen28.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C31.50 H32 B F10 N3' _chemical_formula_weight 653.41 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' 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 9.5902(12) _cell_length_b 11.3185(16) _cell_length_c 15.1442(18) _cell_angle_alpha 85.961(10) _cell_angle_beta 88.454(10) _cell_angle_gamma 75.367(12) _cell_volume 1586.5(4) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3989 _cell_measurement_theta_min 2.1905 _cell_measurement_theta_max 29.2826 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.368 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 674 _exptl_absorpt_coefficient_mu 0.121 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.97514 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Diffraction Xcalibur, Eos' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 16.1419 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 36032 _diffrn_reflns_av_R_equivalents 0.0827 _diffrn_reflns_av_sigmaI/netI 0.0732 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.19 _diffrn_reflns_theta_max 26.37 _reflns_number_total 6468 _reflns_number_gt 4105 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'BRUKER XP' _computing_publication_material SHELXL-97 _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. One half molecule of toluene was found in the asymmetric unit and is disordered across an inversion centre. For refinement, an idealised hexagon was used as a rigid group to model the aromatic ring. ; _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^)+(0.0412P)^2^+0.1258P] 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 6468 _refine_ls_number_parameters 440 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0962 _refine_ls_R_factor_gt 0.0506 _refine_ls_wR_factor_ref 0.1187 _refine_ls_wR_factor_gt 0.0974 _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 B B 0.4551(3) 0.3241(2) 0.24848(17) 0.0185(6) Uani 1 1 d . . . N1 N 0.42246(19) 0.20183(16) 0.23149(12) 0.0181(4) Uani 1 1 d . . . N2 N 0.30111(19) 0.22142(16) 0.17942(12) 0.0198(4) Uani 1 1 d . . . N3 N 0.1887(2) 0.49314(17) 0.24731(12) 0.0210(4) Uani 1 1 d . . . F1 F 0.29462(14) 0.30436(12) 0.40929(9) 0.0300(3) Uani 1 1 d . . . F2 F 0.37290(15) 0.32242(13) 0.57472(9) 0.0382(4) Uani 1 1 d . . . F3 F 0.63630(16) 0.36129(13) 0.60621(9) 0.0397(4) Uani 1 1 d . . . F4 F 0.81258(15) 0.39101(13) 0.46878(9) 0.0351(4) Uani 1 1 d . . . F5 F 0.73983(13) 0.37196(12) 0.30381(8) 0.0275(3) Uani 1 1 d . . . F6 F 0.48828(14) 0.57037(11) 0.23416(8) 0.0260(3) Uani 1 1 d . . . F7 F 0.61738(15) 0.67717(12) 0.10518(9) 0.0332(4) Uani 1 1 d . . . F8 F 0.74938(15) 0.54595(13) -0.03237(9) 0.0380(4) Uani 1 1 d . . . F9 F 0.73329(15) 0.31117(13) -0.04181(9) 0.0368(4) Uani 1 1 d . . . F10 F 0.60092(14) 0.20418(11) 0.08367(8) 0.0293(3) Uani 1 1 d . . . C1 C 0.4902(2) 0.07841(19) 0.23832(14) 0.0200(5) Uani 1 1 d . . . C2 C 0.4092(2) 0.0213(2) 0.19098(15) 0.0226(5) Uani 1 1 d . . . H2 H 0.4277 -0.0639 0.1838 0.027 Uiso 1 1 calc R . . C3 C 0.2940(2) 0.1127(2) 0.15540(15) 0.0216(5) Uani 1 1 d . . . C4 C 0.6260(2) 0.0171(2) 0.29008(15) 0.0237(5) Uani 1 1 d . . . C5 C 0.7518(2) 0.0745(2) 0.26374(16) 0.0299(6) Uani 1 1 d . . . H5A H 0.7780 0.0612 0.2016 0.045 Uiso 1 1 calc R . . H5B H 0.8350 0.0364 0.3012 0.045 Uiso 1 1 calc R . . H5C H 0.7225 0.1626 0.2717 0.045 Uiso 1 1 calc R . . C6 C 0.5971(3) 0.0203(2) 0.39061(15) 0.0304(6) Uani 1 1 d . . . H6A H 0.5762 0.1051 0.4075 0.046 Uiso 1 1 calc R . . H6B H 0.6822 -0.0286 0.4224 0.046 Uiso 1 1 calc R . . H6C H 0.5143 -0.0135 0.4059 0.046 Uiso 1 1 calc R . . C7 C 0.6724(3) -0.1180(2) 0.26875(16) 0.0326(6) Uani 1 1 d . . . H7A H 0.5963 -0.1583 0.2875 0.049 Uiso 1 1 calc R . . H7B H 0.7614 -0.1584 0.3003 0.049 Uiso 1 1 calc R . . H7C H 0.6890 -0.1234 0.2049 0.049 Uiso 1 1 calc R . . C8 C 0.1764(3) 0.1002(2) 0.09441(16) 0.0267(6) Uani 1 1 d . . . C9 C 0.2375(3) 0.0932(3) -0.00015(17) 0.0455(8) Uani 1 1 d . . . H9A H 0.2655 0.1690 -0.0181 0.068 Uiso 1 1 calc R . . H9B H 0.1640 0.0827 -0.0405 0.068 Uiso 1 1 calc R . . H9C H 0.3221 0.0235 -0.0023 0.068 Uiso 1 1 calc R . . C10 C 0.0456(3) 0.2101(2) 0.0988(2) 0.0488(8) Uani 1 1 d . . . H10A H 0.0085 0.2153 0.1598 0.073 Uiso 1 1 calc R . . H10B H -0.0296 0.2001 0.0596 0.073 Uiso 1 1 calc R . . H10C H 0.0743 0.2852 0.0800 0.073 Uiso 1 1 calc R . . C11 C 0.1303(3) -0.0167(2) 0.12162(18) 0.0381(7) Uani 1 1 d . . . H11A H 0.2132 -0.0875 0.1171 0.057 Uiso 1 1 calc R . . H11B H 0.0539 -0.0242 0.0824 0.057 Uiso 1 1 calc R . . H11C H 0.0944 -0.0136 0.1828 0.057 Uiso 1 1 calc R . . C12 C 0.2943(2) 0.4189(2) 0.24585(14) 0.0192(5) Uani 1 1 d . . . C13 C 0.0501(2) 0.5847(2) 0.25142(15) 0.0228(5) Uani 1 1 d . . . C14 C -0.0129(3) 0.5652(2) 0.34301(17) 0.0400(7) Uani 1 1 d . . . H14A H -0.0277 0.4825 0.3504 0.060 Uiso 1 1 calc R . . H14B H -0.1054 0.6255 0.3495 0.060 Uiso 1 1 calc R . . H14C H 0.0538 0.5752 0.3882 0.060 Uiso 1 1 calc R . . C15 C -0.0430(3) 0.5623(3) 0.1786(2) 0.0486(8) Uani 1 1 d . . . H15A H 0.0037 0.5720 0.1211 0.073 Uiso 1 1 calc R . . H15B H -0.1372 0.6214 0.1801 0.073 Uiso 1 1 calc R . . H15C H -0.0557 0.4791 0.1873 0.073 Uiso 1 1 calc R . . C16 C 0.0829(3) 0.7094(2) 0.23783(18) 0.0344(6) Uani 1 1 d . . . H16A H 0.1463 0.7191 0.2850 0.052 Uiso 1 1 calc R . . H16B H -0.0072 0.7737 0.2395 0.052 Uiso 1 1 calc R . . H16C H 0.1306 0.7158 0.1803 0.052 Uiso 1 1 calc R . . C17 C 0.5126(2) 0.33506(19) 0.34766(14) 0.0178(5) Uani 1 1 d . . . C18 C 0.4255(2) 0.3247(2) 0.42119(15) 0.0217(5) Uani 1 1 d . . . C19 C 0.4641(3) 0.3327(2) 0.50712(15) 0.0248(6) Uani 1 1 d . . . C20 C 0.5962(3) 0.3528(2) 0.52322(15) 0.0263(6) Uani 1 1 d . . . C21 C 0.6851(2) 0.3668(2) 0.45316(15) 0.0232(5) Uani 1 1 d . . . C22 C 0.6435(2) 0.3581(2) 0.36849(14) 0.0201(5) Uani 1 1 d . . . C23 C 0.5405(2) 0.38117(19) 0.16748(14) 0.0181(5) Uani 1 1 d . . . C24 C 0.5494(2) 0.5019(2) 0.16652(14) 0.0213(5) Uani 1 1 d . . . C25 C 0.6162(2) 0.5590(2) 0.10119(15) 0.0236(5) Uani 1 1 d . . . C26 C 0.6811(2) 0.4937(2) 0.03195(15) 0.0250(6) Uani 1 1 d . . . C27 C 0.6740(2) 0.3747(2) 0.02807(15) 0.0248(6) Uani 1 1 d . . . C28 C 0.6043(2) 0.3201(2) 0.09443(14) 0.0206(5) Uani 1 1 d . . . C30 C 0.9827(6) -0.0255(5) 0.5189(3) 0.0459(18) Uani 0.50 1 d PG A -1 C31 C 0.9821(5) 0.0973(4) 0.5206(3) 0.039(2) Uani 0.50 1 d PG A -1 H31 H 0.9273 0.1456 0.5644 0.047 Uiso 0.50 1 calc PR A -1 C32 C 1.0616(5) 0.1494(3) 0.4582(3) 0.0395(16) Uani 0.50 1 d PG A -1 H32 H 1.0612 0.2333 0.4594 0.047 Uiso 0.50 1 calc PR A -1 C33 C 1.1417(5) 0.0787(4) 0.3941(3) 0.037(2) Uani 0.50 1 d PG A -1 H33 H 1.1961 0.1143 0.3514 0.045 Uiso 0.50 1 calc PR A -1 C34 C 1.1423(5) -0.0441(4) 0.3924(3) 0.0450(15) Uani 0.50 1 d PG A -1 H34 H 1.1971 -0.0924 0.3485 0.054 Uiso 0.50 1 calc PR A -1 C35 C 1.0628(5) -0.0962(3) 0.4548(3) 0.051(2) Uani 0.50 1 d PG A -1 H35 H 1.0632 -0.1801 0.4536 0.061 Uiso 0.50 1 calc PR A -1 C36 C 0.8955(12) -0.0798(9) 0.5879(6) 0.070(3) Uani 0.50 1 d P A -1 H36A H 0.9605 -0.1316 0.6320 0.105 Uiso 0.50 1 calc PR A -1 H36B H 0.8415 -0.1291 0.5593 0.105 Uiso 0.50 1 calc PR A -1 H36C H 0.8282 -0.0137 0.6172 0.105 Uiso 0.50 1 calc PR A -1 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 0.0146(14) 0.0164(13) 0.0238(15) -0.0022(11) 0.0007(11) -0.0026(11) N1 0.0141(10) 0.0191(10) 0.0213(10) -0.0005(8) -0.0015(8) -0.0049(8) N2 0.0156(10) 0.0207(10) 0.0234(11) -0.0015(8) -0.0019(8) -0.0049(8) N3 0.0175(11) 0.0215(11) 0.0252(11) -0.0035(9) 0.0009(9) -0.0067(9) F1 0.0219(8) 0.0370(8) 0.0325(8) 0.0019(6) 0.0055(6) -0.0116(6) F2 0.0407(9) 0.0457(9) 0.0235(8) 0.0021(7) 0.0139(7) -0.0048(7) F3 0.0509(10) 0.0456(9) 0.0207(8) -0.0058(7) -0.0074(7) -0.0068(8) F4 0.0338(9) 0.0431(9) 0.0334(8) 0.0020(7) -0.0131(7) -0.0187(7) F5 0.0197(7) 0.0425(8) 0.0234(7) 0.0031(6) 0.0003(6) -0.0148(6) F6 0.0327(8) 0.0236(7) 0.0239(7) -0.0039(6) 0.0033(6) -0.0110(6) F7 0.0370(9) 0.0299(8) 0.0369(9) 0.0064(7) -0.0029(7) -0.0183(7) F8 0.0321(9) 0.0546(10) 0.0287(8) 0.0113(7) 0.0056(7) -0.0178(7) F9 0.0341(9) 0.0490(9) 0.0229(8) -0.0051(7) 0.0096(7) -0.0026(7) F10 0.0365(9) 0.0241(7) 0.0264(8) -0.0070(6) 0.0057(6) -0.0049(6) C1 0.0191(13) 0.0177(12) 0.0209(13) 0.0015(10) 0.0034(10) -0.0015(10) C2 0.0215(13) 0.0176(12) 0.0297(14) -0.0018(10) 0.0011(11) -0.0064(10) C3 0.0223(13) 0.0211(13) 0.0241(13) 0.0010(10) 0.0009(10) -0.0111(10) C4 0.0225(13) 0.0242(13) 0.0218(13) -0.0002(10) 0.0007(10) -0.0015(10) C5 0.0178(13) 0.0321(15) 0.0362(15) -0.0025(12) -0.0002(11) 0.0007(11) C6 0.0291(15) 0.0302(14) 0.0243(14) 0.0021(11) -0.0024(11) 0.0057(11) C7 0.0300(15) 0.0264(14) 0.0347(15) -0.0012(12) 0.0011(12) 0.0050(11) C8 0.0279(14) 0.0261(14) 0.0301(14) -0.0017(11) -0.0070(11) -0.0135(11) C9 0.051(2) 0.067(2) 0.0311(16) -0.0037(14) -0.0067(14) -0.0384(17) C10 0.0336(17) 0.0385(17) 0.075(2) -0.0101(15) -0.0283(16) -0.0056(13) C11 0.0370(16) 0.0392(16) 0.0452(17) -0.0001(13) -0.0061(14) -0.0226(13) C12 0.0214(13) 0.0219(13) 0.0171(12) -0.0032(10) 0.0006(10) -0.0102(11) C13 0.0128(12) 0.0235(13) 0.0293(14) -0.0047(11) 0.0016(10) 0.0012(10) C14 0.0299(16) 0.0384(16) 0.0448(18) 0.0064(13) 0.0142(13) 0.0003(13) C15 0.0241(15) 0.0499(19) 0.067(2) -0.0212(16) -0.0154(15) 0.0060(13) C16 0.0285(15) 0.0250(14) 0.0470(17) -0.0004(12) 0.0116(13) -0.0035(11) C17 0.0170(12) 0.0151(11) 0.0204(12) 0.0003(9) 0.0018(10) -0.0029(9) C18 0.0179(13) 0.0193(12) 0.0275(14) 0.0002(10) 0.0007(11) -0.0047(10) C19 0.0288(14) 0.0230(13) 0.0192(13) 0.0011(10) 0.0101(11) -0.0023(11) C20 0.0367(16) 0.0250(13) 0.0159(13) -0.0017(10) -0.0046(11) -0.0043(11) C21 0.0227(13) 0.0222(13) 0.0266(14) -0.0013(10) -0.0052(11) -0.0091(10) C22 0.0201(13) 0.0249(13) 0.0167(12) 0.0004(10) 0.0024(10) -0.0092(10) C23 0.0161(12) 0.0205(12) 0.0172(12) 0.0001(9) -0.0027(10) -0.0036(10) C24 0.0201(13) 0.0274(13) 0.0174(12) -0.0027(10) -0.0011(10) -0.0072(10) C25 0.0233(13) 0.0238(13) 0.0254(14) 0.0038(11) -0.0047(11) -0.0103(11) C26 0.0167(13) 0.0406(16) 0.0180(13) 0.0089(11) 0.0002(10) -0.0110(11) C27 0.0165(13) 0.0378(15) 0.0171(13) -0.0018(11) 0.0018(10) -0.0015(11) C28 0.0198(13) 0.0223(13) 0.0185(13) -0.0013(10) -0.0026(10) -0.0030(10) C30 0.043(4) 0.048(5) 0.053(5) 0.020(3) -0.030(4) -0.026(3) C31 0.030(4) 0.040(5) 0.051(5) -0.018(4) 0.000(4) -0.011(3) C32 0.030(3) 0.030(3) 0.057(5) -0.006(3) 0.004(3) -0.006(3) C33 0.030(4) 0.045(5) 0.038(5) 0.005(4) 0.000(3) -0.015(3) C34 0.050(4) 0.041(4) 0.043(4) -0.006(3) -0.013(3) -0.009(3) C35 0.059(5) 0.034(4) 0.058(5) 0.001(4) -0.027(5) -0.007(4) C36 0.065(6) 0.108(9) 0.052(6) 0.032(6) -0.017(5) -0.058(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 B N1 1.534(3) . ? B C17 1.637(3) . ? B C23 1.641(3) . ? B C12 1.641(3) . ? N1 C1 1.382(3) . ? N1 N2 1.386(2) . ? N2 C3 1.326(3) . ? N3 C12 1.141(3) . ? N3 C13 1.468(3) . ? F1 C18 1.351(2) . ? F2 C19 1.347(3) . ? F3 C20 1.341(2) . ? F4 C21 1.349(2) . ? F5 C22 1.357(2) . ? F6 C24 1.358(2) . ? F7 C25 1.346(2) . ? F8 C26 1.345(2) . ? F9 C27 1.352(3) . ? F10 C28 1.342(2) . ? C1 C2 1.373(3) . ? C1 C4 1.521(3) . ? C2 C3 1.398(3) . ? C3 C8 1.517(3) . ? C4 C7 1.536(3) . ? C4 C5 1.540(3) . ? C4 C6 1.541(3) . ? C8 C11 1.525(3) . ? C8 C10 1.530(3) . ? C8 C9 1.532(3) . ? C13 C15 1.511(3) . ? C13 C16 1.521(3) . ? C13 C14 1.522(3) . ? C17 C18 1.390(3) . ? C17 C22 1.393(3) . ? C18 C19 1.378(3) . ? C19 C20 1.374(3) . ? C20 C21 1.368(3) . ? C21 C22 1.371(3) . ? C23 C24 1.390(3) . ? C23 C28 1.390(3) . ? C24 C25 1.375(3) . ? C25 C26 1.369(3) . ? C26 C27 1.371(3) . ? C27 C28 1.387(3) . ? C30 C31 1.3900 . ? C30 C35 1.3900 . ? C30 C36 1.514(9) . ? C31 C32 1.3900 . ? C32 C33 1.3900 . ? C33 C34 1.3900 . ? C34 C35 1.3900 . ? 