# Electronic Supplementary Material (ESI) for Photochemical & Photobiological Sciences # This journal is (c) The Royal Society of Chemistry and Owner Societies 2011 data_global _journal_name_full Photochem.Photobiol.Sci. _journal_coden_cambridge 0171 #TrackingRef '1-6.cif' # SUBMISSION DETAILS _publ_contact_author_name 'Jianzhuang Jiang' _publ_contact_author_address ; Department of Chemistry, University of Science and Technology Beijing, Beijing 100083, China. ; _publ_contact_author_email jianzhuang@ustb.edu.cn _publ_contact_author_fax ? _publ_contact_author_phone ? # TITLE AND AUTHOR LIST _publ_section_title ; xxx ; loop_ _publ_author_name 'Yuting Chen' 'Liang Wan' 'Daopeng Zhang' 'Yongzhong Bian' ; Jianzhuang Jiang ; #===END data_4 _database_code_depnum_ccdc_archive 'CCDC 798782' #TrackingRef '1-6.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C17 H16 B F2 N3' _chemical_formula_sum 'C17 H16 B F2 N3' _chemical_formula_weight 311.14 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 9.935(5) _cell_length_b 23.900(5) _cell_length_c 13.513(5) _cell_angle_alpha 90.000(5) _cell_angle_beta 103.184(5) _cell_angle_gamma 90.000(5) _cell_volume 3124(2) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 4653 _cell_measurement_theta_min 2.277 _cell_measurement_theta_max 25.441 _exptl_crystal_description block _exptl_crystal_colour black-green _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.323 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1296 _exptl_absorpt_coefficient_mu 0.096 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.975 _exptl_absorpt_correction_T_max 0.983 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART 1000 CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15389 _diffrn_reflns_av_R_equivalents 0.0252 _diffrn_reflns_av_sigmaI/netI 0.0285 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -28 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.70 _diffrn_reflns_theta_max 25.01 _reflns_number_total 5494 _reflns_number_gt 4135 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART (Siemens, 1996)' _computing_cell_refinement 'Bruker SMART (Siemens, 1996)' _computing_data_reduction 'Bruker SAINT (Siemens, 1996)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997a)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997a)' _computing_molecular_graphics 'Bruker SHELXTL (Sheldrick, 1997b)' _computing_publication_material 'Bruker SHELXTL (Sheldrick, 1997b)' _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^)+(0.0510P)^2^+0.5938P] 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 5494 _refine_ls_number_parameters 543 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0569 _refine_ls_R_factor_gt 0.0391 _refine_ls_wR_factor_ref 0.1063 _refine_ls_wR_factor_gt 0.0944 _refine_ls_goodness_of_fit_ref 1.008 _refine_ls_restrained_S_all 1.008 _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 N1 N 0.23970(14) 0.36326(5) 1.08000(11) 0.0429(3) Uani 1 1 d . . . C19 C 1.02099(18) 0.22413(7) 0.21064(13) 0.0445(4) Uani 1 1 d . . . H18 H 0.698(3) 0.4534(10) 0.0106(19) 0.087(8) Uiso 1 1 d . . . H21 H 0.550(3) 0.4377(10) 0.013(2) 0.100(9) Uiso 1 1 d . . . H30 H 0.5572(17) 0.2505(7) 0.0522(12) 0.046(5) Uiso 1 1 d . . . H23A H 0.672(3) -0.0087(11) 0.036(2) 0.105(9) Uiso 1 1 d . . . H23B H 0.607(3) -0.0058(11) -0.079(2) 0.102(9) Uiso 1 1 d . . . H22A H 1.256(3) 0.0916(9) 0.3186(18) 0.086(7) Uiso 1 1 d . . . F2 F 0.32103(12) 0.44495(4) 1.00758(9) 0.0681(3) Uani 1 1 d . . . C22 C 1.1732(3) 0.08359(10) 0.2671(2) 0.0683(6) Uani 1 1 d . . . F1 F 0.10564(13) 0.44762(5) 1.03631(9) 0.0743(4) Uani 1 1 d . . . N5 N 0.97371(14) 0.13502(5) 0.15866(10) 0.0414(3) Uani 1 1 d . . . F3 F 0.85632(14) 0.05076(5) 0.18632(9) 0.0772(4) Uani 1 1 d . . . N2 N 0.14370(14) 0.38956(5) 0.89970(11) 0.0445(4) Uani 1 1 d . . . F4 F 0.97499(13) 0.05036(5) 0.06293(10) 0.0795(4) Uani 1 1 d . . . C12 C 0.19943(17) 0.23341(6) 0.91414(12) 0.0408(4) Uani 1 1 d . . . N6 N 0.76363(15) 0.10333(5) 0.03444(10) 0.0444(3) Uani 1 1 d . . . C28 C 0.80590(17) 0.20295(6) 0.06916(12) 0.0382(4) Uani 1 1 d . . . C10 C 0.24258(16) 0.30745(6) 1.04980(12) 0.0391(4) Uani 1 1 d . . . C18 C 0.92685(17) 0.19004(6) 0.14257(12) 0.0383(4) Uani 1 1 d . . . C29 C 0.76186(17) 0.26178(6) 0.05051(12) 0.0399(4) Uani 1 1 d . . . C30 C 0.62467(18) 0.27814(7) 0.04465(13) 0.0431(4) Uani 1 1 d . . . C31 C 0.58500(19) 0.33326(7) 0.03401(14) 0.0473(4) Uani 1 1 d . . . C9 C 0.14227(17) 0.33280(7) 0.87438(13) 0.0433(4) Uani 1 1 d . . . C15 C 0.19441(19) 0.12389(7) 0.83656(14) 0.0496(5) Uani 1 1 d . . . C34 C 0.85607(19) 0.30408(7) 0.04137(13) 0.0445(4) Uani 1 1 d . . . B2 B 0.8938(2) 0.08269(8) 0.11123(16) 0.0482(5) Uani 1 1 d . . . C11 C 0.19475(16) 0.29194(6) 0.94755(13) 0.0392(4) Uani 1 1 d . . . C27 C 0.72609(18) 0.15934(7) 0.01492(13) 0.0428(4) Uani 1 1 d . . . C21 C 1.09252(19) 0.13538(7) 0.23201(13) 0.0468(4) Uani 1 1 d . . . C32 C 0.68046(19) 0.37516(7) 0.02814(13) 0.0471(4) Uani 1 1 d . . . C13 C 0.25070(19) 0.22139(7) 0.82823(13) 0.0457(4) Uani 1 1 d . . . N8 N 0.6413(3) 0.43075(7) 0.02751(16) 0.0685(5) Uani 1 1 d . . . C24 C 0.6690(2) 0.07116(7) -0.02851(14) 0.0537(5) Uani 1 1 d . . . C20 C 1.1227(2) 0.19030(8) 0.26486(14) 0.0501(4) Uani 1 1 d . . . B1 B 0.2020(2) 0.41341(8) 1.00708(17) 0.0472(5) Uani 1 1 d . . . C14 C 0.2494(2) 0.16811(7) 0.79088(14) 0.0495(4) Uani 1 1 d . . . C1 C 0.30356(19) 0.27593(8) 1.13573(14) 0.0477(4) Uani 1 1 d . . . C33 C 0.81659(19) 0.35947(7) 0.02976(14) 0.0473(4) Uani 1 1 d . . . C3 C 0.29609(19) 0.36575(7) 1.18161(14) 0.0510(5) Uani 1 1 d . . . C5 C 0.08551(19) 0.41855(7) 0.81460(15) 0.0534(5) Uani 1 1 d . . . C17 C 0.15106(19) 0.18861(7) 0.96280(14) 0.0465(4) Uani 1 1 d . . . C7 C 0.0782(2) 0.32808(8) 0.77049(15) 0.0549(5) Uani 1 1 d . . . C16 C 0.1480(2) 0.13489(7) 0.92447(15) 0.0520(5) Uani 1 1 d . . . C26 C 0.6052(2) 0.16009(8) -0.06308(15) 0.0558(5) Uani 1 1 d . . . C6 C 0.0440(2) 0.38087(8) 0.73357(17) 0.0627(5) Uani 1 1 d . . . C25 C 0.5695(2) 0.10561(8) -0.08870(17) 0.0639(6) Uani 1 1 d . . . C2 C 0.3353(2) 0.31201(8) 1.21729(16) 0.0552(5) Uani 1 1 d . . . C4 C 0.3125(3) 0.41920(11) 1.2399(2) 0.0719(6) Uani 1 1 d . . . C8 C 0.0708(3) 0.48061(9) 0.8125(2) 0.0748(7) Uani 1 1 d . . . C23 C 0.6790(3) 0.00879(9) -0.0300(2) 0.0724(7) Uani 1 1 d . . . N3 N 0.1923(2) 0.07085(7) 0.79595(18) 0.0709(5) Uani 1 1 d . . . H19 H 1.0131(16) 0.2649(7) 0.2153(12) 0.042(4) Uiso 1 1 d . . . H31 H 0.490(2) 0.3434(7) 0.0331(13) 0.052(5) Uiso 1 1 d . . . H34 H 0.9485(19) 0.2943(7) 0.0403(13) 0.049(5) Uiso 1 1 d . . . H26 H 0.5599(19) 0.1925(8) -0.0926(14) 0.055(5) Uiso 1 1 d . . . H14 H 0.291(2) 0.1610(7) 0.7348(15) 0.058(5) Uiso 1 1 d . . . H1 H 0.3168(17) 0.2356(7) 1.1353(12) 0.047(5) Uiso 1 1 d . . . H20 H 1.202(2) 0.2019(7) 0.3179(14) 0.055(5) Uiso 1 1 d . . . H33 H 0.885(2) 0.3883(8) 0.0255(13) 0.058(5) Uiso 1 1 d . . . H17 H 0.1109(19) 0.1956(7) 1.0221(15) 0.055(5) Uiso 1 1 d . . . H7 H 0.0610(19) 0.2928(8) 0.7334(14) 0.056(5) Uiso 1 1 d . . . H16 H 0.109(2) 0.1064(8) 0.9582(14) 0.063(6) Uiso 1 1 d . . . H13 H 0.2887(19) 0.2516(8) 0.7942(14) 0.061(5) Uiso 1 1 d . . . H6 H -0.002(2) 0.3910(9) 0.6619(17) 0.076(6) Uiso 1 1 d . . . H10 H 0.141(2) 0.0442(10) 0.8217(17) 0.075(7) Uiso 1 1 d . . . H4A H 0.354(3) 0.4116(11) 1.310(2) 0.112(9) Uiso 1 1 d . . . H25 H 0.492(2) 0.0925(8) -0.1391(16) 0.072(6) Uiso 1 1 d . . . H2 H 0.379(2) 0.3028(8) 1.2871(16) 0.066(6) Uiso 1 1 d . . . H9 H 0.194(3) 0.0677(10) 0.729(2) 0.103(10) Uiso 1 1 d . . . H22B H 1.195(3) 0.0638(11) 0.213(2) 0.097(9) Uiso 1 1 d . . . H8B H 0.040(3) 0.4940(12) 0.747(2) 0.128(11) Uiso 1 1 d . . . H4C H 0.225(3) 0.4363(11) 1.233(2) 0.113(10) Uiso 1 1 d . . . H22C H 1.118(3) 0.0584(12) 0.299(2) 0.120(11) Uiso 1 1 d . . . H23C H 0.766(3) -0.0049(12) -0.042(2) 0.120(11) Uiso 1 1 d . . . H4B H 0.377(4) 0.4459(13) 1.215(2) 0.134(12) Uiso 1 1 d . . . H8C H 0.015(4) 0.4945(15) 0.860(3) 0.169(16) Uiso 1 1 d . . . H8A H 0.155(4) 0.4975(13) 0.842(2) 0.134(12) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0422(8) 0.0363(8) 0.0517(9) -0.0043(6) 0.0135(7) -0.0011(6) C19 0.0505(11) 0.0376(10) 0.0476(10) -0.0028(8) 0.0155(8) -0.0020(8) F2 0.0657(7) 0.0458(6) 0.0849(8) 0.0080(5) 0.0011(6) -0.0189(5) C22 0.0691(16) 0.0558(14) 0.0702(15) 0.0023(12) -0.0044(13) 0.0160(12) F1 0.0804(8) 0.0606(7) 0.0805(8) -0.0110(6) 0.0155(7) 0.0311(6) N5 0.0444(8) 0.0357(8) 0.0442(8) 0.0016(6) 0.0104(6) 0.0043(6) F3 0.0938(9) 0.0554(7) 0.0727(8) 0.0230(6) -0.0009(7) -0.0229(6) N2 0.0455(8) 0.0321(7) 0.0553(9) 0.0023(6) 0.0100(7) 0.0007(6) F4 0.0730(8) 0.0608(7) 0.0978(9) -0.0322(6) 0.0055(7) 0.0207(6) C12 0.0431(9) 0.0349(9) 0.0463(10) 0.0010(7) 0.0139(7) 0.0013(7) N6 0.0518(9) 0.0324(7) 0.0483(8) -0.0028(6) 0.0095(7) -0.0004(6) C28 0.0408(9) 0.0342(8) 0.0429(9) 0.0013(7) 0.0160(7) 0.0010(7) C10 0.0377(9) 0.0325(8) 0.0493(10) -0.0004(7) 0.0147(7) -0.0020(7) C18 0.0432(9) 0.0313(8) 0.0434(9) 0.0005(7) 0.0162(7) 0.0019(7) C29 0.0419(9) 0.0342(9) 0.0450(9) -0.0003(7) 0.0126(7) 0.0002(7) C30 0.0398(10) 0.0351(9) 0.0557(11) 0.0018(7) 0.0134(8) -0.0023(8) C31 0.0412(10) 0.0385(10) 0.0632(12) 0.0010(8) 0.0141(9) 0.0040(8) C9 0.0441(10) 0.0330(9) 0.0535(10) -0.0007(7) 0.0124(8) -0.0001(7) C15 0.0566(11) 0.0348(9) 0.0538(11) -0.0041(8) 0.0050(9) 0.0075(8) C34 0.0409(10) 0.0416(10) 0.0521(10) 0.0033(8) 0.0131(8) 0.0005(8) B2 0.0557(13) 0.0340(10) 0.0530(12) -0.0022(9) 0.0086(10) 0.0024(9) C11 0.0365(9) 0.0332(9) 0.0510(10) 0.0000(7) 0.0165(7) -0.0014(7) C27 0.0464(10) 0.0344(9) 0.0476(10) -0.0002(7) 0.0105(8) 0.0025(7) C21 0.0485(11) 0.0458(10) 0.0464(10) 0.0033(8) 0.0117(8) 0.0036(8) C32 0.0547(11) 0.0335(9) 0.0526(10) 0.0024(7) 0.0113(8) 0.0007(8) C13 0.0517(11) 0.0389(10) 0.0489(10) 0.0045(8) 0.0162(8) 0.0026(8) N8 0.0686(14) 0.0340(9) 0.1042(15) 0.0050(9) 0.0226(12) 0.0037(9) C24 0.0573(12) 0.0424(10) 0.0579(11) -0.0080(9) 0.0061(9) -0.0038(9) C20 0.0511(11) 0.0494(11) 0.0468(10) -0.0001(8) 0.0049(9) -0.0037(9) B1 0.0440(12) 0.0324(10) 0.0644(13) -0.0041(9) 0.0107(10) 0.0014(9) C14 0.0598(12) 0.0442(10) 0.0461(10) -0.0007(8) 0.0156(9) 0.0095(9) C1 0.0496(11) 0.0409(10) 0.0537(11) 0.0043(8) 0.0142(8) -0.0015(8) C33 0.0479(11) 0.0386(10) 0.0563(11) 0.0052(8) 0.0136(8) -0.0072(8) C3 0.0506(11) 0.0507(11) 0.0524(11) -0.0083(8) 0.0131(9) -0.0045(9) C5 0.0541(11) 0.0408(10) 0.0629(12) 0.0086(9) 0.0085(9) 0.0028(8) C17 0.0546(11) 0.0384(10) 0.0501(11) 0.0021(8) 0.0191(9) -0.0010(8) C7 0.0621(12) 0.0451(11) 0.0545(11) -0.0033(9) 0.0067(9) -0.0003(9) C16 0.0629(12) 0.0344(10) 0.0590(12) 0.0068(8) 0.0147(10) -0.0028(8) C26 0.0566(12) 0.0438(11) 0.0613(12) -0.0022(9) 0.0018(10) 0.0068(9) C6 0.0715(14) 0.0534(12) 0.0568(12) 0.0081(10) 0.0012(10) 0.0061(10) C25 0.0622(13) 0.0500(12) 0.0685(13) -0.0118(10) -0.0080(11) -0.0017(10) C2 0.0602(12) 0.0549(12) 0.0488(11) 0.0017(9) 0.0088(9) -0.0043(9) C4 0.0824(18) 0.0616(14) 0.0675(15) -0.0208(12) 0.0086(14) -0.0002(14) C8 0.093(2) 0.0416(12) 0.0824(18) 0.0144(12) 0.0049(15) 0.0080(12) C23 0.0858(18) 0.0399(12) 0.0806(17) -0.0115(11) -0.0035(15) -0.0052(12) N3 0.0974(15) 0.0374(10) 0.0762(14) -0.0089(9) 0.0167(12) 0.0037(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 N1 C3 1.361(2) . ? N1 C10 1.397(2) . ? N1 B1 1.543(2) . ? C19 C20 1.369(3) . ? C19 C18 1.412(2) . ? C19 H19 0.981(16) . ? F2 B1 