Supplementary Material for Organic & Biomolecular Chemistry This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _publ_contact_author_name 'Hiromitsu Maeda' _publ_contact_author_address ; Department of Bioscience and Biotechnology, Faculty of Science and Engineering Ritsumeikan University 1-1-1 Nojihigashi Kusatsu Shiga 525-8577 JAPAN ; _publ_contact_author_email MAEDAHIR@SE.RITSUMEI.AC.JP _publ_section_title ; BF2 complexes of ?-alkyl-substituted dipyrrolyldiketones as acyclic anion receptors ; loop_ _publ_author_name 'Hiromitsu Maeda' 'Yohei Haketa' 'Yukio Kusunose' 'Yuta Mihashi' 'Masahiro Terasaki' # Attachment 'BF2_R_HMaeda_CIF.CIF' data_70105mae _database_code_depnum_ccdc_archive 'CCDC 666247' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C26 H26 B2 F4 N4 O4' _chemical_formula_sum 'C26 H26 B2 F4 N4 O4' _chemical_formula_weight 556.13 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.336(5) _cell_length_b 11.777(9) _cell_length_c 12.965(11) _cell_angle_alpha 84.71(3) _cell_angle_beta 83.95(3) _cell_angle_gamma 87.53(3) _cell_volume 1259.7(16) _cell_formula_units_Z 2 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 4447 _cell_measurement_theta_min 3.1 _cell_measurement_theta_max 27.6 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.466 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 576 _exptl_absorpt_coefficient_mu 0.118 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9543 _exptl_absorpt_correction_T_max 0.9941 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku RAXIS-RAPID' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.00 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12042 _diffrn_reflns_av_R_equivalents 0.0376 _diffrn_reflns_av_sigmaI/netI 0.0585 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.06 _diffrn_reflns_theta_max 27.48 _reflns_number_total 5530 _reflns_number_gt 1854 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0963P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5530 _refine_ls_number_parameters 365 _refine_ls_number_restraints 264 _refine_ls_R_factor_all 0.1329 _refine_ls_R_factor_gt 0.0447 _refine_ls_wR_factor_ref 0.1930 _refine_ls_wR_factor_gt 0.1431 _refine_ls_goodness_of_fit_ref 0.918 _refine_ls_restrained_S_all 0.899 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.5646(6) 0.0681(4) -0.3968(4) 0.0309(13) Uani 1 1 d U . . H1 H 0.5745 -0.0119 -0.3693 0.046 Uiso 1 1 calc R . . H2 H 0.6146 0.0768 -0.4689 0.046 Uiso 1 1 calc R . . H3 H 0.4502 0.0916 -0.3950 0.046 Uiso 1 1 calc R . . C2 C 0.6477(6) 0.1411(4) -0.3319(4) 0.0253(11) Uani 1 1 d U . . C3 C 0.7543(5) 0.2279(4) -0.3612(4) 0.0285(12) Uani 1 1 d U . . H4 H 0.7902 0.2555 -0.4306 0.034 Uiso 1 1 calc R . . C4 C 0.8001(5) 0.2678(4) -0.2702(4) 0.0236(11) Uani 1 1 d U . . H5 H 0.8737 0.3264 -0.2666 0.028 Uiso 1 1 calc R . . C5 C 0.7180(5) 0.2061(4) -0.1867(4) 0.0187(10) Uani 1 1 d U . . C6 C 0.7111(5) 0.2135(4) -0.0766(4) 0.0188(10) Uani 1 1 d U . . C7 C 0.8121(5) 0.2811(4) -0.0317(4) 0.0202(10) Uani 1 1 d U . . H6 H 0.8944 0.3223 -0.0736 0.024 Uiso 1 1 calc R . . C8 C 0.7909(5) 0.2878(4) 0.0759(4) 0.0191(10) Uani 1 1 d U . . C9 C 0.8914(5) 0.3490(4) 0.1315(4) 0.0192(10) Uani 1 1 d U . . C10 C 1.0382(6) 0.4015(4) 0.1005(4) 0.0256(11) Uani 1 1 d U . . H7 H 1.0932 0.4077 0.0323 0.031 Uiso 1 1 calc R . . C11 C 1.0892(6) 0.4434(4) 0.1900(4) 0.0268(12) Uani 1 1 d U . . H8 H 1.1863 0.4818 0.1931 0.032 Uiso 1 1 calc R . . C12 C 0.9732(6) 0.4188(4) 0.2720(4) 0.0251(11) Uani 1 1 d U . . C13 C 0.9643(6) 0.4480(4) 0.3822(4) 0.0306(13) Uani 1 1 d U . . H9 H 0.8987 0.5183 0.3900 0.046 Uiso 1 1 calc R . . H10 H 1.0733 0.4591 0.4004 0.046 Uiso 1 1 calc R . . H11 H 0.9150 0.3856 0.4284 0.046 Uiso 1 1 calc R . . C14 C 0.4339(5) 0.4328(4) 0.8973(5) 0.0322(14) Uani 1 1 d U . . H12 H 0.5412 0.4515 0.8632 0.048 Uiso 1 1 calc R . . H13 H 0.4444 0.3923 0.9659 0.048 Uiso 1 1 calc R . . H14 H 0.3687 0.5033 0.9056 0.048 Uiso 1 1 calc R . . C15 C 0.3535(5) 0.3586(4) 0.8321(4) 0.0224(11) Uani 1 1 d U . . C16 C 0.2455(5) 0.2706(4) 0.8609(4) 0.0270(12) Uani 1 1 d U . . H15 H 0.2095 0.2424 0.9301 0.032 Uiso 1 1 calc R . . C17 C 0.1999(6) 0.2315(4) 0.7702(4) 0.0266(12) Uani 1 1 d U . . H16 H 0.1262 0.1730 0.7664 0.032 Uiso 1 1 calc R . . C18 C 0.2829(5) 0.2943(4) 0.6861(4) 0.0207(11) Uani 1 1 d U . . C19 C 0.2878(5) 0.2869(4) 0.5772(4) 0.0194(10) Uani 1 1 d U . . C20 C 0.1882(5) 0.2184(4) 0.5309(4) 0.0192(10) Uani 1 1 d U . . H17 H 0.1068 0.1761 0.5725 0.023 Uiso 1 1 calc R . . C21 C 0.2089(5) 0.2125(4) 0.4239(4) 0.0189(10) Uani 1 1 d U . . C22 C 0.1069(5) 0.1505(4) 0.3688(4) 0.0194(10) Uani 1 1 d U . . C23 C -0.0386(5) 0.0987(4) 0.3991(4) 0.0239(11) Uani 1 1 d U . . H18 H -0.0938 0.0930 0.4672 0.029 Uiso 1 1 calc R . . C24 C -0.0889(6) 0.0566(4) 0.3116(4) 0.0279(12) Uani 1 1 d U . . H19 H -0.1859 0.0178 0.3094 0.033 Uiso 1 1 calc R . . C25 C 0.0256(6) 0.0807(4) 0.2286(4) 0.0237(11) Uani 1 1 d U . . C26 C 0.0350(6) 0.0526(4) 0.1183(4) 0.0336(13) Uani 1 1 d U . . H20 H 0.0107 0.1216 0.0735 0.050 Uiso 1 1 calc R . . H21 H -0.0435 -0.0053 0.1120 0.050 Uiso 1 1 calc R . . H22 H 0.1439 0.0232 0.0967 0.050 Uiso 1 1 calc R . . N1 N 0.6254(4) 0.1298(3) -0.2269(3) 0.0213(9) Uani 1 1 d U . . H23 H 0.5612 0.0809 -0.1895 0.026 Uiso 1 1 calc R . . N2 N 0.8566(4) 0.3611(3) 0.2358(3) 0.0218(9) Uani 1 1 d U . . H24 H 0.7703 0.3350 0.2741 0.026 Uiso 1 1 calc R . . N3 N 0.3763(4) 0.3711(3) 0.7268(3) 0.0212(9) Uani 1 1 d U . . H25 H 0.4405 0.4203 0.6897 0.025 Uiso 1 1 calc R . . N4 N 0.1438(5) 0.1387(3) 0.2634(3) 0.0219(9) Uani 1 1 d U . . H26 H 0.2302 0.1647 0.2250 0.026 Uiso 1 1 calc R . . O1 O 0.6014(4) 0.1509(3) -0.0204(3) 0.0266(8) Uani 1 1 d U . . O2 O 0.6719(4) 0.2347(3) 0.1340(3) 0.0250(8) Uani 1 1 d U . . O3 O 0.3983(4) 0.3489(3) 0.5204(3) 0.0264(8) Uani 1 1 d U . . O4 O 0.3290(4) 0.2640(3) 0.3662(3) 0.0274(8) Uani 1 1 d U . . B1 B 0.5662(7) 0.1577(6) 0.0920(5) 0.0321(15) Uani 1 1 d U . . B2 B 0.4344(7) 0.3422(6) 0.4078(5) 0.0303(14) Uani 1 1 d U . . F1 F 0.5859(5) 0.0501(3) 0.1418(3) 0.0666(13) Uani 1 1 d U . . F2 F 0.4087(3) 0.1970(4) 0.1109(3) 0.0652(12) Uani 1 1 d U . . F3 F 0.4145(5) 0.4495(3) 0.3580(3) 0.0660(13) Uani 1 1 d U . . F4 F 0.5915(3) 0.3038(4) 0.3890(3) 0.0676(13) Uani 1 1 d U . . 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 C1 0.032(3) 0.037(3) 0.027(3) -0.015(3) -0.005(2) 0.002(2) C2 0.026(3) 0.028(3) 0.024(3) -0.005(2) -0.009(2) 0.007(2) C3 0.027(3) 0.044(3) 0.016(3) -0.009(2) -0.001(2) 0.001(2) C4 0.021(2) 0.030(3) 0.019(3) 0.000(2) 0.002(2) -0.005(2) C5 0.020(2) 0.018(2) 0.019(3) -0.009(2) -0.0020(19) 0.0020(17) C6 0.025(2) 0.019(2) 0.012(2) 0.0010(19) -0.0024(19) 0.0005(19) C7 0.022(2) 0.023(3) 0.015(3) -0.001(2) 0.0014(19) 0.0008(18) C8 0.021(2) 0.021(3) 0.014(3) 0.005(2) -0.0013(19) 0.0003(19) C9 0.023(2) 0.019(2) 0.015(2) 0.0001(19) -0.0014(19) 0.0008(19) C10 0.036(3) 0.022(3) 0.019(3) 0.001(2) -0.003(2) -0.005(2) C11 0.030(2) 0.031(3) 0.022(3) -0.004(2) -0.010(2) -0.009(2) C12 0.033(3) 0.016(2) 0.027(3) -0.004(2) -0.006(2) 0.003(2) C13 0.052(3) 0.025(3) 0.016(3) -0.006(2) -0.011(2) 0.008(2) C14 0.025(3) 0.039(3) 0.037(4) -0.018(3) -0.015(2) 0.009(2) C15 0.016(2) 0.033(3) 0.020(3) -0.011(2) -0.0007(19) 0.0015(19) C16 0.026(2) 0.037(3) 0.017(3) -0.003(2) 0.003(2) -0.006(2) C17 0.027(3) 0.032(3) 0.021(3) -0.007(2) -0.001(2) -0.005(2) C18 0.018(2) 0.027(3) 0.018(3) 0.001(2) -0.0041(19) -0.0034(18) C19 0.015(2) 0.020(2) 0.021(3) 0.002(2) 0.0012(19) -0.0025(18) C20 0.020(2) 0.022(3) 0.016(3) 0.004(2) -0.0037(19) -0.0085(19) C21 0.020(2) 0.017(2) 0.019(3) -0.003(2) 0.001(2) 0.0018(18) C22 0.025(2) 0.021(2) 0.012(2) 0.0019(19) -0.0023(19) -0.0012(19) C23 0.024(2) 0.030(3) 0.018(3) -0.002(2) -0.001(2) -0.008(2) C24 0.039(3) 0.023(3) 0.022(3) 0.003(2) -0.004(2) -0.010(2) C25 0.038(3) 0.021(3) 0.013(3) 0.000(2) -0.009(2) -0.001(2) C26 0.053(3) 0.030(3) 0.020(3) -0.006(2) -0.010(3) -0.001(2) N1 0.022(2) 0.019(2) 0.023(2) -0.0011(17) -0.0025(17) -0.0007(15) N2 0.025(2) 0.025(2) 0.014(2) -0.0008(18) 0.0004(17) 0.0025(16) N3 0.0185(19) 0.026(2) 0.020(2) -0.0055(18) -0.0036(17) -0.0057(16) N4 0.028(2) 0.024(2) 0.014(2) -0.0026(18) -0.0015(17) -0.0025(16) O1 0.0291(18) 0.030(2) 0.021(2) 0.0005(17) 0.0033(15) -0.0140(15) O2 0.0282(17) 0.032(2) 0.0148(19) -0.0012(15) 0.0013(14) -0.0096(15) O3 