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 N1 B C17 115.92(18) . . ? N1 B C23 114.89(19) . . ? C17 B C23 114.71(18) . . ? N1 B C12 102.41(18) . . ? C17 B C12 103.48(18) . . ? C23 B C12 102.77(17) . . ? C1 N1 N2 109.48(17) . . ? C1 N1 B 138.86(18) . . ? N2 N1 B 110.30(16) . . ? C3 N2 N1 106.66(17) . . ? C12 N3 C13 177.5(2) . . ? C2 C1 N1 106.61(19) . . ? C2 C1 C4 126.6(2) . . ? N1 C1 C4 126.8(2) . . ? C1 C2 C3 106.9(2) . . ? N2 C3 C2 110.3(2) . . ? N2 C3 C8 121.0(2) . . ? C2 C3 C8 128.7(2) . . ? C1 C4 C7 108.36(19) . . ? C1 C4 C5 111.97(18) . . ? C7 C4 C5 107.42(19) . . ? C1 C4 C6 111.08(19) . . ? C7 C4 C6 107.30(18) . . ? C5 C4 C6 110.5(2) . . ? C3 C8 C11 109.64(19) . . ? C3 C8 C10 110.55(19) . . ? C11 C8 C10 109.3(2) . . ? C3 C8 C9 108.1(2) . . ? C11 C8 C9 109.4(2) . . ? C10 C8 C9 109.9(2) . . ? N3 C12 B 173.1(2) . . ? N3 C13 C15 107.40(18) . . ? N3 C13 C16 106.64(18) . . ? C15 C13 C16 112.0(2) . . ? N3 C13 C14 106.28(18) . . ? C15 C13 C14 112.2(2) . . ? C16 C13 C14 111.9(2) . . ? C18 C17 C22 113.5(2) . . ? C18 C17 B 119.91(19) . . ? C22 C17 B 126.6(2) . . ? F1 C18 C19 116.8(2) . . ? F1 C18 C17 119.00(19) . . ? C19 C18 C17 124.2(2) . . ? F2 C19 C20 120.2(2) . . ? F2 C19 C18 120.5(2) . . ? C20 C19 C18 119.3(2) . . ? F3 C20 C21 120.5(2) . . ? F3 C20 C19 120.5(2) . . ? C21 C20 C19 119.0(2) . . ? F4 C21 C20 119.0(2) . . ? F4 C21 C22 120.8(2) . . ? C20 C21 C22 120.2(2) . . ? F5 C22 C21 115.63(19) . . ? F5 C22 C17 120.60(19) . . ? C21 C22 C17 123.8(2) . . ? C24 C23 C28 114.1(2) . . ? C24 C23 B 120.1(2) . . ? C28 C23 B 125.8(2) . . ? F6 C24 C25 116.5(2) . . ? F6 C24 C23 118.8(2) . . ? C25 C24 C23 124.7(2) . . ? F7 C25 C26 120.6(2) . . ? F7 C25 C24 120.5(2) . . ? C26 C25 C24 118.9(2) . . ? F8 C26 C25 120.5(2) . . ? F8 C26 C27 120.2(2) . . ? C25 C26 C27 119.3(2) . . ? F9 C27 C26 119.6(2) . . ? F9 C27 C28 120.0(2) . . ? C26 C27 C28 120.4(2) . . ? F10 C28 C27 115.8(2) . . ? F10 C28 C23 121.6(2) . . ? C27 C28 C23 122.5(2) . . ? C31 C30 C35 120.0 . . ? C31 C30 C36 118.8(5) . . ? C35 C30 C36 121.2(5) . . ? C32 C31 C30 120.0 . . ? C31 C32 C33 120.0 . . ? C34 C33 C32 120.0 . . ? C33 C34 C35 120.0 . . ? C34 C35 C30 120.0 . . ? 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 B N1 C1 -53.7(4) . . . . ? C23 B N1 C1 83.8(3) . . . . ? C12 B N1 C1 -165.6(2) . . . . ? C17 B N1 N2 141.73(18) . . . . ? C23 B N1 N2 -80.7(2) . . . . ? C12 B N1 N2 29.9(2) . . . . ? C1 N1 N2 C3 0.4(2) . . . . ? B N1 N2 C3 169.71(18) . . . . ? N2 N1 C1 C2 -0.7(2) . . . . ? B N1 C1 C2 -165.3(2) . . . . ? N2 N1 C1 C4 -179.3(2) . . . . ? B N1 C1 C4 16.1(4) . . . . ? N1 C1 C2 C3 0.7(3) . . . . ? C4 C1 C2 C3 179.3(2) . . . . ? N1 N2 C3 C2 0.0(2) . . . . ? N1 N2 C3 C8 -177.61(19) . . . . ? C1 C2 C3 N2 -0.5(3) . . . . ? C1 C2 C3 C8 177.0(2) . . . . ? C2 C1 C4 C7 9.0(3) . . . . ? N1 C1 C4 C7 -172.7(2) . . . . ? C2 C1 C4 C5 127.3(2) . . . . ? N1 C1 C4 C5 -54.4(3) . . . . ? C2 C1 C4 C6 -108.6(3) . . . . ? N1 C1 C4 C6 69.7(3) . . . . ? N2 C3 C8 C11 -144.0(2) . . . . ? C2 C3 C8 C11 38.8(3) . . . . ? N2 C3 C8 C10 -23.5(3) . . . . ? C2 C3 C8 C10 159.3(2) . . . . ? N2 C3 C8 C9 96.8(3) . . . . ? C2 C3 C8 C9 -80.4(3) . . . . ? C13 N3 C12 B -127(5) . . . . ? N1 B C12 N3 168.9(19) . . . . ? C17 B C12 N3 48(2) . . . . ? C23 B C12 N3 -72(2) . . . . ? C12 N3 C13 C15 -82(5) . . . . ? C12 N3 C13 C16 157(5) . . . . ? C12 N3 C13 C14 38(5) . . . . ? N1 B C17 C18 -61.5(3) . . . . ? C23 B C17 C18 160.91(19) . . . . ? C12 B C17 C18 49.8(2) . . . . ? N1 B C17 C22 120.5(2) . . . . ? C23 B C17 C22 -17.1(3) . . . . ? C12 B C17 C22 -128.2(2) . . . . ? C22 C17 C18 F1 178.93(18) . . . . ? B C17 C18 F1 0.7(3) . . . . ? C22 C17 C18 C19 -1.7(3) . . . . ? B C17 C18 C19 -179.9(2) . . . . ? F1 C18 C19 F2 -1.1(3) . . . . ? C17 C18 C19 F2 179.5(2) . . . . ? F1 C18 C19 C20 179.76(19) . . . . ? C17 C18 C19 C20 0.4(3) . . . . ? F2 C19 C20 F3 0.6(3) . . . . ? C18 C19 C20 F3 179.81(19) . . . . ? F2 C19 C20 C21 -177.9(2) . . . . ? C18 C19 C20 C21 1.2(3) . . . . ? F3 C20 C21 F4 -1.0(3) . . . . ? C19 C20 C21 F4 177.6(2) . . . . ? F3 C20 C21 C22 -180.0(2) . . . . ? C19 C20 C21 C22 -1.4(3) . . . . ? F4 C21 C22 F5 1.7(3) . . . . ? C20 C21 C22 F5 -179.3(2) . . . . ? F4 C21 C22 C17 -179.0(2) . . . . ? C20 C21 C22 C17 -0.1(4) . . . . ? C18 C17 C22 F5 -179.24(19) . . . . ? B C17 C22 F5 -1.1(3) . . . . ? C18 C17 C22 C21 1.6(3) . . . . ? B C17 C22 C21 179.7(2) . . . . ? N1 B C23 C24 166.44(19) . . . . ? C17 B C23 C24 -55.5(3) . . . . ? C12 B C23 C24 56.1(2) . . . . ? N1 B C23 C28 -11.3(3) . . . . ? C17 B C23 C28 126.8(2) . . . . ? C12 B C23 C28 -121.6(2) . . . . ? C28 C23 C24 F6 178.89(18) . . . . ? B C23 C24 F6 0.9(3) . . . . ? C28 C23 C24 C25 -0.9(3) . . . . ? B C23 C24 C25 -178.9(2) . . . . ? F6 C24 C25 F7 -0.9(3) . . . . ? C23 C24 C25 F7 178.9(2) . . . . ? F6 C24 C25 C26 179.2(2) . . . . ? C23 C24 C25 C26 -1.0(3) . . . . ? F7 C25 C26 F8 1.2(3) . . . . ? C24 C25 C26 F8 -178.92(19) . . . . ? F7 C25 C26 C27 -177.80(19) . . . . ? C24 C25 C26 C27 2.1(3) . . . . ? F8 C26 C27 F9 -1.4(3) . . . . ? C25 C26 C27 F9 177.6(2) . . . . ? F8 C26 C27 C28 179.68(19) . . . . ? C25 C26 C27 C28 -1.3(3) . . . . ? F9 C27 C28 F10 -0.1(3) . . . . ? C26 C27 C28 F10 178.79(19) . . . . ? F9 C27 C28 C23 -179.55(19) . . . . ? C26 C27 C28 C23 -0.7(3) . . . . ? C24 C23 C28 F10 -177.73(18) . . . . ? B C23 C28 F10 0.1(3) . . . . ? C24 C23 C28 C27 1.7(3) . . . . ? B C23 C28 C27 179.5(2) . . . . ? C35 C30 C31 C32 0.0 . . . . ? C36 C30 C31 C32 179.8(8) . . . . ? C30 C31 C32 C33 0.0 . . . . ? C31 C32 C33 C34 0.0 . . . . ? C32 C33 C34 C35 0.0 . . . . ? C33 C34 C35 C30 0.0 . . . . ? C31 C30 C35 C34 0.0 . . . . ? C36 C30 C35 C34 -179.7(8) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.251 _refine_diff_density_min -0.241 _refine_diff_density_rms 0.056 # # end of cif data for "eileen28" # Attachment '- eileen32.cif' data_eileen32 _database_code_depnum_ccdc_archive 'CCDC 869101' #TrackingRef '- eileen32.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C27.50 H25 B F10 N2 O' _chemical_formula_weight 600.30 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.2377(6) _cell_length_b 11.5573(10) _cell_length_c 13.2013(12) _cell_angle_alpha 73.287(8) _cell_angle_beta 86.450(6) _cell_angle_gamma 83.350(6) _cell_volume 1340.18(19) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9908 _cell_measurement_theta_min 3.4943 _cell_measurement_theta_max 75.6859 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.488 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 614 _exptl_absorpt_coefficient_mu 1.218 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.51207 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_source 'Nova (Cu) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'Oxford Diffraction Xcalibur, Atlas, Nova' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 10.3543 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14213 _diffrn_reflns_av_R_equivalents 0.0181 _diffrn_reflns_av_sigmaI/netI 0.0179 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.50 _diffrn_reflns_theta_max 74.49 _reflns_number_total 5492 _reflns_number_gt 5037 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'BRUKER XP' _computing_publication_material SHELXL-97 _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. One half disordered molecule of toluene, which could not be refined satisfactorily, was removed using the program SQUEEZE (A.L. Spek, University of Utrecht, Netherlands). The quoted formula and derived parameters are based on a half molecule of toluene per asymmetric unit. ; loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons 1 0.000 0.500 0.500 186.8 49.9 _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^)+(0.0509P)^2^+0.2666P] 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 5492 _refine_ls_number_parameters 349 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0354 _refine_ls_R_factor_gt 0.0332 _refine_ls_wR_factor_ref 0.0929 _refine_ls_wR_factor_gt 0.0909 _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_restrained_S_all 1.051 _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 0.65992(13) 0.35478(11) 0.34777(10) 0.0256(2) Uani 1 1 d . . . N1 N 0.74933(10) 0.47162(8) 0.30467(8) 0.0263(2) Uani 1 1 d . . . N2 N 0.65377(10) 0.56933(8) 0.30859(8) 0.02490(19) Uani 1 1 d . . . O O 0.53910(8) 0.40867(7) 0.40374(6) 0.02670(17) Uani 1 1 d . . . F1 F 0.70495(8) 0.45503(6) 0.10341(6) 0.03549(17) Uani 1 1 d . . . F2 F 0.57097(9) 0.38682(7) -0.03783(6) 0.04079(18) Uani 1 1 d . . . F3 F 0.37560(9) 0.21754(8) 0.02479(6) 0.04382(19) Uani 1 1 d . . . F4 F 0.32324(8) 0.11415(6) 0.23483(6) 0.03515(17) Uani 1 1 d . . . F5 F 0.45734(7) 0.18004(6) 0.37936(5) 0.02985(15) Uani 1 1 d . . . F6 F 0.77917(7) 0.38679(6) 0.53192(6) 0.03387(16) Uani 1 1 d . . . F7 F 0.89645(8) 0.21636(8) 0.69497(6) 0.04128(18) Uani 1 1 d . . . F8 F 0.93726(8) -0.02061(7) 0.69260(6) 0.03833(18) Uani 1 1 d . . . F9 F 0.84643(8) -0.08349(6) 0.52555(6) 0.03362(16) Uani 1 1 d . . . F10 F 0.73889(7) 0.08568(6) 0.35767(6) 0.03049(15) Uani 1 1 d . . . C1 C 0.87645(12) 0.51417(10) 0.26325(10) 0.0284(2) Uani 1 1 d . . . C2 C 0.85727(12) 0.64081(10) 0.24027(10) 0.0285(2) Uani 1 1 d . . . H2 H 0.9287 0.6946 0.2097 0.034 Uiso 1 1 calc R . . C3 C 0.71524(12) 0.67391(10) 0.27008(9) 0.0258(2) Uani 1 1 d . . . C4 C 1.01704(13) 0.43568(11) 0.25277(11) 0.0339(3) Uani 1 1 d . . . C5 C 1.12002(16) 0.51275(13) 0.17251(15) 0.0504(4) Uani 1 1 d . . . H5A H 1.0717 0.5471 0.1048 0.076 Uiso 1 1 calc R . . H5B H 1.2090 0.4617 0.1625 0.076 Uiso 1 1 calc R . . H5C H 1.1451 0.5787 0.1989 0.076 Uiso 1 1 calc R . . C6 C 1.09035(14) 0.39172(13) 0.36105(13) 0.0438(3) Uani 1 1 d . . . H6A H 1.0996 0.4616 0.3873 0.066 Uiso 1 1 calc R . . H6B H 1.1874 0.3504 0.3531 0.066 Uiso 1 1 calc R . . H6C H 1.0307 0.3353 0.4115 0.066 Uiso 1 1 calc R . . C7 C 0.99154(14) 0.32591(12) 0.21580(12) 0.0399(3) Uani 1 1 d . . . H7A H 0.9210 0.2787 0.2641 0.060 Uiso 1 1 calc R . . H7B H 1.0839 0.2749 0.2154 0.060 Uiso 1 1 calc R . . H7C H 0.9534 0.3539 0.1442 0.060 Uiso 1 1 calc R . . C8 C 0.63775(13) 0.79716(10) 0.26931(9) 0.0274(2) Uani 1 1 d . . . C9 C 0.73028(15) 0.89605(10) 0.20336(11) 0.0361(3) Uani 1 1 d . . . H9A H 0.8245 0.8875 0.2364 0.054 Uiso 1 1 calc R . . H9B H 0.6793 0.9762 0.1999 0.054 Uiso 1 1 calc R . . H9C H 0.7461 0.8875 0.1316 0.054 Uiso 1 1 calc R . . C10 C 0.62097(15) 0.80575(11) 0.38358(10) 0.0353(3) Uani 1 1 d . . . H10A H 0.5628 0.7421 0.4259 0.053 Uiso 1 1 calc R . . H10B H 0.5719 0.8855 0.3838 0.053 Uiso 1 1 calc R . . H10C H 0.7175 0.7951 0.4139 0.053 Uiso 1 1 calc R . . C11 C 0.48797(14) 0.81605(11) 0.21981(11) 0.0354(3) Uani 1 1 d . . . H11A H 0.4995 0.8046 0.1489 0.053 Uiso 1 1 calc R . . H11B H 0.4432 0.8986 0.2147 0.053 Uiso 1 1 calc R . . H11C H 0.4254 0.7571 0.2641 0.053 Uiso 1 1 calc R . . C12 C 0.50973(12) 0.53113(10) 0.35186(9) 0.0267(2) Uani 1 1 d . . . H12A H 0.4684 0.5769 0.4017 0.032 Uiso 1 1 calc R . . H12B H 0.4405 0.5437 0.2944 0.032 Uiso 1 1 calc R . . C13 C 0.59243(12) 0.31831(9) 0.25016(9) 0.0259(2) Uani 1 1 d . . . C14 C 0.61348(12) 0.36808(10) 0.14217(10) 0.0289(2) Uani 1 1 d . . . C15 C 0.54369(13) 0.33549(11) 0.06581(10) 0.0318(2) Uani 1 1 d . . . C16 C 0.44507(13) 0.25007(11) 0.09676(10) 0.0320(2) Uani 1 1 d . . . C17 C 0.41843(12) 0.19841(10) 0.20345(10) 0.0289(2) Uani 1 1 d . . . C18 C 0.48971(12) 0.23335(10) 0.27689(9) 0.0264(2) Uani 1 1 d . . . C19 C 0.74673(11) 0.24554(10) 0.43713(9) 0.0256(2) Uani 1 1 d . . . C20 C 0.79204(12) 0.27082(10) 0.52650(10) 0.0281(2) Uani 1 1 d . . . C21 C 0.85402(12) 0.18451(11) 0.61205(10) 0.0307(2) Uani 1 1 d . . . C22 C 0.87259(12) 0.06413(11) 0.61219(10) 0.0305(2) Uani 1 1 d . . . C23 C 0.82891(12) 0.03322(10) 0.52631(10) 0.0281(2) Uani 1 1 d . . . C24 C 0.77061(12) 0.12329(10) 0.44043(9) 0.0261(2) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 B 0.0251(5) 0.0201(5) 0.0324(6) -0.0082(5) 0.0037(5) -0.0058(4) N1 0.0249(4) 0.0188(4) 0.0352(5) -0.0081(4) 0.0030(4) -0.0032(3) N2 0.0243(4) 0.0183(4) 0.0319(5) -0.0074(4) 0.0026(4) -0.0025(3) O 0.0268(4) 0.0182(3) 0.0343(4) -0.0066(3) 0.0048(3) -0.0041(3) F1 0.0395(4) 0.0300(3) 0.0347(4) -0.0025(3) 0.0048(3) -0.0144(3) F2 0.0503(4) 0.0411(4) 0.0282(4) -0.0046(3) 0.0021(3) -0.0084(3) F3 0.0501(4) 0.0486(5) 0.0387(4) -0.0175(4) -0.0059(3) -0.0137(4) F4 0.0333(3) 0.0306(3) 0.0444(4) -0.0120(3) 0.0018(3) -0.0132(3) F5 0.0318(3) 0.0264(3) 0.0308(3) -0.0056(3) 0.0047(3) -0.0099(3) F6 0.0331(3) 0.0276(3) 0.0468(4) -0.0193(3) -0.0018(3) -0.0039(3) F7 0.0401(4) 0.0485(4) 0.0404(4) -0.0192(3) -0.0098(3) -0.0039(3) F8 0.0349(4) 0.0365(4) 0.0376(4) -0.0005(3) -0.0066(3) -0.0020(3) F9 0.0338(3) 0.0188(3) 0.0455(4) -0.0048(3) -0.0008(3) -0.0028(2) F10 0.0358(3) 0.0225(3) 0.0354(4) -0.0117(3) -0.0021(3) -0.0028(3) C1 0.0258(5) 0.0232(5) 0.0365(6) -0.0085(4) 0.0037(4) -0.0060(4) C2 0.0276(5) 0.0213(5) 0.0366(6) -0.0074(4) 0.0033(4) -0.0064(4) C3 0.0292(5) 0.0197(5) 0.0288(5) -0.0064(4) 0.0004(4) -0.0053(4) C4 0.0257(5) 0.0234(5) 0.0510(7) -0.0094(5) 0.0086(5) -0.0038(4) C5 0.0355(7) 0.0326(7) 0.0755(11) -0.0078(7) 0.0232(7) -0.0049(5) C6 0.0292(6) 0.0377(7) 0.0632(9) -0.0136(6) -0.0018(6) -0.0001(5) C7 0.0335(6) 0.0285(6) 0.0585(8) -0.0166(6) 0.0095(6) -0.0010(5) C8 0.0332(5) 0.0182(5) 0.0300(5) -0.0058(4) 0.0039(4) -0.0038(4) C9 0.0439(7) 0.0192(5) 0.0419(7) -0.0051(5) 0.0097(5) -0.0050(5) C10 0.0518(7) 0.0231(5) 0.0325(6) -0.0097(5) 0.0060(5) -0.0088(5) C11 0.0356(6) 0.0260(6) 0.0417(7) -0.0073(5) -0.0005(5) 0.0023(5) C12 0.0242(5) 0.0209(5) 0.0345(6) -0.0071(4) 0.0038(4) -0.0044(4) C13 0.0248(5) 0.0198(5) 0.0327(6) -0.0076(4) 0.0026(4) -0.0021(4) C14 0.0285(5) 0.0219(5) 0.0349(6) -0.0058(4) 0.0036(4) -0.0049(4) C15 0.0360(6) 0.0282(5) 0.0285(6) -0.0052(5) 0.0023(5) -0.0020(5) C16 0.0337(6) 0.0298(6) 0.0351(6) -0.0132(5) -0.0030(5) -0.0029(5) C17 0.0264(5) 0.0222(5) 0.0389(6) -0.0097(5) 0.0017(4) -0.0047(4) C18 0.0266(5) 0.0210(5) 0.0303(6) -0.0060(4) 0.0033(4) -0.0024(4) C19 0.0239(5) 0.0220(5) 0.0313(6) -0.0080(4) 0.0037(4) -0.0053(4) C20 0.0248(5) 0.0246(5) 0.0373(6) -0.0125(5) 0.0029(4) -0.0049(4) C21 0.0256(5) 0.0366(6) 0.0328(6) -0.0135(5) 0.0002(4) -0.0061(4) C22 0.0240(5) 0.0310(6) 0.0327(6) -0.0027(5) 0.0001(4) -0.0040(4) C23 0.0248(5) 0.0212(5) 0.0364(6) -0.0054(4) 0.0038(4) -0.0046(4) C24 0.0250(5) 0.0225(5) 0.0315(6) -0.0082(4) 0.0022(4) -0.0056(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag B O 1.4769(14) . ? B N1 1.6087(14) . ? B C19 1.6293(17) . ? B C13 1.6429(17) . ? N1 C1 1.3488(14) . ? N1 N2 1.3617(13) . ? N2 C3 1.3461(14) . ? N2 C12 1.4793(13) . ? O C12 1.3865(13) . ? F1 C14 1.3539(13) . ? F2 C15 1.3463(14) . ? F3 C16 1.3388(14) . ? F4 C17 1.3470(13) . ? F5 C18 1.3462(13) . ? F6 C20 1.3539(13) . ? F7 C21 1.3437(14) . ? F8 C22 1.3372(14) . ? F9 C23 1.3427(13) . ? F10 C24 1.3456(13) . ? C1 C2 1.3989(15) . ? C1 C4 1.5184(15) . ? C2 C3 1.3890(16) . ? C3 C8 1.5158(15) . ? C4 C7 1.5305(17) . ? C4 C5 1.5328(17) . ? C4 C6 1.544(2) . ? C8 C11 1.5326(17) . ? C8 C9 1.5352(15) . ? C8 C10 1.5373(16) . ? C13 C14 1.3860(17) . ? C13 C18 1.4015(15) . ? C14 C15 1.3889(17) . ? C15 C16 1.3790(17) . ? C16 C17 1.3814(18) . ? C17 C18 1.3793(17) . ? C19 C24 1.3929(15) . ? C19 C20 1.3929(16) . ? C20 C21 1.3777(18) . ? C21 C22 1.3815(17) . ? C22 C23 1.3779(17) . ? C23 C24 1.3878(16) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O B N1 98.57(8) . . ? O B C19 106.67(9) . . ? N1 B C19 112.72(9) . . ? O B C13 108.48(9) . . ? N1 B C13 111.40(9) . . ? C19 B C13 117.13(9) . . ? C1 N1 N2 107.20(9) . . ? C1 N1 B 146.70(9) . . ? N2 N1 B 106.04(8) . . ? C3 N2 N1 111.46(9) . . ? C3 N2 C12 137.57(9) . . ? N1 N2 C12 110.95(8) . . ? C12 O B 109.65(8) . . ? N1 C1 C2 107.82(10) . . ? N1 C1 C4 124.98(10) . . ? C2 C1 C4 127.02(10) . . ? C3 C2 C1 107.84(10) . . ? N2 C3 C2 105.68(9) . . ? N2 C3 C8 123.44(10) . . ? C2 C3 C8 130.79(10) . . ? C1 C4 C7 112.43(10) . . ? C1 C4 C5 108.95(10) . . ? C7 C4 C5 108.71(12) . . ? C1 C4 C6 108.70(11) . . ? C7 C4 C6 109.53(11) . . ? C5 C4 C6 108.43(12) . . ? C3 C8 C11 110.76(9) . . ? C3 C8 C9 108.79(9) . . ? C11 C8 C9 108.72(10) . . ? C3 C8 C10 108.88(9) . . ? C11 C8 C10 110.27(10) . . ? C9 C8 C10 109.40(10) . . ? O C12 N2 103.91(8) . . ? C14 C13 C18 113.96(10) . . ? C14 C13 B 128.62(10) . . ? C18 C13 B 117.16(10) . . ? F1 C14 C13 121.25(10) . . ? F1 C14 C15 114.76(10) . . ? C13 C14 C15 123.99(10) . . ? F2 C15 C16 119.85(11) . . ? F2 C15 C14 120.65(11) . . ? C16 C15 C14 119.50(11) . . ? F3 C16 C15 120.73(11) . . ? F3 C16 C17 120.24(11) . . ? C15 C16 C17 119.03(11) . . ? F4 C17 C18 120.58(11) . . ? F4 C17 C16 119.67(10) . . ? C18 C17 C16 119.74(10) . . ? F5 C18 C17 116.47(10) . . ? F5 C18 C13 119.78(10) . . ? C17 C18 C13 123.74(11) . . ? C24 C19 C20 113.98(10) . . ? C24 C19 B 127.19(10) . . ? C20 C19 B 118.55(9) . . ? F6 C20 C21 115.83(10) . . ? F6 C20 C19 119.94(10) . . ? C21 C20 C19 124.22(10) . . ? F7 C21 C20 120.68(11) . . ? F7 C21 C22 119.88(11) . . ? C20 C21 C22 119.44(11) . . ? F8 C22 C23 120.38(11) . . ? F8 C22 C21 120.50(11) . . ? C23 C22 C21 119.07(11) . . ? F9 C23 C22 119.60(10) . . ? F9 C23 C24 120.67(10) . . ? C22 C23 C24 119.71(10) . . ? F10 C24 C23 115.62(9) . . ? F10 C24 C19 120.86(10) . . ? C23 C24 C19 123.52(11) . . ? 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 O B N1 C1 164.31(16) . . . . ? C19 B N1 C1 52.1(2) . . . . ? C13 B N1 C1 -81.9(2) . . . . ? O B N1 N2 -19.16(11) . . . . ? C19 B N1 N2 -131.35(9) . . . . ? C13 B N1 N2 94.63(10) . . . . ? C1 N1 N2 C3 0.49(13) . . . . ? B N1 N2 C3 -177.52(9) . . . . ? C1 N1 N2 C12 179.19(9) . . . . ? B N1 N2 C12 1.18(12) . . . . ? N1 B O C12 32.14(11) . . . . ? C19 B O C12 149.07(8) . . . . ? C13 B O C12 -83.92(10) . . . . ? N2 N1 C1 C2 -0.71(13) . . . . ? B N1 C1 C2 175.80(15) . . . . ? N2 N1 C1 C4 174.78(11) . . . . ? B N1 C1 C4 -8.7(3) . . . . ? N1 C1 C2 C3 0.68(14) . . . . ? C4 C1 C2 C3 -174.69(12) . . . . ? N1 N2 C3 C2 -0.06(13) . . . . ? C12 N2 C3 C2 -178.26(12) . . . . ? N1 N2 C3 C8 -176.86(10) . . . . ? C12 N2 C3 C8 4.9(2) . . . . ? C1 C2 C3 N2 -0.38(13) . . . . ? C1 C2 C3 C8 176.10(12) . . . . ? N1 C1 C4 C7 41.65(17) . . . . ? C2 C1 C4 C7 -143.73(13) . . . . ? N1 C1 C4 C5 162.23(13) . . . . ? C2 C1 C4 C5 -23.15(19) . . . . ? N1 C1 C4 C6 -79.79(15) . . . . ? C2 C1 C4 C6 94.83(15) . . . . ? N2 C3 C8 C11 -51.13(15) . . . . ? C2 C3 C8 C11 132.94(13) . . . . ? N2 C3 C8 C9 -170.56(11) . . . . ? C2 C3 C8 C9 13.50(17) . . . . ? N2 C3 C8 C10 70.28(14) . . . . ? C2 C3 C8 C10 -105.65(14) . . . . ? B O C12 N2 -32.84(11) . . . . ? C3 N2 C12 O -162.93(12) . . . . ? N1 N2 C12 O 18.86(12) . . . . ? O B C13 C14 113.02(12) . . . . ? N1 B C13 C14 5.58(16) . . . . ? C19 B C13 C14 -126.24(12) . . . . ? O B C13 C18 -60.76(12) . . . . ? N1 B C13 C18 -168.20(9) . . . . ? C19 B C13 C18 59.98(13) . . . . ? C18 C13 C14 F1 177.41(10) . . . . ? B C13 C14 F1 3.47(18) . . . . ? C18 C13 C14 C15 -1.87(17) . . . . ? B C13 C14 C15 -175.82(11) . . . . ? F1 C14 C15 F2 1.47(16) . . . . ? C13 C14 C15 F2 -179.20(10) . . . . ? F1 C14 C15 C16 -178.23(10) . . . . ? C13 C14 C15 C16 1.10(19) . . . . ? F2 C15 C16 F3 -0.12(18) . . . . ? C14 C15 C16 F3 179.58(11) . . . . ? F2 C15 C16 C17 -179.97(10) . . . . ? C14 C15 C16 C17 -0.27(18) . . . . ? F3 C16 C17 F4 0.67(17) . . . . ? C15 C16 C17 F4 -179.47(10) . . . . ? F3 C16 C17 C18 -179.46(10) . . . . ? C15 C16 C17 C18 0.40(18) . . . . ? F4 C17 C18 F5 -0.73(15) . . . . ? C16 C17 C18 F5 179.39(10) . . . . ? F4 C17 C18 C13 178.52(10) . . . . ? C16 C17 C18 C13 -1.35(18) . . . . ? C14 C13 C18 F5 -178.77(9) . . . . ? B C13 C18 F5 -4.08(15) . . . . ? C14 C13 C18 C17 2.00(16) . . . . ? B C13 C18 C17 176.69(10) . . . . ? O B C19 C24 121.66(11) . . . . ? N1 B C19 C24 -131.24(11) . . . . ? C13 B C19 C24 -0.03(16) . . . . ? O B C19 C20 -51.74(12) . . . . ? N1 B C19 C20 55.36(13) . . . . ? C13 B C19 C20 -173.42(9) . . . . ? C24 C19 C20 F6 177.97(9) . . . . ? B C19 C20 F6 -7.79(15) . . . . ? C24 C19 C20 C21 -0.55(16) . . . . ? B C19 C20 C21 173.69(10) . . . . ? F6 C20 C21 F7 0.68(16) . . . . ? C19 C20 C21 F7 179.25(10) . . . . ? F6 C20 C21 C22 -179.28(10) . . . . ? C19 C20 C21 C22 -0.70(18) . . . . ? F7 C21 C22 F8 -2.38(17) . . . . ? C20 C21 C22 F8 177.57(10) . . . . ? F7 C21 C22 C23 -179.77(10) . . . . ? C20 C21 C22 C23 0.19(17) . . . . ? F8 C22 C23 F9 2.61(16) . . . . ? C21 C22 C23 F9 179.99(10) . . . . ? F8 C22 C23 C24 -175.82(10) . . . . ? C21 C22 C23 C24 1.57(17) . . . . ? F9 C23 C24 F10 -2.14(15) . . . . ? C22 C23 C24 F10 176.27(9) . . . . ? F9 C23 C24 C19 178.58(10) . . . . ? C22 C23 C24 C19 -3.01(17) . . . . ? C20 C19 C24 F10 -176.83(9) . . . . ? B C19 C24 F10 9.52(17) . . . . ? C20 C19 C24 C23 2.41(16) . . . . ? B C19 C24 C23 -171.24(10) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 74.49 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.241 _refine_diff_density_min -0.197 _refine_diff_density_rms 0.038 # # end of cif data for "eileen32" # Attachment '- eileen34.cif' data_eileen34 _database_code_depnum_ccdc_archive 'CCDC 869102' #TrackingRef '- eileen34.