1.401(2) . ? C22 C21 1.492(3) . ? C22 H22A 0.97(2) . ? C22 H22B 0.94(3) . ? C22 H22C 0.98(3) . ? F1 B1 1.383(2) . ? N5 C21 1.357(2) . ? N5 C18 1.3953(19) . ? N5 B2 1.540(2) . ? F3 B2 1.387(2) . ? N2 C5 1.354(2) . ? N2 C9 1.398(2) . ? N2 B1 1.544(3) . ? F4 B2 1.383(2) . ? C12 C17 1.398(2) . ? C12 C13 1.400(2) . ? C12 C11 1.474(2) . ? N6 C24 1.354(2) . ? N6 C27 1.399(2) . ? N6 B2 1.543(3) . ? C28 C18 1.407(2) . ? C28 C27 1.410(2) . ? C28 C29 1.477(2) . ? C10 C1 1.401(2) . ? C10 C11 1.404(2) . ? C29 C34 1.402(2) . ? C29 C30 1.403(2) . ? C30 C31 1.373(2) . ? C30 H30 0.964(17) . ? C31 C32 1.394(2) . ? C31 H31 0.972(19) . ? C9 C11 1.403(2) . ? C9 C7 1.408(3) . ? C15 N3 1.380(2) . ? C15 C16 1.394(3) . ? C15 C14 1.396(3) . ? C34 C33 1.379(2) . ? C34 H34 0.950(19) . ? C27 C26 1.406(3) . ? C21 C20 1.396(2) . ? C32 N8 1.384(2) . ? C32 C33 1.399(3) . ? C13 C14 1.369(2) . ? C13 H13 0.977(19) . ? N8 H18 0.85(3) . ? N8 H21 0.90(3) . ? C24 C25 1.397(3) . ? C24 C23 1.494(3) . ? C20 H20 0.975(19) . ? C14 H14 0.96(2) . ? C1 C2 1.378(3) . ? C1 H1 0.973(17) . ? C33 H33 0.982(19) . ? C3 C2 1.396(3) . ? C3 C4 1.490(3) . ? C5 C6 1.405(3) . ? C5 C8 1.490(3) . ? C17 C16 1.382(2) . ? C17 H17 0.99(2) . ? C7 C6 1.371(3) . ? C7 H7 0.977(19) . ? C16 H16 0.95(2) . ? C26 C25 1.373(3) . ? C26 H26 0.939(18) . ? C6 H6 1.00(2) . ? C25 H25 0.96(2) . ? C2 H2 0.97(2) . ? C4 H4A 0.96(3) . ? C4 H4C 0.94(3) . ? C4 H4B 1.02(3) . ? C8 H8B 0.93(3) . ? C8 H8C 1.00(4) . ? C8 H8A 0.94(3) . ? C23 H23A 1.01(3) . ? C23 H23B 0.92(3) . ? C23 H23C 0.97(3) . ? N3 H10 0.93(2) . ? N3 H9 0.91(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 C3 N1 C10 107.78(14) . . ? C3 N1 B1 126.48(14) . . ? C10 N1 B1 124.99(14) . . ? C20 C19 C18 107.84(16) . . ? C20 C19 H19 127.8(9) . . ? C18 C19 H19 124.4(9) . . ? C21 C22 H22A 111.8(14) . . ? C21 C22 H22B 111.7(16) . . ? H22A C22 H22B 111(2) . . ? C21 C22 H22C 109.4(18) . . ? H22A C22 H22C 106(2) . . ? H22B C22 H22C 106(2) . . ? C21 N5 C18 108.15(13) . . ? C21 N5 B2 126.07(14) . . ? C18 N5 B2 125.33(14) . . ? C5 N2 C9 108.07(14) . . ? C5 N2 B1 127.26(14) . . ? C9 N2 B1 124.67(14) . . ? C17 C12 C13 117.52(15) . . ? C17 C12 C11 123.00(15) . . ? C13 C12 C11 119.46(14) . . ? C24 N6 C27 107.95(14) . . ? C24 N6 B2 126.60(14) . . ? C27 N6 B2 125.40(14) . . ? C18 C28 C27 119.54(14) . . ? C18 C28 C29 120.08(14) . . ? C27 C28 C29 120.37(14) . . ? N1 C10 C1 107.76(15) . . ? N1 C10 C11 120.96(14) . . ? C1 C10 C11 131.22(15) . . ? N5 C18 C28 121.17(14) . . ? N5 C18 C19 107.13(14) . . ? C28 C18 C19 131.70(15) . . ? C34 C29 C30 116.98(15) . . ? C34 C29 C28 121.58(15) . . ? C30 C29 C28 121.41(14) . . ? C31 C30 C29 121.68(16) . . ? C31 C30 H30 118.7(10) . . ? C29 C30 H30 119.6(10) . . ? C30 C31 C32 120.83(17) . . ? C30 C31 H31 119.7(10) . . ? C32 C31 H31 119.5(10) . . ? N2 C9 C11 121.43(15) . . ? N2 C9 C7 107.39(15) . . ? C11 C9 C7 131.14(16) . . ? N3 C15 C16 122.31(19) . . ? N3 C15 C14 119.4(2) . . ? C16 C15 C14 118.21(16) . . ? C33 C34 C29 121.58(17) . . ? C33 C34 H34 119.0(11) . . ? C29 C34 H34 119.4(10) . . ? F4 B2 F3 108.71(16) . . ? F4 B2 N5 110.44(16) . . ? F3 B2 N5 109.95(15) . . ? F4 B2 N6 110.53(16) . . ? F3 B2 N6 110.13(16) . . ? N5 B2 N6 107.08(14) . . ? C9 C11 C10 119.84(15) . . ? C9 C11 C12 118.51(15) . . ? C10 C11 C12 121.64(14) . . ? N6 C27 C26 107.40(15) . . ? N6 C27 C28 121.03(15) . . ? C26 C27 C28 131.56(16) . . ? N5 C21 C20 109.04(15) . . ? N5 C21 C22 122.79(17) . . ? C20 C21 C22 128.17(18) . . ? N8 C32 C31 119.73(19) . . ? N8 C32 C33 121.81(18) . . ? C31 C32 C33 118.33(16) . . ? C14 C13 C12 121.47(17) . . ? C14 C13 H13 119.1(11) . . ? C12 C13 H13 119.4(11) . . ? C32 N8 H18 114.2(17) . . ? C32 N8 H21 116.6(16) . . ? H18 N8 H21 121(2) . . ? N6 C24 C25 109.20(16) . . ? N6 C24 C23 122.44(18) . . ? C25 C24 C23 128.34(19) . . ? C19 C20 C21 107.84(17) . . ? C19 C20 H20 126.7(10) . . ? C21 C20 H20 125.5(10) . . ? F1 B1 F2 108.59(15) . . ? F1 B1 N1 111.09(16) . . ? F2 B1 N1 109.48(15) . . ? F1 B1 N2 110.54(15) . . ? F2 B1 N2 109.79(16) . . ? N1 B1 N2 107.34(14) . . ? C13 C14 C15 120.87(19) . . ? C13 C14 H14 119.3(11) . . ? C15 C14 H14 119.8(11) . . ? C2 C1 C10 107.65(17) . . ? C2 C1 H1 128.1(10) . . ? C10 C1 H1 124.2(10) . . ? C34 C33 C32 120.52(16) . . ? C34 C33 H33 119.8(11) . . ? C32 C33 H33 119.6(11) . . ? N1 C3 C2 109.05(15) . . ? N1 C3 C4 122.76(18) . . ? C2 C3 C4 128.17(19) . . ? N2 C5 C6 109.05(16) . . ? N2 C5 C8 123.15(19) . . ? C6 C5 C8 127.80(19) . . ? C16 C17 C12 121.05(18) . . ? C16 C17 H17 118.9(10) . . ? C12 C17 H17 119.9(10) . . ? C6 C7 C9 107.90(17) . . ? C6 C7 H7 127.5(11) . . ? C9 C7 H7 124.6(11) . . ? C17 C16 C15 120.75(17) . . ? C17 C16 H16 117.5(12) . . ? C15 C16 H16 121.6(12) . . ? C25 C26 C27 107.73(17) . . ? C25 C26 H26 127.2(11) . . ? C27 C26 H26 125.0(11) . . ? C7 C6 C5 107.58(18) . . ? C7 C6 H6 126.4(12) . . ? C5 C6 H6 126.0(12) . . ? C26 C25 C24 107.70(18) . . ? C26 C25 H25 127.5(12) . . ? C24 C25 H25 124.8(12) . . ? C1 C2 C3 107.74(17) . . ? C1 C2 H2 127.2(12) . . ? C3 C2 H2 125.0(11) . . ? C3 C4 H4A 109.3(16) . . ? C3 C4 H4C 109.6(17) . . ? H4A C4 H4C 110(2) . . ? C3 C4 H4B 111.2(18) . . ? H4A C4 H4B 107(2) . . ? H4C C4 H4B 109(2) . . ? C5 C8 H8B 111.8(19) . . ? C5 C8 H8C 113(2) . . ? H8B C8 H8C 113(3) . . ? C5 C8 H8A 110(2) . . ? H8B C8 H8A 109(3) . . ? H8C C8 H8A 99(3) . . ? C24 C23 H23A 112.5(15) . . ? C24 C23 H23B 110.0(16) . . ? H23A C23 H23B 106(2) . . ? C24 C23 H23C 113.6(17) . . ? H23A C23 H23C 105(2) . . ? H23B C23 H23C 109(2) . . ? C15 N3 H10 116.1(14) . . ? C15 N3 H9 117.9(16) . . ? H10 N3 H9 117(2) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.142 _refine_diff_density_min -0.195 _refine_diff_density_rms 0.032 data_1 _database_code_depnum_ccdc_archive 'CCDC 798783' #TrackingRef '1-6.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C19 H20 B F2 N3' _chemical_formula_sum 'C19 H20 B F2 N3' _chemical_formula_weight 339.19 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 10.8454(10) _cell_length_b 11.8897(11) _cell_length_c 13.9990(13) _cell_angle_alpha 90.00 _cell_angle_beta 105.2620(10) _cell_angle_gamma 90.00 _cell_volume 1741.5(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2294 _cell_measurement_theta_min 2.280 _cell_measurement_theta_max 25.127 _exptl_crystal_description block _exptl_crystal_colour black-red _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.294 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 712 _exptl_absorpt_coefficient_mu 0.092 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.978 _exptl_absorpt_correction_T_max 0.984 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART 1000 CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10069 _diffrn_reflns_av_R_equivalents 0.0539 _diffrn_reflns_av_sigmaI/netI 0.0569 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.13 _diffrn_reflns_theta_max 27.54 _reflns_number_total 3943 _reflns_number_gt 2227 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART (Siemens, 1996)' _computing_cell_refinement 'Bruker SMART (Siemens, 1996)' _computing_data_reduction 'Bruker SAINT (Siemens, 1996)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997a)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997a)' _computing_molecular_graphics 'Bruker SHELXTL (Sheldrick, 1997b)' _computing_publication_material 'Bruker SHELXTL (Sheldrick, 1997b)' _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^)+(0.0350P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3943 _refine_ls_number_parameters 306 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0836 _refine_ls_R_factor_gt 0.0434 _refine_ls_wR_factor_ref 0.0987 _refine_ls_wR_factor_gt 0.0870 _refine_ls_goodness_of_fit_ref 0.993 _refine_ls_restrained_S_all 0.993 _refine_ls_shift/su_max 0.002 _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 N2 N 0.93254(12) 0.32334(10) 0.01701(9) 0.0446(3) Uani 1 1 d . . . F1 F 1.12377(9) 0.37610(9) -0.02939(6) 0.0687(3) Uani 1 1 d . . . F2 F 1.13047(9) 0.22370(8) 0.06821(7) 0.0709(3) Uani 1 1 d . . . N1 N 1.11711(12) 0.40614(10) 0.13891(9) 0.0445(3) Uani 1 1 d . . . C10 C 1.03646(15) 0.43201(13) 0.19961(11) 0.0440(4) Uani 1 1 d . . . C11 C 0.90790(14) 0.40090(12) 0.17120(11) 0.0420(4) Uani 1 1 d . . . C12 C 0.82515(14) 0.42917(13) 0.23740(11) 0.0437(4) Uani 1 1 d . . . C9 C 0.85561(15) 0.34761(12) 0.08055(11) 0.0439(4) Uani 1 1 d . . . C15 C 0.67603(15) 0.48416(14) 0.36721(12) 0.0516(4) Uani 1 1 d . . . C1 C 1.10956(16) 0.49471(13) 0.28192(12) 0.0527(4) Uani 1 1 d . . . C7 C 0.72861(16) 0.31328(13) 0.03240(13) 0.0531(4) Uani 1 1 d . . . C17 C 0.81427(16) 0.35637(15) 0.31239(12) 0.0513(4) Uani 1 1 d . . . C5 C 0.85787(17) 0.27838(13) -0.06738(12) 0.0525(4) Uani 1 1 d . . . C16 C 0.74010(17) 0.38213(15) 0.37534(13) 0.0546(5) Uani 1 1 d . . . C3 C 1.23266(15) 0.45145(14) 0.17966(12) 0.0521(4) Uani 1 1 d . . . C13 C 0.75909(17) 0.52991(15) 0.22864(14) 0.0565(5) Uani 1 1 d . . . B B 1.07860(18) 0.33220(15) 0.04593(14) 0.0460(4) Uani 1 1 d . . . N3 N 0.59930(18) 0.5102(2) 0.42996(15) 0.0737(5) Uani 1 1 d . . . C8 C 0.9075(3) 0.2427(2) -0.15234(16) 0.0671(6) Uani 1 1 d . . . C14 C 0.68661(18) 0.55665(16) 0.29282(14) 0.0599(5) Uani 1 1 d . . . C4 C 1.3438(2) 0.4388(2) 0.1370(2) 0.0693(6) Uani 1 1 d . . . C6 C 0.73305(19) 0.27096(16) -0.05846(14) 0.0603(5) Uani 1 1 d . . . C2 C 1.22958(18) 0.50673(16) 0.26709(14) 0.0605(5) Uani 1 1 d . . . C19 C 1.0698(3) 0.5434(3) 0.36771(18) 0.0796(7) Uani 1 1 d . . . C18 C 0.6100(2) 0.3215(2) 0.0679(2) 0.0749(6) Uani 1 1 d . . . H6 H 0.6635(16) 0.2415(15) -0.1094(12) 0.068(5) Uiso 1 1 d . . . H14 H 0.6408(17) 0.6252(16) 0.2857(13) 0.080(6) Uiso 1 1 d . . . H13 H 0.7683(16) 0.5816(15) 0.1748(13) 0.075(5) Uiso 1 1 d . . . H17 H 0.8619(14) 0.2826(14) 0.3188(11) 0.062(5) Uiso 1 1 d . . . H18A H 0.541(2) 0.282(2) 0.0215(17) 0.119(8) Uiso 1 1 d . . . H16 H 0.7295(16) 0.3273(15) 0.4285(13) 0.081(6) Uiso 1 1 d . . . H4C H 1.329(2) 0.4769(18) 0.0718(17) 0.103(7) Uiso 1 1 d . . . H18B H 0.588(2) 0.399(2) 0.0714(16) 0.113(9) Uiso 1 1 d . . . H2 H 1.2995(17) 0.5459(16) 0.3093(13) 0.078(6) Uiso 1 1 d . . . H19C H 0.993(2) 0.589(2) 0.3501(17) 0.120(9) Uiso 1 1 d . . . H8A H 0.836(2) 0.2381(19) -0.2095(16) 0.097(7) Uiso 1 1 d . . . H4A H 1.419(3) 0.472(2) 0.1756(18) 0.131(10) Uiso 1 1 d . . . H19A H 1.138(2) 0.590(2) 0.4087(17) 0.126(9) Uiso 1 1 d . . . H3 H 0.584(2) 0.578(2) 0.4362(17) 0.110(10) Uiso 1 1 d . . . H8B H 0.952(2) 0.169(2) -0.1387(15) 0.111(8) Uiso 1 1 d . . . H3A H 0.609(2) 0.4678(19) 0.4850(17) 0.112(9) Uiso 1 1 d . . . H4B H 1.357(2) 0.364(3) 0.1207(18) 0.141(11) Uiso 1 1 d . . . H19B H 1.046(2) 0.489(2) 0.4097(19) 0.125(10) Uiso 1 1 d . . . H8C H 0.971(2) 0.297(2) -0.1657(17) 0.122(9) Uiso 1 1 d . . . H18C H 0.619(2) 0.2852(19) 0.1375(18) 0.118(8) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N2 0.0559(8) 0.0402(7) 0.0433(8) -0.0010(6) 0.0228(7) 0.0041(6) F1 0.0752(7) 0.0889(7) 0.0531(6) 0.0048(6) 0.0365(5) -0.0072(6) F2 0.0843(7) 0.0539(6) 0.0772(7) -0.0005(5) 0.0261(6) 0.0287(5) N1 0.0473(8) 0.0446(8) 0.0467(8) 0.0042(6) 0.0215(6) 0.0069(6) C10 0.0533(10) 0.0414(9) 0.0427(9) 0.0010(7) 0.0223(8) 0.0073(8) C11 0.0526(10) 0.0352(8) 0.0443(9) 0.0049(7) 0.0238(8) 0.0058(7) C12 0.0508(9) 0.0408(9) 0.0460(9) -0.0020(7) 0.0242(8) -0.0007(8) C9 0.0526(9) 0.0387(9) 0.0473(9) 0.0020(7) 0.0255(8) 0.0026(7) C15 0.0567(10) 