0.0286(18) 0.032(2) 0.020(2) -0.0030(17) -0.0003(15) -0.0128(15) O4 0.0258(17) 0.037(2) 0.019(2) -0.0034(17) 0.0067(14) -0.0124(15) B1 0.027(3) 0.050(4) 0.020(3) 0.005(3) -0.003(2) -0.018(3) B2 0.028(3) 0.046(4) 0.017(3) 0.005(3) -0.001(2) -0.017(3) F1 0.108(3) 0.055(2) 0.043(2) 0.026(2) -0.042(2) -0.051(2) F2 0.0240(16) 0.150(4) 0.024(2) -0.022(2) 0.0019(14) -0.013(2) F3 0.108(3) 0.057(2) 0.039(2) 0.023(2) -0.040(2) -0.055(2) F4 0.0234(16) 0.158(4) 0.024(2) -0.024(2) 0.0040(14) -0.014(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.496(6) . ? C1 H1 0.9800 . ? C1 H2 0.9800 . ? C1 H3 0.9800 . ? C2 N1 1.349(7) . ? C2 C3 1.384(7) . ? C3 C4 1.405(7) . ? C3 H4 0.9500 . ? C4 C5 1.382(7) . ? C4 H5 0.9500 . ? C5 N1 1.380(5) . ? C5 C6 1.433(7) . ? C6 O1 1.315(5) . ? C6 C7 1.388(6) . ? C7 C8 1.396(7) . ? C7 H6 0.9500 . ? C8 O2 1.324(5) . ? C8 C9 1.420(6) . ? C9 N2 1.373(7) . ? C9 C10 1.399(6) . ? C10 C11 1.414(7) . ? C10 H7 0.9500 . ? C11 C12 1.378(7) . ? C11 H8 0.9500 . ? C12 N2 1.356(6) . ? C12 C13 1.493(7) . ? C13 H9 0.9800 . ? C13 H10 0.9800 . ? C13 H11 0.9800 . ? C14 C15 1.495(6) . ? C14 H12 0.9800 . ? C14 H13 0.9800 . ? C14 H14 0.9800 . ? C15 N3 1.354(6) . ? C15 C16 1.401(6) . ? C16 C17 1.396(7) . ? C16 H15 0.9500 . ? C17 C18 1.397(7) . ? C17 H16 0.9500 . ? C18 N3 1.392(5) . ? C18 C19 1.419(7) . ? C19 O3 1.319(5) . ? C19 C20 1.397(6) . ? C20 C21 1.387(7) . ? C20 H17 0.9500 . ? C21 O4 1.320(5) . ? C21 C22 1.430(6) . ? C22 C23 1.384(6) . ? C22 N4 1.387(7) . ? C23 C24 1.389(7) . ? C23 H18 0.9500 . ? C24 C25 1.379(7) . ? C24 H19 0.9500 . ? C25 N4 1.360(5) . ? C25 C26 1.491(7) . ? C26 H20 0.9800 . ? C26 H21 0.9800 . ? C26 H22 0.9800 . ? N1 H23 0.8800 . ? N2 H24 0.8800 . ? N3 H25 0.8800 . ? N4 H26 0.8800 . ? O1 B1 1.465(7) . ? O2 B1 1.468(6) . ? O3 B2 1.468(7) . ? O4 B2 1.474(6) . ? B1 F2 1.378(7) . ? B1 F1 1.380(7) . ? B2 F4 1.371(7) . ? B2 F3 1.377(7) . ? 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 C2 C1 H1 109.5 . . ? C2 C1 H2 109.5 . . ? H1 C1 H2 109.5 . . ? C2 C1 H3 109.5 . . ? H1 C1 H3 109.5 . . ? H2 C1 H3 109.5 . . ? N1 C2 C3 107.6(4) . . ? N1 C2 C1 122.1(5) . . ? C3 C2 C1 130.3(5) . . ? C2 C3 C4 107.8(5) . . ? C2 C3 H4 126.1 . . ? C4 C3 H4 126.1 . . ? C5 C4 C3 107.2(4) . . ? C5 C4 H5 126.4 . . ? C3 C4 H5 126.4 . . ? N1 C5 C4 107.2(4) . . ? N1 C5 C6 120.8(4) . . ? C4 C5 C6 132.0(4) . . ? O1 C6 C7 122.0(4) . . ? O1 C6 C5 114.9(4) . . ? C7 C6 C5 123.1(4) . . ? C6 C7 C8 119.1(5) . . ? C6 C7 H6 120.5 . . ? C8 C7 H6 120.5 . . ? O2 C8 C7 120.7(4) . . ? O2 C8 C9 114.9(4) . . ? C7 C8 C9 124.4(4) . . ? N2 C9 C10 106.7(4) . . ? N2 C9 C8 121.9(4) . . ? C10 C9 C8 131.4(5) . . ? C9 C10 C11 106.9(5) . . ? C9 C10 H7 126.5 . . ? C11 C10 H7 126.5 . . ? C12 C11 C10 107.9(4) . . ? C12 C11 H8 126.0 . . ? C10 C11 H8 126.0 . . ? N2 C12 C11 107.6(5) . . ? N2 C12 C13 122.6(5) . . ? C11 C12 C13 129.9(4) . . ? C12 C13 H9 109.5 . . ? C12 C13 H10 109.5 . . ? H9 C13 H10 109.5 . . ? C12 C13 H11 109.5 . . ? H9 C13 H11 109.5 . . ? H10 C13 H11 109.5 . . ? C15 C14 H12 109.5 . . ? C15 C14 H13 109.5 . . ? H12 C14 H13 109.5 . . ? C15 C14 H14 109.5 . . ? H12 C14 H14 109.5 . . ? H13 C14 H14 109.5 . . ? N3 C15 C16 107.7(4) . . ? N3 C15 C14 121.7(5) . . ? C16 C15 C14 130.6(5) . . ? C17 C16 C15 108.1(5) . . ? C17 C16 H15 125.9 . . ? C15 C16 H15 125.9 . . ? C16 C17 C18 107.2(4) . . ? C16 C17 H16 126.4 . . ? C18 C17 H16 126.4 . . ? N3 C18 C17 107.3(4) . . ? N3 C18 C19 121.4(4) . . ? C17 C18 C19 131.3(4) . . ? O3 C19 C20 121.0(5) . . ? O3 C19 C18 114.7(4) . . ? C20 C19 C18 124.3(4) . . ? C21 C20 C19 119.7(5) . . ? C21 C20 H17 120.2 . . ? C19 C20 H17 120.2 . . ? O4 C21 C20 120.8(4) . . ? O4 C21 C22 115.4(4) . . ? C20 C21 C22 123.8(4) . . ? C23 C22 N4 107.2(4) . . ? C23 C22 C21 132.0(5) . . ? N4 C22 C21 120.7(4) . . ? C22 C23 C24 107.4(5) . . ? C22 C23 H18 126.3 . . ? C24 C23 H18 126.3 . . ? C25 C24 C23 108.5(4) . . ? C25 C24 H19 125.8 . . ? C23 C24 H19 125.8 . . ? N4 C25 C24 107.6(4) . . ? N4 C25 C26 121.3(5) . . ? C24 C25 C26 131.1(4) . . ? C25 C26 H20 109.5 . . ? C25 C26 H21 109.5 . . ? H20 C26 H21 109.5 . . ? C25 C26 H22 109.5 . . ? H20 C26 H22 109.5 . . ? H21 C26 H22 109.5 . . ? C2 N1 C5 110.1(4) . . ? C2 N1 H23 124.9 . . ? C5 N1 H23 124.9 . . ? C12 N2 C9 110.9(4) . . ? C12 N2 H24 124.6 . . ? C9 N2 H24 124.6 . . ? C15 N3 C18 109.7(4) . . ? C15 N3 H25 125.2 . . ? C18 N3 H25 125.2 . . ? C25 N4 C22 109.3(4) . . ? C25 N4 H26 125.3 . . ? C22 N4 H26 125.3 . . ? C6 O1 B1 122.0(4) . . ? C8 O2 B1 122.6(4) . . ? C19 O3 B2 122.6(4) . . ? C21 O4 B2 122.7(4) . . ? F2 B1 F1 110.1(5) . . ? F2 B1 O1 107.9(4) . . ? F1 B1 O1 108.7(5) . . ? F2 B1 O2 108.7(5) . . ? F1 B1 O2 108.3(4) . . ? O1 B1 O2 113.1(4) . . ? F4 B2 F3 109.9(5) . . ? F4 B2 O3 108.2(4) . . ? F3 B2 O3 108.8(5) . . ? F4 B2 O4 108.7(5) . . ? F3 B2 O4 108.6(4) . . ? O3 B2 O4 112.6(4) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C2 C3 C4 1.4(5) . . . . ? C1 C2 C3 C4 -178.8(5) . . . . ? C2 C3 C4 C5 -1.1(5) . . . . ? C3 C4 C5 N1 0.4(5) . . . . ? C3 C4 C5 C6 -176.6(5) . . . . ? N1 C5 C6 O1 -6.0(6) . . . . ? C4 C5 C6 O1 170.7(5) . . . . ? N1 C5 C6 C7 174.0(4) . . . . ? C4 C5 C6 C7 -9.3(8) . . . . ? O1 C6 C7 C8 -3.5(7) . . . . ? C5 C6 C7 C8 176.5(4) . . . . ? C6 C7 C8 O2 -3.1(7) . . . . ? C6 C7 C8 C9 176.5(4) . . . . ? O2 C8 C9 N2 -6.3(6) . . . . ? C7 C8 C9 N2 174.0(4) . . . . ? O2 C8 C9 C10 170.3(4) . . . . ? C7 C8 C9 C10 -9.4(8) . . . . ? N2 C9 C10 C11 0.7(5) . . . . ? C8 C9 C10 C11 -176.3(5) . . . . ? C9 C10 C11 C12 -1.4(5) . . . . ? C10 C11 C12 N2 1.5(5) . . . . ? C10 C11 C12 C13 -177.4(5) . . . . ? N3 C15 C16 C17 -1.4(5) . . . . ? C14 C15 C16 C17 177.3(5) . . . . ? C15 C16 C17 C18 1.2(5) . . . . ? C16 C17 C18 N3 -0.5(5) . . . . ? C16 C17 C18 C19 176.8(5) . . . . ? N3 C18 C19 O3 6.7(7) . . . . ? C17 C18 C19 O3 -170.3(5) . . . . ? N3 C18 C19 C20 -174.8(4) . . . . ? C17 C18 C19 C20 8.2(9) . . . . ? O3 C19 C20 C21 2.0(7) . . . . ? C18 C19 C20 C21 -176.4(4) . . . . ? C19 C20 C21 O4 5.1(7) . . . . ? C19 C20 C21 C22 -176.0(4) . . . . ? O4 C21 C22 C23 -170.9(5) . . . . ? C20 C21 C22 C23 10.1(8) . . . . ? O4 C21 C22 N4 5.5(6) . . . . ? C20 C21 C22 N4 -173.5(4) . . . . ? N4 C22 C23 C24 -0.4(5) . . . . ? C21 C22 C23 C24 176.4(5) . . . . ? C22 C23 C24 C25 0.9(6) . . . . ? C23 C24 C25 N4 -1.1(6) . . . . ? C23 C24 C25 C26 178.1(5) . . . . ? C3 C2 N1 C5 -1.1(5) . . . . ? C1 C2 N1 C5 179.1(4) . . . . ? C4 C5 N1 C2 0.4(5) . . . . ? C6 C5 N1 C2 177.9(4) . . . . ? C11 C12 N2 C9 -1.1(5) . . . . ? C13 C12 N2 C9 177.9(4) . . . . ? C10 C9 N2 C12 0.2(5) . . . . ? C8 C9 N2 C12 177.6(4) . . . . ? C16 C15 N3 C18 1.1(5) . . . . ? C14 C15 N3 C18 -177.8(4) . . . . ? C17 C18 N3 C15 -0.4(5) . . . . ? C19 C18 N3 C15 -178.1(4) . . . . ? C24 C25 N4 C22 0.9(5) . . . . ? C26 C25 N4 C22 -178.4(5) . . . . ? C23 C22 N4 C25 -0.3(5) . . . . ? C21 C22 N4 C25 -177.5(4) . . . . ? C7 C6 O1 B1 6.8(7) . . . . ? C5 C6 O1 B1 -173.2(5) . . . . ? C7 C8 O2 B1 6.2(7) . . . . ? C9 C8 O2 B1 -173.5(5) . . . . ? C20 C19 O3 B2 -5.9(7) . . . . ? C18 C19 O3 B2 172.7(5) . . . . ? C20 C21 O4 B2 -8.2(7) . . . . ? C22 C21 O4 B2 172.8(5) . . . . ? C6 O1 B1 F2 116.7(5) . . . . ? C6 O1 B1 F1 -123.9(4) . . . . ? C6 O1 B1 O2 -3.6(7) . . . . ? C8 O2 B1 F2 -122.8(5) . . . . ? C8 O2 B1 F1 117.6(5) . . . . ? C8 O2 B1 O1 -2.9(7) . . . . ? C19 O3 B2 F4 -117.2(5) . . . . ? C19 O3 B2 F3 123.3(5) . . . . ? C19 O3 B2 O4 2.9(7) . . . . ? C21 O4 B2 F4 124.1(5) . . . . ? C21 O4 B2 F3 -116.3(5) . . . . ? C21 O4 B2 O3 4.3(7) . . . . ? _diffrn_measured_fraction_theta_max 0.959 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.959 _refine_diff_density_max 0.262 _refine_diff_density_min -0.330 _refine_diff_density_rms 0.069 #============================================================================== # End of CIF #============================================================================== data_70616mae _database_code_depnum_ccdc_archive 'CCDC 666248' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H17 B F2 N2 O2' _chemical_formula_sum 'C15 H17 B F2 N2 O2' _chemical_formula_weight 306.12 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.272(11) _cell_length_b 11.368(17) _cell_length_c 16.05(3) _cell_angle_alpha 98.48(5) _cell_angle_beta 104.48(6) _cell_angle_gamma 109.80(3) _cell_volume 1491(4) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prizm _exptl_crystal_colour yellow _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.364 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 640 _exptl_absorpt_coefficient_mu 0.107 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9487 _exptl_absorpt_correction_T_max 0.9790 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku RAXIS-RAPID' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.00 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12504 _diffrn_reflns_av_R_equivalents 0.1076 _diffrn_reflns_av_sigmaI/netI 0.1713 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.02 _diffrn_reflns_theta_max 27.48 _reflns_number_total 6399 _reflns_number_gt 3324 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1080P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6399 _refine_ls_number_parameters 401 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1228 _refine_ls_R_factor_gt 0.0744 _refine_ls_wR_factor_ref 0.2386 _refine_ls_wR_factor_gt 0.1738 _refine_ls_goodness_of_fit_ref 0.995 _refine_ls_restrained_S_all 0.995 _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 C1 C 0.8519(5) -0.5986(3) -0.1680(3) 0.0437(11) Uani 1 1 d . . . H1 H 0.9025 -0.6332 -0.1218 0.066 Uiso 1 1 calc R . . H2 H 0.8890 -0.6117 -0.2193 0.066 Uiso 1 1 calc R . . H3 H 0.7339 -0.6436 -0.1864 0.066 Uiso 1 1 calc R . . C2 C 0.8992(5) -0.4543(3) -0.1311(2) 0.0303(9) Uani 1 1 d . . . H4 H 1.0186 -0.4097 -0.1116 0.036 Uiso 1 1 calc R . . H5 H 0.8534 -0.4189 -0.1791 0.036 Uiso 1 1 calc R . . C3 C 0.8413(4) -0.4265(3) -0.0548(2) 0.0262(8) Uani 1 1 d . . . C4 C 0.7596(5) -0.5065(3) -0.0100(3) 0.0300(9) Uani 1 1 d . . . H6 H 0.7252 -0.5978 -0.0229 0.036 Uiso 1 1 calc R . . C5 C 0.7369(4) -0.4296(3) 0.0570(2) 0.0288(9) Uani 1 1 d . . . H7 H 0.6853 -0.4590 0.0986 0.035 Uiso 1 1 calc R . . C6 C 0.8024(4) -0.3027(3) 0.0528(2) 0.0258(8) Uani 1 1 d . . . C7 C 0.8157(4) -0.1841(3) 0.1051(2) 0.0241(8) Uani 1 1 d . . . C8 C 0.7786(4) -0.1736(3) 0.1833(2) 0.0276(9) Uani 1 1 d . . . H8 H 0.7254 -0.2489 0.2004 0.033 Uiso 1 1 calc R . . C9 C 0.8197(4) -0.0518(3) 0.2367(2) 0.0234(8) Uani 1 1 d . . . C10 C 0.8124(4) -0.0292(3) 0.3241(2) 0.0276(8) Uani 1 1 d . . . C11 C 0.7589(4) -0.1134(3) 0.3744(2) 0.0294(9) Uani 1 1 d . . . H9 H 0.7140 -0.2052 0.3553 0.035 Uiso 1 1 calc R . . C12 C 0.7825(4) -0.0398(3) 0.4579(2) 0.0288(8) Uani 1 1 d . . . H10 H 0.7550 -0.0725 0.5054 0.035 Uiso 1 1 calc R . . C13 C 0.8532(4) 0.0893(3) 0.4595(2) 0.0262(8) Uani 1 1 d . . . C14 C 0.9088(5) 0.2079(3) 0.5320(2) 0.0315(9) Uani 1 1 d . . . H11 H 0.8642 0.2687 0.5087 0.038 Uiso 1 1 calc R . . H12 H 1.0284 0.2503 0.5506 0.038 Uiso 1 1 calc R . . C15 C 0.8590(5) 0.1824(4) 0.6128(3) 0.0420(10) Uani 1 1 d . . . H13 H 0.7406 0.1423 0.5953 0.063 Uiso 1 1 calc R . . H14 H 0.8992 0.2642 0.6579 0.063 Uiso 1 1 calc R . . H15 H 0.9050 0.1241 0.6373 0.063 Uiso 1 1 calc R . . C16 C 1.4667(5) 0.7639(3) 0.9114(2) 0.0320(9) Uani 1 1 d . . . H16 H 1.4715 0.6958 0.9416 0.048 Uiso 1 1 calc R . . H17 H 1.4363 0.8246 0.9459 0.048 Uiso 1 1 calc R . . H18 H 1.5730 0.8102 0.9060 0.048 Uiso 1 1 calc R . . C17 C 1.3428(5) 0.7043(3) 0.8202(3) 0.0328(9) Uani 1 1 d . . . H19 H 1.2361 0.6565 0.8260 0.039 Uiso 1 1 calc R . . H20 H 1.3337 0.7739 0.7914 0.039 Uiso 1 1 calc R . . C18 C 1.3845(4) 0.6139(3) 0.7621(2) 0.0254(8) Uani 1 1 d . . . C19 C 1.5011(4) 0.5613(3) 0.7837(2) 0.0284(8) Uani 1 1 d . . . H21 H 1.5727 0.5750 0.8414 0.034 Uiso 1 1 calc R . . C20 C 1.4926(4) 0.4850(3) 0.7046(2) 0.0282(8) Uani 1 1 d . . . H22 H 1.5581 0.4376 0.6987 0.034 Uiso 1 1 calc R . . C21 C 1.3705(4) 0.4905(3) 0.6354(2) 0.0237(8) Uani 1 1 d . . . C22 C 1.3197(4) 0.4360(3) 0.5430(2) 0.0215(7) Uani 1 1 d . . . C23 C 1.3788(4) 0.3547(3) 0.5036(2) 0.0247(8) Uani 1 1 d . . . H23 H 1.4646 0.3377 0.5389 0.030 Uiso 1 1 calc R . . C24 C 1.3142(4) 0.2973(3) 0.4127(3) 0.0249(8) Uani 1 1 d . . . C25 C 1.3615(4) 0.2061(3) 0.3700(2) 0.0241(8) Uani 1 1 d . . . C26 C 1.4792(4) 0.1596(3) 0.4023(3) 0.0292(9) Uani 1 1 d . . . H24 H 1.5524 0.1863 0.4612 0.035 Uiso 1 1 calc R . . C27 C 1.4697(4) 0.0659(3) 0.3314(2) 0.0278(8) Uani 1 1 d . . . H25 H 1.5367 0.0182 0.3340 0.033 Uiso 1 1 calc R . . C28 C 1.3468(4) 0.0542(3) 0.2568(2) 0.0240(8) Uani 1 1 d . . . C29 C 1.2809(5) -0.0365(3) 0.1676(3) 0.0312(9) Uani 1 1 d . . . H26 H 1.2449 0.0077 0.1229 0.037 Uiso 1 1 calc R . . H27 H 1.1845 -0.1109 0.1655 0.037 Uiso 1 1 calc R . . C30 C 1.4003(5) -0.0873(3) 0.1419(3) 0.0358(10) Uani 1 1 d . . . H28 H 1.4931 -0.0150 0.1397 0.054 Uiso 1 1 calc R . . H29 H 1.3468 -0.1491 0.0833 0.054 Uiso 1 1 calc R . . H30 H 1.4379 -0.1304 0.1861 0.054 Uiso 1 1 calc R . . N1 N 0.8654(3) -0.3036(2) -0.01601(19) 0.0243(7) Uani 1 1 d . . . H31 H 0.9144 -0.2346 -0.0327 0.029 Uiso 1 1 calc R . . N2 N 0.8689(4) 0.0940(3) 0.37830(19) 0.0258(7) Uani 1 1 d . . . H32 H 0.9096 0.1656 0.3623 0.031 Uiso 1 1 calc R . . N3 N 1.3083(3) 0.5696(2) 0.67359(19) 0.0232(7) Uani 1 1 d . . . H33 H 1.2292 0.5888 0.6442 0.028 Uiso 1 1 calc R . . N4 N 1.2854(3) 0.1412(2) 0.2822(2) 0.0261(7) Uani 1 1 d . . . H34 H 1.2064 0.1541 0.2466 0.031 Uiso 1 1 calc R . . O1 O 0.8773(3) -0.0813(2) 0.07669(15) 0.0246(6) Uani 1 1 d . . . O2 O 0.8788(3) 0.0533(2) 0.21025(16) 0.0259(6) Uani 1 1 d . . . O3 O 1.2044(3) 0.4653(2) 0.49521(16) 0.0274(6) Uani 1 1 d . . . O4 O 1.1978(3) 0.3235(2) 0.36232(16) 0.0284(6) Uani 1 1 d . . . B1 B 0.8880(5) 0.0462(4) 0.1198(3) 0.0242(9) Uani 1 1 d . . . B2 B 1.1471(5) 0.4241(4) 0.3976(3) 0.0248(9) Uani 1 1 d . . . F1 F 1.0371(2) 0.13766(17) 0.12557(13) 0.0308(5) Uani 1 1 d . . . F2 F 0.7651(3) 0.07300(19) 0.06814(14) 0.0372(6) Uani 1 1 d . . . F3 F 1.1971(3) 0.52848(18) 0.36422(14) 0.0360(6) Uani 1 1 d . . . F4 F 0.9766(2) 0.36778(17) 0.37000(13) 0.0306(5) 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 C1 0.066(3) 0.031(2) 0.046(3) 0.0076(19) 0.030(3) 0.025(2) C2 0.039(2) 0.0281(19) 0.032(2) 0.0085(17) 0.017(2) 0.0171(17) C3 0.030(2) 0.0192(17) 0.032(2) 0.0033(15) 0.0155(19) 0.0101(15) C4 0.039(2) 0.0197(17) 0.037(2) 0.0091(16) 0.020(2) 0.0117(16) C5 0.042(2) 0.0208(18) 0.029(2) 0.0093(16) 0.022(2) 0.0101(16) C6 0.032(2) 0.0224(18) 0.028(2) 0.0070(15) 0.0179(19) 0.0116(16) C7 0.0237(19) 0.0211(17) 0.035(2) 0.0126(15) 0.0154(18) 0.0115(15) C8 0.035(2) 0.0225(18) 0.035(2) 0.0120(16) 0.023(2) 0.0131(16) C9 0.0220(19) 0.0254(18) 0.028(2) 0.0089(15) 0.0124(17) 0.0114(15) C10 0.033(2) 0.0205(17) 0.036(2) 0.0090(16) 0.021(2) 0.0110(16) C11 0.037(2) 0.0180(17) 0.037(2) 0.0051(16) 0.021(2) 0.0097(16) C12 0.032(2) 0.0245(18) 0.029(2) 0.0054(16) 0.0131(19) 0.0084(16) C13 0.031(2) 0.0257(18) 0.028(2) 0.0093(16) 0.0165(18) 0.0126(16) C14 0.036(2) 0.030(2) 0.032(2) 0.0068(17) 0.016(2) 0.0131(17) C15 0.057(3) 0.036(2) 0.034(3) 0.0039(19) 0.017(2) 0.020(2) C16 0.036(2) 0.029(2) 0.026(2) -0.0003(17) 0.0073(19) 0.0119(17) C17 0.033(2) 0.032(2) 0.034(2) 0.0013(18) 0.014(2) 0.0138(18) C18 0.0212(19) 0.0228(17) 0.031(2) 0.0052(16) 0.0103(18) 0.0057(15) C19 0.027(2) 0.0299(19) 0.031(2) 0.0069(17) 0.0120(19) 0.0127(16) C20 0.029(2) 0.0219(18) 0.035(2) 0.0045(16) 0.0125(19) 0.0105(16) C21 0.0256(19) 0.0172(16) 0.031(2) 0.0065(15) 0.0153(18) 0.0070(15) C22 0.0168(18) 0.0208(17) 0.026(2) 0.0093(15) 0.0075(17) 0.0050(14) C23 0.0222(19) 0.0192(17) 0.036(2) 0.0086(16) 0.0134(18) 0.0084(15) C24 0.0206(19) 0.0177(16) 0.037(2) 0.0089(16) 0.0120(18) 0.0050(14) C25 0.025(2) 0.0172(16) 0.031(2) 0.0042(15) 0.0123(18) 0.0070(15) C26 0.028(2) 0.0281(19) 0.032(2) 0.0044(17) 0.0127(19) 0.0115(16) C27 0.029(2) 0.0298(19) 0.029(2) 0.0039(16) 0.0136(19) 0.0151(17) C28 0.0247(19) 0.0182(16) 0.030(2) 0.0046(15) 0.0118(18) 0.0076(15) C29 0.035(2) 0.0228(18) 0.038(2) 0.0033(17) 0.016(2) 0.0124(16) C30 0.042(2) 0.0234(19) 0.044(3) 0.0033(17) 0.021(2) 0.0129(18) N1 0.0326(18) 0.0175(14) 0.0286(18) 0.0089(13) 0.0174(15) 0.0100(13) N2 0.0318(18) 0.0210(15) 0.0274(18) 0.0064(13) 0.0168(16) 0.0083(13) N3 0.0205(16) 0.0230(15) 0.0281(18) 0.0061(13) 0.0081(14) 0.0106(12) N4 0.0276(17) 0.0198(14) 0.0347(19) 0.0056(13) 0.0140(16) 0.0113(13) O1 0.0291(14) 0.0213(12) 0.0245(14) 0.0072(10) 0.0109(12) 0.0091(11) O2 0.0333(15) 0.0189(12) 0.0276(15) 0.0085(11) 0.0149(13) 0.0082(11) O3 0.0302(15) 0.0267(13) 0.0259(15) 0.0022(11) 0.0081(13) 0.0143(11) O4 0.0324(15) 0.0269(13) 0.0293(15) 0.0032(11) 0.0127(13) 0.0154(12) B1 0.018(2) 