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H28 B F10 N3 S' _chemical_formula_weight 639.40 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 '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/n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 11.1232(2) _cell_length_b 13.5996(2) _cell_length_c 19.3628(2) _cell_angle_alpha 90.00 _cell_angle_beta 96.913(2) _cell_angle_gamma 90.00 _cell_volume 2907.74(7) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 45154 _cell_measurement_theta_min 3.2470 _cell_measurement_theta_max 75.6980 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.461 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1312 _exptl_absorpt_coefficient_mu 1.795 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.36801 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_source 'Nova (Cu) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'Oxford Diffraction Xcalibur, Atlas, Nova' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 10.3543 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 54092 _diffrn_reflns_av_R_equivalents 0.0272 _diffrn_reflns_av_sigmaI/netI 0.0099 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 3.98 _diffrn_reflns_theta_max 74.50 _reflns_number_total 5941 _reflns_number_gt 5857 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'BRUKER XP' _computing_publication_material SHELXL-97 _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^)+(0.0346P)^2^+1.2666P] 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 5941 _refine_ls_number_parameters 397 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0286 _refine_ls_R_factor_gt 0.0283 _refine_ls_wR_factor_ref 0.0735 _refine_ls_wR_factor_gt 0.0733 _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_restrained_S_all 1.048 _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 S S 0.11186(2) 0.17786(2) 0.197877(14) 0.02065(7) Uani 1 1 d . . . B B 0.10302(11) 0.05365(9) 0.24710(6) 0.0169(2) Uani 1 1 d . . . N1 N -0.01244(8) 0.00665(7) 0.20468(4) 0.01610(18) Uani 1 1 d . . . N2 N -0.05800(8) 0.05456(7) 0.14428(4) 0.01648(18) Uani 1 1 d . . . N3 N -0.03085(9) 0.18592(7) 0.07157(5) 0.0219(2) Uani 1 1 d . . . F1 F -0.10823(6) 0.15430(5) 0.27944(3) 0.02563(15) Uani 1 1 d . . . F2 F -0.16630(7) 0.20477(6) 0.40388(4) 0.03213(17) Uani 1 1 d . . . F3 F -0.02137(7) 0.15261(6) 0.52146(4) 0.03625(19) Uani 1 1 d . . . F4 F 0.18487(7) 0.04732(6) 0.51081(4) 0.03359(18) Uani 1 1 d . . . F5 F 0.24611(6) -0.00251(5) 0.38800(3) 0.02402(15) Uani 1 1 d . . . F6 F 0.34089(6) 0.11891(5) 0.30066(4) 0.02744(16) Uani 1 1 d . . . F7 F 0.55347(6) 0.03507(6) 0.28128(5) 0.0386(2) Uani 1 1 d . . . F8 F 0.55811(7) -0.12659(6) 0.19864(5) 0.0401(2) Uani 1 1 d . . . F9 F 0.34569(7) -0.20452(6) 0.13745(4) 0.03395(18) Uani 1 1 d . . . F10 F 0.13632(6) -0.13032(5) 0.16103(3) 0.02381(15) Uani 1 1 d . . . C1 C -0.15846(9) 0.00562(8) 0.11347(6) 0.0180(2) Uani 1 1 d . . . C2 C -0.17256(10) -0.07419(8) 0.15553(6) 0.0196(2) Uani 1 1 d . . . H2 H -0.2342 -0.1226 0.1474 0.024 Uiso 1 1 calc R . . C3 C -0.08193(10) -0.07268(8) 0.21197(5) 0.0175(2) Uani 1 1 d . . . C4 C -0.24106(10) 0.03077(9) 0.04722(6) 0.0212(2) Uani 1 1 d . . . C5 C -0.17183(11) 0.02503(9) -0.01681(6) 0.0244(2) Uani 1 1 d . . . H5A H -0.1125 0.0785 -0.0150 0.037 Uiso 1 1 calc R . . H5B H -0.2290 0.0312 -0.0592 0.037 Uiso 1 1 calc R . . H5C H -0.1299 -0.0383 -0.0170 0.037 Uiso 1 1 calc R . . C6 C -0.30256(12) 0.13130(10) 0.05302(7) 0.0297(3) Uani 1 1 d . . . H6A H -0.3504 0.1304 0.0924 0.044 Uiso 1 1 calc R . . H6B H -0.3559 0.1448 0.0100 0.044 Uiso 1 1 calc R . . H6C H -0.2406 0.1827 0.0604 0.044 Uiso 1 1 calc R . . C7 C -0.34215(11) -0.04721(10) 0.03724(6) 0.0277(3) Uani 1 1 d . . . H7A H -0.3061 -0.1125 0.0337 0.042 Uiso 1 1 calc R . . H7B H -0.3960 -0.0330 -0.0054 0.042 Uiso 1 1 calc R . . H7C H -0.3886 -0.0457 0.0771 0.042 Uiso 1 1 calc R . . C8 C -0.07327(10) -0.14726(8) 0.27148(6) 0.0200(2) Uani 1 1 d . . . C9 C 0.05526(10) -0.17286(9) 0.30430(6) 0.0222(2) Uani 1 1 d . . . H9A H 0.0982 -0.2070 0.2700 0.033 Uiso 1 1 calc R . . H9B H 0.0510 -0.2156 0.3447 0.033 Uiso 1 1 calc R . . H9C H 0.0987 -0.1123 0.3191 0.033 Uiso 1 1 calc R . . C10 C -0.14846(11) -0.10817(10) 0.32745(6) 0.0271(3) Uani 1 1 d . . . H10A H -0.1072 -0.0515 0.3509 0.041 Uiso 1 1 calc R . . H10B H -0.1573 -0.1600 0.3616 0.041 Uiso 1 1 calc R . . H10C H -0.2287 -0.0881 0.3055 0.041 Uiso 1 1 calc R . . C11 C -0.13161(13) -0.24332(10) 0.24226(7) 0.0319(3) Uani 1 1 d . . . H11A H -0.2179 -0.2323 0.2274 0.048 Uiso 1 1 calc R . . H11B H -0.1224 -0.2941 0.2784 0.048 Uiso 1 1 calc R . . H11C H -0.0918 -0.2649 0.2024 0.048 Uiso 1 1 calc R . . C12 C 0.00246(10) 0.14547(8) 0.12875(6) 0.0177(2) Uani 1 1 d . . . C13 C 0.01653(12) 0.28085(9) 0.04783(6) 0.0262(3) Uani 1 1 d . . . C14 C -0.01388(14) 0.36382(9) 0.09536(7) 0.0336(3) Uani 1 1 d . . . H14A H -0.1011 0.3636 0.0988 0.050 Uiso 1 1 calc R . . H14B H 0.0090 0.4269 0.0762 0.050 Uiso 1 1 calc R . . H14C H 0.0308 0.3545 0.1417 0.050 Uiso 1 1 calc R . . C15 C 0.15240(15) 0.27621(11) 0.04356(9) 0.0423(4) Uani 1 1 d . . . H15A H 0.1956 0.2677 0.0904 0.063 Uiso 1 1 calc R . . H15B H 0.1788 0.3374 0.0233 0.063 Uiso 1 1 calc R . . H15C H 0.1701 0.2206 0.0143 0.063 Uiso 1 1 calc R . . C16 C -0.0506(2) 0.29765(12) -0.02503(8) 0.0546(5) Uani 1 1 d . . . H16A H -0.0303 0.2449 -0.0561 0.082 Uiso 1 1 calc R . . H16B H -0.0263 0.3611 -0.0430 0.082 Uiso 1 1 calc R . . H16C H -0.1381 0.2977 -0.0226 0.082 Uiso 1 1 calc R . . C17 C 0.07477(10) 0.07682(8) 0.32608(6) 0.0179(2) Uani 1 1 d . . . C18 C -0.03037(10) 0.12866(8) 0.33536(6) 0.0204(2) Uani 1 1 d . . . C19 C -0.06348(11) 0.15492(9) 0.39923(6) 0.0235(2) Uani 1 1 d . . . C20 C 0.00990(12) 0.12847(9) 0.45885(6) 0.0258(2) Uani 1 1 d . . . C21 C 0.11406(11) 0.07609(9) 0.45322(6) 0.0241(2) Uani 1 1 d . . . C22 C 0.14442(10) 0.05146(8) 0.38800(6) 0.0201(2) Uani 1 1 d . . . C23 C 0.22738(10) -0.00386(8) 0.23549(5) 0.0186(2) Uani 1 1 d . . . C24 C 0.33872(10) 0.03601(9) 0.26232(6) 0.0226(2) Uani 1 1 d . . . C25 C 0.44921(10) -0.00390(10) 0.25137(7) 0.0275(3) Uani 1 1 d . . . C26 C 0.45201(11) -0.08600(10) 0.20971(7) 0.0285(3) Uani 1 1 d . . . C27 C 0.34498(11) -0.12645(9) 0.17983(6) 0.0250(2) Uani 1 1 d . . . C28 C 0.23598(10) -0.08556(9) 0.19336(6) 0.0204(2) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S 0.02179(14) 0.01840(13) 0.02068(13) 0.00258(10) -0.00180(10) -0.00276(10) B 0.0162(5) 0.0171(5) 0.0172(5) 0.0010(4) 0.0004(4) -0.0001(4) N1 0.0163(4) 0.0174(4) 0.0145(4) 0.0016(3) 0.0015(3) 0.0020(3) N2 0.0168(4) 0.0180(4) 0.0144(4) 0.0017(3) 0.0010(3) 0.0017(3) N3 0.0290(5) 0.0185(5) 0.0178(4) 0.0009(4) 0.0017(4) -0.0018(4) F1 0.0233(3) 0.0309(4) 0.0219(3) 0.0005(3) -0.0002(3) 0.0106(3) F2 0.0315(4) 0.0358(4) 0.0306(4) -0.0025(3) 0.0103(3) 0.0130(3) F3 0.0434(4) 0.0473(5) 0.0195(4) -0.0053(3) 0.0098(3) 0.0064(4) F4 0.0339(4) 0.0488(5) 0.0167(3) 0.0029(3) -0.0024(3) 0.0048(3) F5 0.0200(3) 0.0293(4) 0.0219(3) 0.0027(3) -0.0008(2) 0.0058(3) F6 0.0229(3) 0.0260(4) 0.0323(4) -0.0002(3) -0.0013(3) -0.0048(3) F7 0.0162(3) 0.0410(4) 0.0574(5) 0.0118(4) -0.0009(3) -0.0043(3) F8 0.0235(4) 0.0469(5) 0.0530(5) 0.0153(4) 0.0175(3) 0.0152(3) F9 0.0403(4) 0.0327(4) 0.0310(4) -0.0007(3) 0.0130(3) 0.0153(3) F10 0.0248(3) 0.0249(3) 0.0219(3) -0.0045(3) 0.0030(3) 0.0013(3) C1 0.0152(5) 0.0214(5) 0.0174(5) -0.0013(4) 0.0023(4) 0.0013(4) C2 0.0170(5) 0.0220(5) 0.0198(5) 0.0009(4) 0.0019(4) -0.0015(4) C3 0.0162(5) 0.0189(5) 0.0177(5) -0.0001(4) 0.0034(4) 0.0002(4) C4 0.0185(5) 0.0253(6) 0.0189(5) 0.0021(4) -0.0015(4) 0.0014(4) C5 0.0273(6) 0.0276(6) 0.0178(5) -0.0001(4) 0.0004(4) -0.0024(5) C6 0.0259(6) 0.0322(7) 0.0298(6) 0.0023(5) -0.0010(5) 0.0092(5) C7 0.0199(6) 0.0370(7) 0.0247(6) 0.0036(5) -0.0045(4) -0.0036(5) C8 0.0207(5) 0.0205(5) 0.0186(5) 0.0034(4) 0.0016(4) -0.0021(4) C9 0.0229(6) 0.0214(5) 0.0220(5) 0.0052(4) 0.0014(4) 0.0020(4) C10 0.0250(6) 0.0327(6) 0.0250(6) 0.0088(5) 0.0088(5) 0.0033(5) C11 0.0406(7) 0.0245(6) 0.0282(6) 0.0068(5) -0.0053(5) -0.0113(5) C12 0.0187(5) 0.0166(5) 0.0182(5) -0.0015(4) 0.0042(4) 0.0012(4) C13 0.0387(7) 0.0191(6) 0.0204(5) 0.0028(4) 0.0017(5) -0.0050(5) C14 0.0451(8) 0.0198(6) 0.0367(7) 0.0013(5) 0.0082(6) 0.0014(5) C15 0.0481(9) 0.0291(7) 0.0549(9) 0.0084(6) 0.0274(7) -0.0022(6) C16 0.0939(14) 0.0363(8) 0.0279(7) 0.0136(6) -0.0161(8) -0.0262(9) C17 0.0189(5) 0.0164(5) 0.0183(5) 0.0001(4) 0.0017(4) -0.0010(4) C18 0.0209(5) 0.0201(5) 0.0196(5) 0.0008(4) 0.0001(4) 0.0010(4) C19 0.0236(6) 0.0219(6) 0.0259(6) -0.0015(4) 0.0066(5) 0.0034(4) C20 0.0322(6) 0.0279(6) 0.0185(5) -0.0037(5) 0.0077(5) -0.0012(5) C21 0.0261(6) 0.0279(6) 0.0174(5) 0.0013(4) -0.0010(4) -0.0015(5) C22 0.0185(5) 0.0201(5) 0.0214(5) 0.0004(4) 0.0014(4) 0.0005(4) C23 0.0180(5) 0.0207(5) 0.0174(5) 0.0043(4) 0.0036(4) 0.0013(4) C24 0.0209(5) 0.0234(6) 0.0235(5) 0.0051(4) 0.0026(4) -0.0005(4) C25 0.0158(5) 0.0322(6) 0.0344(6) 0.0126(5) 0.0025(5) -0.0015(5) C26 0.0206(6) 0.0340(7) 0.0331(6) 0.0145(5) 0.0122(5) 0.0106(5) C27 0.0295(6) 0.0256(6) 0.0217(5) 0.0056(4) 0.0098(5) 0.0092(5) C28 0.0203(5) 0.0236(6) 0.0176(5) 0.0042(4) 0.0041(4) 0.0023(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S C12 1.7533(11) . ? S B 1.9479(12) . ? B N1 1.5744(14) . ? B C23 1.6280(16) . ? B C17 1.6287(16) . ? N1 C3 1.3445(14) . ? N1 N2 1.3807(12) . ? N2 C1 1.3737(14) . ? N2 C12 1.4560(14) . ? N3 C12 1.2518(15) . ? N3 C13 1.4879(15) . ? F1 C18 1.3485(13) . ? F2 C19 1.3419(14) . ? F3 C20 1.3417(13) . ? F4 C21 1.3437(13) . ? F5 C22 1.3484(13) . ? F6 C24 1.3485(14) . ? F7 C25 1.3415(14) . ? F8 C26 1.3433(13) . ? F9 C27 1.3424(15) . ? F10 C28 1.3507(13) . ? C1 C2 1.3772(16) . ? C1 C4 1.5241(14) . ? C2 C3 1.3948(15) . ? C3 C8 1.5294(15) . ? C4 C5 1.5382(16) . ? C4 C6 1.5389(17) . ? C4 C7 1.5407(16) . ? C8 C9 1.5331(15) . ? C8 C11 1.5360(16) . ? C8 C10 1.5411(16) . ? C13 C14 1.5197(18) . ? C13 C15 1.525(2) . ? C13 C16 1.5319(18) . ? C17 C22 1.3902(15) . ? C17 C18 1.3956(16) . ? C18 C19 1.3791(16) . ? C19 C20 1.3789(17) . ? C20 C21 1.3755(18) . ? C21 C22 1.3870(16) . ? C23 C28 1.3885(16) . ? C23 C24 1.3938(16) . ? C24 C25 1.3831(17) . ? C25 C26 1.380(2) . ? C26 C27 1.3744(19) . ? C27 C28 1.3871(16) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C12 S B 94.84(5) . . ? N1 B C23 112.72(9) . . ? N1 B C17 109.33(9) . . ? C23 B C17 119.06(9) . . ? N1 B S 100.54(7) . . ? C23 B S 104.79(7) . . ? C17 B S 108.57(7) . . ? C3 N1 N2 108.10(8) . . ? C3 N1 B 135.57(9) . . ? N2 N1 B 116.33(8) . . ? C1 N2 N1 109.61(9) . . ? C1 N2 C12 133.91(9) . . ? N1 N2 C12 116.36(8) . . ? C12 N3 C13 125.19(10) . . ? N2 C1 C2 105.63(9) . . ? N2 C1 C4 129.29(10) . . ? C2 C1 C4 125.07(10) . . ? C1 C2 C3 109.20(10) . . ? N1 C3 C2 107.45(9) . . ? N1 C3 C8 128.79(10) . . ? C2 C3 C8 123.68(10) . . ? C1 C4 C5 110.94(9) . . ? C1 C4 C6 111.48(10) . . ? C5 C4 C6 111.96(10) . . ? C1 C4 C7 107.93(9) . . ? C5 C4 C7 107.01(10) . . ? C6 C4 C7 107.25(10) . . ? C3 C8 C9 115.72(9) . . ? C3 C8 C11 107.52(9) . . ? C9 C8 C11 106.92(10) . . ? C3 C8 C10 108.10(9) . . ? C9 C8 C10 110.16(9) . . ? C11 C8 C10 108.15(10) . . ? N3 C12 N2 117.44(10) . . ? N3 C12 S 132.00(9) . . ? N2 C12 S 110.55(7) . . ? N3 C13 C14 110.14(10) . . ? N3 C13 C15 111.78(10) . . ? C14 C13 C15 110.97(11) . . ? N3 C13 C16 105.21(10) . . ? C14 C13 C16 109.12(12) . . ? C15 C13 C16 109.43(13) . . ? C22 C17 C18 113.76(10) . . ? C22 C17 B 127.68(10) . . ? C18 C17 B 118.56(9) . . ? F1 C18 C19 115.98(10) . . ? F1 C18 C17 119.63(10) . . ? C19 C18 C17 124.38(10) . . ? F2 C19 C20 119.94(10) . . ? F2 C19 C18 120.85(11) . . ? C20 C19 C18 119.21(11) . . ? F3 C20 C21 120.71(11) . . ? F3 C20 C19 120.06(11) . . ? C21 C20 C19 119.22(11) . . ? F4 C21 C20 120.02(11) . . ? F4 C21 C22 120.17(11) . . ? C20 C21 C22 119.80(11) . . ? F5 C22 C21 115.31(10) . . ? F5 C22 C17 121.03(10) . . ? C21 C22 C17 123.62(11) . . ? C28 C23 C24 114.16(10) . . ? C28 C23 B 125.83(10) . . ? C24 C23 B 119.55(10) . . ? F6 C24 C25 117.07(11) . . ? F6 C24 C23 119.12(10) . . ? C25 C24 C23 123.80(11) . . ? F7 C25 C26 119.53(11) . . ? F7 C25 C24 121.12(12) . . ? C26 C25 C24 119.35(11) . . ? F8 C26 C27 120.10(12) . . ? F8 C26 C25 120.52(12) . . ? C27 C26 C25 119.38(11) . . ? F9 C27 C26 120.35(11) . . ? F9 C27 C28 120.14(11) . . ? C26 C27 C28 119.51(11) . . ? F10 C28 C27 114.77(10) . . ? F10 C28 C23 121.48(10) . . ? C27 C28 C23 123.74(11) . . ? 