0.0529(10) 0.0559(10) -0.0139(9) 0.0338(9) -0.0118(9) C1 0.0597(11) 0.0510(10) 0.0486(10) -0.0028(8) 0.0165(8) 0.0060(9) C7 0.0549(11) 0.0472(10) 0.0614(11) -0.0002(8) 0.0227(9) -0.0006(8) C17 0.0669(11) 0.0443(10) 0.0508(10) 0.0010(8) 0.0300(9) 0.0021(9) C5 0.0691(12) 0.0428(9) 0.0469(10) -0.0028(8) 0.0177(9) 0.0045(9) C16 0.0700(11) 0.0526(10) 0.0505(10) 0.0003(9) 0.0322(9) -0.0065(9) C3 0.0494(10) 0.0519(10) 0.0574(11) 0.0085(9) 0.0183(9) 0.0070(8) C13 0.0699(12) 0.0478(10) 0.0652(12) 0.0098(9) 0.0413(10) 0.0079(9) B 0.0570(11) 0.0430(10) 0.0460(10) 0.0075(9) 0.0274(9) 0.0124(9) N3 0.0874(13) 0.0711(13) 0.0846(14) -0.0160(11) 0.0615(11) -0.0089(10) C8 0.0870(16) 0.0673(14) 0.0505(12) -0.0109(11) 0.0242(12) 0.0093(13) C14 0.0715(12) 0.0445(10) 0.0783(13) 0.0016(10) 0.0456(11) 0.0089(10) C4 0.0542(13) 0.0849(17) 0.0777(15) 0.0111(14) 0.0329(12) 0.0047(12) C6 0.0640(12) 0.0580(12) 0.0582(12) -0.0092(10) 0.0150(10) -0.0043(10) C2 0.0518(11) 0.0663(13) 0.0611(12) -0.0069(10) 0.0108(9) -0.0009(10) C19 0.0791(17) 0.0974(19) 0.0660(14) -0.0322(15) 0.0256(13) -0.0019(15) C18 0.0560(13) 0.0877(18) 0.0895(18) -0.0116(15) 0.0339(12) -0.0129(13) _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 N2 C5 1.3540(19) . ? N2 C9 1.4005(17) . ? N2 B 1.532(2) . ? F1 B 1.3770(18) . ? F2 B 1.4092(19) . ? N1 C3 1.3453(19) . ? N1 C10 1.4046(18) . ? N1 B 1.535(2) . ? C10 C11 1.395(2) . ? C10 C1 1.425(2) . ? C11 C9 1.398(2) . ? C11 C12 1.4884(19) . ? C12 C13 1.384(2) . ? C12 C17 1.389(2) . ? C9 C7 1.425(2) . ? C15 C14 1.380(2) . ? C15 C16 1.388(2) . ? C15 N3 1.394(2) . ? C1 C2 1.378(2) . ? C1 C19 1.495(3) . ? C7 C6 1.380(2) . ? C7 C18 1.500(2) . ? C17 C16 1.375(2) . ? C17 H17 1.010(17) . ? C5 C6 1.395(2) . ? C5 C8 1.490(2) . ? C16 H16 1.019(18) . ? C3 C2 1.397(2) . ? C3 C4 1.488(2) . ? C13 C14 1.378(2) . ? C13 H13 0.997(18) . ? N3 H3 0.83(2) . ? N3 H3A 0.90(2) . ? C8 H8A 0.96(2) . ? C8 H8B 1.00(2) . ? C8 H8C 0.99(2) . ? C14 H14 0.946(19) . ? C4 H4C 0.99(2) . ? C4 H4A 0.94(3) . ? C4 H4B 0.93(3) . ? C6 H6 0.957(17) . ? C2 H2 0.951(18) . ? C19 H19C 0.97(2) . ? C19 H19A 0.98(3) . ? C19 H19B 0.95(3) . ? C18 H18A 0.97(2) . ? C18 H18B 0.95(2) . ? C18 H18C 1.05(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 C5 N2 C9 108.42(13) . . ? C5 N2 B 126.66(13) . . ? C9 N2 B 124.43(13) . . ? C3 N1 C10 108.34(13) . . ? C3 N1 B 127.17(13) . . ? C10 N1 B 124.39(13) . . ? C11 C10 N1 120.27(13) . . ? C11 C10 C1 132.11(14) . . ? N1 C10 C1 107.53(13) . . ? C10 C11 C9 121.00(13) . . ? C10 C11 C12 118.93(13) . . ? C9 C11 C12 120.03(13) . . ? C13 C12 C17 117.46(14) . . ? C13 C12 C11 121.53(14) . . ? C17 C12 C11 120.99(14) . . ? C11 C9 N2 120.18(14) . . ? C11 C9 C7 132.07(14) . . ? N2 C9 C7 107.69(13) . . ? C14 C15 C16 117.94(15) . . ? C14 C15 N3 121.27(18) . . ? C16 C15 N3 120.74(17) . . ? C2 C1 C10 106.19(15) . . ? C2 C1 C19 124.32(18) . . ? C10 C1 C19 129.46(17) . . ? C6 C7 C9 106.05(14) . . ? C6 C7 C18 124.75(18) . . ? C9 C7 C18 129.18(17) . . ? C16 C17 C12 121.72(16) . . ? C16 C17 H17 120.6(9) . . ? C12 C17 H17 117.7(9) . . ? N2 C5 C6 108.57(15) . . ? N2 C5 C8 123.35(18) . . ? C6 C5 C8 128.07(18) . . ? C17 C16 C15 120.47(16) . . ? C17 C16 H16 121.6(10) . . ? C15 C16 H16 118.0(10) . . ? N1 C3 C2 108.99(14) . . ? N1 C3 C4 123.53(17) . . ? C2 C3 C4 127.46(18) . . ? C14 C13 C12 120.84(16) . . ? C14 C13 H13 122.6(10) . . ? C12 C13 H13 116.6(10) . . ? F1 B F2 108.34(13) . . ? F1 B N2 112.04(13) . . ? F2 B N2 108.68(14) . . ? F1 B N1 111.10(14) . . ? F2 B N1 109.46(13) . . ? N2 B N1 107.17(12) . . ? C15 N3 H3 116.6(16) . . ? C15 N3 H3A 117.1(16) . . ? H3 N3 H3A 116(2) . . ? C5 C8 H8A 107.7(12) . . ? C5 C8 H8B 110.9(12) . . ? H8A C8 H8B 110.6(19) . . ? C5 C8 H8C 112.3(14) . . ? H8A C8 H8C 108.9(19) . . ? H8B C8 H8C 106.5(18) . . ? C13 C14 C15 121.55(17) . . ? C13 C14 H14 120.3(11) . . ? C15 C14 H14 118.1(11) . . ? C3 C4 H4C 111.9(12) . . ? C3 C4 H4A 113.6(15) . . ? H4C C4 H4A 104.1(19) . . ? C3 C4 H4B 113.0(16) . . ? H4C C4 H4B 101.8(19) . . ? H4A C4 H4B 111(2) . . ? C7 C6 C5 109.24(17) . . ? C7 C6 H6 127.4(10) . . ? C5 C6 H6 123.3(10) . . ? C1 C2 C3 108.93(17) . . ? C1 C2 H2 126.0(11) . . ? C3 C2 H2 125.1(11) . . ? C1 C19 H19C 115.0(14) . . ? C1 C19 H19A 110.7(14) . . ? H19C C19 H19A 107.9(19) . . ? C1 C19 H19B 114.7(15) . . ? H19C C19 H19B 100(2) . . ? H19A C19 H19B 108(2) . . ? C7 C18 H18A 108.6(14) . . ? C7 C18 H18B 108.9(14) . . ? H18A C18 H18B 110(2) . . ? C7 C18 H18C 113.9(13) . . ? H18A C18 H18C 106.8(18) . . ? H18B C18 H18C 108.2(18) . . ? _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 27.54 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 0.164 _refine_diff_density_min -0.201 _refine_diff_density_rms 0.044 #===END data_2 _database_code_depnum_ccdc_archive 'CCDC 798784' #TrackingRef '1-6.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H21 B F2 N2 O0' _chemical_formula_sum 'C20 H21 B F2 N2 O0' _chemical_formula_weight 338.20 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21 ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 11.882(3) _cell_length_b 8.409(2) _cell_length_c 44.412(10) _cell_angle_alpha 90.00 _cell_angle_beta 91.766(4) _cell_angle_gamma 90.00 _cell_volume 4435.4(18) _cell_formula_units_Z 10 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2716 _cell_measurement_theta_min 2.597 _cell_measurement_theta_max 21.596 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.266 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1780 _exptl_absorpt_coefficient_mu 0.088 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9774 _exptl_absorpt_correction_T_max 0.9843 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART 1000 CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18795 _diffrn_reflns_av_R_equivalents 0.0446 _diffrn_reflns_av_sigmaI/netI 0.0846 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -42 _diffrn_reflns_limit_l_max 49 _diffrn_reflns_theta_min 1.38 _diffrn_reflns_theta_max 23.25 _reflns_number_total 11782 _reflns_number_gt 6734 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART (Siemens, 1996)' _computing_cell_refinement 'Bruker SMART (Siemens, 1996)' _computing_data_reduction 'Bruker SAINT (Siemens, 1996)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997a)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997a)' _computing_molecular_graphics 'Bruker SHELXTL (Sheldrick, 1997b)' _computing_publication_material 'Bruker SHELXTL (Sheldrick, 1997b)' _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^)+(0.1100P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 1.2(13) _refine_ls_number_reflns 11782 _refine_ls_number_parameters 1126 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1302 _refine_ls_R_factor_gt 0.0754 _refine_ls_wR_factor_ref 0.2155 _refine_ls_wR_factor_gt 0.1882 _refine_ls_goodness_of_fit_ref 1.001 _refine_ls_restrained_S_all 1.001 _refine_ls_shift/su_max 0.016 _refine_ls_shift/su_mean 0.003 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 C60 C 0.5515(6) 1.3334(10) 0.17648(14) 0.075(2) Uani 1 1 d . . . H60A H 0.6290 1.3293 0.1710 0.113 Uiso 1 1 calc R . . H60B H 0.5446 1.2928 0.1965 0.113 Uiso 1 1 calc R . . H60C H 0.5257 1.4416 0.1757 0.113 Uiso 1 1 calc R . . C01 C 0.0755(6) 0.9327(10) 0.39311(15) 0.074(2) Uani 1 1 d . . . H01A H 0.0469 0.8288 0.3976 0.111 Uiso 1 1 calc R . . H01B H 0.1221 0.9267 0.3759 0.111 Uiso 1 1 calc R . . H01C H 0.0138 1.0038 0.3889 0.111 Uiso 1 1 calc R . . C02 C 0.1432(5) 0.9924(10) 0.41939(16) 0.059(2) Uani 1 1 d . . . C03 C 0.1973(6) 1.1429(10) 0.42237(17) 0.066(2) Uani 1 1 d . . . H03 H 0.1965 1.2223 0.4078 0.079 Uiso 1 1 calc R . . C04 C 0.2507(5) 1.1522(9) 0.45005(16) 0.0541(19) Uani 1 1 d . . . C05 C 0.3184(5) 1.2942(9) 0.46041(15) 0.062(2) Uani 1 1 d . . . H05A H 0.3461 1.2772 0.4807 0.092 Uiso 1 1 calc R . . H05B H 0.2716 1.3873 0.4597 0.092 Uiso 1 1 calc R . . H05C H 0.3808 1.3087 0.4475 0.092 Uiso 1 1 calc R . . C06 C 0.2288(5) 1.0030(8) 0.46464(15) 0.0483(17) Uani 1 1 d . . . C07 C 0.2634(5) 0.9477(9) 0.49306(14) 0.0423(16) Uani 1 1 d . . . C08 C 0.2314(5) 0.7953(9) 0.50213(14) 0.0466(18) Uani 1 1 d . . . C09 C 0.2532(5) 0.7071(9) 0.52899(14) 0.0495(18) Uani 1 1 d . . . C010 C 0.3344(5) 0.7463(11) 0.55525(14) 0.068(2) Uani 1 1 d . . . H01D H 0.3682 0.8482 0.5519 0.102 Uiso 1 1 calc R . . H01E H 0.3920 0.6664 0.5567 0.102 Uiso 1 1 calc R . . H01F H 0.2939 0.7489 0.5736 0.102 Uiso 1 1 calc R . . C011 C 0.1916(6) 0.5710(10) 0.52684(14) 0.0563(19) Uani 1 1 d . . . H011 H 0.1882 0.4926 0.5415 0.068 Uiso 1 1 calc R . . C012 C 0.1350(5) 0.5685(9) 0.49930(15) 0.0547(18) Uani 1 1 d . . . C013 C 0.0561(5) 0.4429(10) 0.48674(16) 0.069(2) Uani 1 1 d . . . H01G H 0.0285 0.4745 0.4671 0.103 Uiso 1 1 calc R . . H01H H -0.0060 0.4305 0.4998 0.103 Uiso 1 1 calc R . . H01I H 0.0956 0.3438 0.4853 0.103 Uiso 1 1 calc R . . C014 C 0.3347(5) 1.0479(8) 0.51374(13) 0.0440(17) Uani 1 1 d . . . C015 C 0.4512(5) 1.0585(9) 0.51178(13) 0.0528(18) Uani 1 1 d . . . H015 H 0.4873 1.0038 0.4966 0.063 Uiso 1 1 calc R . . C016 C 0.5126(5) 1.1478(8) 0.53176(13) 0.0510(18) Uani 1 1 d . . . H016 H 0.5904 1.1530 0.5301 0.061 Uiso 1 1 calc R . . C017 C 0.4632(6) 1.2301(9) 0.55422(14) 0.0535(18) Uani 1 1 d . . . C018 C 0.3468(6) 1.2217(9) 0.55634(15) 0.061(2) Uani 1 1 d . . . H018 H 0.3115 1.2783 0.5714 0.074 Uiso 1 1 calc R . . C019 C 0.2832(6) 1.1304(9) 0.53645(14) 0.0535(19) Uani 1 1 d . . . H019 H 0.2055 1.1244 0.5383 0.064 Uiso 1 1 calc R . . C020 C 0.5300(6) 1.3349(11) 0.57640(14) 0.080(2) Uani 1 1 d . . . H02A H 0.6086 1.3294 0.5721 0.120 Uiso 1 1 calc R . . H02B H 0.5189 1.2983 0.5966 0.120 Uiso 1 1 calc R . . H02C H 0.5045 1.4429 0.5745 0.120 Uiso 1 1 calc R . . N9 N 0.1636(4) 0.9106(7) 0.44487(12) 0.0465(16) Uani 1 1 d . . . N10 N 0.1577(4) 0.7020(7) 0.48428(11) 0.0451(13) Uani 1 1 d . . . F9 F 0.1654(4) 0.6333(5) 0.43163(8) 0.0714(12) Uani 1 1 d . . . F10 F 0.0027(3) 0.7359(5) 0.44832(8) 0.0711(12) Uani 1 1 d . . . B5 B 0.1197(6) 0.7408(12) 0.45131(19) 0.056(2) Uani 1 1 d . . . C4 C 0.0901(7) 0.8707(12) 0.19269(15) 0.091(3) Uani 1 1 d . . . H4A H 0.0640 0.9751 0.1978 0.137 Uiso 1 1 calc R . . H4B H 0.0270 0.8049 0.1870 0.137 Uiso 1 1 calc R . . H4C H 0.1402 0.8780 0.1762 0.137 Uiso 1 1 calc R . . C3 C 0.1506(6) 0.8001(9) 0.21911(15) 0.056(2) Uani 1 1 d . . . C2 C 0.2040(6) 0.6500(9) 0.22239(15) 0.059(2) Uani 1 1 d . . . H2 H 0.2004 0.5690 0.2081 0.071 Uiso 1 1 calc R . . C1 C 0.2617(5) 0.6415(9) 0.24960(14) 0.0485(17) Uani 1 1 d . . . C19 C 0.3288(6) 0.5031(9) 0.26061(15) 0.067(2) Uani 1 1 d . . . H5A H 0.3608 0.5263 0.2802 0.101 Uiso 1 1 calc R . . H5B H 0.3881 0.4821 0.2470 0.101 Uiso 1 1 calc R . . H5C H 0.2810 0.4115 0.2617 0.101 Uiso 1 1 calc R . . C10 C 0.2403(5) 0.7892(8) 0.26447(13) 0.0458(18) Uani 1 1 d . . . C11 C 0.2722(5) 0.8497(9) 0.29271(13) 0.0446(18) Uani 1 1 d . . . C9 C 0.2384(5) 0.9988(9) 0.30240(14) 0.0461(18) Uani 1 1 d . . . C7 C 0.2629(5) 1.0866(10) 0.32871(14) 0.0523(19) Uani 1 1 d . . . C6 C 0.2000(5) 1.2247(9) 0.32619(15) 0.0568(19) Uani 1 1 d . . . H10 H 0.1982 1.3050 0.3406 0.068 Uiso 1 1 calc R . . C5 C 0.1403(6) 1.2248(10) 0.29903(14) 0.0543(18) Uani 1 1 d . . . C8 C 0.0644(6) 1.3491(10) 0.28644(16) 0.074(2) Uani 1 1 d . . . H12A H 0.0366 1.3170 0.2668 0.111 Uiso 1 1 calc R . . H12B H 0.1051 1.4472 0.2848 0.111 Uiso 1 1 calc R . . H12C H 0.0023 1.3637 