0.028(2) 0.030(2) 0.0112(19) 0.008(2) 0.0118(17) B2 0.021(2) 0.024(2) 0.036(3) 0.0096(18) 0.014(2) 0.0130(17) F1 0.0382(13) 0.0200(10) 0.0331(13) 0.0082(9) 0.0183(11) 0.0045(9) F2 0.0445(14) 0.0376(13) 0.0312(13) 0.0045(10) 0.0086(12) 0.0223(11) F3 0.0501(15) 0.0258(11) 0.0417(15) 0.0142(10) 0.0246(12) 0.0170(10) F4 0.0218(11) 0.0303(11) 0.0365(14) 0.0009(10) 0.0052(11) 0.0128(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.527(5) . ? C1 H1 0.9800 . ? C1 H2 0.9800 . ? C1 H3 0.9800 . ? C2 C3 1.490(5) . ? C2 H4 0.9900 . ? C2 H5 0.9900 . ? C3 N1 1.361(4) . ? C3 C4 1.383(5) . ? C4 C5 1.389(5) . ? C4 H6 0.9500 . ? C5 C6 1.382(5) . ? C5 H7 0.9500 . ? C6 N1 1.374(4) . ? C6 C7 1.428(5) . ? C7 O1 1.318(4) . ? C7 C8 1.381(5) . ? C8 C9 1.387(5) . ? C8 H8 0.9500 . ? C9 O2 1.315(4) . ? C9 C10 1.412(5) . ? C10 N2 1.381(4) . ? C10 C11 1.386(5) . ? C11 C12 1.395(5) . ? C11 H9 0.9500 . ? C12 C13 1.383(5) . ? C12 H10 0.9500 . ? C13 N2 1.355(5) . ? C13 C14 1.484(5) . ? C14 C15 1.516(5) . ? C14 H11 0.9900 . ? C14 H12 0.9900 . ? C15 H13 0.9800 . ? C15 H14 0.9800 . ? C15 H15 0.9800 . ? C16 C17 1.504(6) . ? C16 H16 0.9800 . ? C16 H17 0.9800 . ? C16 H18 0.9800 . ? C17 C18 1.498(5) . ? C17 H19 0.9900 . ? C17 H20 0.9900 . ? C18 N3 1.348(5) . ? C18 C19 1.399(5) . ? C19 C20 1.397(5) . ? C19 H21 0.9500 . ? C20 C21 1.399(5) . ? C20 H22 0.9500 . ? C21 N3 1.371(4) . ? C21 C22 1.409(5) . ? C22 O3 1.322(4) . ? C22 C23 1.378(4) . ? C23 C24 1.390(5) . ? C23 H23 0.9500 . ? C24 O4 1.326(4) . ? C24 C25 1.410(4) . ? C25 N4 1.367(5) . ? C25 C26 1.389(5) . ? C26 C27 1.403(5) . ? C26 H24 0.9500 . ? C27 C28 1.385(5) . ? C27 H25 0.9500 . ? C28 N4 1.358(4) . ? C28 C29 1.479(5) . ? C29 C30 1.523(4) . ? C29 H26 0.9900 . ? C29 H27 0.9900 . ? C30 H28 0.9800 . ? C30 H29 0.9800 . ? C30 H30 0.9800 . ? N1 H31 0.8800 . ? N2 H32 0.8800 . ? N3 H33 0.8800 . ? N4 H34 0.8800 . ? O1 B1 1.471(5) . ? O2 B1 1.467(5) . ? O3 B2 1.468(5) . ? O4 B2 1.469(4) . ? B1 F2 1.385(5) . ? B1 F1 1.392(4) . ? B2 F3 1.360(4) . ? B2 F4 1.409(5) . ? 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 C2 C1 H1 109.5 . . ? C2 C1 H2 109.5 . . ? H1 C1 H2 109.5 . . ? C2 C1 H3 109.5 . . ? H1 C1 H3 109.5 . . ? H2 C1 H3 109.5 . . ? C3 C2 C1 112.8(3) . . ? C3 C2 H4 109.0 . . ? C1 C2 H4 109.0 . . ? C3 C2 H5 109.0 . . ? C1 C2 H5 109.0 . . ? H4 C2 H5 107.8 . . ? N1 C3 C4 107.1(3) . . ? N1 C3 C2 121.1(3) . . ? C4 C3 C2 131.8(3) . . ? C3 C4 C5 107.9(3) . . ? C3 C4 H6 126.0 . . ? C5 C4 H6 126.0 . . ? C6 C5 C4 108.1(3) . . ? C6 C5 H7 126.0 . . ? C4 C5 H7 126.0 . . ? N1 C6 C5 106.7(3) . . ? N1 C6 C7 120.8(3) . . ? C5 C6 C7 132.5(3) . . ? O1 C7 C8 121.2(3) . . ? O1 C7 C6 114.9(3) . . ? C8 C7 C6 123.7(3) . . ? C7 C8 C9 119.3(3) . . ? C7 C8 H8 120.3 . . ? C9 C8 H8 120.3 . . ? O2 C9 C8 121.3(3) . . ? O2 C9 C10 114.7(3) . . ? C8 C9 C10 123.9(3) . . ? N2 C10 C11 106.3(3) . . ? N2 C10 C9 122.2(3) . . ? C11 C10 C9 131.5(3) . . ? C10 C11 C12 107.9(3) . . ? C10 C11 H9 126.0 . . ? C12 C11 H9 126.0 . . ? C13 C12 C11 108.1(3) . . ? C13 C12 H10 126.0 . . ? C11 C12 H10 126.0 . . ? N2 C13 C12 107.1(3) . . ? N2 C13 C14 122.2(3) . . ? C12 C13 C14 130.8(3) . . ? C13 C14 C15 113.5(3) . . ? C13 C14 H11 108.9 . . ? C15 C14 H11 108.9 . . ? C13 C14 H12 108.9 . . ? C15 C14 H12 108.9 . . ? H11 C14 H12 107.7 . . ? C14 C15 H13 109.5 . . ? C14 C15 H14 109.5 . . ? H13 C15 H14 109.5 . . ? C14 C15 H15 109.5 . . ? H13 C15 H15 109.5 . . ? H14 C15 H15 109.5 . . ? C17 C16 H16 109.5 . . ? C17 C16 H17 109.5 . . ? H16 C16 H17 109.5 . . ? C17 C16 H18 109.5 . . ? H16 C16 H18 109.5 . . ? H17 C16 H18 109.5 . . ? C18 C17 C16 112.6(3) . . ? C18 C17 H19 109.1 . . ? C16 C17 H19 109.1 . . ? C18 C17 H20 109.1 . . ? C16 C17 H20 109.1 . . ? H19 C17 H20 107.8 . . ? N3 C18 C19 107.5(3) . . ? N3 C18 C17 122.3(3) . . ? C19 C18 C17 130.2(4) . . ? C20 C19 C18 107.2(3) . . ? C20 C19 H21 126.4 . . ? C18 C19 H21 126.4 . . ? C19 C20 C21 108.0(3) . . ? C19 C20 H22 126.0 . . ? C21 C20 H22 126.0 . . ? N3 C21 C20 106.4(3) . . ? N3 C21 C22 123.3(3) . . ? C20 C21 C22 130.3(3) . . ? O3 C22 C23 121.1(3) . . ? O3 C22 C21 114.7(3) . . ? C23 C22 C21 124.1(3) . . ? C22 C23 C24 120.7(3) . . ? C22 C23 H23 119.6 . . ? C24 C23 H23 119.6 . . ? O4 C24 C23 120.1(3) . . ? O4 C24 C25 116.7(3) . . ? C23 C24 C25 123.1(3) . . ? N4 C25 C26 106.6(3) . . ? N4 C25 C24 122.2(3) . . ? C26 C25 C24 131.2(4) . . ? C25 C26 C27 107.0(4) . . ? C25 C26 H24 126.5 . . ? C27 C26 H24 126.5 . . ? C28 C27 C26 108.8(3) . . ? C28 C27 H25 125.6 . . ? C26 C27 H25 125.6 . . ? N4 C28 C27 105.9(3) . . ? N4 C28 C29 123.9(3) . . ? C27 C28 C29 130.1(3) . . ? C28 C29 C30 114.3(3) . . ? C28 C29 H26 108.7 . . ? C30 C29 H26 108.7 . . ? C28 C29 H27 108.7 . . ? C30 C29 H27 108.7 . . ? H26 C29 H27 107.6 . . ? C29 C30 H28 109.5 . . ? C29 C30 H29 109.5 . . ? H28 C30 H29 109.5 . . ? C29 C30 H30 109.5 . . ? H28 C30 H30 109.5 . . ? H29 C30 H30 109.5 . . ? C3 N1 C6 110.2(3) . . ? C3 N1 H31 124.9 . . ? C6 N1 H31 124.9 . . ? C13 N2 C10 110.7(3) . . ? C13 N2 H32 124.7 . . ? C10 N2 H32 124.7 . . ? C18 N3 C21 111.0(3) . . ? C18 N3 H33 124.5 . . ? C21 N3 H33 124.5 . . ? C28 N4 C25 111.7(3) . . ? C28 N4 H34 124.1 . . ? C25 N4 H34 124.1 . . ? C7 O1 B1 121.2(3) . . ? C9 O2 B1 121.4(3) . . ? C22 O3 B2 121.3(3) . . ? C24 O4 B2 121.7(3) . . ? F2 B1 F1 109.4(3) . . ? F2 B1 O2 110.2(3) . . ? F1 B1 O2 108.0(3) . . ? F2 B1 O1 109.2(3) . . ? F1 B1 O1 107.8(3) . . ? O2 B1 O1 112.2(3) . . ? F3 B2 F4 109.9(3) . . ? F3 B2 O3 109.7(3) . . ? F4 B2 O3 107.2(3) . . ? F3 B2 O4 110.8(3) . . ? F4 B2 O4 106.0(3) . . ? O3 B2 O4 113.1(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 C2 C3 N1 -176.9(3) . . . . ? C1 C2 C3 C4 3.0(6) . . . . ? N1 C3 C4 C5 -0.8(4) . . . . ? C2 C3 C4 C5 179.4(4) . . . . ? C3 C4 C5 C6 0.8(4) . . . . ? C4 C5 C6 N1 -0.6(4) . . . . ? C4 C5 C6 C7 -179.0(4) . . . . ? N1 C6 C7 O1 6.2(5) . . . . ? C5 C6 C7 O1 -175.5(4) . . . . ? N1 C6 C7 C8 -169.3(3) . . . . ? C5 C6 C7 C8 8.9(7) . . . . ? O1 C7 C8 C9 -5.6(5) . . . . ? C6 C7 C8 C9 169.7(3) . . . . ? C7 C8 C9 O2 6.8(5) . . . . ? C7 C8 C9 C10 -169.0(3) . . . . ? O2 C9 C10 N2 -2.4(5) . . . . ? C8 C9 C10 N2 173.6(3) . . . . ? O2 C9 C10 C11 -180.0(4) . . . . ? C8 C9 C10 C11 -3.9(6) . . . . ? N2 C10 C11 C12 0.6(4) . . . . ? C9 C10 C11 C12 178.4(4) . . . . ? C10 C11 C12 C13 -1.1(4) . . . . ? C11 C12 C13 N2 1.2(4) . . . . ? C11 C12 C13 C14 -177.8(4) . . . . ? N2 C13 C14 C15 171.9(3) . . . . ? C12 C13 C14 C15 -9.2(6) . . . . ? C16 C17 C18 N3 -166.9(3) . . . . ? C16 C17 C18 C19 12.2(5) . . . . ? N3 C18 C19 C20 0.5(4) . . . . ? C17 C18 C19 C20 -178.7(3) . . . . ? C18 C19 C20 C21 -0.4(4) . . . . ? C19 C20 C21 N3 0.1(4) . . . . ? C19 C20 C21 C22 176.6(3) . . . . ? N3 C21 C22 O3 -1.0(4) . . . . ? C20 C21 C22 O3 -176.9(3) . . . . ? N3 C21 C22 C23 -178.9(3) . . . . ? C20 C21 C22 C23 5.2(5) . . . . ? O3 C22 C23 C24 -2.5(5) . . . . ? C21 C22 C23 C24 175.3(3) . . . . ? C22 C23 C24 O4 2.0(5) . . . . ? C22 C23 C24 C25 -175.1(3) . . . . ? O4 C24 C25 N4 -3.9(5) . . . . ? C23 C24 C25 N4 173.3(3) . . . . ? O4 C24 C25 C26 178.7(3) . . . . ? C23 C24 C25 C26 -4.1(5) . . . . ? N4 C25 C26 C27 -0.1(4) . . . . ? C24 C25 C26 C27 177.6(3) . . . . ? C25 C26 C27 C28 -0.6(4) . . . . ? C26 C27 C28 N4 1.0(4) . . . . ? C26 C27 C28 C29 -175.3(3) . . . . ? N4 C28 C29 C30 158.1(3) . . . . ? C27 C28 C29 C30 -26.1(5) . . . . ? C4 C3 N1 C6 0.4(4) . . . . ? C2 C3 N1 C6 -179.7(3) . . . . ? C5 C6 N1 C3 0.1(4) . . . . ? C7 C6 N1 C3 178.7(3) . . . . ? C12 C13 N2 C10 -0.9(4) . . . . ? C14 C13 N2 C10 178.2(3) . . . . ? C11 C10 N2 C13 0.2(4) . . . . ? C9 C10 N2 C13 -177.9(3) . . . . ? C19 C18 N3 C21 -0.5(4) . . . . ? C17 C18 N3 C21 178.8(3) . . . . ? C20 C21 N3 C18 0.2(3) . . . . ? C22 C21 N3 C18 -176.5(3) . . . . ? C27 C28 N4 C25 -1.2(4) . . . . ? C29 C28 N4 C25 175.5(3) . . . . ? C26 C25 N4 C28 0.8(4) . . . . ? C24 C25 N4 C28 -177.2(3) . . . . ? C8 C7 O1 B1 -8.7(5) . . . . ? C6 C7 O1 B1 175.6(3) . . . . ? C8 C9 O2 B1 6.5(5) . . . . ? C10 C9 O2 B1 -177.4(3) . . . . ? C23 C22 O3 B2 -6.7(4) . . . . ? C21 C22 O3 B2 175.3(3) . . . . ? C23 C24 O4 B2 7.6(4) . . . . ? C25 C24 O4 B2 -175.1(3) . . . . ? C9 O2 B1 F2 103.0(3) . . . . ? C9 O2 B1 F1 -137.6(3) . . . . ? C9 O2 B1 O1 -18.9(4) . . . . ? C7 O1 B1 F2 -102.4(4) . . . . ? C7 O1 B1 F1 138.8(3) . . . . ? C7 O1 B1 O2 20.0(4) . . . . ? C22 O3 B2 F3 -109.4(3) . . . . ? C22 O3 B2 F4 