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 C12 S B N1 -10.48(7) . . . . ? C12 S B C23 106.62(7) . . . . ? C12 S B C17 -125.16(8) . . . . ? C23 B N1 C3 77.65(14) . . . . ? C17 B N1 C3 -57.18(15) . . . . ? S B N1 C3 -171.28(10) . . . . ? C23 B N1 N2 -101.85(10) . . . . ? C17 B N1 N2 123.32(9) . . . . ? S B N1 N2 9.21(10) . . . . ? C3 N1 N2 C1 0.78(11) . . . . ? B N1 N2 C1 -179.59(9) . . . . ? C3 N1 N2 C12 177.44(9) . . . . ? B N1 N2 C12 -2.93(12) . . . . ? N1 N2 C1 C2 -0.95(11) . . . . ? C12 N2 C1 C2 -176.80(11) . . . . ? N1 N2 C1 C4 178.67(10) . . . . ? C12 N2 C1 C4 2.82(19) . . . . ? N2 C1 C2 C3 0.77(12) . . . . ? C4 C1 C2 C3 -178.87(10) . . . . ? N2 N1 C3 C2 -0.27(12) . . . . ? B N1 C3 C2 -179.80(11) . . . . ? N2 N1 C3 C8 -177.07(10) . . . . ? B N1 C3 C8 3.39(19) . . . . ? C1 C2 C3 N1 -0.32(13) . . . . ? C1 C2 C3 C8 176.69(10) . . . . ? N2 C1 C4 C5 64.46(15) . . . . ? C2 C1 C4 C5 -115.99(12) . . . . ? N2 C1 C4 C6 -61.06(15) . . . . ? C2 C1 C4 C6 118.49(12) . . . . ? N2 C1 C4 C7 -178.59(11) . . . . ? C2 C1 C4 C7 0.96(15) . . . . ? N1 C3 C8 C9 -36.39(16) . . . . ? C2 C3 C8 C9 147.28(11) . . . . ? N1 C3 C8 C11 -155.79(11) . . . . ? C2 C3 C8 C11 27.88(15) . . . . ? N1 C3 C8 C10 87.67(13) . . . . ? C2 C3 C8 C10 -88.66(13) . . . . ? C13 N3 C12 N2 177.39(10) . . . . ? C13 N3 C12 S -2.04(18) . . . . ? C1 N2 C12 N3 -10.03(17) . . . . ? N1 N2 C12 N3 174.33(9) . . . . ? C1 N2 C12 S 169.51(10) . . . . ? N1 N2 C12 S -6.12(11) . . . . ? B S C12 N3 -170.54(12) . . . . ? B S C12 N2 10.00(8) . . . . ? C12 N3 C13 C14 -63.37(16) . . . . ? C12 N3 C13 C15 60.49(16) . . . . ? C12 N3 C13 C16 179.17(13) . . . . ? N1 B C17 C22 130.17(11) . . . . ? C23 B C17 C22 -1.37(17) . . . . ? S B C17 C22 -121.03(11) . . . . ? N1 B C17 C18 -50.29(13) . . . . ? C23 B C17 C18 178.17(10) . . . . ? S B C17 C18 58.51(11) . . . . ? C22 C17 C18 F1 -177.44(10) . . . . ? B C17 C18 F1 2.96(15) . . . . ? C22 C17 C18 C19 1.11(17) . . . . ? B C17 C18 C19 -178.49(11) . . . . ? F1 C18 C19 F2 -1.33(17) . . . . ? C17 C18 C19 F2 -179.93(11) . . . . ? F1 C18 C19 C20 178.02(10) . . . . ? C17 C18 C19 C20 -0.58(19) . . . . ? F2 C19 C20 F3 -0.07(18) . . . . ? C18 C19 C20 F3 -179.42(11) . . . . ? F2 C19 C20 C21 179.03(11) . . . . ? C18 C19 C20 C21 -0.32(18) . . . . ? F3 C20 C21 F4 0.95(18) . . . . ? C19 C20 C21 F4 -178.14(11) . . . . ? F3 C20 C21 C22 179.68(11) . . . . ? C19 C20 C21 C22 0.59(18) . . . . ? F4 C21 C22 F5 0.72(16) . . . . ? C20 C21 C22 F5 -178.01(10) . . . . ? F4 C21 C22 C17 178.74(10) . . . . ? C20 C21 C22 C17 0.02(19) . . . . ? C18 C17 C22 F5 177.09(10) . . . . ? B C17 C22 F5 -3.35(17) . . . . ? C18 C17 C22 C21 -0.82(17) . . . . ? B C17 C22 C21 178.73(11) . . . . ? N1 B C23 C28 0.11(15) . . . . ? C17 B C23 C28 130.14(11) . . . . ? S B C23 C28 -108.28(11) . . . . ? N1 B C23 C24 171.86(9) . . . . ? C17 B C23 C24 -58.11(14) . . . . ? S B C23 C24 63.46(11) . . . . ? C28 C23 C24 F6 176.21(9) . . . . ? B C23 C24 F6 3.55(15) . . . . ? C28 C23 C24 C25 -2.99(16) . . . . ? B C23 C24 C25 -175.66(10) . . . . ? F6 C24 C25 F7 4.00(17) . . . . ? C23 C24 C25 F7 -176.79(10) . . . . ? F6 C24 C25 C26 -176.89(10) . . . . ? C23 C24 C25 C26 2.32(18) . . . . ? F7 C25 C26 F8 -0.40(17) . . . . ? C24 C25 C26 F8 -179.53(11) . . . . ? F7 C25 C26 C27 179.22(11) . . . . ? C24 C25 C26 C27 0.09(18) . . . . ? F8 C26 C27 F9 -2.39(17) . . . . ? C25 C26 C27 F9 177.99(10) . . . . ? F8 C26 C27 C28 178.08(10) . . . . ? C25 C26 C27 C28 -1.54(17) . . . . ? F9 C27 C28 F10 -0.05(15) . . . . ? C26 C27 C28 F10 179.49(10) . . . . ? F9 C27 C28 C23 -178.79(10) . . . . ? C26 C27 C28 C23 0.74(17) . . . . ? C24 C23 C28 F10 -177.22(9) . . . . ? B C23 C28 F10 -5.09(16) . . . . ? C24 C23 C28 C27 1.44(16) . . . . ? B C23 C28 C27 173.57(10) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 74.50 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.285 _refine_diff_density_min -0.222 _refine_diff_density_rms 0.038 # # end of cif data for "eileen34" # Attachment '- eileen36.cif' data_eileen36 _database_code_depnum_ccdc_archive 'CCDC 869103' #TrackingRef '- eileen36.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C38 H33 B F10 N2' _chemical_formula_weight 718.47 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0727 0.0534 '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 11.0480(6) _cell_length_b 13.2011(7) _cell_length_c 13.2014(7) _cell_angle_alpha 73.524(5) _cell_angle_beta 69.985(5) _cell_angle_gamma 78.473(5) _cell_volume 1723.48(16) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 43373 _cell_measurement_theta_min 3.5114 _cell_measurement_theta_max 75.7778 _exptl_crystal_description block _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 ? _exptl_crystal_density_diffrn 1.384 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 740 _exptl_absorpt_coefficient_mu 1.022 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.26342 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_source 'Oxford Diffraction Nova (Cu) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'Oxford Diffraction Xcalibur, Atlas, Nova' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 10.3543 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 63138 _diffrn_reflns_av_R_equivalents 0.0222 _diffrn_reflns_av_sigmaI/netI 0.0084 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.51 _diffrn_reflns_theta_max 75.97 _reflns_number_total 7144 _reflns_number_gt 6902 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker XP' _computing_publication_material SHELXL-97 _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. H1 (at nitrogen) was refined freely. The methyl groups were refined as idealized rigid groups allowed to rotate but not tip. Other hydrogens were included using a riding model starting from calculated positions. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0423P)^2^+0.7142P] 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 7144 _refine_ls_number_parameters 471 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0335 _refine_ls_R_factor_gt 0.0326 _refine_ls_wR_factor_ref 0.0849 _refine_ls_wR_factor_gt 0.0841 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.038 _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 B B 0.78408(11) 0.30341(9) 0.28091(10) 0.0161(2) Uani 1 1 d . . . N1 N 0.64390(8) 0.32451(7) 0.25976(7) 0.01567(17) Uani 1 1 d . . . N2 N 0.58687(8) 0.42642(7) 0.25693(7) 0.01621(17) Uani 1 1 d . . . H1 H 0.6251(15) 0.4675(12) 0.2747(13) 0.029(4) Uiso 1 1 d . . . F1 F 0.96748(6) 0.09682(5) 0.25227(5) 0.02113(14) Uani 1 1 d . . . F2 F 0.97539(6) -0.07597(5) 0.41209(6) 0.02443(15) Uani 1 1 d . . . F3 F 0.81846(7) -0.08180(5) 0.62386(6) 0.02711(15) Uani 1 1 d . . . F4 F 0.64384(7) 0.08954(6) 0.66887(5) 0.02782(15) Uani 1 1 d . . . F5 F 0.62404(6) 0.26070(5) 0.50785(5) 0.02322(14) Uani 1 1 d . . . F6 F 1.05190(6) 0.27938(5) 0.26781(5) 0.02225(14) Uani 1 1 d . . . F7 F 1.25431(6) 0.32678(6) 0.08838(6) 0.02627(15) Uani 1 1 d . . . F8 F 1.22283(6) 0.39871(5) -0.11623(5) 0.02472(15) Uani 1 1 d . . . F9 F 0.98031(6) 0.42102(5) -0.13747(5) 0.02384(14) Uani 1 1 d . . . F10 F 0.77673(6) 0.37762(5) 0.03878(5) 0.02160(14) Uani 1 1 d . . . C1 C 0.47773(10) 0.44486(8) 0.22932(8) 0.0165(2) Uani 1 1 d . . . C2 C 0.46234(10) 0.34999(8) 0.21231(9) 0.0178(2) Uani 1 1 d . . . H2 H 0.3933 0.3375 0.1915 0.021 Uiso 1 1 calc R . . C3 C 0.56647(10) 0.27597(8) 0.23119(8) 0.0163(2) Uani 1 1 d . . . C4 C 0.39832(10) 0.55270(8) 0.21906(9) 0.0186(2) Uani 1 1 d . . . C5 C 0.42504(12) 0.61789(9) 0.28695(11) 0.0268(2) Uani 1 1 d . . . H5A H 0.4037 0.5794 0.3650 0.040 Uiso 1 1 calc R . . H5B H 0.3716 0.6869 0.2802 0.040 Uiso 1 1 calc R . . H5C H 0.5169 0.6291 0.2590 0.040 Uiso 1 1 calc R . . C6 C 0.25417(11) 0.53707(9) 0.26116(10) 0.0251(2) Uani 1 1 d . . . H6A H 0.2371 0.4958 0.2174 0.038 Uiso 1 1 calc R . . H6B H 0.2020 0.6066 0.2536 0.038 Uiso 1 1 calc R . . H6C H 0.2313 0.4989 0.3393 0.038 Uiso 1 1 calc R . . C7 C 0.43492(12) 0.61130(10) 0.09635(10) 0.0283(3) Uani 1 1 d . . . H7A H 0.5271 0.6214 0.0697 0.042 Uiso 1 1 calc R . . H7B H 0.3827 0.6807 0.0879 0.042 Uiso 1 1 calc R . . H7C H 0.4184 0.5692 0.0531 0.042 Uiso 1 1 calc R . . C8 C 0.58767(10) 0.16094(8) 0.22144(9) 0.0181(2) Uani 1 1 d . . . C9 C 0.55997(11) 0.08337(9) 0.33647(9) 0.0219(2) Uani 1 1 d . . . H9A H 0.6211 0.0889 0.3732 0.033 Uiso 1 1 calc R . . H9B H 0.5701 0.0105 0.3279 0.033 Uiso 1 1 calc R . . H9C H 0.4711 0.1013 0.3815 0.033 Uiso 1 1 calc R . . C10 C 0.72535(11) 0.13364(9) 0.14779(9) 0.0215(2) Uani 1 1 d . . . H10A H 0.7374 0.1785 0.0727 0.032 Uiso 1 1 calc R . . H10B H 0.7378 0.0587 0.1452 0.032 Uiso 1 1 calc R . . H10C H 0.7887 0.1463 0.1785 0.032 Uiso 1 1 calc R . . C11 C 0.49186(11) 0.14639(9) 0.16647(9) 0.0223(2) Uani 1 1 d . . . H11A H 0.4029 0.1580 0.2146 0.033 Uiso 1 1 calc R . . H11B H 0.5088 0.0741 0.1550 0.033 Uiso 1 1 calc R . . H11C H 0.5029 0.1978 0.0948 0.033 Uiso 1 1 calc R . . C12 C 0.78576(10) 0.39623(8) 0.33531(8) 0.0173(2) Uani 1 1 d . . . C13 C 0.78712(10) 0.47060(8) 0.37081(9) 0.0181(2) Uani 1 1 d . . . C14 C 0.78764(10) 0.55788(8) 0.41552(8) 0.0181(2) Uani 1 1 d . . . C15 C 0.67101(11) 0.61848(9) 0.45867(9) 0.0212(2) Uani 1 1 d . . . H15 H 0.5917 0.6033 0.4563 0.025 Uiso 1 1 calc R . . C16 C 0.67145(12) 0.70052(9) 0.50479(10) 0.0265(2) Uani 1 1 d . . . H16 H 0.5924 0.7417 0.5335 0.032 Uiso 1 1 calc R . . C17 C 0.78700(14) 0.72271(10) 0.50916(10) 0.0304(3) Uani 1 1 d . . . H17 H 0.7867 0.7782 0.5420 0.036 Uiso 1 1 calc R . . C18 C 0.90279(13) 0.66400(10) 0.46562(10) 0.0299(3) Uani 1 1 d . . . H18 H 0.9818 0.6797 0.4682 0.036 Uiso 1 1 calc R . . C19 C 0.90372(11) 0.58226(9) 0.41829(9) 