0.2995 0.111 Uiso 1 1 calc R . . C12 C 0.3405(5) 0.7487(8) 0.31361(14) 0.0450(17) Uani 1 1 d . . . C13 C 0.4560(5) 0.7394(9) 0.31180(14) 0.0539(18) Uani 1 1 d . . . H14 H 0.4926 0.7964 0.2971 0.065 Uiso 1 1 calc R . . C14 C 0.5187(5) 0.6431(10) 0.33241(15) 0.064(2) Uani 1 1 d . . . H15 H 0.5962 0.6347 0.3305 0.077 Uiso 1 1 calc R . . C15 C 0.4674(6) 0.5612(9) 0.35533(14) 0.0567(19) Uani 1 1 d . . . C16 C 0.3519(6) 0.5734(10) 0.35650(15) 0.062(2) Uani 1 1 d . . . H17 H 0.3149 0.5164 0.3712 0.075 Uiso 1 1 calc R . . C17 C 0.2888(6) 0.6674(9) 0.33663(14) 0.059(2) Uani 1 1 d . . . H18 H 0.2114 0.6760 0.3387 0.071 Uiso 1 1 calc R . . C18 C 0.5356(7) 0.4632(12) 0.37708(16) 0.093(3) Uani 1 1 d . . . H19A H 0.4869 0.4143 0.3912 0.140 Uiso 1 1 calc R . . H19B H 0.5891 0.5300 0.3877 0.140 Uiso 1 1 calc R . . H19C H 0.5750 0.3824 0.3664 0.140 Uiso 1 1 calc R . . C20 C 0.3413(6) 1.0426(11) 0.35477(14) 0.075(2) Uani 1 1 d . . . H20A H 0.3748 0.9409 0.3510 0.113 Uiso 1 1 calc R . . H20B H 0.2997 1.0374 0.3729 0.113 Uiso 1 1 calc R . . H20C H 0.3994 1.1214 0.3570 0.113 Uiso 1 1 calc R . . N1 N 0.1712(5) 0.8833(7) 0.24502(13) 0.0541(17) Uani 1 1 d . . . N2 N 0.1661(4) 1.0919(7) 0.28375(11) 0.0500(15) Uani 1 1 d . . . F1 F 0.1743(4) 1.1587(5) 0.23148(8) 0.0766(13) Uani 1 1 d . . . F2 F 0.0123(3) 1.0543(6) 0.24824(8) 0.0767(13) Uani 1 1 d . . . B1 B 0.1276(6) 1.0510(10) 0.25146(16) 0.047(2) Uani 1 1 d . . . C61 C 0.8663(6) 0.3018(10) 0.38097(16) 0.062(2) Uani 1 1 d . . . C62 C 0.9305(7) 0.3734(12) 0.40718(16) 0.093(3) Uani 1 1 d . . . H62A H 0.9531 0.4795 0.4022 0.139 Uiso 1 1 calc R . . H62B H 0.9961 0.3102 0.4118 0.139 Uiso 1 1 calc R . . H62C H 0.8835 0.3763 0.4244 0.139 Uiso 1 1 calc R . . C63 C 0.8153(6) 0.1518(10) 0.37668(15) 0.056(2) Uani 1 1 d . . . H63 H 0.8213 0.0689 0.3905 0.067 Uiso 1 1 calc R . . C64 C 0.7577(6) 0.1424(9) 0.35069(14) 0.0513(18) Uani 1 1 d . . . C65 C 0.7768(5) 0.2900(9) 0.33532(14) 0.0474(18) Uani 1 1 d . . . C66 C 0.7437(5) 0.3501(10) 0.30766(13) 0.0447(18) Uani 1 1 d . . . C67 C 0.7778(5) 0.5001(8) 0.29773(14) 0.0427(17) Uani 1 1 d . . . C68 C 0.7521(6) 0.5854(10) 0.27092(14) 0.056(2) Uani 1 1 d . . . C69 C 0.8159(5) 0.7262(10) 0.27420(15) 0.0597(19) Uani 1 1 d . . . H69 H 0.8178 0.8071 0.2599 0.072 Uiso 1 1 calc R . . C70 C 0.8743(5) 0.7274(10) 0.30112(14) 0.0512(18) Uani 1 1 d . . . C71 C 0.9514(6) 0.8514(10) 0.31307(15) 0.068(2) Uani 1 1 d . . . H71A H 0.9803 0.8202 0.3326 0.102 Uiso 1 1 calc R . . H71B H 0.9113 0.9500 0.3147 0.102 Uiso 1 1 calc R . . H71C H 1.0127 0.8645 0.2997 0.102 Uiso 1 1 calc R . . C72 C 0.6750(6) 0.5436(10) 0.24565(14) 0.069(2) Uani 1 1 d . . . H72A H 0.6409 0.4424 0.2495 0.104 Uiso 1 1 calc R . . H72B H 0.7162 0.5378 0.2274 0.104 Uiso 1 1 calc R . . H72C H 0.6174 0.6233 0.2435 0.104 Uiso 1 1 calc R . . C73 C 0.6884(6) 0.0030(9) 0.33970(16) 0.072(2) Uani 1 1 d . . . H73A H 0.6567 0.0260 0.3200 0.108 Uiso 1 1 calc R . . H73B H 0.6289 -0.0163 0.3534 0.108 Uiso 1 1 calc R . . H73C H 0.7354 -0.0896 0.3387 0.108 Uiso 1 1 calc R . . C74 C 0.6765(5) 0.2500(8) 0.28619(14) 0.0454(17) Uani 1 1 d . . . C75 C 0.7271(6) 0.1663(9) 0.26381(14) 0.0528(19) Uani 1 1 d . . . H75 H 0.8049 0.1706 0.2622 0.063 Uiso 1 1 calc R . . C76 C 0.6636(5) 0.0754(9) 0.24360(13) 0.0530(18) Uani 1 1 d . . . H76 H 0.6999 0.0213 0.2284 0.064 Uiso 1 1 calc R . . C77 C 0.5484(6) 0.0625(10) 0.24528(14) 0.0572(19) Uani 1 1 d . . . C78 C 0.4978(5) 0.1447(9) 0.26806(14) 0.0573(19) Uani 1 1 d . . . H78 H 0.4201 0.1383 0.2698 0.069 Uiso 1 1 calc R . . C79 C 0.5607(5) 0.2380(9) 0.28874(13) 0.0509(18) Uani 1 1 d . . . H79 H 0.5249 0.2914 0.3041 0.061 Uiso 1 1 calc R . . C80 C 0.4792(6) -0.0359(11) 0.22335(14) 0.073(2) Uani 1 1 d . . . H80A H 0.5279 -0.0865 0.2094 0.110 Uiso 1 1 calc R . . H80B H 0.4268 0.0314 0.2125 0.110 Uiso 1 1 calc R . . H80C H 0.4388 -0.1155 0.2341 0.110 Uiso 1 1 calc R . . N7 N 0.8526(4) 0.5938(8) 0.31639(11) 0.0511(15) Uani 1 1 d . . . N8 N 0.8450(4) 0.3863(6) 0.35525(13) 0.0444(15) Uani 1 1 d . . . F7 F 1.0057(3) 0.5550(6) 0.35154(8) 0.0764(13) Uani 1 1 d . . . F8 F 0.8434(4) 0.6588(6) 0.36870(9) 0.0807(14) Uani 1 1 d . . . B4 B 0.8887(6) 0.5540(11) 0.34883(17) 0.050(2) Uani 1 1 d . . . C21 C 0.9630(5) -0.0482(9) 0.11508(15) 0.0600(18) Uani 1 1 d . . . H21A H 0.9857 -0.0178 0.1352 0.090 Uiso 1 1 calc R . . H21B H 1.0285 -0.0613 0.1032 0.090 Uiso 1 1 calc R . . H21C H 0.9222 -0.1467 0.1156 0.090 Uiso 1 1 calc R . . C22 C 0.8889(5) 0.0787(9) 0.10134(14) 0.0525(17) Uani 1 1 d . . . C23 C 0.8391(5) 0.0859(9) 0.07304(13) 0.0544(17) Uani 1 1 d . . . H23 H 0.8486 0.0107 0.0580 0.065 Uiso 1 1 calc R . . C24 C 0.7741(5) 0.2182(8) 0.07013(12) 0.0455(16) Uani 1 1 d . . . C25 C 0.7026(6) 0.2594(10) 0.04276(14) 0.077(2) Uani 1 1 d . . . H25A H 0.6678 0.3611 0.0456 0.115 Uiso 1 1 calc R . . H25B H 0.6454 0.1799 0.0397 0.115 Uiso 1 1 calc R . . H25C H 0.7489 0.2636 0.0254 0.115 Uiso 1 1 calc R . . C26 C 0.7899(5) 0.3036(9) 0.09824(13) 0.0457(17) Uani 1 1 d . . . C27 C 0.7539(5) 0.4514(8) 0.10762(14) 0.0399(15) Uani 1 1 d . . . C28 C 0.7859(5) 0.5109(8) 0.13638(14) 0.0445(16) Uani 1 1 d . . . C29 C 0.7649(5) 0.6580(8) 0.15015(14) 0.0505(17) Uani 1 1 d . . . C30 C 0.8174(6) 0.6478(11) 0.17893(15) 0.062(2) Uani 1 1 d . . . H30 H 0.8153 0.7253 0.1938 0.075 Uiso 1 1 calc R . . C31 C 0.8726(5) 0.5043(9) 0.18135(15) 0.0567(19) Uani 1 1 d . . . C32 C 0.9374(6) 0.4391(10) 0.20833(13) 0.068(2) Uani 1 1 d . . . H32A H 0.9648 0.3347 0.2038 0.102 Uiso 1 1 calc R . . H32B H 0.8888 0.4333 0.2252 0.102 Uiso 1 1 calc R . . H32C H 0.9998 0.5078 0.2132 0.102 Uiso 1 1 calc R . . C33 C 0.6828(5) 0.5521(8) 0.08696(12) 0.0418(15) Uani 1 1 d . . . C34 C 0.7316(5) 0.6522(9) 0.06707(15) 0.060(2) Uani 1 1 d . . . H34 H 0.8095 0.6599 0.0664 0.072 Uiso 1 1 calc R . . C35 C 0.6631(5) 0.7424(9) 0.04782(14) 0.0609(19) Uani 1 1 d . . . H35 H 0.6970 0.8118 0.0346 0.073 Uiso 1 1 calc R . . C36 C 0.5495(5) 0.7342(9) 0.04742(12) 0.0501(17) Uani 1 1 d . . . C37 C 0.5018(4) 0.6373(8) 0.06821(13) 0.0486(16) Uani 1 1 d . . . H37 H 0.4238 0.6325 0.0691 0.058 Uiso 1 1 calc R . . C38 C 0.5659(5) 0.5477(8) 0.08760(13) 0.0567(18) Uani 1 1 d . . . H38 H 0.5311 0.4828 0.1015 0.068 Uiso 1 1 calc R . . C39 C 0.4792(6) 0.8354(11) 0.02535(15) 0.083(3) Uani 1 1 d . . . H39A H 0.4007 0.8144 0.0280 0.125 Uiso 1 1 calc R . . H39B H 0.4984 0.8093 0.0051 0.125 Uiso 1 1 calc R . . H39C H 0.4943 0.9459 0.0291 0.125 Uiso 1 1 calc R . . C40 C 0.6955(5) 0.7961(8) 0.13957(15) 0.0616(19) Uani 1 1 d . . . H40A H 0.6994 0.8789 0.1544 0.092 Uiso 1 1 calc R . . H40B H 0.6186 0.7630 0.1365 0.092 Uiso 1 1 calc R . . H40C H 0.7237 0.8352 0.1210 0.092 Uiso 1 1 calc R . . C41 C 0.1374(5) 1.0083(9) 0.02275(14) 0.0535(18) Uani 1 1 d . . . C42 C 0.1934(6) 1.1538(10) 0.02522(15) 0.062(2) Uani 1 1 d . . . H42 H 0.1892 1.2350 0.0110 0.074 Uiso 1 1 calc R . . C43 C 0.2554(5) 1.1591(9) 0.05173(14) 0.0537(18) Uani 1 1 d . . . C44 C 0.2388(5) 1.0077(7) 0.06553(12) 0.0369(14) Uani 1 1 d . . . C45 C 0.0588(5) 0.9499(9) -0.00128(14) 0.064(2) Uani 1 1 d . . . H45A H 0.0366 0.8429 0.0032 0.097 Uiso 1 1 calc R . . H45B H 0.0954 0.9521 -0.0202 0.097 Uiso 1 1 calc R . . H45C H -0.0067 1.0169 -0.0024 0.097 Uiso 1 1 calc R . . C46 C 0.3310(5) 1.2946(8) 0.06114(14) 0.0625(19) Uani 1 1 d . . . H46A H 0.3658 1.2717 0.0805 0.094 Uiso 1 1 calc R . . H46B H 0.2874 1.3903 0.0624 0.094 Uiso 1 1 calc R . . H46C H 0.3882 1.3083 0.0466 0.094 Uiso 1 1 calc R . . C47 C 0.2789(4) 0.9497(8) 0.09321(13) 0.0380(14) Uani 1 1 d . . . C48 C 0.2476(4) 0.7957(7) 0.10292(12) 0.0314(14) Uani 1 1 d . . . C49 C 0.2752(5) 0.7094(9) 0.12932(13) 0.0430(16) Uani 1 1 d . . . C50 C 0.2134(5) 0.5738(9) 0.12770(13) 0.0542(18) Uani 1 1 d . . . H50 H 0.2120 0.4952 0.1424 0.065 Uiso 1 1 calc R . . C51 C 0.1517(5) 0.5712(8) 0.10021(13) 0.0446(15) Uani 1 1 d . . . C52 C 0.0707(5) 0.4422(9) 0.08873(15) 0.064(2) Uani 1 1 d . . . H52A H 0.0414 0.4707 0.0691 0.096 Uiso 1 1 calc R . . H52B H 0.0098 0.4321 0.1023 0.096 Uiso 1 1 calc R . . H52C H 0.1100 0.3428 0.0876 0.096 Uiso 1 1 calc R . . C53 C 0.3555(5) 0.7455(9) 0.15485(13) 0.061(2) Uani 1 1 d . . . H53A H 0.3885 0.8483 0.1519 0.091 Uiso 1 1 calc R . . H53B H 0.4136 0.6663 0.1557 0.091 Uiso 1 1 calc R . . H53C H 0.3160 0.7453 0.1734 0.091 Uiso 1 1 calc R . . C54 C 0.4668(5) 1.0620(8) 0.11147(12) 0.0485(16) Uani 1 1 d . . . H54 H 0.5020 1.0102 0.0959 0.058 Uiso 1 1 calc R . . C55 C 0.3504(5) 1.0485(8) 0.11391(12) 0.0436(16) Uani 1 1 d . . . C56 C 0.3020(5) 1.1299(9) 0.13682(13) 0.0540(19) Uani 1 1 d . . . H56 H 0.2245 1.1250 0.1389 0.065 Uiso 1 1 calc R . . C57 C 0.3667(6) 1.2192(8) 0.15696(13) 0.0554(18) Uani 1 1 d . . . H57 H 0.3314 1.2713 0.1725 0.066 Uiso 1 1 calc R . . C58 C 0.4812(5) 1.2338(8) 0.15476(13) 0.0495(16) Uani 1 1 d . . . C59 C 0.5301(5) 1.1501(8) 0.13161(13) 0.0501(17) Uani 1 1 d . . . H59 H 0.6078 1.1540 0.1297 0.060 Uiso 1 1 calc R . . N3 N 0.8546(4) 0.4182(7) 0.15632(12) 0.0461(15) Uani 1 1 d . . . N4 N 0.8606(4) 0.2087(6) 0.11685(9) 0.0385(12) Uani 1 1 d . . . N5 N 0.1712(4) 0.7056(6) 0.08519(9) 0.0364(11) Uani 1 1 d . . . N6 N 0.1669(4) 0.9194(6) 0.04751(11) 0.0401(14) Uani 1 1 d . . . F3 F 1.0119(3) 0.2410(5) 0.15380(7) 0.0675(11) Uani 1 1 d . . . F4 F 0.8474(3) 0.1405(5) 0.16931(8) 0.0716(12) Uani 1 1 d . . . F5 F 0.1720(3) 0.6433(5) 0.03234(7) 0.0592(11) Uani 1 1 d . . . F6 F 0.0106(2) 0.7378(4) 0.05183(7) 0.0543(9) Uani 1 1 d . . . B2 B 0.8957(6) 0.2517(10) 0.15009(17) 0.050(2) Uani 1 1 d . . . B3 B 0.1276(6) 0.7469(10) 0.05320(15) 0.0425(18) 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 C60 0.082(5) 0.070(6) 0.071(5) 0.001(5) -0.039(4) -0.020(5) C01 0.061(5) 0.075(5) 0.084(6) -0.006(5) -0.036(4) -0.005(4) C02 0.038(4) 0.070(6) 0.068(5) -0.007(5) -0.008(4) 0.004(4) C03 0.060(5) 0.057(5) 0.080(6) 0.011(5) 0.002(4) 0.003(4) C04 0.035(4) 0.052(5) 0.075(5) -0.006(4) -0.005(4) 0.006(4) C05 0.040(4) 0.055(5) 0.089(5) -0.001(4) -0.003(4) -0.003(4) C06 0.037(4) 0.039(4) 0.069(5) -0.002(4) 0.005(4) 0.014(3) C07 0.034(4) 0.033(4) 0.059(4) -0.004(4) 0.004(3) -0.001(3) C08 0.040(4) 0.055(5) 0.045(4) -0.008(4) -0.007(3) 0.011(4) C09 0.043(4) 0.051(5) 0.054(4) -0.010(4) 0.004(3) 0.011(4) C010 0.051(4) 0.089(7) 0.064(4) -0.004(5) -0.005(3) 0.005(4) C011 0.066(5) 0.051(5) 0.052(4) 0.013(4) 0.009(4) 0.004(4) C012 0.056(5) 0.044(5) 0.065(5) 0.000(4) 0.011(4) -0.002(4) C013 0.047(4) 0.067(5) 0.092(6) -0.019(5) 0.004(4) -0.018(4) C014 0.040(4) 0.048(5) 0.044(4) -0.013(3) -0.007(3) -0.003(3) C015 0.037(4) 0.060(5) 0.061(4) 0.001(4) 0.000(3) 0.000(4) C016 0.044(4) 0.054(5) 0.054(4) 0.001(4) -0.011(3) -0.008(4) C017 0.055(5) 0.046(4) 0.058(4) 0.012(4) -0.016(3) -0.010(4) C018 0.081(6) 0.045(4) 0.058(4) -0.015(4) -0.007(4) 0.005(4) C019 0.045(4) 0.053(5) 0.062(4) -0.006(4) -0.005(3) -0.015(4) C020 0.099(6) 0.076(6) 0.063(5) 0.003(5) -0.033(4) -0.019(5) N9 0.043(3) 0.061(5) 0.035(3) 0.005(3) -0.008(3) -0.001(3) N10 0.040(3) 0.045(4) 0.051(3) -0.003(3) 0.000(3) -0.005(3) F9 0.098(3) 0.053(3) 0.064(2) -0.012(2) 0.004(2) 0.005(2) F10 0.051(2) 0.080(3) 0.080(3) 0.004(2) -0.0213(18) -0.014(2) B5 0.036(5) 0.060(6) 0.072(6) -0.011(5) 0.000(4) 0.007(5) C4 0.086(6) 0.135(9) 0.053(5) -0.015(5) -0.019(4) 0.028(6) C3 0.054(4) 0.053(5) 0.059(5) -0.010(4) -0.010(4) -0.005(4) C2 0.072(5) 0.045(5) 0.060(5) -0.013(4) -0.014(4) 0.007(4) C1 