131.3(3) . . . . ? C22 O3 B2 O4 14.8(4) . . . . ? C24 O4 B2 F3 108.3(4) . . . . ? C24 O4 B2 F4 -132.5(3) . . . . ? C24 O4 B2 O3 -15.3(4) . . . . ? _diffrn_measured_fraction_theta_max 0.935 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.935 _refine_diff_density_max 0.411 _refine_diff_density_min -0.433 _refine_diff_density_rms 0.095 #============================================================================== # End of CIF #============================================================================== data_70920mae _database_code_depnum_ccdc_archive 'CCDC 666249' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C19 H25 B F2 N2 O2' _chemical_formula_sum 'C19 H25 B F2 N2 O2' _chemical_formula_weight 362.22 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M Pc _symmetry_space_group_name_Hall P-2yc _symmetry_Int_Tables_number 7 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' _cell_length_a 8.526(6) _cell_length_b 12.160(6) _cell_length_c 8.797(5) _cell_angle_alpha 90.00 _cell_angle_beta 93.64(3) _cell_angle_gamma 90.00 _cell_volume 910.2(10) _cell_formula_units_Z 2 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.322 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 384 _exptl_absorpt_coefficient_mu 0.098 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9524 _exptl_absorpt_correction_T_max 0.9806 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku RAXIS-RAPID' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.00 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8741 _diffrn_reflns_av_R_equivalents 0.0386 _diffrn_reflns_av_sigmaI/netI 0.0481 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 3.35 _diffrn_reflns_theta_max 27.48 _reflns_number_total 3728 _reflns_number_gt 3171 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0387P)^2^+0.1654P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.8(7) _refine_ls_number_reflns 3728 _refine_ls_number_parameters 237 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0482 _refine_ls_R_factor_gt 0.0376 _refine_ls_wR_factor_ref 0.0895 _refine_ls_wR_factor_gt 0.0781 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.056 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group B1 B 0.1415(3) 0.56207(19) 0.2375(3) 0.0215(5) Uani 1 1 d . . . O1 O 0.06481(18) 0.63109(11) 0.34992(16) 0.0244(4) Uani 1 1 d . . . O2 O 0.1784(2) 0.62306(11) 0.10017(17) 0.0253(3) Uani 1 1 d . . . N1 N -0.0621(2) 0.74521(15) 0.5848(2) 0.0207(4) Uani 1 1 d . . . H1N H -0.0436 0.6760 0.6089 0.025 Uiso 1 1 calc R . . N2 N 0.2787(2) 0.71512(13) -0.1566(2) 0.0191(4) Uani 1 1 d . . . H2N H 0.2864 0.6430 -0.1543 0.023 Uiso 1 1 calc R . . F1 F 0.28177(16) 0.52155(10) 0.30597(14) 0.0280(3) Uani 1 1 d . . . F2 F 0.04388(16) 0.47578(10) 0.19582(15) 0.0299(3) Uani 1 1 d . . . C1 C -0.1347(3) 0.81866(17) 0.6730(2) 0.0202(4) Uani 1 1 d . . . C2 C -0.1415(3) 0.91774(18) 0.5948(2) 0.0229(5) Uani 1 1 d . . . H2A H -0.1873 0.9839 0.6286 0.027 Uiso 1 1 calc R . . C3 C -0.0700(3) 0.90373(17) 0.4587(2) 0.0209(4) Uani 1 1 d . . . H3A H -0.0565 0.9587 0.3839 0.025 Uiso 1 1 calc R . . C4 C -0.0217(2) 0.79502(18) 0.4517(2) 0.0186(4) Uani 1 1 d . . . C5 C 0.0491(3) 0.73770(16) 0.3321(2) 0.0186(4) Uani 1 1 d . . . C6 C 0.0981(2) 0.79068(17) 0.2036(2) 0.0199(4) Uani 1 1 d . . . H6A H 0.0869 0.8681 0.1937 0.024 Uiso 1 1 calc R . . C7 C 0.1631(3) 0.73050(16) 0.0903(3) 0.0190(4) Uani 1 1 d . . . C8 C 0.2179(3) 0.77797(17) -0.0447(2) 0.0197(4) Uani 1 1 d . . . C9 C 0.2267(3) 0.88659(18) -0.0904(3) 0.0236(5) Uani 1 1 d . . . H9A H 0.1938 0.9490 -0.0359 0.028 Uiso 1 1 calc R . . C10 C 0.2932(3) 0.88736(17) -0.2316(2) 0.0238(5) Uani 1 1 d . . . H10A H 0.3129 0.9508 -0.2904 0.029 Uiso 1 1 calc R . . C11 C 0.3254(2) 0.77967(17) -0.2712(3) 0.0209(5) Uani 1 1 d . . . C12 C -0.1970(3) 0.79130(17) 0.8249(2) 0.0232(5) Uani 1 1 d . . . H12A H -0.3001 0.8278 0.8315 0.028 Uiso 1 1 calc R . . H12B H -0.1246 0.8225 0.9062 0.028 Uiso 1 1 calc R . . C13 C -0.2169(3) 0.66972(16) 0.8558(2) 0.0234(5) Uani 1 1 d . . . H13A H -0.1119 0.6349 0.8676 0.028 Uiso 1 1 calc R . . H13B H -0.2747 0.6355 0.7667 0.028 Uiso 1 1 calc R . . C14 C -0.3055(3) 0.64653(19) 0.9985(2) 0.0262(5) Uani 1 1 d . . . H14A H -0.2395 0.6697 1.0896 0.031 Uiso 1 1 calc R . . H14B H -0.4030 0.6909 0.9944 0.031 Uiso 1 1 calc R . . C15 C -0.3473(4) 0.5265(2) 1.0141(3) 0.0391(6) Uani 1 1 d . . . H15A H -0.4177 0.5042 0.9272 0.059 Uiso 1 1 calc R . . H15B H -0.4001 0.5155 1.1087 0.059 Uiso 1 1 calc R . . H15C H -0.2513 0.4821 1.0166 0.059 Uiso 1 1 calc R . . C16 C 0.4000(3) 0.73448(17) -0.4069(2) 0.0214(5) Uani 1 1 d . . . H16A H 0.3274 0.6810 -0.4590 0.026 Uiso 1 1 calc R . . H16B H 0.4970 0.6946 -0.3725 0.026 Uiso 1 1 calc R . . C17 C 0.4409(3) 0.82343(18) -0.5202(2) 0.0216(5) Uani 1 1 d . . . H17A H 0.3424 0.8562 -0.5654 0.026 Uiso 1 1 calc R . . H17B H 0.5009 0.8823 -0.4649 0.026 Uiso 1 1 calc R . . C18 C 0.5371(3) 0.78049(18) -0.6479(2) 0.0224(5) Uani 1 1 d . . . H18A H 0.6378 0.7504 -0.6037 0.027 Uiso 1 1 calc R . . H18B H 0.4790 0.7201 -0.7018 0.027 Uiso 1 1 calc R . . C19 C 0.5704(3) 0.87073(19) -0.7610(2) 0.0278(5) Uani 1 1 d . . . H19A H 0.4749 0.8863 -0.8253 0.042 Uiso 1 1 calc R . . H19B H 0.6539 0.8466 -0.8251 0.042 Uiso 1 1 calc R . . H19C H 0.6040 0.9375 -0.7056 0.042 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 B1 0.0249(13) 0.0192(11) 0.0209(11) -0.0003(10) 0.0048(9) 0.0000(9) O1 0.0359(9) 0.0185(7) 0.0200(7) 0.0014(6) 0.0108(7) 0.0022(6) O2 0.0373(9) 0.0180(7) 0.0217(7) 0.0010(6) 0.0107(7) 0.0020(7) N1 0.0229(9) 0.0193(9) 0.0204(9) 0.0009(7) 0.0045(7) 0.0024(7) N2 0.0236(9) 0.0157(8) 0.0185(8) 0.0007(8) 0.0057(7) -0.0008(7) F1 0.0305(7) 0.0256(6) 0.0286(7) 0.0031(5) 0.0074(5) 0.0029(6) F2 0.0372(8) 0.0256(6) 0.0279(6) -0.0058(6) 0.0098(6) -0.0106(6) C1 0.0198(11) 0.0212(10) 0.0196(10) -0.0044(9) 0.0023(8) -0.0006(9) C2 0.0250(12) 0.0199(11) 0.0239(10) -0.0020(9) 0.0030(9) 0.0023(8) C3 0.0232(11) 0.0200(10) 0.0195(10) -0.0012(9) 0.0002(8) -0.0012(9) C4 0.0173(10) 0.0200(10) 0.0183(10) -0.0002(9) -0.0001(8) -0.0006(8) C5 0.0181(10) 0.0159(9) 0.0214(10) -0.0024(9) -0.0022(8) -0.0009(8) C6 0.0242(12) 0.0161(10) 0.0195(10) -0.0009(9) 0.0020(8) -0.0024(8) C7 0.0184(10) 0.0187(9) 0.0200(10) 0.0016(9) 0.0003(8) -0.0023(9) C8 0.0210(11) 0.0191(10) 0.0190(10) -0.0020(9) 0.0015(8) -0.0004(9) C9 0.0286(12) 0.0180(10) 0.0244(10) 0.0012(9) 0.0040(9) 0.0015(8) C10 0.0302(12) 0.0173(10) 0.0243(11) 0.0056(9) 0.0052(9) 0.0003(9) C11 0.0183(11) 0.0209(11) 0.0234(10) -0.0008(9) 0.0016(8) -0.0021(8) C12 0.0283(13) 0.0219(10) 0.0201(11) -0.0011(9) 0.0070(9) 0.0011(9) C13 0.0277(12) 0.0231(10) 0.0200(10) -0.0034(9) 0.0067(9) 0.0014(9) C14 0.0262(13) 0.0292(12) 0.0236(11) -0.0005(10) 0.0051(10) -0.0002(9) C15 0.0481(16) 0.0331(13) 0.0367(13) 0.0104(11) 0.0076(12) -0.0050(12) C16 0.0246(12) 0.0188(10) 0.0215(11) -0.0002(9) 0.0058(9) 0.0017(9) C17 0.0221(11) 0.0231(10) 0.0201(10) -0.0005(9) 0.0058(9) -0.0030(9) C18 0.0212(11) 0.0252(11) 0.0213(11) -0.0013(10) 0.0052(8) -0.0011(9) C19 0.0312(13) 0.0286(12) 0.0246(11) -0.0001(10) 0.0092(10) -0.0010(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag B1 F2 1.374(3) . ? B1 F1 1.395(3) . ? B1 O2 1.469(3) . ? B1 O1 1.481(3) . ? O1 C5 1.312(2) . ? O2 C7 1.315(2) . ? N1 C1 1.357(3) . ? N1 C4 1.382(3) . ? N1 H1N 0.8800 . ? N2 C11 1.357(3) . ? N2 C8 1.374(3) . ? N2 H2N 0.8800 . ? C1 C2 1.387(3) . ? C1 C12 1.506(3) . ? C2 C3 1.388(3) . ? C2 H2A 0.9500 . ? C3 C4 1.387(3) . ? C3 H3A 0.9500 . ? C4 C5 1.427(3) . ? C5 C6 1.388(3) . ? C6 C7 1.381(3) . ? C6 H6A 0.9500 . ? C7 C8 1.425(3) . ? C8 C9 1.384(3) . ? C9 C10 1.397(3) . ? C9 H9A 0.9500 . ? C10 C11 1.387(3) . ? C10 H10A 0.9500 . ? C11 C16 1.493(3) . ? C12 C13 1.515(3) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.532(3) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C15 1.511(3) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 C17 1.526(3) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 C18 1.525(3) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 C19 1.520(3) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag F2 B1 F1 109.49(18) . . ? F2 B1 O2 108.91(18) . . ? F1 B1 O2 108.11(18) . . ? F2 B1 O1 109.00(18) . . ? F1 B1 O1 108.33(18) . . ? O2 B1 O1 112.96(17) . . ? C5 O1 B1 121.78(17) . . ? C7 O2 B1 122.04(17) . . ? C1 N1 C4 