0.0235(2) Uani 1 1 d . . . H19 H 0.9835 0.5428 0.3877 0.028 Uiso 1 1 calc R . . C20 C 0.79615(10) 0.19004(8) 0.37092(9) 0.0168(2) Uani 1 1 d . . . C21 C 0.88319(10) 0.10017(8) 0.35339(9) 0.0174(2) Uani 1 1 d . . . C22 C 0.88973(10) 0.00834(8) 0.43556(9) 0.0193(2) Uani 1 1 d . . . C23 C 0.80955(11) 0.00449(8) 0.54248(9) 0.0207(2) Uani 1 1 d . . . C24 C 0.72187(11) 0.09167(9) 0.56517(9) 0.0203(2) Uani 1 1 d . . . C25 C 0.71610(10) 0.18063(8) 0.48016(9) 0.0182(2) Uani 1 1 d . . . C26 C 0.90356(10) 0.32138(8) 0.16380(8) 0.0161(2) Uani 1 1 d . . . C27 C 1.02949(10) 0.31240(8) 0.16860(9) 0.0177(2) Uani 1 1 d . . . C28 C 1.13573(10) 0.33723(8) 0.07718(9) 0.0192(2) Uani 1 1 d . . . C29 C 1.12039(10) 0.37349(8) -0.02716(9) 0.0188(2) Uani 1 1 d . . . C30 C 0.99813(10) 0.38451(8) -0.03715(9) 0.0180(2) Uani 1 1 d . . . C31 C 0.89357(10) 0.35953(8) 0.05695(9) 0.0167(2) Uani 1 1 d . . . C91 C 0.89807(14) 0.85172(10) 0.12238(11) 0.0345(3) Uani 1 1 d . . . C92 C 0.89945(14) 0.89430(10) 0.01277(11) 0.0336(3) Uani 1 1 d . . . H92 H 0.9783 0.9137 -0.0422 0.040 Uiso 1 1 calc R . . C93 C 0.78838(16) 0.90881(12) -0.01752(14) 0.0433(3) Uani 1 1 d . . . H93 H 0.7911 0.9380 -0.0927 0.052 Uiso 1 1 calc R . . C94 C 0.67266(17) 0.88070(13) 0.06189(18) 0.0527(4) Uani 1 1 d . . . H94 H 0.5959 0.8901 0.0415 0.063 Uiso 1 1 calc R . . C95 C 0.67038(17) 0.83877(12) 0.17111(16) 0.0525(5) Uani 1 1 d . . . H95 H 0.5913 0.8199 0.2260 0.063 Uiso 1 1 calc R . . C96 C 0.78168(17) 0.82404(11) 0.20117(13) 0.0444(4) Uani 1 1 d . . . H96 H 0.7786 0.7947 0.2764 0.053 Uiso 1 1 calc R . . C97 C 1.01881(17) 0.83463(12) 0.15650(13) 0.0446(4) Uani 1 1 d . . . H97A H 1.0006 0.8648 0.2207 0.067 Uiso 1 1 calc R . . H97B H 1.0878 0.8697 0.0948 0.067 Uiso 1 1 calc R . . H97C H 1.0466 0.7583 0.1762 0.067 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 B 0.0153(5) 0.0169(5) 0.0162(5) -0.0038(4) -0.0055(4) -0.0007(4) N1 0.0162(4) 0.0141(4) 0.0165(4) -0.0041(3) -0.0048(3) -0.0007(3) N2 0.0164(4) 0.0142(4) 0.0183(4) -0.0042(3) -0.0057(3) -0.0010(3) F1 0.0216(3) 0.0208(3) 0.0180(3) -0.0059(2) -0.0030(2) 0.0008(2) F2 0.0265(3) 0.0167(3) 0.0300(4) -0.0055(3) -0.0114(3) 0.0028(2) F3 0.0362(4) 0.0203(3) 0.0230(3) 0.0038(3) -0.0124(3) -0.0059(3) F4 0.0319(4) 0.0306(4) 0.0158(3) -0.0030(3) -0.0004(3) -0.0080(3) F5 0.0214(3) 0.0224(3) 0.0217(3) -0.0075(3) -0.0018(3) 0.0014(2) F6 0.0205(3) 0.0287(3) 0.0188(3) -0.0030(3) -0.0098(2) -0.0024(3) F7 0.0151(3) 0.0362(4) 0.0281(3) -0.0053(3) -0.0080(3) -0.0047(3) F8 0.0194(3) 0.0277(3) 0.0217(3) -0.0026(3) 0.0001(3) -0.0066(3) F9 0.0260(3) 0.0284(3) 0.0158(3) -0.0004(2) -0.0075(3) -0.0052(3) F10 0.0168(3) 0.0285(3) 0.0198(3) -0.0014(3) -0.0088(2) -0.0035(2) C1 0.0149(5) 0.0198(5) 0.0130(4) -0.0020(4) -0.0031(4) -0.0023(4) C2 0.0160(5) 0.0206(5) 0.0171(5) -0.0041(4) -0.0052(4) -0.0030(4) C3 0.0162(5) 0.0185(5) 0.0134(4) -0.0033(4) -0.0026(4) -0.0041(4) C4 0.0167(5) 0.0184(5) 0.0186(5) -0.0024(4) -0.0054(4) -0.0001(4) C5 0.0283(6) 0.0211(5) 0.0347(6) -0.0100(5) -0.0147(5) 0.0035(4) C6 0.0166(5) 0.0246(6) 0.0296(6) -0.0028(5) -0.0056(4) -0.0001(4) C7 0.0247(6) 0.0287(6) 0.0216(6) 0.0027(5) -0.0045(5) 0.0020(5) C8 0.0195(5) 0.0172(5) 0.0185(5) -0.0052(4) -0.0055(4) -0.0031(4) C9 0.0259(5) 0.0192(5) 0.0210(5) -0.0030(4) -0.0070(4) -0.0063(4) C10 0.0218(5) 0.0202(5) 0.0226(5) -0.0086(4) -0.0042(4) -0.0021(4) C11 0.0251(5) 0.0213(5) 0.0239(5) -0.0062(4) -0.0094(4) -0.0056(4) C12 0.0159(5) 0.0186(5) 0.0167(5) -0.0028(4) -0.0055(4) -0.0008(4) C13 0.0169(5) 0.0196(5) 0.0170(5) -0.0029(4) -0.0054(4) -0.0017(4) C14 0.0219(5) 0.0176(5) 0.0144(5) -0.0028(4) -0.0046(4) -0.0041(4) C15 0.0226(5) 0.0217(5) 0.0183(5) -0.0045(4) -0.0051(4) -0.0027(4) C16 0.0333(6) 0.0221(5) 0.0213(5) -0.0077(4) -0.0038(5) -0.0012(5) C17 0.0443(7) 0.0246(6) 0.0249(6) -0.0097(5) -0.0059(5) -0.0123(5) C18 0.0316(6) 0.0338(6) 0.0288(6) -0.0084(5) -0.0069(5) -0.0160(5) C19 0.0211(5) 0.0272(6) 0.0222(5) -0.0065(4) -0.0035(4) -0.0066(4) C20 0.0166(5) 0.0175(5) 0.0176(5) -0.0040(4) -0.0067(4) -0.0025(4) C21 0.0171(5) 0.0194(5) 0.0165(5) -0.0049(4) -0.0050(4) -0.0029(4) C22 0.0194(5) 0.0164(5) 0.0241(5) -0.0052(4) -0.0096(4) -0.0007(4) C23 0.0255(5) 0.0174(5) 0.0204(5) 0.0017(4) -0.0109(4) -0.0068(4) C24 0.0215(5) 0.0238(5) 0.0160(5) -0.0038(4) -0.0039(4) -0.0075(4) C25 0.0171(5) 0.0184(5) 0.0200(5) -0.0060(4) -0.0058(4) -0.0012(4) C26 0.0176(5) 0.0137(4) 0.0171(5) -0.0040(4) -0.0051(4) -0.0017(4) C27 0.0202(5) 0.0170(5) 0.0176(5) -0.0039(4) -0.0083(4) -0.0015(4) C28 0.0152(5) 0.0196(5) 0.0243(5) -0.0055(4) -0.0076(4) -0.0023(4) C29 0.0180(5) 0.0164(5) 0.0194(5) -0.0040(4) -0.0015(4) -0.0039(4) C30 0.0229(5) 0.0156(5) 0.0158(5) -0.0018(4) -0.0075(4) -0.0029(4) C31 0.0155(5) 0.0159(5) 0.0203(5) -0.0039(4) -0.0075(4) -0.0018(4) C91 0.0472(8) 0.0187(6) 0.0315(7) -0.0089(5) -0.0022(6) -0.0030(5) C92 0.0402(7) 0.0271(6) 0.0287(6) -0.0108(5) -0.0014(5) -0.0036(5) C93 0.0518(9) 0.0349(7) 0.0469(8) -0.0180(6) -0.0158(7) 0.0003(6) C94 0.0450(9) 0.0365(8) 0.0848(13) -0.0326(9) -0.0180(9) 0.0007(7) C95 0.0454(9) 0.0309(7) 0.0677(11) -0.0224(7) 0.0131(8) -0.0127(6) C96 0.0606(10) 0.0241(6) 0.0349(7) -0.0070(5) 0.0056(7) -0.0103(6) C97 0.0606(10) 0.0332(7) 0.0389(8) -0.0082(6) -0.0145(7) -0.0042(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 C12 1.5921(15) . ? B N1 1.6229(14) . ? B C20 1.6400(15) . ? B C26 1.6459(15) . ? N1 N2 1.3627(12) . ? N1 C3 1.3644(13) . ? N2 C1 1.3338(13) . ? F1 C21 1.3480(12) . ? F2 C22 1.3433(12) . ? F3 C23 1.3398(12) . ? F4 C24 1.3409(12) . ? F5 C25 1.3491(12) . ? F6 C27 1.3497(12) . ? F7 C28 1.3439(12) . ? F8 C29 1.3386(12) . ? F9 C30 1.3430(12) . ? F10 C31 1.3554(12) . ? C1 C2 1.3851(15) . ? C1 C4 1.5124(14) . ? C2 C3 1.3961(14) . ? C3 C8 1.5251(14) . ? C4 C6 1.5323(15) . ? C4 C5 1.5334(15) . ? C4 C7 1.5337(15) . ? C8 C10 1.5350(15) . ? C8 C11 1.5395(14) . ? C8 C9 1.5406(15) . ? C12 C13 1.2065(16) . ? C13 C14 1.4376(15) . ? C14 C19 1.3976(15) . ? C14 C15 1.4031(15) . ? C15 C16 1.3864(16) . ? C16 C17 1.3886(19) . ? C17 C18 1.3858(19) . ? C18 C19 1.3887(17) . ? C20 C21 1.3904(14) . ? C20 C25 1.3952(15) . ? C21 C22 1.3871(15) . ? C22 C23 1.3788(16) . ? C23 C24 1.3798(16) . ? C24 C25 1.3836(15) . ? C26 C31 1.3918(14) . ? C26 C27 1.3943(14) . ? C27 C28 1.3789(15) . ? C28 C29 1.3816(15) . ? C29 C30 1.3768(15) . ? C30 C31 1.3870(15) . ? C91 C96 1.388(2) . ? C91 C92 1.3917(19) . ? C91 C97 1.506(2) . ? C92 C93 1.379(2) . ? C93 C94 1.387(2) . ? C94 C95 1.383(3) . ? C95 C96 1.379(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 C12 B N1 105.46(8) . . ? C12 B C20 107.90(8) . . ? N1 B C20 110.10(8) . . ? C12 B C26 104.26(8) . . ? N1 B C26 111.85(8) . . ? C20 B C26 116.44(8) . . ? N2 N1 C3 105.70(8) . . ? N2 N1 B 113.45(8) . . ? C3 N1 B 140.36(9) . . ? C1 N2 N1 112.60(9) . . ? N2 C1 C2 105.81(9) . . ? N2 C1 C4 122.26(9) . . ? C2 C1 C4 131.91(9) . . ? C1 C2 C3 107.71(9) . . ? N1 C3 C2 108.19(9) . . ? N1 C3 C8 126.72(9) . . ? C2 C3 C8 125.09(9) . . ? C1 C4 C6 108.90(9) . . ? C1 C4 C5 110.81(9) . . ? C6 C4 C5 109.51(9) . . ? C1 C4 C7 108.33(9) . . ? C6 C4 C7 109.64(9) . . ? C5 C4 C7 109.63(10) . . ? C3 C8 C10 110.96(9) . . ? C3 C8 C11 108.82(9) . . ? C10 C8 C11 107.64(9) . . ? C3 C8 C9 111.24(8) . . ? C10 C8 C9 110.87(9) . . ? C11 C8 C9 107.15(9) . . ? C13 C12 B 176.25(11) . . ? C12 C13 C14 178.75(11) . . ? C19 C14 C15 119.24(10) . . ? C19 C14 C13 120.52(10) . . ? C15 C14 C13 120.23(10) . . ? C16 C15 C14 120.05(11) . . ? C15 C16 C17 120.25(11) . . ? C18 C17 C16 120.05(11) . . ? C17 C18 C19 120.22(11) . . ? C18 C19 C14 120.16(11) . . ? C21 C20 C25 113.82(9) . . ? C21 C20 B 127.51(9) . . ? C25 C20 B 118.59(9) . . ? F1 C21 C22 115.17(9) . . ? F1 C21 C20 121.04(9) . . ? C22 C21 C20 123.78(10) . . ? F2 C22 C23 119.85(10) . . ? F2 C22 C21 120.44(10) . . ? C23 C22 C21 119.70(10) . . ? F3 C23 C22 120.52(10) . . ? F3 C23 C24 120.33(10) . . ? C22 C23 C24 119.14(10) . . ? F4 C24 C23 119.90(10) . . ? F4 C24 C25 120.81(10) . . ? C23 C24 C25 119.29(10) . . ? F5 C25 C24 115.78(9) . . ? F5 C25 C20 119.98(9) . . ? C24 C25 C20 124.23(10) . . ? C31 C26 C27 113.63(9) . . ? C31 C26 B 127.28(9) . . ? C27 C26 B 118.46(9) . . ? F6 C27 C28 116.28(9) . . ? F6 C27 C26 119.59(9) . . ? C28 C27 C26 124.11(10) . . ? F7 C28 C27 120.72(10) . . ? F7 C28 C29 119.49(10) . . ? C27 C28 C29 119.78(10) . . ? F8 C29 C30 121.05(10) . . ? F8 C29 C28 120.16(10) . . ? C30 C29 C28 118.78(10) . . ? F9 C30 C29 119.96(9) . . ? F9 C30 C31 120.35(9) . . ? C29 C30 C31 119.68(10) . . ? F10 C31 C30 115.09(9) . . ? F10 C31 C26 120.88(9) . . ? C30 C31 C26 124.01(10) . . ? C96 C91 C92 118.37(15) . . ? C96 C91 C97 119.86(14) . . ? C92 C91 C97 121.77(13) . . ? C93 C92 C91 121.19(14) . . ? C92 C93 C94 119.95(16) . . ? C95 C94 C93 119.21(17) . . ? C96 C95 C94 120.74(15) . . ? C95 C96 C91 120.54(15) . . ? 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 C12 B N1 N2 20.51(11) . . . . ? C20 B N1 N2 136.67(9) . . . . ? C26 B N1 N2 -92.21(10) . . . . ? C12 B N1 C3 -169.16(11) . . . . ? C20 B N1 C3 -53.00(16) . . . . ? C26 B N1 C3 78.12(15) . . . . ? C3 N1 N2 C1 0.56(11) . . . . ? B N1 N2 C1 174.16(8) . . . . ? N1 N2 C1 C2 -0.38(12) . . . . ? N1 N2 C1 C4 -179.05(9) . . . . ? N2 C1 C2 C3 0.06(11) . . . . ? C4 C1 C2 C3 178.55(10) . . . . ? N2 N1 C3 C2 -0.49(11) . . . . ? B N1 C3 C2 -171.28(11) . . . . ? N2 N1 C3 C8 179.71(9) . . . . ? B N1 C3 C8 8.92(19) . . . . ? C1 C2 C3 N1 0.28(12) . . . . ? C1 C2 C3 C8 -179.92(9) . . . . ? N2 C1 C4 C6 -143.55(10) . . . . ? C2 C1 C4 C6 38.17(15) . . . . ? N2 C1 C4 C5 -23.03(14) . . . . ? C2 C1 C4 C5 158.68(11) . . . . ? N2 C1 C4 C7 97.26(12) . . . . ? C2 C1 C4 C7 -81.02(14) . . . . ? N1 C3 C8 C10 -51.25(14) . . . . ? C2 C3 C8 C10 128.98(11) . . . . ? N1 C3 C8 C11 -169.50(10) . . . . ? C2 C3 C8 C11 10.73(14) . . . . ? N1 C3 C8 C9 72.68(13) . . . . ? C2 C3 C8 C9 -107.09(12) . . . . ? N1 B C12 C13 -67.8(16) . . . . ? C20 B C12 C13 174.6(16) . . . . ? C26 B C12 C13 50.2(16) . . . . ? B C12 C13 C14 159(4) . . . . ? C12 C13 C14 C19 104(5) . . . . ? C12 C13 C14 C15 -75(5) . . . . ? C19 C14 C15 C16 -0.90(16) . . . . ? C13 C14 C15 C16 178.03(10) . . . . ? C14 C15 C16 C17 -0.40(17) . . . . ? C15 C16 C17 C18 1.12(18) . . . . ? C16 C17 C18 C19 -0.52(19) . . . . ? C17 C18 C19 C14 -0.79(18) . . . . ? C15 C14 C19 C18 1.49(17) . . . . ? C13 C14 C19 C18 -177.43(11) . . . . ? C12 B C20 C21 -128.66(11) . . . . ? N1 B C20 C21 116.72(11) . . . . ? C26 B C20 C21 -11.94(15) . . . . ? C12 B C20 C25 47.90(12) . . . . ? N1 B C20 C25 -66.72(12) . . . . ? C26 B C20 C25 164.62(9) . . . . ? C25 C20 C21 F1 -179.81(9) . . . . ? B C20 C21 F1 -3.11(16) . . . . ? C25 C20 C21 C22 0.99(15) . . . . ? B C20 C21 C22 177.69(10) . . . . ? F1 C21 C22 F2 -0.09(14) . . . . ? C20 C21 C22 F2 179.15(9) . . . . ? F1 C21 C22 C23 178.56(9) . . . . ? C20 C21 C22 C23 -2.20(16) . . . . ? F2 C22 C23 F3 1.60(15) . . . . ? C21 C22 C23 F3 -177.06(9) . . . . ? F2 C22 C23 C24 -179.85(9) . . . . ? C21 