0.056(4) 0.042(4) 0.048(4) -0.005(4) 0.009(3) -0.002(4) C19 0.076(5) 0.045(5) 0.080(5) -0.009(4) 0.007(4) 0.013(4) C10 0.040(4) 0.052(5) 0.046(4) 0.011(4) 0.000(3) 0.005(3) C11 0.032(4) 0.061(5) 0.040(4) 0.006(4) -0.010(3) -0.011(4) C9 0.042(4) 0.050(5) 0.046(4) 0.005(4) 0.004(3) 0.013(4) C7 0.043(4) 0.060(5) 0.052(4) -0.005(4) -0.010(3) -0.007(4) C6 0.056(4) 0.043(4) 0.071(5) -0.006(4) 0.003(4) 0.009(4) C5 0.053(4) 0.059(5) 0.051(4) 0.005(4) 0.002(3) 0.001(4) C8 0.078(6) 0.051(5) 0.093(6) -0.027(5) 0.001(4) 0.016(5) C12 0.032(4) 0.042(4) 0.060(4) -0.004(4) 0.000(3) -0.003(3) C13 0.048(4) 0.055(5) 0.058(4) -0.003(4) -0.001(3) 0.005(4) C14 0.040(4) 0.064(5) 0.086(5) -0.019(5) -0.010(4) 0.006(4) C15 0.073(5) 0.046(5) 0.049(4) -0.006(4) -0.015(4) 0.013(4) C16 0.054(5) 0.071(5) 0.062(4) 0.006(5) -0.004(4) -0.003(4) C17 0.053(5) 0.063(6) 0.062(4) 0.007(4) 0.000(4) -0.002(4) C18 0.108(7) 0.093(7) 0.076(5) -0.004(6) -0.030(5) 0.039(6) C20 0.072(5) 0.084(7) 0.068(5) -0.029(5) -0.021(4) 0.007(5) N1 0.050(4) 0.059(5) 0.053(4) 0.004(3) 0.000(3) 0.008(3) N2 0.036(3) 0.053(4) 0.060(4) 0.002(3) -0.001(3) 0.005(3) F1 0.115(4) 0.059(3) 0.056(2) 0.014(2) 0.012(2) 0.010(3) F2 0.051(2) 0.100(4) 0.078(3) -0.004(3) -0.0173(19) 0.021(3) B1 0.055(5) 0.044(5) 0.042(4) 0.009(4) -0.008(4) 0.007(4) C61 0.061(5) 0.063(6) 0.061(5) 0.004(4) -0.010(4) -0.001(4) C62 0.085(6) 0.133(9) 0.060(5) 0.001(5) -0.018(4) -0.014(6) C63 0.069(5) 0.049(5) 0.049(4) 0.017(4) -0.015(4) 0.009(4) C64 0.062(5) 0.043(5) 0.049(4) 0.001(4) 0.013(4) 0.002(4) C65 0.038(4) 0.054(5) 0.050(4) -0.006(4) -0.006(3) 0.002(4) C66 0.033(4) 0.069(5) 0.032(4) 0.008(4) 0.002(3) 0.010(4) C67 0.034(4) 0.037(4) 0.057(4) -0.001(4) 0.008(3) -0.006(3) C68 0.051(4) 0.068(6) 0.048(4) 0.000(4) 0.000(3) 0.009(4) C69 0.053(4) 0.058(5) 0.068(5) 0.011(4) -0.006(4) 0.004(4) C70 0.046(4) 0.056(5) 0.051(4) 0.004(4) 0.006(3) -0.004(4) C71 0.082(6) 0.060(5) 0.062(5) 0.014(5) 0.005(4) -0.015(5) C72 0.076(5) 0.072(6) 0.058(4) 0.022(4) -0.022(4) -0.009(5) C73 0.079(6) 0.050(5) 0.088(5) 0.015(5) 0.005(4) 0.001(4) C74 0.040(4) 0.034(4) 0.062(4) -0.001(4) 0.006(3) 0.005(3) C75 0.048(4) 0.056(5) 0.054(4) -0.006(4) -0.004(3) 0.011(4) C76 0.052(4) 0.061(5) 0.046(4) -0.004(4) -0.006(3) -0.001(4) C77 0.062(5) 0.057(5) 0.052(4) 0.003(4) -0.017(3) -0.010(4) C78 0.049(4) 0.065(5) 0.058(4) 0.018(4) -0.004(3) -0.007(4) C79 0.041(4) 0.055(5) 0.056(4) 0.003(4) 0.000(3) 0.009(4) C80 0.079(5) 0.074(6) 0.066(5) -0.002(5) -0.018(4) -0.021(5) N7 0.038(3) 0.056(4) 0.060(4) -0.005(3) -0.001(3) 0.001(3) N8 0.048(3) 0.038(4) 0.046(4) -0.005(3) -0.005(3) -0.005(3) F7 0.047(2) 0.098(4) 0.083(3) 0.007(3) -0.0127(19) -0.018(3) F8 0.115(4) 0.064(3) 0.063(3) -0.021(3) 0.005(2) -0.007(3) B4 0.055(5) 0.049(6) 0.048(5) 0.000(4) -0.008(4) -0.008(5) C21 0.047(4) 0.056(5) 0.076(5) 0.000(4) -0.005(3) 0.012(4) C22 0.044(4) 0.043(4) 0.071(5) -0.003(4) 0.008(3) -0.007(3) C23 0.070(5) 0.052(4) 0.041(4) -0.003(3) -0.005(3) -0.004(4) C24 0.046(4) 0.051(4) 0.039(3) -0.007(3) -0.003(3) -0.001(4) C25 0.079(5) 0.092(7) 0.058(4) -0.004(4) -0.025(4) 0.006(5) C26 0.029(4) 0.059(5) 0.049(4) 0.013(4) -0.005(3) -0.004(3) C27 0.033(4) 0.033(4) 0.054(4) 0.024(4) 0.000(3) -0.004(3) C28 0.037(4) 0.044(4) 0.052(4) 0.002(4) -0.001(3) -0.002(3) C29 0.038(4) 0.048(5) 0.065(5) 0.000(4) 0.000(3) -0.002(3) C30 0.062(5) 0.068(6) 0.058(5) -0.007(4) 0.011(4) 0.007(4) C31 0.047(4) 0.065(5) 0.058(4) -0.013(4) 0.005(3) -0.002(4) C32 0.084(5) 0.072(5) 0.047(4) -0.017(4) -0.026(4) 0.006(4) C33 0.035(4) 0.044(4) 0.046(4) 0.003(3) -0.003(3) 0.000(3) C34 0.032(4) 0.070(6) 0.078(5) 0.023(4) 0.007(3) 0.000(4) C35 0.055(5) 0.060(5) 0.067(4) 0.014(4) -0.004(3) -0.002(4) C36 0.048(4) 0.059(5) 0.043(4) -0.007(4) -0.004(3) 0.007(4) C37 0.021(3) 0.056(4) 0.068(4) 0.001(4) -0.010(3) 0.002(3) C38 0.042(4) 0.057(5) 0.071(4) 0.014(4) 0.000(3) -0.001(4) C39 0.063(5) 0.104(7) 0.081(5) 0.019(5) -0.030(4) 0.020(5) C40 0.045(4) 0.060(5) 0.079(5) 0.003(4) 0.005(3) -0.009(4) C41 0.047(4) 0.067(5) 0.045(4) 0.004(4) -0.006(3) 0.005(4) C42 0.066(5) 0.064(6) 0.056(4) 0.020(4) 0.004(4) 0.022(4) C43 0.053(4) 0.048(5) 0.060(4) -0.003(4) 0.001(3) 0.007(3) C44 0.036(3) 0.032(4) 0.043(4) 0.005(3) 0.003(3) 0.008(3) C45 0.072(5) 0.065(5) 0.054(4) 0.016(4) -0.030(4) 0.002(4) C46 0.063(5) 0.054(5) 0.070(5) 0.021(4) -0.008(4) -0.008(4) C47 0.025(3) 0.034(4) 0.055(4) 0.005(3) 0.005(3) -0.003(3) C48 0.028(3) 0.029(4) 0.037(3) 0.009(3) -0.005(3) 0.011(3) C49 0.045(4) 0.046(4) 0.038(3) 0.003(3) 0.004(3) -0.002(4) C50 0.067(5) 0.049(5) 0.048(4) 0.018(4) 0.013(3) 0.003(4) C51 0.034(3) 0.049(4) 0.051(4) 0.005(4) 0.003(3) 0.000(3) C52 0.062(5) 0.057(4) 0.074(5) -0.020(4) 0.003(4) -0.012(4) C53 0.046(4) 0.077(6) 0.057(4) 0.005(4) -0.013(3) 0.004(4) C54 0.042(4) 0.054(4) 0.050(4) -0.001(3) 0.004(3) -0.007(3) C55 0.037(4) 0.046(4) 0.047(4) 0.002(3) -0.006(3) -0.002(3) C56 0.028(4) 0.082(6) 0.051(4) -0.002(4) -0.013(3) -0.004(4) C57 0.067(5) 0.053(4) 0.047(4) 0.004(4) -0.007(3) -0.004(4) C58 0.057(4) 0.042(4) 0.049(4) 0.009(3) -0.014(3) -0.008(4) C59 0.035(4) 0.047(4) 0.066(4) 0.013(4) -0.013(3) -0.016(3) N3 0.042(3) 0.056(4) 0.041(4) -0.006(3) -0.001(3) -0.003(3) N4 0.037(3) 0.040(3) 0.039(3) -0.002(3) -0.002(2) -0.001(2) N5 0.038(3) 0.027(3) 0.045(3) 0.006(3) 0.001(2) 0.000(2) N6 0.036(3) 0.045(4) 0.039(3) 0.011(3) -0.011(2) -0.006(3) F3 0.047(2) 0.080(3) 0.073(2) -0.007(2) -0.0193(17) 0.015(2) F4 0.090(3) 0.067(3) 0.058(2) 0.004(2) 0.014(2) -0.003(2) F5 0.065(2) 0.061(3) 0.051(2) -0.008(2) -0.0008(18) 0.006(2) F6 0.0383(19) 0.063(2) 0.061(2) 0.0051(19) -0.0136(15) -0.0066(18) B2 0.036(4) 0.058(6) 0.056(5) 0.012(4) 0.000(3) -0.006(4) B3 0.035(4) 0.052(5) 0.040(4) -0.008(4) 0.001(3) 0.007(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 C60 C58 1.510(8) . ? C60 H60A 0.9600 . ? C60 H60B 0.9600 . ? C60 H60C 0.9600 . ? C01 C02 1.485(9) . ? C01 H01A 0.9600 . ? C01 H01B 0.9600 . ? C01 H01C 0.9600 . ? C02 N9 1.340(9) . ? C02 C03 1.423(11) . ? C03 C04 1.368(9) . ? C03 H03 0.9300 . ? C04 C06 1.439(10) . ? C04 C05 1.504(10) . ? C05 H05A 0.9600 . ? C05 H05B 0.9600 . ? C05 H05C 0.9600 . ? C06 N9 1.390(8) . ? C06 C07 1.395(8) . ? C07 C08 1.399(10) . ? C07 C014 1.491(8) . ? C08 N10 1.403(8) . ? C08 C09 1.422(9) . ? C09 C011 1.360(10) . ? C09 C010 1.526(9) . ? C010 H01D 0.9600 . ? C010 H01E 0.9600 . ? C010 H01F 0.9600 . ? C011 C012 1.377(8) . ? C011 H011 0.9300 . ? C012 N10 1.337(9) . ? C012 C013 1.508(10) . ? C013 H01G 0.9600 . ? C013 H01H 0.9600 . ? C013 H01I 0.9600 . ? C014 C019 1.383(8) . ? C014 C015 1.393(7) . ? C015 C016 1.358(8) . ? C015 H015 0.9300 . ? C016 C017 1.362(9) . ? C016 H016 0.9300 . ? C017 C018 1.391(9) . ? C017 C020 1.526(9) . ? C018 C019 1.378(9) . ? C018 H018 0.9300 . ? C019 H019 0.9300 . ? C020 H02A 0.9600 . ? C020 H02B 0.9600 . ? C020 H02C 0.9600 . ? N9 B5 1.550(11) . ? N10 B5 1.554(9) . ? F9 B5 1.381(9) . ? F10 B5 1.393(8) . ? C4 C3 1.481(9) . ? C4 H4A 0.9600 . ? C4 H4B 0.9600 . ? C4 H4C 0.9600 . ? C3 N1 1.362(8) . ? C3 C2 1.417(10) . ? C2 C1 1.373(8) . ? C2 H2 0.9300 . ? C1 C10 1.433(9) . ? C1 C19 1.485(9) . ? C19 H5A 0.9600 . ? C19 H5B 0.9600 . ? C19 H5C 0.9600 . ? C10 C11 1.395(8) . ? C10 N1 1.416(8) . ? C11 C9 1.388(10) . ? C11 C12 1.482(9) . ? C9 C7 1.405(9) . ? C9 N2 1.412(8) . ? C7 C6 1.384(10) . ? C7 C20 1.509(9) . ? C6 C5 1.380(8) . ? C6 H10 0.9300 . ? C5 N2 1.347(9) . ? C5 C8 1.479(10) . ? C8 H12A 0.9600 . ? C8 H12B 0.9600 . ? C8 H12C 0.9600 . ? C12 C13 1.379(8) . ? C12 C17 1.389(8) . ? C13 C14 1.417(9) . ? C13 H14 0.9300 . ? C14 C15 1.386(9) . ? C14 H15 0.9300 . ? C15 C16 1.379(9) . ? C15 C18 1.490(9) . ? C16 C17 1.387(9) . ? C16 H17 0.9300 . ? C17 H18 0.9300 . ? C18 H19A 0.9600 . ? C18 H19B 0.9600 . ? C18 H19C 0.9600 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? N1 B1 1.532(10) . ? N2 B1 1.531(9) . ? F1 B1 1.395(8) . ? F2 B1 1.373(8) . ? C61 N8 1.362(9) . ? C61 C63 1.411(11) . ? C61 C62 1.498(10) . ? C62 H62A 0.9600 . ? C62 H62B 0.9600 . ? C62 H62C 0.9600 . ? C63 C64 1.326(8) . ? C63 H63 0.9300 . ? C64 C65 1.437(9) . ? C64 C73 1.505(10) . ? C65 C66 1.374(8) . ? C65 N8 1.433(8) . ? C66 C67 1.400(10) . ? C66 C74 1.487(9) . ? C67 C68 1.415(9) . ? C67 N7 1.432(8) . ? C68 C69 1.411(10) . ? C68 C72 1.469(8) . ? C69 C70 1.364(8) . ? C69 H69 0.9300 . ? C70 N7 1.341(9) . ? C70 C71 1.476(10) . ? C71 H71A 0.9600 . ? C71 H71B 0.9600 . ? C71 H71C 0.9600 . ? C72 H72A 0.9600 . ? C72 H72B 0.9600 . ? C72 H72C 0.9600 . ? C73 H73A 0.9600 . ? C73 H73B 0.9600 . ? C73 H73C 0.9600 . ? C74 C75 1.372(8) . ? C74 C79 1.387(8) . ? C75 C76 1.384(9) . ? C75 H75 0.9300 . ? C76 C77 1.377(8) . ? C76 H76 0.9300 . ? C77 C78 1.379(9) . ? C77 C80 1.503(9) . ? C78 C79 1.405(9) . ? C78 H78 0.9300 . ? C79 H79 0.9300 . ? C80 H80A 0.9600 . ? C80 H80B 0.9600 . ? C80 H80C 0.9600 . ? N7 B4 1.527(9) . ? N8 B4 1.532(10) . ? F7 B4 1.392(8) . ? F8 B4 1.369(9) . ? C21 C22 1.501(9) . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? C22 N4 1.341(8) . ? C22 C23 1.374(8) . ? C23 C24 1.359(9) . ? C23 H23 0.9300 . ? C24 C26 1.447(8) . ? C24 C25 1.502(8) . ? C25 H25A 0.9600 . ? C25 H25B 0.9600 . ? C25 H25C 0.9600 . ? C26 C27 1.383(9) . ? C26 N4 1.408(7) . ? C27 C28 1.413(8) . ? C27 C33 1.491(8) . ? C28 C29 1.405(9) . ? C28 N3 1.419(8) . ? C29 C30 1.407(9) . ? C29 C40 1.492(9) . ? C30 C31 1.376(10) . ? C30 H30 0.9300 . ? C31 N3 1.338(8) . ? C31 C32 1.508(9) . ? C32 H32A 0.9600 . ? C32 H32B 0.9600 . ? C32 H32C 0.9600 . ? C33 C34 1.362(8) . ? C33 C38 1.391(7) . ? C34 C35 1.388(9) . ? C34 H34 0.9300 . ? C35 C36 1.351(8) . ? C35 H35 0.9300 . ? C36 C37 1.367(8) . ? C36 C39 1.527(9) . ? C37 C38 1.359(8) . ? C37 H37 0.9300 . ? C38 H38 0.9300 . ? C39 H39A 0.9600 . ? C39 H39B 0.9600 . ? C39 H39C 0.9600 . ? C40 H40A 0.9600 . ? C40 H40B 0.9600 . ? C40 H40C 0.9600 . ? C41 N6 1.367(8) . ? C41 C42 1.395(10) . ? C41 C45 1.480(8) . ? C42 C43 1.371(9) . ? C42 H42 0.9300 . ? C43 C44 1.429(9) . ? C43 C46 1.503(9) . ? C44 N6 1.372(7) . ? C44 C47 1.392(7) . ? C45 H45A 0.9600 . ? C45 H45B 0.9600 . ? C45 H45C 0.9600 . ? C46 H46A 0.9600 . ? C46 H46B 0.9600 . ? C46 H46C 0.9600 . ? C47 C48 1.419(8) . ? C47 C55 1.487(8) . ? C48 N5 1.405(7) . ? C48 C49 1.409(8) . ? C49 C50 1.357(9) . ? C49 C53 1.490(8) . ? C50 C51 1.405(8) . ? C50 H50 0.9300 . ? C51 N5 1.336(7) . ? C51 C52 1.527(9) . ? C52 H52A 0.9600 . ? C52 H52B 0.9600 . ? C52 H52C 0.9600 . ? C53 H53A 0.9600 . ? C53 H53B 0.9600 . ? C53 H53C 0.9600 . ? C54 C59 1.369(8) . ? C54 C55 1.394(7) . ? C54 H54 0.9300 . ? C55 C56 1.368(8) . ? C56 C57 1.383(8) . ? C56 H56 0.9300 . ? C57 C58 1.372(8) . ? C57 H57 0.9300 . ? C58 C59 1.388(8) . ? C59 H59 0.9300 . ? N3 B2 1.512(10) . ? N4 B2 1.564(8) . ? N5 B3 1.537(8) . ? N6 B3 1.546(9) . ? F3 B2 1.388(7) . ? F4 B2 1.401(8) . ? F5 B3 1.388(7) . ? F6 B3 1.392(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 C58 C60 H60A 109.5 . . ? C58 C60 H60B 109.5 . . ? H60A C60 H60B 109.5 . . ? C58 C60 H60C 109.5 . . ? H60A C60 H60C 109.5 . . ? H60B C60 H60C 109.5 . . ? C02 C01 H01A 109.5 . . ? C02 C01 H01B 109.5 . . ? H01A C01 H01B 109.5 . . ? C02 C01 H01C 109.5 . . ? H01A C01 H01C 109.5 . . ? H01B C01 H01C 109.5 . . ? N9 C02 C03 108.0(6) . . ? N9 C02 C01 124.7(7) . . ? C03 C02 C01 127.3(8) . . ? C04 C03 C02 109.3(7) . . ? C04 C03 H03 125.4 . . ? C02 C03 H03 125.4 . . ? C03 C04 C06 105.6(7) . . ? C03 C04 C05 