110.08(18) . . ? C1 N1 H1N 125.0 . . ? C4 N1 H1N 125.0 . . ? C11 N2 C8 110.64(16) . . ? C11 N2 H2N 124.7 . . ? C8 N2 H2N 124.7 . . ? N1 C1 C2 107.12(19) . . ? N1 C1 C12 124.10(19) . . ? C2 C1 C12 128.8(2) . . ? C1 C2 C3 108.3(2) . . ? C1 C2 H2A 125.8 . . ? C3 C2 H2A 125.8 . . ? C4 C3 C2 107.66(19) . . ? C4 C3 H3A 126.2 . . ? C2 C3 H3A 126.2 . . ? N1 C4 C3 106.80(18) . . ? N1 C4 C5 123.41(19) . . ? C3 C4 C5 129.72(19) . . ? O1 C5 C6 121.47(19) . . ? O1 C5 C4 116.08(18) . . ? C6 C5 C4 122.45(18) . . ? C7 C6 C5 119.83(19) . . ? C7 C6 H6A 120.1 . . ? C5 C6 H6A 120.1 . . ? O2 C7 C6 121.40(19) . . ? O2 C7 C8 114.90(18) . . ? C6 C7 C8 123.70(17) . . ? N2 C8 C9 107.01(18) . . ? N2 C8 C7 122.03(18) . . ? C9 C8 C7 130.94(19) . . ? C8 C9 C10 107.3(2) . . ? C8 C9 H9A 126.4 . . ? C10 C9 H9A 126.4 . . ? C11 C10 C9 108.4(2) . . ? C11 C10 H10A 125.8 . . ? C9 C10 H10A 125.8 . . ? N2 C11 C10 106.69(19) . . ? N2 C11 C16 122.76(18) . . ? C10 C11 C16 130.53(19) . . ? C1 C12 C13 115.12(18) . . ? C1 C12 H12A 108.5 . . ? C13 C12 H12A 108.5 . . ? C1 C12 H12B 108.5 . . ? C13 C12 H12B 108.5 . . ? H12A C12 H12B 107.5 . . ? C12 C13 C14 113.17(17) . . ? C12 C13 H13A 108.9 . . ? C14 C13 H13A 108.9 . . ? C12 C13 H13B 108.9 . . ? C14 C13 H13B 108.9 . . ? H13A C13 H13B 107.8 . . ? C15 C14 C13 112.58(19) . . ? C15 C14 H14A 109.1 . . ? C13 C14 H14A 109.1 . . ? C15 C14 H14B 109.1 . . ? C13 C14 H14B 109.1 . . ? H14A C14 H14B 107.8 . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C11 C16 C17 112.83(17) . . ? C11 C16 H16A 109.0 . . ? C17 C16 H16A 109.0 . . ? C11 C16 H16B 109.0 . . ? C17 C16 H16B 109.0 . . ? H16A C16 H16B 107.8 . . ? C18 C17 C16 113.24(17) . . ? C18 C17 H17A 108.9 . . ? C16 C17 H17A 108.9 . . ? C18 C17 H17B 108.9 . . ? C16 C17 H17B 108.9 . . ? H17A C17 H17B 107.7 . . ? C19 C18 C17 111.52(18) . . ? C19 C18 H18A 109.3 . . ? C17 C18 H18A 109.3 . . ? C19 C18 H18B 109.3 . . ? C17 C18 H18B 109.3 . . ? H18A C18 H18B 108.0 . . ? C18 C19 H19A 109.5 . . ? C18 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C18 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag F2 B1 O1 C5 -128.1(2) . . . . ? F1 B1 O1 C5 112.9(2) . . . . ? O2 B1 O1 C5 -6.9(3) . . . . ? F2 B1 O2 C7 129.8(2) . . . . ? F1 B1 O2 C7 -111.4(2) . . . . ? O1 B1 O2 C7 8.5(3) . . . . ? C4 N1 C1 C2 0.2(2) . . . . ? C4 N1 C1 C12 178.86(19) . . . . ? N1 C1 C2 C3 -0.8(2) . . . . ? C12 C1 C2 C3 -179.4(2) . . . . ? C1 C2 C3 C4 1.2(2) . . . . ? C1 N1 C4 C3 0.5(2) . . . . ? C1 N1 C4 C5 -176.65(19) . . . . ? C2 C3 C4 N1 -1.0(2) . . . . ? C2 C3 C4 C5 175.9(2) . . . . ? B1 O1 C5 C6 2.6(3) . . . . ? B1 O1 C5 C4 -177.73(19) . . . . ? N1 C4 C5 O1 4.6(3) . . . . ? C3 C4 C5 O1 -171.9(2) . . . . ? N1 C4 C5 C6 -175.7(2) . . . . ? C3 C4 C5 C6 7.8(3) . . . . ? O1 C5 C6 C7 0.9(3) . . . . ? C4 C5 C6 C7 -178.8(2) . . . . ? B1 O2 C7 C6 -5.8(3) . . . . ? B1 O2 C7 C8 174.3(2) . . . . ? C5 C6 C7 O2 0.8(3) . . . . ? C5 C6 C7 C8 -179.4(2) . . . . ? C11 N2 C8 C9 -0.1(3) . . . . ? C11 N2 C8 C7 -178.7(2) . . . . ? O2 C7 C8 N2 1.3(3) . . . . ? C6 C7 C8 N2 -178.5(2) . . . . ? O2 C7 C8 C9 -176.9(2) . . . . ? C6 C7 C8 C9 3.2(4) . . . . ? N2 C8 C9 C10 0.2(2) . . . . ? C7 C8 C9 C10 178.7(2) . . . . ? C8 C9 C10 C11 -0.3(2) . . . . ? C8 N2 C11 C10 -0.1(3) . . . . ? C8 N2 C11 C16 178.41(19) . . . . ? C9 C10 C11 N2 0.2(3) . . . . ? C9 C10 C11 C16 -178.1(2) . . . . ? N1 C1 C12 C13 -16.9(3) . . . . ? C2 C1 C12 C13 161.5(2) . . . . ? C1 C12 C13 C14 -170.42(19) . . . . ? C12 C13 C14 C15 170.8(2) . . . . ? N2 C11 C16 C17 179.6(2) . . . . ? C10 C11 C16 C17 -2.2(3) . . . . ? C11 C16 C17 C18 172.08(19) . . . . ? C16 C17 C18 C19 178.04(19) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.182 _refine_diff_density_min -0.167 _refine_diff_density_rms 0.042 #============================================================================== # End of CIF #============================================================================== data_71103mae _database_code_depnum_ccdc_archive 'CCDC 666250' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '(C15 H17 N2 O2 B F2), (C16 H36 N), Cl' _chemical_formula_sum 'C31 H53 B Cl F2 N3 O2' _chemical_formula_weight 584.02 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' Cl Cl 0.1484 0.1585 '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 1 2/c 1' _symmetry_space_group_name_Hall '-C 2yc' _symmetry_Int_Tables_number 15 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 27.621(8) _cell_length_b 13.498(3) _cell_length_c 22.643(6) _cell_angle_alpha 90.00 _cell_angle_beta 128.066(10) _cell_angle_gamma 90.00 _cell_volume 6647(3) _cell_formula_units_Z 8 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 25410 _cell_measurement_theta_min 3.0 _cell_measurement_theta_max 27.5 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.167 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2528 _exptl_absorpt_coefficient_mu 0.157 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9258 _exptl_absorpt_correction_T_max 0.9545 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku RAXIS-RAPID' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.00 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 31576 _diffrn_reflns_av_R_equivalents 0.0430 _diffrn_reflns_av_sigmaI/netI 0.0370 _diffrn_reflns_limit_h_min -35 _diffrn_reflns_limit_h_max 35 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 3.02 _diffrn_reflns_theta_max 27.48 _reflns_number_total 7573 _reflns_number_gt 6082 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0375P)^2^+154.6432P] 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 7573 _refine_ls_number_parameters 387 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1324 _refine_ls_R_factor_gt 0.1199 _refine_ls_wR_factor_ref 0.3307 _refine_ls_wR_factor_gt 0.3261 _refine_ls_goodness_of_fit_ref 1.083 _refine_ls_restrained_S_all 1.083 _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 C1 C 0.0611(6) -0.5310(8) -0.0785(6) 0.085(4) Uani 1 1 d . . . H1 H 0.1021 -0.5248 -0.0650 0.127 Uiso 1 1 calc R . . H2 H 0.0316 -0.5501 -0.1314 0.127 Uiso 1 1 calc R . . H3 H 0.0618 -0.5819 -0.0471 0.127 Uiso 1 1 calc R . . C2 C 0.0422(4) -0.4339(6) -0.0663(4) 0.0482(18) Uani 1 1 d . . . H4 H -0.0007 -0.4389 -0.0844 0.058 Uiso 1 1 calc R . . H5 H 0.0436 -0.3822 -0.0962 0.058 Uiso 1 1 calc R . . C3 C 0.0830(3) -0.4034(5) 0.0148(4) 0.0373(15) Uani 1 1 d . . . C4 C 0.1053(3) -0.4540(5) 0.0808(4) 0.0433(16) Uani 1 1 d . . . H6 H 0.0967 -0.5211 0.0840 0.052 Uiso 1 1 calc R . . C5 C 0.1417(3) -0.3909(5) 0.1404(4) 0.0370(14) Uani 1 1 d . . . H7 H 0.1625 -0.4066 0.1917 0.044 Uiso 1 1 calc R . . C6 C 0.1426(3) -0.2996(5) 0.1122(3) 0.0310(13) Uani 1 1 d . . . C7 C 0.1748(3) -0.2108(5) 0.1486(3) 0.0305(13) Uani 1 1 d . . . C8 C 0.1776(3) -0.1327(5) 0.1112(3) 0.0338(13) Uani 1 1 d . . . H8 H 0.1615 -0.1406 0.0604 0.041 Uiso 1 1 calc R . . C9 C 0.2035(3) -0.0434(5) 0.1468(3) 0.0301(12) Uani 1 1 d . . . C10 C 0.2014(3) 0.0415(5) 0.1081(4) 0.0334(13) Uani 1 1 d . . . C11 C 0.2254(3) 0.1368(5) 0.1343(4) 0.0394(15) Uani 1 1 d . . . H9 H 0.2475 0.1596 0.1844 0.047 Uiso 1 1 calc R . . C12 C 0.2108(4) 0.1916(5) 0.0735(4) 0.0433(17) Uani 1 1 d . . . H10 H 0.2208 0.2592 0.0745 0.052 Uiso 1 1 calc R . . C13 C 0.1788(3) 0.1297(5) 0.0104(4) 0.0390(15) Uani 1 1 d . . . C14 C 0.1551(5) 0.1506(6) -0.0687(5) 0.060(2) Uani 1 1 d . . . H11 H 0.1867 0.1298 -0.0740 0.072 Uiso 1 1 calc R . . H12 H 0.1179 0.1101 -0.1037 0.072 Uiso 1 1 calc R . . C15 C 0.1401(7) 0.2548(7) -0.0905(6) 0.098(5) Uani 1 1 d . . . H13 H 0.1104 0.2772 -0.0831 0.147 Uiso 1 1 calc R . . H14 H 0.1222 0.2622 -0.1434 0.147 Uiso 1 1 calc R . . H15 H 0.1776 0.2948 -0.0594 0.147 Uiso 1 1 calc R . . C16 C 0.3207(3) -0.3689(5) 0.1982(3) 0.0315(13) Uani 1 1 d . . . H16 H 0.3046 -0.4238 0.2107 0.038 Uiso 1 1 calc R . . H17 H 0.2991 -0.3077 0.1942 0.038 Uiso 1 1 calc R . . C17 C 0.3046(3) -0.3896(6) 0.1234(4) 0.0402(16) Uani 1 1 d . . . H18 H 0.3178 -0.4576 0.1229 0.048 Uiso 1 1 calc R . . H19 H 0.3269 -0.3428 0.1142 0.048 Uiso 1 1 calc R . . C18 C 0.2358(3) -0.3794(7) 0.0615(4) 0.050(2) Uani 1 1 d . . . H20 H 0.2227 -0.3115 0.0623 0.061 Uiso 1 1 calc R . . H21 H 0.2137 -0.4264 0.0708 0.061 Uiso 1 1 calc R . . C19 C 0.2186(4) -0.4000(9) -0.0155(4) 0.073(3) Uani 1 1 d . . . H22 H 0.2510 -0.3749 -0.0172 0.109 Uiso 1 1 calc R . . H23 H 0.1797 -0.3667 -0.0541 0.109 Uiso 1 1 calc R . . H24 H 0.2139 -0.4715 -0.0249 0.109 Uiso 1 1 calc R . . C20 C 0.4258(3) -0.4452(5) 0.2697(4) 0.0329(13) Uani 1 1 d . . . H25 H 0.4215 -0.4499 0.2230 0.039 Uiso 1 1 calc R . . H26 H 0.4697 -0.4320 0.3113 0.039 Uiso 1 1 calc R . . C21 C 0.4093(3) -0.5449(5) 0.2837(4) 0.0364(14) Uani 1 1 d . . . H27 H 0.3662 -0.5619 0.2413 0.044 Uiso 1 1 calc R . . H28 H 0.4130 -0.5422 0.3300 0.044 Uiso 1 1 calc R . . C22 C 0.4525(3) -0.6236(5) 0.2916(5) 0.0442(17) Uani 1 1 d . . . H29 H 0.4488 -0.6249 0.2452 0.053 Uiso 1 1 calc R . . H30 H 0.4954 -0.6054 0.3337 0.053 Uiso 1 1 calc R . . C23 C 0.4391(4) -0.7261(5) 0.3057(4) 0.0478(18) Uani 1 1 d . . . H31 H 0.4432 -0.7255 0.3519 0.072 Uiso 1 1 calc R . . H32 H 0.4683 -0.7737 0.3108 0.072 Uiso 1 1 calc R . . H33 H 0.3971 -0.7454 0.2634 0.072 Uiso 1 1 calc R . . C24 C 0.4159(3) -0.2688(5) 0.2501(4) 0.0305(13) Uani 1 1 d . . . H34 H 0.4140 -0.2832 0.2058 0.037 Uiso 1 1 calc R . . H35 H 0.4598 -0.2632 0.2940 0.037 Uiso 1 1 calc R . . C25 C 0.3852(3) -0.1690(5) 0.2380(4) 0.0367(14) Uani 1 1 d . . . H36 H 0.3412 -0.1724 0.1937 0.044 Uiso 1 1 calc R . . H37 H 0.3878 -0.1518 0.2823 0.044 Uiso 1 1 calc R . . C26 C 0.4177(3) -0.0903(5) 0.2257(4) 0.0349(14) Uani 1 1 d . . . H38 H 0.4142 -0.1077 0.1807 0.042 Uiso 1 1 calc R . . H39 H 0.4619 -0.0894 0.2694 0.042 Uiso 1 1 calc R . . C27 C 0.3905(4) 0.0130(6) 0.2152(5) 0.053(2) Uani 1 1 d . . . H40 H 0.3457 0.0099 0.1779 0.080 Uiso 1 1 calc R . . H41 H 0.4069 0.0587 0.1978 0.080 Uiso 1 1 calc R . . H42 H 0.4016 0.0365 0.2631 0.080 Uiso 1 1 calc R . . C28 C 0.3927(3) -0.3435(5) 0.3319(3) 0.0350(14) Uani 1 1 d . . . H47 H 0.3676 -0.3953 0.3326 0.042 Uiso 0.515(17) 1 calc PR A 1 H48 H 0.3753 -0.2783 0.3297 0.042 Uiso 0.515(17) 1 calc PR A 1 H49 H 0.3861 -0.4090 0.3456 0.042 Uiso 0.485(17) 1 calc PR A 2 H50 H 0.3584 -0.3001 0.3188 0.042 Uiso 0.485(17) 1 calc PR A 2 N1 N 0.1057(2) -0.3099(4) 0.0347(3) 0.0315(11) Uani 1 1 d . . . H51 H 0.0982 -0.2628 0.0032 0.038 Uiso 1 1 calc R . . N2 N 0.1731(3) 0.0405(4) 0.0317(3) 0.0359(12) Uani 1 1 d . . . H52 H 0.1543 -0.0109 0.0019 0.043 Uiso 1 1 calc R . . N3 N 0.3885(2) -0.3565(4) 0.2627(3) 0.0291(10) Uani 1 1 d . A . O1 O 0.2016(2) -0.2038(3) 0.2209(2) 0.0356(10) Uani 1 1 d . . . O2 O 0.2287(2) -0.0305(3) 0.2183(2) 0.0331(10) Uani 1 1 d . . . B1 B 0.2453(3) -0.1213(5) 0.2659(4) 0.0301(14) Uani 1 1 d . . . F1 F 0.30369(18) -0.1499(3) 0.2944(2) 0.0420(9) Uani 1 1 d . . . F2 F 0.24090(17) -0.0972(3) 0.3210(2) 0.0352(8) Uani 1 1 d . . . Cl1 Cl 0.08914(6) -0.14652(12) -0.08530(7) 0.0306(3) Uani 1 1 d . . . C29 C 0.4603(7) -0.3503(14) 0.4058(9) 0.036(3) Uani 0.515(17) 1 d P A 1 H53 H 0.4867 -0.3019 0.4048 0.044 Uiso 0.515(17) 1 calc PR A 1 H54 H 0.4770 -0.4176 0.4118 0.044 Uiso 0.515(17) 1 calc PR A 1 C30 C 0.4536(8) -0.2995(17) 0.4026(9) 0.037(4) Uani 0.485(17) 1 d P A 2 H55 H 0.4539 -0.2267 0.3976 0.045 Uiso 0.485(17) 1 calc PR A 2 H56 H 0.4892 -0.3276 0.4080 0.045 Uiso 0.485(17) 1 calc PR A 2 C31 C 0.4581(4) -0.3256(11) 0.4734(5) 0.080(4) Uani 1 1 d . . . H63 H 0.4317 -0.3770 0.4718 0.096 Uiso 0.515(17) 1 calc PR A 1 H64 H 0.5002 -0.3371 0.5203 0.096 Uiso 0.515(17) 1 calc PR A 1 H65 H 0.4902 -0.2812 0.5137 0.096 Uiso 0.485(17) 1 calc PR A 2 H66 H 0.4187 -0.3031 0.4613 0.096 Uiso 0.485(17) 1 calc PR A 2 C33 C 0.4402(7) -0.2417(12) 0.4819(8) 0.047(4) Uani 0.515(17) 1 d P A 1 H57 H 0.3960 -0.2336 0.4421 0.071 Uiso 0.515(17) 1 calc PR A 1 H58 H 0.4625 -0.1876 0.4793 0.071 Uiso 0.515(17) 1 calc PR A 1 H59 H 0.4488 -0.2405 0.5308 0.071 Uiso 0.515(17) 1 calc PR A 1 C34 C 0.4683(9) -0.4083(14) 0.5038(10) 0.058(5) Uani 0.485(17) 1 d P A 2 H60 H 0.4608 -0.4049 0.5407 0.087 Uiso 0.485(17) 1 calc PR A 2 H61 H 0.5112 -0.4271 0.5290 0.087 Uiso 0.485(17) 1 calc PR A 2 H62 H 0.4410 -0.4578 0.4655 0.087 Uiso 0.485(17) 1 calc PR A 2 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 C1 0.111(9) 0.056(6) 0.053(5) -0.016(5) 0.033(6) 0.014(6) C2 0.048(4) 0.052(5) 0.034(4) -0.013(3) 0.020(3) -0.005(4) C3 0.030(3) 0.040(4) 0.034(3) -0.011(3) 0.016(3) -0.004(3) C4 0.047(4) 0.028(3) 0.051(4) -0.002(3) 0.029(4) -0.006(3) C5 0.044(4) 0.034(3) 0.031(3) 0.001(3) 0.021(3) 0.000(3) C6 0.031(3) 0.031(3) 0.028(3) -0.003(2) 0.016(3) -0.004(2) C7 0.032(3) 0.030(3) 0.025(3) 0.000(2) 0.015(2) 0.003(2) C8 0.043(3) 0.033(3) 0.025(3) -0.002(2) 0.020(3) -0.002(3) C9 0.029(3) 0.034(3) 0.023(3) 0.001(2) 0.014(2) 0.002(2) C10 0.040(3) 0.029(3) 0.030(3) 0.001(2) 0.021(3) 0.002(3) C11 0.044(4) 0.031(3) 0.034(3) -0.005(3) 0.020(3) -0.002(3) C12 0.061(5) 0.024(3) 0.044(4) 0.000(3) 0.032(4) -0.002(3) C13 0.050(4) 0.030(3) 0.033(3) 0.001(3) 0.023(3) -0.003(3) C14 0.095(7) 0.036(4) 0.053(5) 0.008(4) 0.048(5) -0.002(4) C15 0.191(14) 0.044(5) 0.060(6) 0.018(5) 0.078(8) 0.028(7) C16 0.025(3) 0.033(3) 0.032(3) 0.003(3) 0.015(3) -0.001(2) C17 0.025(3) 0.053(4) 0.037(3) -0.005(3) 0.017(3) -0.001(3) C18 0.027(3) 0.078(6) 0.036(4) 0.000(4) 0.014(3) 0.001(3) C19 0.047(5) 0.124(9) 0.029(4) -0.007(5) 0.013(4) 0.001(5) C20 0.026(3) 0.034(3) 0.036(3) 0.001(3) 0.018(3) 0.001(2) C21 0.030(3) 0.035(3) 0.044(4) 0.002(3) 0.022(3) 0.003(3) C22 0.043(4) 0.034(4) 0.063(5) 0.005(3) 0.037(4) 0.005(3) C23 0.050(4) 0.034(4) 0.049(4) 0.004(3) 0.026(4) 0.007(3) C24 0.029(3) 0.032(3) 0.032(3) -0.002(2) 0.020(3) -0.007(2) C25 0.047(4) 0.027(3) 0.048(4) 0.000(3) 0.035(3) -0.002(3) C26 0.041(3) 0.037(3) 0.029(3) 0.001(3) 0.023(3) -0.006(3) C27 0.071(5) 0.039(4) 0.061(5) 0.006(4) 0.046(5) 0.004(4) C28 0.031(3) 0.046(4) 0.031(3) 0.003(3) 0.022(3) -0.001(3) N1 0.031(3) 0.032(3) 0.027(2) 0.000(2) 0.016(2) 0.002(2) N2 0.042(3) 0.032(3) 0.026(3) -0.003(2) 0.017(2) -0.003(2) N3 0.028(2) 0.028(3) 0.032(3) 0.000(2) 0.020(2) -0.001(2) O1 0.043(3) 0.033(2) 0.024(2) -0.0008(18) 0.018(2) -0.003(2) O2 0.042(2) 0.026(2) 0.024(2) -0.0002(17) 0.0166(19) 0.0014(18) B1 0.030(3) 0.028(3) 0.025(3) 0.002(3) 0.013(3) 0.003(3) F1 0.040(2) 0.038(2) 0.052(2) 0.0047(19) 0.030(2) 0.0079(17) F2 0.038(2) 0.038(2) 0.0291(18) -0.0018(15) 0.0209(17) 0.0029(16) Cl1 0.0230(6) 0.0474(9) 0.0190(6) -0.0013(6) 0.0117(5) -0.0044(6) C29 0.038(7) 0.033(8) 0.036(7) -0.004(7) 0.021(6) 0.003(7) C30 0.040(8) 0.049(11) 0.028(7) -0.007(8) 0.024(7) -0.011(9) C31 0.049(5) 0.163(12) 0.036(4) -0.022(6) 0.030(4) -0.022(6) C33 0.049(8) 0.055(9) 0.032(7) -0.004(6) 0.023(7) 0.011(7) C34 0.070(12) 0.070(12) 0.041(9) 0.025(9) 0.038(9) 0.008(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.497(12) . ? C1 H1 0.9800 . ? C1 H2 0.9800 . ? C1 H3 0.9800 . ? C2 C3 1.504(9) . ? C2 H4 0.9900 . ? C2 H5 0.9900 . ? C3 N1 1.356(8) . ? C3 C4 1.393(10) . ? C4 C5 1.372(10) . ? C4 H6 0.9500 . ? C5 C6 1.395(9) . ? C5 H7 0.9500 . ? C6 N1 1.390(8) . ? C6 C7 1.416(8) . ? C7 O1 1.321(7) . ? C7 C8 1.384(9) . ? C8 C9 1.379(9) . ? C8 H8 0.9500 . ? C9 O2 1.320(7) . ? C9 C10 1.423(9) . ? C10 N2 1.391(8) . ? C10 C11 1.400(9) . ? C11 C12 1.385(10) . ? C11 H9 0.9500 . ? C12 C13 1.401(9) . ? C12 H10 0.9500 . ? C13 N2 1.342(8) . ? C13 C14 1.509(10) . ? C14 C15 1.463(12) . ? C14 H11 0.9900 . ? C14 H12 0.9900 . ? C15 H13 0.9800 . ? C15 H14 0.9800 . ? C15 H15 0.9800 . ? C16 C17 1.489(9) . ? C16 N3 1.515(7) . ? C16 H16 0.9900 . ? C16 H17 0.9900 . ? C17 C18 1.522(9) . ? C17 H18 0.9900 . ? C17 H19 0.9900 . ? C18 C19 1.523(11) . ? C18 H20 0.9900 . ? C18 H21 0.9900 . ? C19 H22 0.9800 . ? C19 H23 0.9800 . ? C19 H24 0.9800 . ? C20 C21 1.516(9) . ? C20 N3 1.522(8) . ? C20 H25 0.9900 . ? C20 H26 0.9900 . ? C21 C22 1.523(9) . ? C21 H27 0.9900 . ? C21 H28 0.9900 . ? C22 C23 1.517(10) . ? C22 H29 0.9900 . ? C22 H30 0.9900 . ? C23 H31 0.9800 . ? C23 H32 0.9800 . ? C23 H33 0.9800 . ? C24 N3 1.522(7) . ? C24 C25 1.524(9) . ? C24 H34 0.9900 . ? C24 H35 0.9900 . ? C25 C26 1.522(9) . ? C25 H36 0.9900 . ? C25 H37 0.9900 . ? C26 C27 1.530(10) . ? C26 H38 0.9900 . ? C26 H39 0.9900 . ? C27 H40 0.9800 . ? C27 H41 0.9800 . ? C27 H42 0.9800 . ? C28 N3 1.509(8) . ? C28 C30 1.558(17) . ? C28 C29 1.563(17) . ? C28 H47 0.9900 . ? C28 H48 0.9900 . ? C28 H49 0.9900 . ? C28 H50 0.9900 . ? N1 H51 0.8800 . ? N2 H52 0.8800 . ? O1 B1 1.491(8) . ? O2 B1 1.505(8) . ? B1 F2 1.365(8) . ? B1 F1 1.372(8) . ? C29 C31 1.605(18) . ? C29 H53 0.9900 . ? C29 H54 0.9900 . ? C30 C31 1.570(18) . ? C30 H55 0.9900 . ? C30 H56 0.9900 . ? C31 C34 1.25(2) . ? C31 C33 1.296(18) . ? C31 H63 0.9900 . ? C31 H64 0.9900 . ? C31 H65 0.9900 . ? C31 H66 0.9900 . ? C33 H57 0.9800 . ? C33 H58 0.9800 . ? C33 H59 0.9800 . ? C34 H60 0.9800 . ? C34 H61 0.9800 . ? C34 H62 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 H1 109.5 . . ? C2 C1 H2 109.5 . . ? H1 C1 H2 109.5 . . ? C2 C1 H3 109.5 . . ? H1 C1 H3 109.5 . . ? H2 C1 H3 109.5 . . ? C1 C2 C3 112.4(7) . . ? C1 C2 H4 109.1 . . ? C3 C2 H4 109.1 . . ? C1 C2 H5 109.1 . . ? C3 C2 H5 109.1 . . ? H4 C2 H5 107.9 . . ? N1 C3 C4 107.0(6) . . ? N1 C3 C2 120.3(7) . . ? C4 C3 C2 132.7(7) . . ? C5 C4 C3 108.7(6) . . ? C5 C4 H6 125.6 . . ? C3 C4 H6 125.6 . . ? C4 C5 C6 107.9(6) . . ? C4 C5 H7 126.0 . . ? C6 C5 H7 126.0 . . ? N1 C6 C5 106.4(5) . . ? N1 C6 C7 121.9(6) . . ? C5 C6 C7 131.6(6) . . ? O1 C7 C8 120.3(6) . . ? O1 C7 C6 116.9(6) . . ? C8 C7 C6 122.7(6) . . ? C9 C8 C7 120.8(6) . . ? C9 C8 H8 119.6 . . ? C7 C8 H8 119.6 . . ? O2 C9 C8 121.6(6) . . ? O2 C9 C10 116.1(6) . . ? C8 C9 C10 122.2(5) . . ? N2 C10 C11 107.0(6) . . ? N2 C10 C9 122.4(6) . . ? C11 C10 C9 130.6(6) . . ? C12 C11 C10 107.3(6) . . ? C12 C11 H9 126.3 . . ? C10 C11 H9 126.3 . . ? C11 C12 C13 108.0(6) . . ? C11 C12 H10 126.0 . . ? C13 C12 H10 126.0 . . ? N2 C13 C12 108.0(6) . . ? N2 C13 C14 122.4(6) . . ? C12 C13 C14 129.6(7) . . ? C15 C14 C13 113.9(7) . . ? C15 C14 H11 108.8 . . ? C13 C14 H11 108.8 . . ? C15 C14 H12 108.8 . . ? C13 C14 H12 108.8 . . ? H11 C14 H12 107.7 . . ? C14 C15 H13 109.5 . . ? C14 C15 H14 109.5 . . ? H13 C15 H14 109.5 . . ? C14 C15 H15 109.5 . . ? H13 C15 H15 109.5 . . ? H14 C15 H15 109.5 . . ? C17 C16 N3 116.1(5) . . ? C17 C16 H16 108.3 . . ? N3 C16 H16 108.3 . . ? C17 C16 H17 108.3 . . ? N3 C16 H17 108.3 . . ? H16 C16 H17 107.4 . . ? C16 C17 C18 111.0(6) . . ? C16 C17 H18 109.4 . . ? C18 C17 H18 109.4 . . ? C16 C17 H19 109.4 . . ? C18 C17 H19 109.4 . . ? H18 C17 H19 108.0 . . ? C17 C18 C19 111.7(7) . . ? C17 C18 H20 109.3 . . ? C19 C18 H20 109.3 . . ? C17 C18 H21 109.3 . . ? C19 C18 H21 109.3 . . ? H20 C18 H21 107.9 . . ? C18 C19 H22 109.5 . . ? C18 C19 H23 109.5 . . ? H22 C19 H23 109.5 . . ? C18 C19 H24 109.5 . . ? H22 C19 H24 109.5 . . ? H23 C19 H24 109.5 . . ? C21 C20 N3 116.7(5) . . ? C21 C20 H25 108.1 . . ? N3 C20 H25 108.1 . . ? C21 C20 H26 108.1 . . ? N3 C20 H26 108.1 . . ? H25 C20 H26 107.3 . . ? C20 C21 C22 109.2(5) . . ? C20 C21 H27 109.8 . . ? C22 C21 H27 109.8 . . ? C20 C21 H28 109.8 . . ? C22 C21 H28 109.8 . . ? H27 C21 H28 108.3 . . ? C23 C22 C21 112.7(6) . . ? C23 C22 H29 109.1 . . ? C21 C22 H29 109.1 . . ? C23 C22 H30 109.1 . . ? C21 C22 H30 109.1 . . ? H29 C22 H30 107.8 . . ? C22 C23 H31 109.5 . . ? C22 C23 H32 109.5 . . ? H31 C23 H32 109.5 . . ? C22 C23 H33 109.5 . . ? H31 C23 H33 109.5 . . ? H32 C23 H33 109.5 . . ? N3 C24 C25 115.9(5) . . ? N3 C24 H34 108.3 . . ? C25 C24 H34 108.3 . . ? N3 C24 H35 108.3 . . ? C25 C24 H35 108.3 . . ? H34 C24 H35 107.4 . . ? C26 C25 C24 109.0(5) . . ? C26 C25 H36 109.9 . . ? C24 C25 H36 109.9 . . ? C26 C25 H37 109.9 . . ? C24 C25 H37 109.9 . . ? H36 C25 H37 108.3 . . ? C25 C26 C27 112.1(6) . . ? C25 C26 H38 109.2 . . ? C27 C26 H38 109.2 . . ? C25 C26 H39 109.2 . . ? C27 C26 H39 109.2 . . ? H38 C26 H39 107.9 . . ? C26 C27 H40 109.5 . . ? C26 C27 H41 109.5 . . ? H40 C27 H41 109.5 . . ? C26 C27 H42 109.5 . . ? H40 C27 H42 109.5 . . ? H41 C27 H42 109.5 . . ? N3 C28 C30 117.0(7) . . ? N3 C28 C29 112.4(7) . . ? C30 C28 C29 26.0(7) . . ? N3 C28 H47 109.1 . . ? C30 C28 H47 125.1 . . ? C29 C28 H47 109.1 . . ? N3 C28 H48 109.1 . . ? C30 C28 H48 83.9 . . ? C29 C28 H48 109.1 . . ? H47 C28 H48 107.9 . . ? N3 C28 H49 108.0 . . ? C30 C28 H49 108.0 . . ? C29 C28 H49 86.7 . . ? H47 C28 H49 25.9 . . ? H48 C28 H49 129.3 . . ? N3 C28 H50 108.0 . . ? C30 C28 H50 108.0 . . ? C29 C28 H50 130.3 . . ? H47 C28 H50 82.8 . . ? H48 C28 H50 27.6 . . ? H49 C28 H50 107.3 . . ? C3 N1 C6 109.9(5) . . ? C3 N1 H51 125.0 . . ? C6 N1 H51 125.0 . . ? C13 N2 C10 109.7(5) . . ? C13 N2 H52 125.1 . . ? C10 N2 H52 125.1 . . ? C28 N3 C16 105.7(4) . . ? C28 N3 C20 111.7(5) . . ? C16 N3 C20 111.6(5) . . ? C28 N3 C24 112.0(5) . . ? C16 N3 C24 111.5(5) . . ? C20 N3 C24 104.4(4) . . ? C7 O1 B1 119.9(5) . . ? C9 O2 B1 117.9(5) . . ? F2 B1 F1 112.2(5) . . ? F2 B1 O1 108.1(5) . . ? F1 B1 O1 109.5(5) . . ? F2 B1 O2 107.6(5) . . ? F1 B1 O2 108.5(5) . . ? O1 B1 O2 111.0(5) . . ? C28 C29 C31 106.6(10) . . ? C28 C29 H53 110.4 . . ? C31 C29 H53 110.4 . . ? C28 C29 H54 110.4 . . ? C31 C29 H54 110.4 . . ? H53 C29 H54 108.6 . . ? C28 C30 C31 108.6(11) . . ? C28 C30 H55 110.0 . . ? C31 C30 H55 110.0 . . ? C28 C30 H56 110.0 . . ? C31 C30 H56 110.0 . . ? H55 C30 H56 108.3 . . ? C34 C31 C33 132.7(13) . . ? C34 C31 C30 127.7(16) . . ? C33 C31 C30 99.0(15) . . ? C34 C31 C29 102.2(14) . . ? C33 C31 C29 124.3(14) . . ? C30 C31 C29 25.5(7) . . ? C34 C31 H63 46.1 . . ? C33 C31 H63 106.2 . . ? C30 C31 H63 121.8 . . ? C29 C31 H63 106.2 . . ? C34 C31 H64 63.4 . . ? C33 C31 H64 106.2 . . ? C30 C31 H64 115.5 . . ? C29 C31 H64 106.2 . . ? H63 C31 H64 106.4 . . ? C34 C31 H65 105.4 . . ? C33 C31 H65 62.6 . . ? C30 C31 H65 105.4 . . ? C29 C31 H65 117.6 . . ? H63 C31 H65 132.9 . . ? H64 C31 H65 46.7 . . ? C34 C31 H66 105.4 . . ? C33 C31 H66 47.2 . . ? C30 C31 H66 105.4 . . ? C29 C31 H66 118.7 . . ? H63 C31 H66 63.2 . . ? H64 C31 H66 135.1 . . ? H65 C31 H66 106.0 . . ? C31 C33 H57 109.5 . . ? C31 C33 H58 109.5 . . ? C31 C33 H59 109.5 . . ? C31 C34 H60 109.5 . . ? C31 C34 H61 109.5 . . ? H60 C34 H61 109.5 . . ? C31 C34 H62 109.5 . . ? H60 C34 H62 109.5 . . ? H61 C34 H62 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 C2 C3 N1 132.7(9) . . . . ? C1 C2 C3 C4 -46.9(12) . . . . ? N1 C3 C4 C5 -0.3(8) . . . . ? C2 C3 C4 C5 179.3(8) . . . . ? C3 C4 C5 C6 -0.1(9) . . . . ? C4 C5 C6 N1 0.4(8) . . . . ? C4 C5 C6 C7 -176.5(7) . . . . ? N1 C6 C7 O1 170.8(6) . . . . ? C5 C6 C7 O1 -12.7(11) . . . . ? N1 C6 C7 C8 -7.5(10) . . . . ? C5 C6 C7 C8 169.0(7) . . . . ? O1 C7 C8 C9 -5.7(10) . . . . ? C6 C7 C8 C9 172.5(6) . . . . ? C7 C8 C9 O2 2.9(10) . . . . ? C7 C8 C9 C10 -173.3(6) . . . . ? O2 C9 C10 N2 -176.3(6) . . . . ? C8 C9 C10 N2 0.2(10) . . . . ? O2 C9 C10 C11 4.6(11) . . . . ? C8 C9 C10 C11 -179.0(7) . . . . ? N2 C10 C11 C12 0.4(8) . . . . ? C9 C10 C11 C12 179.7(7) . . . . ? C10 C11 C12 C13 -0.8(9) . . . . ? C11 C12 C13 N2 0.9(9) . . . . ? C11 C12 C13 C14 -176.7(8) . . . . ? N2 C13 C14 C15 154.1(10) . . . . ? C12 C13 C14 C15 -28.5(15) . . . . ? N3 C16 C17 C18 -168.3(6) . . . . ? C16 C17 C18 C19 179.8(8) . . . . ? N3 C20 C21 C22 -178.2(6) . . . . ? C20 C21 C22 C23 -179.9(6) . . . . ? N3 C24 C25 C26 -179.5(5) . . . . ? C24 C25 C26 C27 -178.4(6) . . . . ? C4 C3 N1 C6 0.5(8) . . . . ? C2 C3 N1 C6 -179.2(6) . . . . ? C5 C6 N1 C3 -0.6(7) . . . . ? C7 C6 N1 C3 176.7(6) . . . . ? C12 C13 N2 C10 -0.6(8) . . . . ? C14 C13 N2 C10 177.2(7) . . . . ? C11 C10 N2 C13 0.1(8) . . . . ? C9 C10 N2 C13 -179.2(6) . . . . ? C30 C28 N3 C16 -162.9(11) . . . . ? C29 C28 N3 C16 168.8(9) . . . . ? C30 C28 N3 C20 75.5(12) . . . . ? C29 C28 N3 C20 47.3(10) . . . . ? C30 C28 N3 C24 -41.2(12) . . . . ? C29 C28 N3 C24 -69.5(10) . . . . ? C17 C16 N3 C28 -176.2(6) . . . . ? C17 C16 N3 C20 -54.6(7) . . . . ? C17 C16 N3 C24 61.8(7) . . . . ? C21 C20 N3 C28 58.1(7) . . . . ? C21 C20 N3 C16 -60.0(7) . . . . ? C21 C20 N3 C24 179.3(5) . . . . ? C25 C24 N3 C28 -61.3(7) . . . . ? C25 C24 N3 C16 57.0(7) . . . . ? C25 C24 N3 C20 177.7(5) . . . . ? C8 C7 O1 B1 -12.6(9) . . . . ? C6 C7 O1 B1 169.1(6) . . . . ? C8 C9 O2 B1 17.5(9) . . . . ? C10 C9 O2 B1 -166.1(6) . . . . ? C7 O1 B1 F2 148.0(5) . . . . ? C7 O1 B1 F1 -89.5(7) . . . . ? C7 O1 B1 O2 30.2(8) . . . . ? C9 O2 B1 F2 -150.4(5) . . . . ? C9 O2 B1 F1 87.9(6) . . . . ? C9 O2 B1 O1 -32.4(8) . . . . ? N3 C28 C29 C31 175.1(10) . . . . ? C30 C28 C29 C31 69(2) . . . . ? N3 C28 C30 C31 -160.7(11) . . . . ? C29 C28 C30 C31 -75(2) . . . . ? C28 C30 C31 C34 72(2) . . . . ? C28 C30 C31 C33 -100.3(15) . . . . ? C28 C30 C31 C29 73(2) . . . . ? C28 C29 C31 C34 108.5(15) . . . . ? C28 C29 C31 C33 -62.5(18) . . . . ? C28 C29 C31 C30 -70(2) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.970 _refine_diff_density_min -0.578 _refine_diff_density_rms 0.119 #============================================================================== # End of CIF #==============================================================================