C22 C23 C24 1.49(16) . . . . ? F3 C23 C24 F4 -0.96(16) . . . . ? C22 C23 C24 F4 -179.51(9) . . . . ? F3 C23 C24 C25 178.80(9) . . . . ? C22 C23 C24 C25 0.25(16) . . . . ? F4 C24 C25 F5 -3.11(15) . . . . ? C23 C24 C25 F5 177.12(9) . . . . ? F4 C24 C25 C20 178.26(10) . . . . ? C23 C24 C25 C20 -1.50(17) . . . . ? C21 C20 C25 F5 -177.70(9) . . . . ? B C20 C25 F5 5.28(14) . . . . ? C21 C20 C25 C24 0.87(15) . . . . ? B C20 C25 C24 -176.15(10) . . . . ? C12 B C26 C31 -107.58(11) . . . . ? N1 B C26 C31 5.89(14) . . . . ? C20 B C26 C31 133.70(11) . . . . ? C12 B C26 C27 62.71(11) . . . . ? N1 B C26 C27 176.18(9) . . . . ? C20 B C26 C27 -56.02(12) . . . . ? C31 C26 C27 F6 178.00(9) . . . . ? B C26 C27 F6 6.42(14) . . . . ? C31 C26 C27 C28 -0.77(15) . . . . ? B C26 C27 C28 -172.35(10) . . . . ? F6 C27 C28 F7 1.02(15) . . . . ? C26 C27 C28 F7 179.83(9) . . . . ? F6 C27 C28 C29 -178.83(9) . . . . ? C26 C27 C28 C29 -0.03(17) . . . . ? F7 C28 C29 F8 -0.49(15) . . . . ? C27 C28 C29 F8 179.37(9) . . . . ? F7 C28 C29 C30 -179.52(9) . . . . ? C27 C28 C29 C30 0.34(16) . . . . ? F8 C29 C30 F9 0.03(15) . . . . ? C28 C29 C30 F9 179.06(9) . . . . ? F8 C29 C30 C31 -178.83(9) . . . . ? C28 C29 C30 C31 0.20(16) . . . . ? F9 C30 C31 F10 -1.69(14) . . . . ? C29 C30 C31 F10 177.16(9) . . . . ? F9 C30 C31 C26 -179.97(9) . . . . ? C29 C30 C31 C26 -1.11(16) . . . . ? C27 C26 C31 F10 -176.84(9) . . . . ? B C26 C31 F10 -6.15(16) . . . . ? C27 C26 C31 C30 1.34(15) . . . . ? B C26 C31 C30 172.02(10) . . . . ? C96 C91 C92 C93 -0.06(19) . . . . ? C97 C91 C92 C93 179.51(13) . . . . ? C91 C92 C93 C94 0.0(2) . . . . ? C92 C93 C94 C95 0.3(2) . . . . ? C93 C94 C95 C96 -0.5(2) . . . . ? C94 C95 C96 C91 0.4(2) . . . . ? C92 C91 C96 C95 -0.1(2) . . . . ? C97 C91 C96 C95 -179.71(13) . . . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 75.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.378 _refine_diff_density_min -0.258 _refine_diff_density_rms 0.040 # # end of cif data for "eileen36" # Attachment '- eileen38.cif' data_eileen38 _database_code_depnum_ccdc_archive 'CCDC 869104' #TrackingRef '- eileen38.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H24 B F10 N3' _chemical_formula_weight 627.33 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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/n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 11.8154(3) _cell_length_b 15.1224(5) _cell_length_c 15.9346(5) _cell_angle_alpha 90.00 _cell_angle_beta 97.556(3) _cell_angle_gamma 90.00 _cell_volume 2822.43(15) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 12443 _cell_measurement_theta_min 2.1949 _cell_measurement_theta_max 28.7293 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.476 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1280 _exptl_absorpt_coefficient_mu 0.133 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.95281 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Diffraction Xcalibur, Eos' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 16.1419 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 67513 _diffrn_reflns_av_R_equivalents 0.0515 _diffrn_reflns_av_sigmaI/netI 0.0236 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.20 _diffrn_reflns_theta_max 25.03 _reflns_number_total 4972 _reflns_number_gt 4119 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker XP' _computing_publication_material SHELXL-97 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. The C6F5 group C19 to F5 is disordered over two positions with relative occupancy 0.788(4)/0.212(4). A system of appropriate restraints was employed to ensure stability of refinement, but the dimensions of disordered groups should always be interpreted with caution. ; _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^)+(0.0326P)^2^+1.5980P] 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 4972 _refine_ls_number_parameters 448 _refine_ls_number_restraints 248 _refine_ls_R_factor_all 0.0488 _refine_ls_R_factor_gt 0.0371 _refine_ls_wR_factor_ref 0.0854 _refine_ls_wR_factor_gt 0.0802 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.021 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.27023(10) 0.19885(9) 0.26532(8) 0.0162(3) Uani 1 1 d . A . N2 N 0.22360(10) 0.16672(9) 0.33454(8) 0.0165(3) Uani 1 1 d . . . N3 N 0.41612(11) 0.15032(9) 0.37441(8) 0.0172(3) Uani 1 1 d . A . F6 F 0.36192(9) 0.00567(6) 0.27217(6) 0.0308(3) Uani 1 1 d . A . F7 F 0.44641(10) -0.10954(7) 0.17000(7) 0.0425(3) Uani 1 1 d . . . F8 F 0.58045(9) -0.05269(8) 0.05423(7) 0.0420(3) Uani 1 1 d . A . F9 F 0.63434(9) 0.12142(8) 0.04650(7) 0.0388(3) Uani 1 1 d . . . F10 F 0.55090(8) 0.23810(7) 0.14659(6) 0.0280(2) Uani 1 1 d . A . C1 C 0.10671(13) 0.16441(10) 0.31582(10) 0.0178(3) Uani 1 1 d . . . C2 C 0.08262(13) 0.19781(11) 0.23510(10) 0.0195(4) Uani 1 1 d . . . H2 H 0.0083 0.2056 0.2052 0.023 Uiso 1 1 calc R . . C3 C 0.18452(13) 0.21837(10) 0.20416(10) 0.0167(3) Uani 1 1 d . . . C4 C 0.01937(13) 0.12652(11) 0.36879(11) 0.0213(4) Uani 1 1 d . . . C5 C 0.04839(15) 0.02985(12) 0.39166(12) 0.0280(4) Uani 1 1 d . . . H5A H 0.0580 -0.0032 0.3402 0.042 Uiso 1 1 calc R . . H5B H -0.0137 0.0036 0.4184 0.042 Uiso 1 1 calc R . . H5C H 0.1194 0.0274 0.4310 0.042 Uiso 1 1 calc R . . C6 C 0.00938(15) 0.18191(13) 0.44793(11) 0.0294(4) Uani 1 1 d . . . H6A H 0.0803 0.1772 0.4872 0.044 Uiso 1 1 calc R . . H6B H -0.0545 0.1601 0.4756 0.044 Uiso 1 1 calc R . . H6C H -0.0040 0.2439 0.4317 0.044 Uiso 1 1 calc R . . C7 C -0.09779(14) 0.12830(13) 0.31422(12) 0.0307(4) Uani 1 1 d . . . H7A H -0.1187 0.1896 0.2994 0.046 Uiso 1 1 calc R . . H7B H -0.1551 0.1023 0.3460 0.046 Uiso 1 1 calc R . . H7C H -0.0943 0.0941 0.2624 0.046 Uiso 1 1 calc R . . C8 C 0.19736(13) 0.25557(11) 0.11729(10) 0.0193(4) Uani 1 1 d . . . C9 C 0.23383(15) 0.18224(12) 0.05938(11) 0.0266(4) Uani 1 1 d . . . H9A H 0.3070 0.1573 0.0846 0.040 Uiso 1 1 calc R . . H9B H 0.2419 0.2072 0.0037 0.040 Uiso 1 1 calc R . . H9C H 0.1757 0.1356 0.0530 0.040 Uiso 1 1 calc R . . C10 C 0.28403(14) 0.33145(11) 0.12372(11) 0.0228(4) Uani 1 1 d . . . H10A H 0.2602 0.3778 0.1607 0.034 Uiso 1 1 calc R . . H10B H 0.2879 0.3559 0.0672 0.034 Uiso 1 1 calc R . . H10C H 0.3594 0.3091 0.1474 0.034 Uiso 1 1 calc R . . C11 C 0.08117(14) 0.29161(13) 0.07712(11) 0.0284(4) Uani 1 1 d . . . H11A H 0.0255 0.2432 0.0698 0.043 Uiso 1 1 calc R . . H11B H 0.0889 0.3176 0.0218 0.043 Uiso 1 1 calc R . . H11C H 0.0550 0.3369 0.1141 0.043 Uiso 1 1 calc R . . C12 C 0.32003(13) 0.14220(10) 0.39900(10) 0.0165(3) Uani 1 1 d . . . C13 C 0.30688(12) 0.11266(11) 0.48622(10) 0.0170(3) Uani 1 1 d . . . C14 C 0.34469(13) 0.02786(11) 0.51050(10) 0.0204(4) Uani 1 1 d . . . H14 H 0.3682 -0.0116 0.4698 0.024 Uiso 1 1 calc R . . C15 C 0.34793(14) 0.00111(12) 0.59409(11) 0.0261(4) Uani 1 1 d . . . H15 H 0.3728 -0.0568 0.6105 0.031 Uiso 1 1 calc R . . C16 C 0.31486(14) 0.05909(13) 0.65333(11) 0.0284(4) Uani 1 1 d . . . H16 H 0.3157 0.0404 0.7103 0.034 Uiso 1 1 calc R . . C17 C 0.28051(14) 0.14415(13) 0.63016(11) 0.0275(4) Uani 1 1 d . . . H17 H 0.2593 0.1840 0.6715 0.033 Uiso 1 1 calc R . . C18 C 0.27707(13) 0.17130(11) 0.54684(11) 0.0222(4) Uani 1 1 d . . . H18 H 0.2544 0.2299 0.5311 0.027 Uiso 1 1 calc R . . B B 0.40669(15) 0.19282(12) 0.28672(11) 0.0175(4) Uani 1 1 d D . . C19 C 0.4729(3) 0.2862(2) 0.3060(3) 0.0187(9) Uani 0.788(4) 1 d PDU A 1 C20 C 0.5900(3) 0.2913(2) 0.31557(17) 0.0200(6) Uani 0.788(4) 1 d PDU A 1 C21 C 0.6528(2) 0.36516(19) 0.33852(15) 0.0259(6) Uani 0.788(4) 1 d PDU A 1 C22 C 0.5975(3) 0.44120(19) 0.35754(17) 0.0308(7) Uani 0.788(4) 1 d PDU A 1 C23 C 0.4808(3) 0.44084(15) 0.35270(16) 0.0312(6) Uani 0.788(4) 1 d PDU A 1 C24 C 0.4224(3) 0.36434(19) 0.3269(2) 0.0264(9) Uani 0.788(4) 1 d PDU A 1 F1 F 0.65242(13) 0.21694(15) 0.30430(11) 0.0268(4) Uani 0.788(4) 1 d PDU A 1 F2 F 0.76809(13) 0.36326(13) 0.34369(9) 0.0388(5) Uani 0.788(4) 1 d PDU A 1 F3 F 0.65787(18) 0.51461(10) 0.38217(11) 0.0529(7) Uani 0.788(4) 1 d PD A 1 F4 F 0.4252(2) 0.51364(10) 0.37285(11) 0.0542(6) Uani 0.788(4) 1 d PDU A 1 F5 F 0.3065(2) 0.36888(15) 0.32600(14) 0.0338(5) Uani 0.788(4) 1 d PDU A 1 C19' C 0.4530(9) 0.2969(9) 0.3059(14) 0.013(4) Uiso 0.212(4) 1 d PDU A 2 C20' C 0.5688(9) 0.3154(7) 0.3243(10) 0.032(4) Uiso 0.212(4) 1 d PDU A 2 C21' C 0.6162(8) 0.3964(7) 0.3493(7) 0.023(3) Uiso 0.212(4) 1 d PDU A 2 C22' C 0.5441(9) 0.4599(6) 0.3700(7) 0.026(3) Uiso 0.212(4) 1 d PDU A 2 C23' C 0.4290(8) 0.4464(6) 0.3594(7) 0.030(3) Uiso 0.212(4) 1 d PDU A 2 C24' C 0.3881(11) 0.3647(6) 0.3311(8) 0.008(3) Uiso 0.212(4) 1 d PDU A 2 F1' F 0.6422(8) 0.2513(6) 0.3107(5) 0.032(2) Uiso 0.212(4) 1 d PDU A 2 F2' F 0.7289(6) 0.4079(5) 0.3565(4) 0.0430(18) Uiso 0.212(4) 1 d PDU A 2 F3' F 0.5880(6) 0.5397(4) 0.3974(4) 0.0461(19) Uiso 0.212(4) 1 d PD A 2 F4' F 0.3570(7) 0.5099(4) 0.3801(4) 0.048(2) Uiso 0.212(4) 1 d PDU A 2 F5' F 0.2738(8) 0.3554(7) 0.3291(7) 0.034(3) Uiso 0.212(4) 1 d PDU A 2 C25 C 0.45633(13) 0.12766(11) 0.21834(10) 0.0187(3) Uani 1 1 d . A . C26 C 0.43153(14) 0.03775(11) 0.21859(10) 0.0226(4) Uani 1 1 d . . . C27 C 0.47271(16) -0.02341(12) 0.16571(11) 0.0282(4) Uani 1 1 d . A . C28 C 0.54214(15) 0.00475(13) 0.10827(11) 0.0294(4) Uani 1 1 d . . . C29 C 0.56870(14) 0.09292(13) 0.10425(11) 0.0267(4) Uani 1 1 d . A . C30 C 0.52507(13) 0.15192(11) 0.15761(10) 0.0222(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 N1 0.0170(7) 0.0171(7) 0.0152(7) 0.0029(6) 0.0049(5) 0.0001(5) N2 0.0157(7) 0.0185(7) 0.0162(7) 0.0031(6) 0.0050(5) 0.0002(5) N3 0.0173(7) 0.0160(7) 0.0183(7) 0.0002(6) 0.0020(5) -0.0002(5) F6 0.0418(6) 0.0229(5) 0.0294(6) 0.0001(4) 0.0115(5) -0.0082(5) F7 0.0663(8) 0.0204(6) 0.0394(7) -0.0055(5) 0.0025(6) 0.0051(5) F8 0.0467(7) 0.0506(7) 0.0270(6) -0.0127(5) -0.0012(5) 0.0274(6) F9 0.0315(6) 0.0586(8) 0.0295(6) 0.0005(5) 0.0164(5) 0.0067(5) F10 0.0275(5) 0.0306(6) 0.0276(5) 0.0058(4) 0.0106(4) -0.0034(4) C1 0.0161(8) 0.0164(8) 0.0214(9) -0.0008(7) 0.0035(6) 0.0012(6) C2 0.0156(8) 0.0208(9) 0.0218(9) 0.0026(7) 0.0015(6) 0.0025(7) C3 0.0179(8) 0.0139(8) 0.0181(8) 0.0003(6) 0.0017(6) 0.0024(6) C4 0.0168(8) 0.0250(9) 0.0230(9) 0.0039(7) 0.0063(7) 0.0002(7) C5 0.0255(9) 0.0269(10) 0.0325(10) 0.0069(8) 0.0067(8) -0.0031(8) C6 0.0234(9) 0.0374(11) 0.0299(10) -0.0006(8) 0.0124(8) 0.0003(8) C7 0.0197(9) 0.0422(12) 0.0310(10) 0.0089(9) 0.0060(8) -0.0034(8) C8 0.0193(8) 0.0217(9) 0.0169(8) 0.0034(7) 0.0021(6) 0.0010(7) C9 0.0321(10) 0.0290(10) 0.0181(9) -0.0012(8) 0.0016(7) -0.0001(8) C10 0.0238(9) 0.0227(9) 0.0220(9) 0.0052(7) 0.0036(7) -0.0005(7) C11 0.0223(9) 0.0375(11) 0.0247(9) 0.0129(8) 0.0013(7) 0.0015(8) C12 0.0177(8) 0.0130(8) 0.0184(8) -0.0015(6) 0.0014(6) 0.0005(6) C13 0.0127(7) 0.0207(9) 0.0174(8) 0.0020(7) 0.0015(6) -0.0015(6) C14 0.0196(8) 0.0202(9) 0.0215(9) -0.0004(7) 0.0033(7) -0.0008(7) C15 0.0220(9) 0.0292(10) 0.0269(10) 0.0093(8) 0.0028(7) 0.0014(7) C16 0.0220(9) 0.0439(12) 0.0193(9) 0.0093(8) 0.0032(7) 