123.3(7) . . ? C06 C04 C05 131.1(6) . . ? C04 C05 H05A 109.5 . . ? C04 C05 H05B 109.5 . . ? H05A C05 H05B 109.5 . . ? C04 C05 H05C 109.5 . . ? H05A C05 H05C 109.5 . . ? H05B C05 H05C 109.5 . . ? N9 C06 C07 121.9(6) . . ? N9 C06 C04 107.9(6) . . ? C07 C06 C04 130.2(7) . . ? C06 C07 C08 119.3(6) . . ? C06 C07 C014 121.0(6) . . ? C08 C07 C014 119.6(6) . . ? C07 C08 N10 121.3(6) . . ? C07 C08 C09 132.5(6) . . ? N10 C08 C09 106.0(6) . . ? C011 C09 C08 107.2(6) . . ? C011 C09 C010 124.2(7) . . ? C08 C09 C010 128.5(7) . . ? C09 C010 H01D 109.5 . . ? C09 C010 H01E 109.5 . . ? H01D C010 H01E 109.5 . . ? C09 C010 H01F 109.5 . . ? H01D C010 H01F 109.5 . . ? H01E C010 H01F 109.5 . . ? C09 C011 C012 108.8(6) . . ? C09 C011 H011 125.6 . . ? C012 C011 H011 125.6 . . ? N10 C012 C011 109.2(7) . . ? N10 C012 C013 122.4(6) . . ? C011 C012 C013 128.3(7) . . ? C012 C013 H01G 109.5 . . ? C012 C013 H01H 109.5 . . ? H01G C013 H01H 109.5 . . ? C012 C013 H01I 109.5 . . ? H01G C013 H01I 109.5 . . ? H01H C013 H01I 109.5 . . ? C019 C014 C015 118.5(6) . . ? C019 C014 C07 118.5(6) . . ? C015 C014 C07 123.0(6) . . ? C016 C015 C014 120.6(6) . . ? C016 C015 H015 119.7 . . ? C014 C015 H015 119.7 . . ? C015 C016 C017 121.6(6) . . ? C015 C016 H016 119.2 . . ? C017 C016 H016 119.2 . . ? C016 C017 C018 118.4(6) . . ? C016 C017 C020 122.6(7) . . ? C018 C017 C020 119.0(7) . . ? C019 C018 C017 120.8(7) . . ? C019 C018 H018 119.6 . . ? C017 C018 H018 119.6 . . ? C018 C019 C014 120.0(7) . . ? C018 C019 H019 120.0 . . ? C014 C019 H019 120.0 . . ? C017 C020 H02A 109.5 . . ? C017 C020 H02B 109.5 . . ? H02A C020 H02B 109.5 . . ? C017 C020 H02C 109.5 . . ? H02A C020 H02C 109.5 . . ? H02B C020 H02C 109.5 . . ? C02 N9 C06 109.2(6) . . ? C02 N9 B5 125.1(6) . . ? C06 N9 B5 125.6(6) . . ? C012 N10 C08 108.7(6) . . ? C012 N10 B5 126.1(6) . . ? C08 N10 B5 125.0(6) . . ? F9 B5 F10 109.3(6) . . ? F9 B5 N9 110.2(6) . . ? F10 B5 N9 110.6(6) . . ? F9 B5 N10 110.5(6) . . ? F10 B5 N10 110.1(6) . . ? N9 B5 N10 106.1(6) . . ? C3 C4 H4A 109.5 . . ? C3 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C3 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? N1 C3 C2 107.6(6) . . ? N1 C3 C4 122.2(7) . . ? C2 C3 C4 130.0(7) . . ? C1 C2 C3 110.3(6) . . ? C1 C2 H2 124.8 . . ? C3 C2 H2 124.9 . . ? C2 C1 C10 105.6(6) . . ? C2 C1 C19 125.4(6) . . ? C10 C1 C19 128.9(6) . . ? C1 C19 H5A 109.5 . . ? C1 C19 H5B 109.5 . . ? H5A C19 H5B 109.5 . . ? C1 C19 H5C 109.5 . . ? H5A C19 H5C 109.5 . . ? H5B C19 H5C 109.5 . . ? C11 C10 N1 118.7(6) . . ? C11 C10 C1 133.1(6) . . ? N1 C10 C1 108.1(6) . . ? C9 C11 C10 122.4(6) . . ? C9 C11 C12 118.8(6) . . ? C10 C11 C12 118.8(7) . . ? C11 C9 C7 132.7(7) . . ? C11 C9 N2 119.7(6) . . ? C7 C9 N2 107.6(7) . . ? C6 C7 C9 106.0(6) . . ? C6 C7 C20 125.9(7) . . ? C9 C7 C20 128.0(7) . . ? C5 C6 C7 109.4(7) . . ? C5 C6 H10 125.3 . . ? C7 C6 H10 125.3 . . ? N2 C5 C6 108.7(7) . . ? N2 C5 C8 122.7(6) . . ? C6 C5 C8 128.4(7) . . ? C5 C8 H12A 109.5 . . ? C5 C8 H12B 109.5 . . ? H12A C8 H12B 109.5 . . ? C5 C8 H12C 109.5 . . ? H12A C8 H12C 109.5 . . ? H12B C8 H12C 109.5 . . ? C13 C12 C17 118.6(6) . . ? C13 C12 C11 121.5(6) . . ? C17 C12 C11 119.8(6) . . ? C12 C13 C14 119.9(6) . . ? C12 C13 H14 120.0 . . ? C14 C13 H14 120.0 . . ? C15 C14 C13 121.6(6) . . ? C15 C14 H15 119.2 . . ? C13 C14 H15 119.2 . . ? C16 C15 C14 116.9(6) . . ? C16 C15 C18 122.6(7) . . ? C14 C15 C18 120.5(7) . . ? C15 C16 C17 122.5(7) . . ? C15 C16 H17 118.7 . . ? C17 C16 H17 118.7 . . ? C16 C17 C12 120.4(7) . . ? C16 C17 H18 119.8 . . ? C12 C17 H18 119.8 . . ? C15 C18 H19A 109.5 . . ? C15 C18 H19B 109.5 . . ? H19A C18 H19B 109.5 . . ? C15 C18 H19C 109.5 . . ? H19A C18 H19C 109.5 . . ? H19B C18 H19C 109.5 . . ? C7 C20 H20A 109.5 . . ? C7 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C7 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C3 N1 C10 108.3(6) . . ? C3 N1 B1 125.3(6) . . ? C10 N1 B1 126.4(6) . . ? C5 N2 C9 107.9(6) . . ? C5 N2 B1 126.3(6) . . ? C9 N2 B1 125.7(6) . . ? F2 B1 F1 109.6(6) . . ? F2 B1 N2 111.2(6) . . ? F1 B1 N2 109.7(6) . . ? F2 B1 N1 110.0(6) . . ? F1 B1 N1 109.6(6) . . ? N2 B1 N1 106.8(6) . . ? N8 C61 C63 106.6(6) . . ? N8 C61 C62 121.3(7) . . ? C63 C61 C62 132.1(7) . . ? C61 C62 H62A 109.5 . . ? C61 C62 H62B 109.5 . . ? H62A C62 H62B 109.5 . . ? C61 C62 H62C 109.5 . . ? H62A C62 H62C 109.5 . . ? H62B C62 H62C 109.5 . . ? C64 C63 C61 112.3(7) . . ? C64 C63 H63 123.9 . . ? C61 C63 H63 123.9 . . ? C63 C64 C65 106.1(7) . . ? C63 C64 C73 126.2(7) . . ? C65 C64 C73 127.6(6) . . ? C66 C65 N8 119.0(7) . . ? C66 C65 C64 134.2(7) . . ? N8 C65 C64 106.8(5) . . ? C65 C66 C67 122.4(7) . . ? C65 C66 C74 119.9(7) . . ? C67 C66 C74 117.6(6) . . ? C66 C67 C68 131.6(7) . . ? C66 C67 N7 119.6(6) . . ? C68 C67 N7 108.8(6) . . ? C69 C68 C67 103.7(6) . . ? C69 C68 C72 126.9(7) . . ? C67 C68 C72 129.4(8) . . ? C70 C69 C68 110.8(7) . . ? C70 C69 H69 124.6 . . ? C68 C69 H69 124.6 . . ? N7 C70 C69 109.6(7) . . ? N7 C70 C71 122.5(6) . . ? C69 C70 C71 127.9(7) . . ? C70 C71 H71A 109.5 . . ? C70 C71 H71B 109.5 . . ? H71A C71 H71B 109.5 . . ? C70 C71 H71C 109.5 . . ? H71A C71 H71C 109.5 . . ? H71B C71 H71C 109.5 . . ? C68 C72 H72A 109.5 . . ? C68 C72 H72B 109.5 . . ? H72A C72 H72B 109.5 . . ? C68 C72 H72C 109.5 . . ? H72A C72 H72C 109.5 . . ? H72B C72 H72C 109.5 . . ? C64 C73 H73A 109.5 . . ? C64 C73 H73B 109.5 . . ? H73A C73 H73B 109.5 . . ? C64 C73 H73C 109.5 . . ? H73A C73 H73C 109.5 . . ? H73B C73 H73C 109.5 . . ? C75 C74 C79 118.7(6) . . ? C75 C74 C66 121.1(6) . . ? C79 C74 C66 120.3(6) . . ? C74 C75 C76 120.7(6) . . ? C74 C75 H75 119.7 . . ? C76 C75 H75 119.7 . . ? C77 C76 C75 122.1(7) . . ? C77 C76 H76 119.0 . . ? C75 C76 H76 119.0 . . ? C76 C77 C78 117.2(6) . . ? C76 C77 C80 122.2(7) . . ? C78 C77 C80 120.6(7) . . ? C77 C78 C79 121.6(6) . . ? C77 C78 H78 119.2 . . ? C79 C78 H78 119.2 . . ? C74 C79 C78 119.8(6) . . ? C74 C79 H79 120.1 . . ? C78 C79 H79 120.1 . . ? C77 C80 H80A 109.5 . . ? C77 C80 H80B 109.5 . . ? H80A C80 H80B 109.5 . . ? C77 C80 H80C 109.5 . . ? H80A C80 H80C 109.5 . . ? H80B C80 H80C 109.5 . . ? C70 N7 C67 107.1(6) . . ? C70 N7 B4 127.4(6) . . ? C67 N7 B4 125.2(6) . . ? C61 N8 C65 108.0(6) . . ? C61 N8 B4 125.5(6) . . ? C65 N8 B4 126.4(6) . . ? F8 B4 F7 110.6(6) . . ? F8 B4 N7 111.3(6) . . ? F7 B4 N7 109.3(5) . . ? F8 B4 N8 109.3(6) . . ? F7 B4 N8 109.4(6) . . ? N7 B4 N8 106.9(6) . . ? C22 C21 H21A 109.5 . . ? C22 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C22 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? N4 C22 C23 109.1(6) . . ? N4 C22 C21 121.6(6) . . ? C23 C22 C21 129.3(7) . . ? C24 C23 C22 110.5(6) . . ? C24 C23 H23 124.7 . . ? C22 C23 H23 124.7 . . ? C23 C24 C26 105.4(5) . . ? C23 C24 C25 124.9(6) . . ? C26 C24 C25 129.7(6) . . ? C24 C25 H25A 109.5 . . ? C24 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C24 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C27 C26 N4 121.1(6) . . ? C27 C26 C24 132.2(6) . . ? N4 C26 C24 106.5(6) . . ? C26 C27 C28 120.9(6) . . ? C26 C27 C33 120.0(6) . . ? C28 C27 C33 119.1(6) . . ? C29 C28 C27 131.2(6) . . ? C29 C28 N3 108.5(5) . . ? C27 C28 N3 120.2(6) . . ? C28 C29 C30 105.2(6) . . ? C28 C29 C40 130.7(6) . . ? C30 C29 C40 124.0(6) . . ? C31 C30 C29 108.7(7) . . ? C31 C30 H30 125.6 . . ? C29 C30 H30 125.6 . . ? N3 C31 C30 110.3(6) . . ? N3 C31 C32 121.9(7) . . ? C30 C31 C32 127.7(7) . . ? C31 C32 H32A 109.5 . . ? C31 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C31 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? C34 C33 C38 118.3(6) . . ? C34 C33 C27 120.4(5) . . ? C38 C33 C27 121.3(6) . . ? C33 C34 C35 119.0(6) . . ? C33 C34 H34 120.5 . . ? C35 C34 H34 120.5 . . ? C36 C35 C34 123.2(7) . . ? C36 C35 H35 118.4 . . ? C34 C35 H35 118.4 . . ? C35 C36 C37 117.1(6) . . ? C35 C36 C39 120.4(6) . . ? C37 C36 C39 122.4(6) . . ? C38 C37 C36 121.5(5) . . ? C38 C37 H37 119.2 . . ? C36 C37 H37 119.2 . . ? C37 C38 C33 120.8(6) . . ? C37 C38 H38 119.6 . . ? C33 C38 H38 119.6 . . ? C36 C39 H39A 109.5 . . ? C36 C39 H39B 109.5 . . ? H39A C39 H39B 109.5 . . ? C36 C39 H39C 109.5 . . ? H39A C39 H39C 109.5 . . ? H39B C39 H39C 109.5 . . ? C29 C40 H40A 109.5 . . ? C29 C40 H40B 109.5 . . ? H40A C40 H40B 109.5 . . ? C29 C40 H40C 109.5 . . ? H40A C40 H40C 109.5 . . ? H40B C40 H40C 109.5 . . ? N6 C41 C42 107.8(6) . . ? N6 C41 C45 122.6(7) . . ? C42 C41 C45 129.5(7) . . ? C43 C42 C41 109.8(6) . . ? C43 C42 H42 125.1 . . ? C41 C42 H42 125.1 . . ? C42 C43 C44 105.2(6) . . ? C42 C43 C46 124.4(7) . . ? C44 C43 C46 130.2(6) . . ? N6 C44 C47 121.0(5) . . ? N6 C44 C43 108.9(5) . . ? C47 C44 C43 130.0(6) . . ? C41 C45 H45A 109.5 . . ? C41 C45 H45B 109.5 . . ? H45A C45 H45B 109.5 . . ? C41 C45 H45C 109.5 . . ? H45A C45 H45C 109.5 . . ? H45B C45 H45C 109.5 . . ? C43 C46 H46A 109.5 . . ? C43 C46 H46B 109.5 . . ? H46A C46 H46B 109.5 . . ? C43 C46 H46C 109.5 . . ? H46A C46 H46C 109.5 . . ? H46B C46 H46C 109.5 . . ? C44 C47 C48 120.2(6) . . ? C44 C47 C55 121.6(6) . . ? C48 C47 C55 118.2(5) . . ? N5 C48 C49 108.6(5) . . ? N5 C48 C47 119.5(5) . . ? C49 C48 C47 131.8(6) . . ? C50 C49 C48 106.1(5) . . ? C50 C49 C53 123.0(6) . . ? C48 C49 C53 130.9(6) . . ? C49 C50 C51 109.0(6) . . ? C49 C50 H50 125.5 . . ? C51 C50 H50 125.5 . . ? N5 C51 C50 109.1(6) . . ? N5 C51 C52 123.5(5) . . ? C50 C51 C52 127.4(6) . . ? C51 C52 H52A 109.5 . . ? C51 C52 H52B 109.5 . . ? H52A C52 H52B 109.5 . . ? C51 C52 H52C 109.5 . . ? H52A C52 H52C 109.5 . . ? H52B C52 H52C 109.5 . . ? C49 C53 H53A 109.5 . . ? C49 C53 H53B 109.5 . . ? H53A C53 H53B 109.5 . . ? C49 C53 H53C 109.5 . . ? H53A C53 H53C 109.5 . . ? H53B C53 H53C 109.5 . . ? C59 C54 C55 121.3(6) . . ? C59 C54 H54 119.3 . . ? C55 C54 H54 119.3 . . ? C56 C55 C54 117.2(5) . . ? C56 C55 C47 119.6(5) . . ? C54 C55 C47 123.2(5) . . ? C55 C56 C57 121.0(6) . . ? C55 C56 H56 119.5 . . ? C57 C56 H56 119.5 . . ? C58 C57 C56 122.3(6) . . ? C58 C57 H57 118.8 . . ? C56 C57 H57 118.8 . . ? C57 C58 C59 116.5(6) . . ? C57 C58 C60 122.3(6) . . ? C59 C58 C60 121.2(6) . . ? C54 C59 C58 121.6(6) . . ? C54 C59 H59 119.2 . . ? C58 C59 H59 119.2 . . ? C31 N3 C28 107.2(6) . . ? C31 N3 B2 127.5(6) . . ? C28 N3 B2 125.3(5) . . ? C22 N4 C26 108.4(5) . . ? C22 N4 B2 127.6(5) . . ? C26 N4 B2 124.1(6) . . ? C51 N5 C48 107.2(4) . . ? C51 N5 B3 126.4(5) . . ? C48 N5 B3 126.1(5) . . ? C41 N6 C44 108.3(5) . . ? C41 N6 B3 125.0(5) . . ? C44 N6 B3 126.7(5) . . ? F3 B2 F4 108.0(6) . . ? F3 B2 N3 111.4(6) . . ? F4 B2 N3 111.5(5) . . ? F3 B2 N4 109.4(5) . . ? F4 B2 N4 108.6(5) . . ? N3 B2 N4 108.0(6) . . ? F5 B3 F6 109.6(5) . . ? F5 B3 N5 110.5(5) . . ? F6 B3 N5 109.6(5) . . ? F5 B3 N6 110.9(5) . . ? F6 B3 N6 110.5(5) . . ? N5 B3 N6 105.6(5) . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 23.25 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.330 _refine_diff_density_min -0.298 _refine_diff_density_rms 0.058 #===END data_5 _database_code_depnum_ccdc_archive 'CCDC 798785' #TrackingRef '1-6.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H17 B F2 N2 O0' _chemical_formula_sum 'C18 H17 B F2 N2 O0' _chemical_formula_weight 310.15 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 C2/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 6.554(3) _cell_length_b 26.198(11) _cell_length_c 9.732(4) _cell_angle_alpha 90.00 _cell_angle_beta 105.458(8) _cell_angle_gamma 90.00 _cell_volume 1610.4(12) _cell_formula_units_Z 4 _cell_measurement_temperature 273(2) _cell_measurement_reflns_used 687 _cell_measurement_theta_min 2.667 _cell_measurement_theta_max 21.364 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.279 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 648 _exptl_absorpt_coefficient_mu 0.091 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.978 _exptl_absorpt_correction_T_max 0.984 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 273(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART 1000 CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3953 _diffrn_reflns_av_R_equivalents 0.0379 _diffrn_reflns_av_sigmaI/netI 0.0473 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -30 _diffrn_reflns_limit_k_max 28 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.67 _diffrn_reflns_theta_max 25.01 _reflns_number_total 1418 _reflns_number_gt 871 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART (Siemens, 1996)' _computing_cell_refinement 'Bruker SMART (Siemens, 1996)' _computing_data_reduction 'Bruker SAINT (Siemens, 1996)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997a)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997a)' _computing_molecular_graphics 'Bruker SHELXTL (Sheldrick, 1997b)' _computing_publication_material 'Bruker SHELXTL (Sheldrick, 1997b)' _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^)+(0.0580P)^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 1418 _refine_ls_number_parameters 109 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0820 _refine_ls_R_factor_gt 0.0445 _refine_ls_wR_factor_ref 0.1208 _refine_ls_wR_factor_gt 0.1031 _refine_ls_goodness_of_fit_ref 1.006 _refine_ls_restrained_S_all 1.006 _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 0.1906(2) 0.37004(6) 0.31940(16) 0.0464(5) Uani 1 1 d . . . C11 C 0.0000 0.44984(9) 0.2500 0.0433(7) Uani 1 2 d S . . C10 C 0.1864(3) 0.42313(7) 0.3140(2) 0.0440(5) Uani 1 1 d . . . F1 F 0.04919(19) 0.30447(5) 0.14671(15) 0.0939(6) Uani 1 1 d . . . C1 C 0.3887(3) 0.44070(8) 0.3886(2) 0.0543(6) Uani 1 1 d . . . H1 H 0.4312 0.4746 0.4016 0.065 Uiso 1 1 calc R . . C13 C -0.1248(3) 0.53399(8) 0.3191(2) 0.0587(6) Uani 1 1 d . . . H13 H -0.2107 0.5167 0.3660 0.070 Uiso 1 1 calc R . . C12 C 0.0000 0.50634(10) 0.2500 0.0472(7) Uani 1 2 d S . . C2 C 0.5113(3) 0.39900(8) 0.4382(2) 0.0602(6) Uani 1 1 d . . . H2 H 0.6525 0.3995 0.4907 0.072 Uiso 1 1 calc R . . C3 C 0.3869(3) 0.35536(8) 0.3961(2) 0.0552(6) Uani 1 1 d . . . C15 C 0.0000 0.61413(11) 0.2500 0.0604(9) Uani 1 2 d S . . C14 C -0.1228(4) 0.58651(8) 0.3190(2) 0.0658(7) Uani 1 1 d . . . H14 H -0.2066 0.6040 0.3669 0.079 Uiso 1 1 calc R . . B1 B 0.0000 0.33503(13) 0.2500 0.0561(9) Uani 1 2 d S . . C4 C 0.4486(3) 0.30106(8) 0.4289(3) 0.0794(8) Uani 1 1 d . . . H4A H 0.4243 0.2919 0.5187 0.119 Uiso 1 1 calc R . . H4B H 0.5959 0.2968 0.4339 0.119 Uiso 1 1 calc R . . H4C H 0.3654 0.2795 0.3551 0.119 Uiso 1 1 calc R . . C18 C 0.0000 0.67177(11) 0.2500 0.0927(13) Uani 1 2 d S . . H18A H -0.0898 0.6840 0.1614 0.139 Uiso 0.50 1 calc PR . . H18B H 0.1416 0.6840 0.2612 0.139 Uiso 0.50 1 calc PR . . H18C H -0.0519 0.6840 0.3274 0.139 Uiso 0.50 1 calc PR . . 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 0.0409(10) 0.0465(10) 0.0506(10) 0.0010(8) 0.0099(8) 0.0025(7) C11 0.0522(18) 0.0449(17) 0.0390(15) 0.000 0.0228(14) 0.000 C10 0.0441(12) 0.0483(12) 0.0415(11) -0.0030(9) 0.0146(9) -0.0029(9) F1 0.0670(9) 0.0809(10) 0.1263(13) -0.0502(8) 0.0125(8) 0.0059(7) C1 0.0544(13) 0.0595(14) 0.0507(13) -0.0072(10) 0.0172(11) -0.0096(11) C13 0.0710(15) 0.0519(14) 0.0627(14) -0.0001(10) 0.0345(12) 0.0019(11) C12 0.0551(18) 0.0441(17) 0.0452(16) 0.000 0.0183(14) 0.000 C2 0.0460(13) 0.0776(16) 0.0537(13) 0.0016(12) 0.0075(11) 0.0013(12) C3 0.0474(13) 0.0637(14) 0.0545(13) 0.0042(11) 0.0138(11) 0.0067(12) C15 0.080(2) 0.0456(19) 0.0490(18) 0.000 0.0060(18) 0.000 C14 0.0820(17) 0.0528(15) 0.0670(16) -0.0077(11) 0.0275(14) 0.0130(12) B1 0.051(2) 0.045(2) 0.073(2) 0.000 0.0191(19) 0.000 C4 0.0621(16) 0.0755(17) 0.0958(19) 0.0160(14) 0.0126(14) 0.0180(12) C18 0.125(3) 0.052(2) 0.090(3) 0.000 0.008(3) 0.000 _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 1.360(2) . ? N1 C10 1.392(2) . ? N1 B1 1.552(2) . ? C11 C10 1.401(2) 2 ? C11 C10 1.401(2) . ? C11 C12 1.480(3) . ? C10 C1 1.409(3) . ? F1 B1 1.388(2) . ? C1 C2 1.366(3) . ? C1 H1 0.9300 . ? C13 C14 1.376(3) . ? C13 C12 1.393(2) . ? C13 H13 0.9300 . ? C12 C13 1.393(2) 2 ? C2 C3 1.401(3) . ? C2 H2 0.9300 . ? C3 C4 1.490(3) . ? C15 C14 1.382(2) 2 ? C15 C14 1.382(2) . ? C15 C18 1.510(4) . ? C14 H14 0.9300 . ? B1 F1 1.388(2) 2 ? B1 N1 1.552(2) 2 ? C4 H4A 0.9600 . ? C4 H4B 0.9600 . ? C4 H4C 0.9600 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? 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 C10 108.03(16) . . ? C3 N1 B1 127.30(18) . . ? C10 N1 B1 124.67(17) . . ? C10 C11 C10 120.1(2) 2 . ? C10 C11 C12 119.96(12) 2 . ? C10 C11 C12 119.96(12) . . ? N1 C10 C11 121.46(18) . . ? N1 C10 C1 107.50(17) . . ? C11 C10 C1 130.93(19) . . ? C2 C1 C10 107.76(18) . . ? C2 C1 H1 126.1 . . ? C10 C1 H1 126.1 . . ? C14 C13 C12 120.8(2) . . ? C14 C13 H13 119.6 . . ? C12 C13 H13 119.6 . . ? C13 C12 C13 117.3(3) 2 . ? C13 C12 C11 121.34(13) 2 . ? C13 C12 C11 121.34(13) . . ? C1 C2 C3 107.92(19) . . ? C1 C2 H2 126.0 . . ? C3 C2 H2 126.0 . . ? N1 C3 C2 108.76(18) . . ? N1 C3 C4 123.41(19) . . ? C2 C3 C4 127.82(19) . . ? C14 C15 C14 116.9(3) 2 . ? C14 C15 C18 121.57(14) 2 . ? C14 C15 C18 121.57(14) . . ? C13 C14 C15 122.1(2) . . ? C13 C14 H14 119.0 . . ? C15 C14 H14 119.0 . . ? F1 B1 F1 109.6(3) . 2 ? F1 B1 N1 109.92(8) . . ? F1 B1 N1 109.94(8) 2 . ? F1 B1 N1 109.94(8) . 2 ? F1 B1 N1 109.92(8) 2 2 ? N1 B1 N1 107.5(2) . 2 ? C3 C4 H4A 109.5 . . ? C3 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C3 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C15 C18 H18A 109.5 . . ? C15 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C15 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.126 _refine_diff_density_min -0.138 _refine_diff_density_rms 0.030 #===END data_6 _database_code_depnum_ccdc_archive 'CCDC 798786' #TrackingRef '1-6.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H14 B F2 N3 O2' _chemical_formula_weight 341.12 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' 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.4804(7) _cell_length_b 8.3217(9) _cell_length_c 14.6304(16) _cell_angle_alpha 80.583(2) _cell_angle_beta 84.666(2) _cell_angle_gamma 85.576(2) _cell_volume 773.44(15) _cell_formula_units_Z 2 _cell_measurement_temperature 273(2) _cell_measurement_reflns_used 2016 _cell_measurement_theta_min 2.665 _cell_measurement_theta_max 27.420 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.465 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 352 _exptl_absorpt_coefficient_mu 0.113 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9690 _exptl_absorpt_correction_T_max 0.9854 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 273(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART 1000 CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3860 _diffrn_reflns_av_R_equivalents 0.0143 _diffrn_reflns_av_sigmaI/netI 0.0274 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.49 _diffrn_reflns_theta_max 25.01 _reflns_number_total 2701 _reflns_number_gt 2309 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART (Siemens, 1996)' _computing_cell_refinement 'Bruker SMART (Siemens, 1996)' _computing_data_reduction 'Bruker SAINT (Siemens, 1996)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997a)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997a)' _computing_molecular_graphics 'Bruker SHELXTL (Sheldrick, 1997b)' _computing_publication_material 'Bruker SHELXTL (Sheldrick, 1997b)' _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^)+(0.0600P)^2^+0.2304P] 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 2701 _refine_ls_number_parameters 228 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0445 _refine_ls_R_factor_gt 0.0376 _refine_ls_wR_factor_ref 0.1102 _refine_ls_wR_factor_gt 0.1034 _refine_ls_goodness_of_fit_ref 0.993 _refine_ls_restrained_S_all 0.993 _refine_ls_shift/su_max 0.008 _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 F2 F 0.83956(18) 0.40825(12) 0.14408(8) 0.0568(3) Uani 1 1 d . . . N1 N 0.9268(2) 0.12522(15) 0.13381(9) 0.0353(3) Uani 1 1 d . . . N2 N 0.5847(2) 0.21635(15) 0.20785(9) 0.0358(3) Uani 1 1 d . . . C11 C 0.7567(2) -0.04494(18) 0.26564(10) 0.0336(4) Uani 1 1 d . . . F1 F 0.67390(18) 0.29231(14) 0.04399(7) 0.0615(3) Uani 1 1 d . . . C10 C 0.9253(2) -0.01558(18) 0.20028(11) 0.0350(4) Uani 1 1 d . . . O1 O 0.7448(2) -0.65365(17) 0.59378(9) 0.0611(4) Uani 1 1 d . . . C15 C 0.7574(2) -0.49743(19) 0.44729(11) 0.0373(4) Uani 1 1 d . . . N3 N 0.7619(2) -0.65511(19) 0.50992(11) 0.0467(4) Uani 1 1 d . . . C12 C 0.7555(2) -0.20264(18) 0.33040(11) 0.0337(4) Uani 1 1 d . . . C17 C 0.7727(3) -0.34870(19) 0.29455(11) 0.0387(4) Uani 1 1 d . . . H17 H 0.7845 -0.3462 0.2305 0.046 Uiso 1 1 calc R . . C9 C 0.5872(2) 0.06868(18) 0.26904(11) 0.0355(4) Uani 1 1 d . . . C16 C 0.7725(3) -0.49692(19) 0.35279(12) 0.0403(4) Uani 1 1 d . . . H16 H 0.7824 -0.5942 0.3287 0.048 Uiso 1 1 calc R . . C13 C 0.7365(2) -0.20737(19) 0.42638(11) 0.0379(4) Uani 1 1 d . . . H13 H 0.7229 -0.1105 0.4510 0.045 Uiso 1 1 calc R . . O2 O 0.7849(3) -0.78008(16) 0.47529(11) 0.0685(4) Uani 1 1 d . . . C14 C 0.7378(2) -0.3554(2) 0.48527(11) 0.0399(4) Uani 1 1 d . . . H14 H 0.7257 -0.3591 0.5494 0.048 Uiso 1 1 calc R . . C3 C 1.1066(3) 0.1189(2) 0.07939(11) 0.0410(4) Uani 1 1 d . . . C7 C 0.3973(3) 0.0634(2) 0.32437(12) 0.0421(4) Uani 1 1 d . . . H7 H 0.3561 -0.0211 0.3707 0.050 Uiso 1 1 calc R . . C5 C 0.4020(3) 0.3000(2) 0.22542(12) 0.0411(4) Uani 1 1 d . . . C1 C 1.1137(3) -0.1078(2) 0.18558(12) 0.0423(4) Uani 1 1 d . . . H1 H 1.1552 -0.2067 0.2205 0.051 Uiso 1 1 calc R . . C8 C 0.3476(3) 0.4667(2) 0.17586(15) 0.0559(5) Uani 1 1 d . . . H8A H 0.4018 0.4755 0.1120 0.084 Uiso 1 1 calc R . . H8B H 0.4066 0.5461 0.2047 0.084 Uiso 1 1 calc R . . H8C H 0.1993 0.4860 0.1789 0.084 Uiso 1 1 calc R . . C2 C 1.2241(3) -0.0256(2) 0.11094(13) 0.0469(4) Uani 1 1 d . . . H2 H 1.3540 -0.0590 0.0854 0.056 Uiso 1 1 calc R . . C6 C 0.2844(3) 0.2069(2) 0.29690(13) 0.0453(4) Uani 1 1 d . . . H6 H 0.1523 0.2370 0.3216 0.054 Uiso 1 1 calc R . . C4 C 1.1600(3) 0.2468(2) -0.00095(13) 0.0544(5) Uani 1 1 d . . . H4A H 1.1050 0.3515 0.0127 0.082 Uiso 1 1 calc R . . H4B H 1.1013 0.2241 -0.0550 0.082 Uiso 1 1 calc R . . H4C H 1.3082 0.2475 -0.0125 0.082 Uiso 1 1 calc R . . B1 B 0.7557(3) 0.2672(2) 0.12921(13) 0.0387(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 F2 0.0643(7) 0.0332(5) 0.0719(7) -0.0111(5) 0.0091(5) -0.0083(5) N1 0.0382(7) 0.0342(7) 0.0335(7) -0.0061(5) -0.0016(5) -0.0016(6) N2 0.0378(7) 0.0301(7) 0.0399(7) -0.0081(5) -0.0061(6) 0.0036(5) C11 0.0385(8) 0.0309(8) 0.0330(8) -0.0089(6) -0.0049(6) -0.0016(6) F1 0.0670(7) 0.0747(8) 0.0387(6) -0.0022(5) -0.0129(5) 0.0174(6) C10 0.0401(9) 0.0299(8) 0.0352(8) -0.0066(6) -0.0037(7) 0.0006(6) O1 0.0595(9) 0.0673(9) 0.0484(8) 0.0157(7) -0.0052(6) -0.0049(7) C15 0.0295(8) 0.0374(9) 0.0423(9) 0.0029(7) -0.0052(6) -0.0016(6) N3 0.0330(8) 0.0473(9) 0.0547(10) 