0.0012(8) C17 0.0231(9) 0.0404(11) 0.0198(9) -0.0062(8) 0.0061(7) 0.0035(8) C18 0.0199(8) 0.0223(9) 0.0245(9) -0.0002(7) 0.0028(7) 0.0040(7) B 0.0137(9) 0.0199(10) 0.0184(9) 0.0022(8) 0.0005(7) 0.0008(7) C19 0.0211(16) 0.0187(16) 0.0159(15) 0.0045(12) 0.0006(15) 0.0013(13) C20 0.0236(14) 0.0210(16) 0.0157(13) 0.0012(12) 0.0036(11) -0.0015(14) C21 0.0223(13) 0.0345(15) 0.0197(12) 0.0034(11) -0.0024(10) -0.0162(13) C22 0.0416(19) 0.0189(15) 0.0287(14) 0.0000(12) -0.0073(13) -0.0136(14) C23 0.042(2) 0.0174(13) 0.0318(15) -0.0023(10) -0.0057(14) 0.0014(13) C24 0.0194(17) 0.0318(18) 0.0274(16) 0.0012(10) 0.0011(15) -0.0007(13) F1 0.0146(7) 0.0320(11) 0.0335(9) -0.0028(8) 0.0022(5) 0.0024(8) F2 0.0267(8) 0.0546(12) 0.0331(8) 0.0029(8) -0.0031(6) -0.0224(8) F3 0.0690(14) 0.0291(9) 0.0533(11) 0.0010(7) -0.0185(9) -0.0270(9) F4 0.0715(16) 0.0210(9) 0.0649(12) -0.0159(7) -0.0111(10) 0.0085(8) F5 0.0322(15) 0.0266(11) 0.0423(11) -0.0103(7) 0.0043(10) 0.0088(10) C25 0.0152(8) 0.0225(9) 0.0177(8) 0.0027(7) -0.0004(6) 0.0030(7) C26 0.0239(9) 0.0241(9) 0.0195(9) 0.0022(7) 0.0015(7) 0.0016(7) C27 0.0368(10) 0.0216(10) 0.0237(9) -0.0002(8) -0.0045(8) 0.0062(8) C28 0.0298(10) 0.0380(11) 0.0190(9) -0.0067(8) -0.0020(7) 0.0175(8) C29 0.0196(9) 0.0418(11) 0.0193(9) 0.0020(8) 0.0052(7) 0.0065(8) C30 0.0186(8) 0.0262(9) 0.0213(9) 0.0034(7) 0.0014(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 N1 C3 1.343(2) . ? N1 N2 1.3842(17) . ? N1 B 1.606(2) . ? N2 C1 1.375(2) . ? N2 C12 1.477(2) . ? N3 C12 1.255(2) . ? N3 B 1.529(2) . ? F6 C26 1.3511(19) . ? F7 C27 1.343(2) . ? F8 C28 1.343(2) . ? F9 C29 1.3498(19) . ? F10 C30 1.355(2) . ? C1 C2 1.376(2) . ? C1 C4 1.528(2) . ? C2 C3 1.395(2) . ? C3 C8 1.520(2) . ? C4 C6 1.531(2) . ? C4 C5 1.534(2) . ? C4 C7 1.535(2) . ? C8 C10 1.532(2) . ? C8 C11 1.536(2) . ? C8 C9 1.540(2) . ? C12 C13 1.487(2) . ? C13 C18 1.390(2) . ? C13 C14 1.396(2) . ? C14 C15 1.388(2) . ? C15 C16 1.382(3) . ? C16 C17 1.384(3) . ? C17 C18 1.385(2) . ? B C19 1.624(4) . ? B C25 1.634(2) . ? B C19' 1.681(12) . ? C19 C20 1.374(5) . ? C19 C24 1.384(5) . ? C20 C21 1.365(3) . ? C20 F1 1.369(4) . ? C21 F2 1.354(3) . ? C21 C22 1.376(4) . ? C22 F3 1.350(3) . ? C22 C23 1.370(4) . ? C23 F4 1.342(3) . ? C23 C24 1.382(4) . ? C24 F5 1.369(4) . ? C19' C24' 1.373(11) . ? C19' C20' 1.389(12) . ? C20' F1' 1.337(10) . ? C20' C21' 1.384(11) . ? C21' F2' 1.332(10) . ? C21' C22' 1.353(10) . ? C22' F3' 1.362(10) . ? C22' C23' 1.363(10) . ? C23' F4' 1.352(10) . ? C23' C24' 1.381(11) . ? C24' F5' 1.354(10) . ? C25 C26 1.391(2) . ? C25 C30 1.392(2) . ? C26 C27 1.382(2) . ? C27 C28 1.375(3) . ? C28 C29 1.373(3) . ? C29 C30 1.378(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C3 N1 N2 108.32(12) . . ? C3 N1 B 143.79(13) . . ? N2 N1 B 107.73(11) . . ? C1 N2 N1 109.26(12) . . ? C1 N2 C12 143.66(13) . . ? N1 N2 C12 106.90(11) . . ? C12 N3 B 111.49(13) . . ? N2 C1 C2 105.78(13) . . ? N2 C1 C4 128.46(14) . . ? C2 C1 C4 125.60(14) . . ? C1 C2 C3 109.26(14) . . ? N1 C3 C2 107.35(13) . . ? N1 C3 C8 125.89(13) . . ? C2 C3 C8 126.76(14) . . ? C1 C4 C6 112.37(14) . . ? C1 C4 C5 110.03(13) . . ? C6 C4 C5 111.38(14) . . ? C1 C4 C7 107.74(13) . . ? C6 C4 C7 107.19(14) . . ? C5 C4 C7 107.93(14) . . ? C3 C8 C10 111.23(13) . . ? C3 C8 C11 108.66(13) . . ? C10 C8 C11 108.35(14) . . ? C3 C8 C9 110.39(13) . . ? C10 C8 C9 110.01(13) . . ? C11 C8 C9 108.11(14) . . ? N3 C12 N2 113.89(14) . . ? N3 C12 C13 122.08(14) . . ? N2 C12 C13 124.01(13) . . ? C18 C13 C14 119.63(15) . . ? C18 C13 C12 121.66(14) . . ? C14 C13 C12 117.78(14) . . ? C15 C14 C13 120.09(16) . . ? C16 C15 C14 119.74(16) . . ? C15 C16 C17 120.45(16) . . ? C16 C17 C18 120.11(16) . . ? C17 C18 C13 119.92(16) . . ? N3 B N1 99.70(12) . . ? N3 B C19 102.5(2) . . ? N1 B C19 115.8(2) . . ? N3 B C25 111.50(13) . . ? N1 B C25 109.32(13) . . ? C19 B C25 116.4(2) . . ? N3 B C19' 104.2(8) . . ? N1 B C19' 106.2(4) . . ? C19 B C19' 9.7(4) . . ? C25 B C19' 123.3(6) . . ? C20 C19 C24 112.7(3) . . ? C20 C19 B 121.5(3) . . ? C24 C19 B 125.2(3) . . ? C21 C20 F1 115.1(3) . . ? C21 C20 C19 125.4(4) . . ? F1 C20 C19 119.5(2) . . ? F2 C21 C20 120.4(3) . . ? F2 C21 C22 120.5(2) . . ? C20 C21 C22 119.0(3) . . ? F3 C22 C23 120.6(3) . . ? F3 C22 C21 120.2(2) . . ? C23 C22 C21 119.2(2) . . ? F4 C23 C22 120.2(3) . . ? F4 C23 C24 121.1(3) . . ? C22 C23 C24 118.7(3) . . ? F5 C24 C23 114.9(3) . . ? F5 C24 C19 120.2(3) . . ? C23 C24 C19 124.9(3) . . ? C24' C19' C20' 111.1(11) . . ? C24' C19' B 124.8(9) . . ? C20' C19' B 121.0(9) . . ? F1' C20' C21' 116.2(9) . . ? F1' C20' C19' 117.4(9) . . ? C21' C20' C19' 126.1(10) . . ? F2' C21' C22' 122.7(9) . . ? F2' C21' C20' 120.2(9) . . ? C22' C21' C20' 117.0(9) . . ? C21' C22' F3' 118.7(9) . . ? C21' C22' C23' 120.9(8) . . ? F3' C22' C23' 120.2(8) . . ? F4' C23' C22' 120.9(8) . . ? F4' C23' C24' 120.6(8) . . ? C22' C23' C24' 118.4(9) . . ? F5' C24' C19' 120.7(9) . . ? F5' C24' C23' 114.0(9) . . ? C19' C24' C23' 125.4(10) . . ? C26 C25 C30 113.71(15) . . ? C26 C25 B 119.56(14) . . ? C30 C25 B 126.73(15) . . ? F6 C26 C27 115.93(15) . . ? F6 C26 C25 119.92(15) . . ? C27 C26 C25 124.15(16) . . ? F7 C27 C28 119.79(16) . . ? F7 C27 C26 121.05(16) . . ? C28 C27 C26 119.17(17) . . ? F8 C28 C29 119.99(17) . . ? F8 C28 C27 120.50(18) . . ? C29 C28 C27 119.46(16) . . ? F9 C29 C28 119.81(16) . . ? F9 C29 C30 120.59(17) . . ? C28 C29 C30 119.57(16) . . ? F10 C30 C29 115.70(14) . . ? F10 C30 C25 120.37(15) . . ? C29 C30 C25 123.91(16) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C3 N1 N2 C1 1.21(17) . . . . ? B N1 N2 C1 -175.30(12) . . . . ? C3 N1 N2 C12 177.51(12) . . . . ? B N1 N2 C12 1.00(15) . . . . ? N1 N2 C1 C2 -1.59(17) . . . . ? C12 N2 C1 C2 -175.60(19) . . . . ? N1 N2 C1 C4 173.98(15) . . . . ? C12 N2 C1 C4 0.0(3) . . . . ? N2 C1 C2 C3 1.39(18) . . . . ? C4 C1 C2 C3 -174.34(15) . . . . ? N2 N1 C3 C2 -0.32(17) . . . . ? B N1 C3 C2 174.04(19) . . . . ? N2 N1 C3 C8 179.95(14) . . . . ? B N1 C3 C8 -5.7(3) . . . . ? C1 C2 C3 N1 -0.68(18) . . . . ? C1 C2 C3 C8 179.05(15) . . . . ? N2 C1 C4 C6 70.2(2) . . . . ? C2 C1 C4 C6 -115.05(18) . . . . ? N2 C1 C4 C5 -54.5(2) . . . . ? C2 C1 C4 C5 120.23(18) . . . . ? N2 C1 C4 C7 -171.95(16) . . . . ? C2 C1 C4 C7 2.8(2) . . . . ? N1 C3 C8 C10 -45.5(2) . . . . ? C2 C3 C8 C10 134.87(16) . . . . ? N1 C3 C8 C11 -164.64(15) . . . . ? C2 C3 C8 C11 15.7(2) . . . . ? N1 C3 C8 C9 76.96(19) . . . . ? C2 C3 C8 C9 -102.72(18) . . . . ? B N3 C12 N2 5.91(18) . . . . ? B N3 C12 C13 -172.59(14) . . . . ? C1 N2 C12 N3 169.65(19) . . . . ? N1 N2 C12 N3 -4.44(18) . . . . ? C1 N2 C12 C13 -11.9(3) . . . . ? N1 N2 C12 C13 174.03(14) . . . . ? N3 C12 C13 C18 105.93(19) . . . . ? N2 C12 C13 C18 -72.4(2) . . . . ? N3 C12 C13 C14 -63.0(2) . . . . ? N2 C12 C13 C14 118.69(16) . . . . ? C18 C13 C14 C15 2.7(2) . . . . ? C12 C13 C14 C15 171.80(15) . . . . ? C13 C14 C15 C16 -0.8(2) . . . . ? C14 C15 C16 C17 -1.2(3) . . . . ? C15 C16 C17 C18 1.2(3) . . . . ? C16 C17 C18 C13 0.8(2) . . . . ? C14 C13 C18 C17 -2.7(2) . . . . ? C12 C13 C18 C17 -171.37(15) . . . . ? C12 N3 B N1 -4.71(17) . . . . ? C12 N3 B C19 114.7(2) . . . . ? C12 N3 B C25 -120.06(14) . . . . ? C12 N3 B C19' 104.9(4) . . . . ? C3 N1 B N3 -172.49(19) . . . . ? N2 N1 B N3 1.89(15) . . . . ? C3 N1 B C19 78.4(3) . . . . ? N2 N1 B C19 -107.2(3) . . . . ? C3 N1 B C25 -55.5(3) . . . . ? N2 N1 B C25 118.89(13) . . . . ? C3 N1 B C19' 79.5(9) . . . . ? N2 N1 B C19' -106.1(8) . . . . ? N3 B C19 C20 80.2(4) . . . . ? N1 B C19 C20 -172.4(3) . . . . ? C25 B C19 C20 -41.8(5) . . . . ? C19' B C19 C20 -179(6) . . . . ? N3 B C19 C24 -89.7(5) . . . . ? N1 B C19 C24 17.7(6) . . . . ? C25 B C19 C24 148.3(4) . . . . ? C19' B C19 C24 11(5) . . . . ? C24 C19 C20 C21 -3.4(6) . . . . ? B C19 C20 C21 -174.4(3) . . . . ? C24 C19 C20 F1 174.5(3) . . . . ? B C19 C20 F1 3.4(5) . . . . ? F1 C20 C21 F2 4.0(3) . . . . ? C19 C20 C21 F2 -178.1(3) . . . . ? F1 C20 C21 C22 -175.1(2) . . . . ? C19 C20 C21 C22 2.8(4) . . . . ? F2 C21 C22 F3 -0.5(3) . . . . ? C20 C21 C22 F3 178.6(2) . . . . ? F2 C21 C22 C23 -179.2(2) . . . . ? C20 C21 C22 C23 -0.2(3) . . . . ? F3 C22 C23 F4 -0.3(4) . . . . ? C21 C22 C23 F4 178.5(2) . . . . ? F3 C22 C23 C24 179.8(3) . . . . ? C21 C22 C23 C24 -1.5(4) . . . . ? F4 C23 C24 F5 -1.6(4) . . . . ? C22 C23 C24 F5 178.3(3) . . . . ? F4 C23 C24 C19 -179.1(4) . . . . ? C22 C23 C24 C19 0.8(5) . . . . ? C20 C19 C24 F5 -175.9(3) . . . . ? B C19 C24 F5 -5.3(7) . . . . ? C20 C19 C24 C23 1.5(6) . . . . ? B C19 C24 C23 172.2(3) . . . . ? N3 B C19' C24' -81.5(19) . . . . ? N1 B C19' C24' 23(2) . . . . ? C19 B C19' C24' -163(8) . . . . ? C25 B C19' C24' 150.3(15) . . . . ? N3 B C19' C20' 77.1(17) . . . . ? N1 B C19' C20' -178.2(15) . . . . ? C19 B C19' C20' -4(4) . . . . ? C25 B C19' C20' -51(2) . . . . ? C24' C19' C20' F1' 173.5(16) . . . . ? B C19' C20' F1' 12(3) . . . . ? C24' C19' C20' C21' -12(3) . . . . ? B C19' C20' C21' -173.0(14) . . . . ? F1' C20' C21' F2' 2(2) . . . . ? C19' C20' C21' F2' -172.9(16) . . . . ? F1' C20' C21' C22' -174.8(13) . . . . ? C19' C20' C21' C22' 10(2) . . . . ? F2' C21' C22' F3' 1.5(18) . . . . ? C20' C21' C22' F3' 178.1(11) . . . . ? F2' C21' C22' C23' 178.1(10) . . . . ? C20' C21' C22' C23' -5.4(19) . . . . ? C21' C22' C23' F4' 179.9(10) . . . . ? F3' C22' C23' F4' -3.6(17) . . . . ? C21' C22' C23' C24' 3.2(18) . . . . ? F3' C22' C23' C24' 179.7(10) . . . . ? C20' C19' C24' F5' -171.5(14) . . . . ? B C19' C24' F5' -11(3) . . . . ? C20' C19' C24' C23' 9(3) . . . . ? B C19' C24' C23' 169.5(13) . . . . ? F4' C23' C24' F5' -1.7(17) . . . . ? C22' C23' C24' F5' 175.0(12) . . . . ? F4' C23' C24' C19' 177.7(16) . . . . ? C22' C23' C24' C19' -6(2) . . . . ? N3 B C25 C26 41.69(19) . . . . ? N1 B C25 C26 -67.58(18) . . . . ? C19 B C25 C26 158.8(2) . . . . ? C19' B C25 C26 166.7(8) . . . . ? N3 B C25 C30 -137.30(16) . . . . ? N1 B C25 C30 113.43(17) . . . . ? C19 B C25 C30 -20.2(3) . . . . ? C19' B C25 C30 -12.3(8) . . . . ? C30 C25 C26 F6 -177.43(14) . . . . ? B C25 C26 F6 3.5(2) . . . . ? C30 C25 C26 C27 1.6(2) . . . . ? B C25 C26 C27 -177.47(15) . . . . ? F6 C26 C27 F7 -1.7(2) . . . . ? C25 C26 C27 F7 179.21(15) . . . . ? F6 C26 C27 C28 178.66(15) . . . . ? C25 C26 C27 C28 -0.4(3) . . . . ? F7 C27 C28 F8 2.5(3) . . . . ? C26 C27 C28 F8 -177.85(15) . . . . ? F7 C27 C28 C29 -179.98(16) . . . . ? C26 C27 C28 C29 -0.3(3) . . . . ? F8 C28 C29 F9 -0.7(2) . . . . ? C27 C28 C29 F9 -178.25(15) . . . . ? F8 C28 C29 C30 177.30(15) . . . . ? C27 C28 C29 C30 -0.2(3) . . . . ? F9 C29 C30 F10 1.1(2) . . . . ? C28 C29 C30 F10 -176.86(15) . . . . ? F9 C29 C30 C25 179.63(15) . . . . ? C28 C29 C30 C25 1.6(3) . . . . ? C26 C25 C30 F10 176.19(14) . . . . ? B C25 C30 F10 -4.8(2) . . . . ? C26 C25 C30 C29 -2.2(2) . . . . ? B C25 C30 C29 176.80(15) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.298 _refine_diff_density_min -0.244 _refine_diff_density_rms 0.041 # # end of cif data for "eileen38"