0.0086(7) -0.0053(6) -0.0033(6) C12 0.0315(8) 0.0326(8) 0.0367(8) -0.0053(6) -0.0035(6) 0.0008(6) C17 0.0454(9) 0.0360(8) 0.0344(8) -0.0065(7) -0.0028(7) 0.0006(7) C9 0.0392(9) 0.0320(8) 0.0360(8) -0.0076(6) -0.0041(6) 0.0005(7) C16 0.0414(9) 0.0325(8) 0.0478(10) -0.0092(7) -0.0040(7) -0.0003(7) C13 0.0399(9) 0.0372(9) 0.0376(9) -0.0097(7) -0.0029(7) -0.0002(7) O2 0.0841(11) 0.0362(7) 0.0802(10) 0.0031(7) -0.0036(8) -0.0022(7) C14 0.0366(9) 0.0487(10) 0.0337(8) -0.0044(7) -0.0038(7) -0.0019(7) C3 0.0414(9) 0.0470(9) 0.0364(9) -0.0126(7) 0.0000(7) -0.0051(7) C7 0.0416(9) 0.0430(9) 0.0419(9) -0.0101(7) 0.0011(7) -0.0027(7) C5 0.0401(9) 0.0369(9) 0.0499(10) -0.0168(7) -0.0111(7) 0.0065(7) C1 0.0436(9) 0.0367(9) 0.0458(9) -0.0084(7) -0.0033(7) 0.0068(7) C8 0.0537(11) 0.0408(10) 0.0738(13) -0.0123(9) -0.0171(10) 0.0136(8) C2 0.0403(9) 0.0509(10) 0.0489(10) -0.0150(8) 0.0055(8) 0.0041(8) C6 0.0364(9) 0.0489(10) 0.0524(10) -0.0186(8) -0.0009(8) 0.0056(8) C4 0.0569(12) 0.0619(12) 0.0429(10) -0.0044(9) 0.0045(8) -0.0126(9) B1 0.0471(11) 0.0317(9) 0.0368(10) -0.0037(7) -0.0062(8) 0.0015(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag F2 B1 1.387(2) . ? N1 C3 1.351(2) . ? N1 C10 1.395(2) . ? N1 B1 1.554(2) . ? N2 C5 1.352(2) . ? N2 C9 1.397(2) . ? N2 B1 1.552(2) . ? C11 C10 1.392(2) . ? C11 C9 1.396(2) . ? C11 C12 1.488(2) . ? F1 B1 1.378(2) . ? C10 C1 1.410(2) . ? O1 N3 1.224(2) . ? C15 C16 1.376(2) . ? C15 C14 1.378(2) . ? C15 N3 1.472(2) . ? N3 O2 1.223(2) . ? C12 C13 1.393(2) . ? C12 C17 1.393(2) . ? C17 C16 1.380(2) . ? C17 H17 0.9300 . ? C9 C7 1.408(2) . ? C16 H16 0.9300 . ? C13 C14 1.383(2) . ? C13 H13 0.9300 . ? C14 H14 0.9300 . ? C3 C2 1.408(2) . ? C3 C4 1.485(2) . ? C7 C6 1.373(2) . ? C7 H7 0.9300 . ? C5 C6 1.397(3) . ? C5 C8 1.489(2) . ? C1 C2 1.363(2) . ? C1 H1 0.9300 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C2 H2 0.9300 . ? C6 H6 0.9300 . ? C4 H4A 0.9600 . ? C4 H4B 0.9600 . ? C4 H4C 0.9600 . ? 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 C10 107.90(13) . . ? C3 N1 B1 127.13(14) . . ? C10 N1 B1 124.86(13) . . ? C5 N2 C9 107.86(14) . . ? C5 N2 B1 126.68(14) . . ? C9 N2 B1 125.30(13) . . ? C10 C11 C9 121.01(14) . . ? C10 C11 C12 119.05(14) . . ? C9 C11 C12 119.91(14) . . ? C11 C10 N1 121.14(14) . . ? C11 C10 C1 131.16(15) . . ? N1 C10 C1 107.70(14) . . ? C16 C15 C14 122.25(15) . . ? C16 C15 N3 118.84(15) . . ? C14 C15 N3 118.91(15) . . ? O2 N3 O1 123.66(15) . . ? O2 N3 C15 118.23(16) . . ? O1 N3 C15 118.10(15) . . ? C13 C12 C17 119.20(14) . . ? C13 C12 C11 121.29(14) . . ? C17 C12 C11 119.51(14) . . ? C16 C17 C12 120.88(15) . . ? C16 C17 H17 119.6 . . ? C12 C17 H17 119.6 . . ? C11 C9 N2 120.61(14) . . ? C11 C9 C7 131.46(15) . . ? N2 C9 C7 107.89(14) . . ? C15 C16 C17 118.48(15) . . ? C15 C16 H16 120.8 . . ? C17 C16 H16 120.8 . . ? C14 C13 C12 120.29(15) . . ? C14 C13 H13 119.9 . . ? C12 C13 H13 119.9 . . ? C15 C14 C13 118.88(15) . . ? C15 C14 H14 120.6 . . ? C13 C14 H14 120.6 . . ? N1 C3 C2 108.95(15) . . ? N1 C3 C4 123.11(16) . . ? C2 C3 C4 127.93(16) . . ? C6 C7 C9 106.95(15) . . ? C6 C7 H7 126.5 . . ? C9 C7 H7 126.5 . . ? N2 C5 C6 109.01(15) . . ? N2 C5 C8 123.06(16) . . ? C6 C5 C8 127.89(16) . . ? C2 C1 C10 107.57(15) . . ? C2 C1 H1 126.2 . . ? C10 C1 H1 126.2 . . ? C5 C8 H8A 109.5 . . ? C5 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C5 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C1 C2 C3 107.86(15) . . ? C1 C2 H2 126.1 . . ? C3 C2 H2 126.1 . . ? C7 C6 C5 108.27(15) . . ? C7 C6 H6 125.9 . . ? C5 C6 H6 125.9 . . ? C3 C4 H4A 109.5 . . ? C3 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C3 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? F1 B1 F2 110.16(14) . . ? F1 B1 N2 110.20(15) . . ? F2 B1 N2 109.68(14) . . ? F1 B1 N1 110.24(14) . . ? F2 B1 N1 109.58(14) . . ? N2 B1 N1 106.92(13) . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.226 _refine_diff_density_min -0.181 _refine_diff_density_rms 0.035 #===END #===END data_3 _database_code_depnum_ccdc_archive 'CCDC 798787' #TrackingRef '1-6.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H15 B Cl2 F2 N3 O2' _chemical_formula_sum 'C20 H15 B Cl2 F2 N3 O2' _chemical_formula_weight 449.06 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' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.3639 0.7018 '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 8.3449(7) _cell_length_b 11.6005(8) _cell_length_c 12.0810(8) _cell_angle_alpha 100.343(6) _cell_angle_beta 97.027(6) _cell_angle_gamma 111.076(7) _cell_volume 1051.05(14) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3751 _cell_measurement_theta_min 3.123 _cell_measurement_theta_max 63.884 _exptl_crystal_description block _exptl_crystal_colour black-red _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.419 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 458 _exptl_absorpt_coefficient_mu 3.131 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.465 _exptl_absorpt_correction_T_max 0.535 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART 1000 CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10300 _diffrn_reflns_av_R_equivalents 0.0337 _diffrn_reflns_av_sigmaI/netI 0.0377 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.80 _diffrn_reflns_theta_max 63.98 _reflns_number_total 3431 _reflns_number_gt 2655 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART (Siemens, 1996)' _computing_cell_refinement 'Bruker SMART (Siemens, 1996)' _computing_data_reduction 'Bruker SAINT (Siemens, 1996)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997a)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997a)' _computing_molecular_graphics 'Bruker SHELXTL (Sheldrick, 1997b)' _computing_publication_material 'Bruker SHELXTL (Sheldrick, 1997b)' _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^)+(0.1220P)^2^+0.2492P] 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 3431 _refine_ls_number_parameters 283 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0784 _refine_ls_R_factor_gt 0.0643 _refine_ls_wR_factor_ref 0.1953 _refine_ls_wR_factor_gt 0.1719 _refine_ls_goodness_of_fit_ref 1.005 _refine_ls_restrained_S_all 1.005 _refine_ls_shift/su_max 0.002 _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 F2 F 0.4220(2) 0.07703(18) 0.17306(16) 0.0652(5) Uani 1 1 d . . . F1 F 0.2032(3) -0.04903(17) 0.02131(16) 0.0712(6) Uani 1 1 d . . . N2 N 0.1251(3) 0.0378(2) 0.1936(2) 0.0495(6) Uani 1 1 d . . . C8 C 0.0890(3) 0.2351(2) 0.1944(2) 0.0438(6) Uani 1 1 d . . . N1 N 0.2662(3) 0.1754(2) 0.06851(19) 0.0495(6) Uani 1 1 d . . . N3 N -0.2352(4) 0.5789(2) 0.3309(2) 0.0592(7) Uani 1 1 d . . . C15 C 0.0157(4) 0.5173(3) 0.3538(2) 0.0542(7) Uani 1 1 d . . . H15 H 0.0748 0.5903 0.4128 0.065 Uiso 1 1 calc R . . C11 C 0.0049(3) 0.3246(2) 0.2340(2) 0.0447(6) Uani 1 1 d . . . C10 C 0.1958(3) 0.2621(3) 0.1138(2) 0.0480(6) Uani 1 1 d . . . C14 C -0.1516(4) 0.4898(2) 0.2978(2) 0.0482(7) Uani 1 1 d . . . C9 C 0.0524(3) 0.1240(2) 0.2328(2) 0.0452(6) Uani 1 1 d . . . O2 O -0.1568(4) 0.6706(2) 0.4120(3) 0.0885(8) Uani 1 1 d . . . C7 C -0.0551(4) 0.0738(3) 0.3101(2) 0.0521(7) Uani 1 1 d . . . C1 C 0.2420(4) 0.3632(3) 0.0562(3) 0.0547(7) Uani 1 1 d . . . C16 C 0.0944(4) 0.4341(3) 0.3204(2) 0.0529(7) Uani 1 1 d . . . H16 H 0.2086 0.4519 0.3563 0.063 Uiso 1 1 calc R . . C13 C -0.2449(4) 0.3810(3) 0.2118(3) 0.0541(7) Uani 1 1 d . . . H13 H -0.3587 0.3641 0.1757 0.065 Uiso 1 1 calc R . . O1 O -0.3794(4) 0.5581(3) 0.2764(2) 0.0854(8) Uani 1 1 d . . . C3 C 0.3496(4) 0.2179(3) -0.0133(2) 0.0568(8) Uani 1 1 d . . . C5 C 0.0678(4) -0.0614(3) 0.2418(3) 0.0580(8) Uani 1 1 d . . . C12 C -0.1657(4) 0.2983(3) 0.1808(2) 0.0528(7) Uani 1 1 d . . . H12 H -0.2270 0.2240 0.1236 0.063 Uiso 1 1 calc R . . B B 0.2573(4) 0.0566(3) 0.1120(3) 0.0509(8) Uani 1 1 d . . . C19 C 0.2037(5) 0.4801(4) 0.0731(4) 0.0765(10) Uani 1 1 d . . . H19A H 0.0805 0.4573 0.0705 0.115 Uiso 1 1 calc R . . H19C H 0.2372 0.5227 0.0134 0.115 Uiso 1 1 calc R . . H19B H 0.2687 0.5358 0.1465 0.115 Uiso 1 1 calc R . . C17 C -0.1664(5) 0.1271(3) 0.3736(3) 0.0643(8) Uani 1 1 d . . . H17B H -0.1002 0.2157 0.4092 0.096 Uiso 1 1 calc R . . H17C H -0.2018 0.0820 0.4315 0.096 Uiso 1 1 calc R . . H17A H -0.2685 0.1177 0.3206 0.096 Uiso 1 1 calc R . . C18 C 0.1170(5) -0.1741(3) 0.2167(4) 0.0796(10) Uani 1 1 d . . . H18A H 0.0445 -0.2316 0.1459 0.119 Uiso 1 1 calc R . . H18C H 0.1003 -0.2168 0.2780 0.119 Uiso 1 1 calc R . . H18B H 0.2379 -0.1460 0.2102 0.119 Uiso 1 1 calc R . . C2 C 0.3367(4) 0.3336(3) -0.0224(3) 0.0624(8) Uani 1 1 d . . . H2 H 0.3839 0.3819 -0.0729 0.075 Uiso 1 1 calc R . . C6 C -0.0425(4) -0.0415(3) 0.3140(3) 0.0623(8) Uani 1 1 d . . . H6 H -0.0984 -0.0963 0.3575 0.075 Uiso 1 1 calc R . . C4 C 0.4410(5) 0.1502(4) -0.0813(3) 0.0726(10) Uani 1 1 d . . . H4B H 0.5003 0.1153 -0.0321 0.109 Uiso 1 1 calc R . . H4C H 0.5249 0.2091 -0.1132 0.109 Uiso 1 1 calc R . . H4A H 0.3565 0.0827 -0.1423 0.109 Uiso 1 1 calc R . . Cl Cl 0.50080(17) 0.65804(13) 0.56505(11) 0.1104(5) Uani 1 1 d . . . C20 C 0.5860(6) 0.8059(4) 0.5376(4) 0.0852(12) Uani 1 1 d . . . Cl1 Cl 0.46730(18) 0.81793(14) 0.41482(12) 0.1155(5) Uani 1 1 d . . . H20 H 0.708(8) 0.838(5) 0.539(4) 0.115(17) Uiso 1 1 d . . . H20A H 0.570(8) 0.869(5) 0.593(5) 0.15(2) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 F2 0.0444(10) 0.0778(11) 0.0745(11) 0.0143(9) 0.0031(8) 0.0299(9) F1 0.0779(13) 0.0584(10) 0.0651(11) -0.0071(8) 0.0093(9) 0.0249(9) N2 0.0427(13) 0.0482(12) 0.0544(13) 0.0089(10) 0.0049(10) 0.0172(10) C8 0.0343(14) 0.0471(14) 0.0415(13) 0.0039(10) -0.0009(11) 0.0119(11) N1 0.0414(12) 0.0571(13) 0.0462(12) 0.0055(10) 0.0058(10) 0.0192(10) N3 0.0682(18) 0.0595(15) 0.0605(15) 0.0185(12) 0.0234(13) 0.0318(13) C15 0.0568(18) 0.0445(14) 0.0520(15) 0.0032(11) 0.0071(13) 0.0144(13) C11 0.0415(15) 0.0475(14) 0.0428(13) 0.0101(11) 0.0083(11) 0.0155(12) C10 0.0388(14) 0.0504(14) 0.0503(14) 0.0072(11) 0.0029(12) 0.0167(12) C14 0.0506(16) 0.0474(14) 0.0497(14) 0.0139(11) 0.0147(12) 0.0201(12) C9 0.0397(14) 0.0447(13) 0.0454(14) 0.0035(11) 0.0021(11) 0.0153(11) O2 0.0898(19) 0.0685(15) 0.1007(19) -0.0087(14) 0.0165(16) 0.0381(14) C7 0.0437(15) 0.0542(15) 0.0518(15) 0.0102(12) 0.0049(12) 0.0146(13) C1 0.0428(16) 0.0656(17) 0.0599(17) 0.0221(14) 0.0084(13) 0.0232(14) C16 0.0443(16) 0.0503(15) 0.0555(16) 0.0047(12) -0.0003(13) 0.0159(13) C13 0.0408(15) 0.0630(17) 0.0555(16) 0.0069(13) 0.0060(12) 0.0215(13) O1 0.0856(19) 0.1042(19) 0.0851(17) 0.0157(14) 0.0123(15) 0.0635(16) C3 0.0427(16) 0.076(2) 0.0452(15) 0.0077(13) 0.0063(12) 0.0201(14) C5 0.0488(17) 0.0546(16) 0.0672(18) 0.0154(13) 0.0022(14) 0.0190(14) C12 0.0424(16) 0.0543(16) 0.0519(15) -0.0013(12) -0.0004(12) 0.0175(13) B 0.0468(18) 0.0514(17) 0.0502(17) 0.0036(13) 0.0051(14) 0.0198(14) C19 0.075(2) 0.084(2) 0.099(3) 0.053(2) 0.035(2) 0.0444(19) C17 0.062(2) 0.0662(19) 0.0633(18) 0.0130(15) 0.0221(15) 0.0217(16) C18 0.075(2) 0.066(2) 0.106(3) 0.0263(19) 0.016(2) 0.0349(19) C2 0.0511(18) 0.083(2) 0.0584(17) 0.0270(15) 0.0138(14) 0.0266(16) C6 0.0545(18) 0.0594(17) 0.073(2) 0.0254(15) 0.0143(16) 0.0179(15) C4 0.060(2) 0.095(2) 0.0620(19) 0.0058(17) 0.0150(16) 0.0343(19) Cl 0.0963(9) 0.1182(9) 0.1098(9) 0.0560(7) 0.0237(7) 0.0195(7) C20 0.065(3) 0.088(3) 0.085(3) 0.009(2) 0.000(2) 0.020(2) Cl1 0.1072(10) 0.1298(10) 0.1100(9) 0.0477(8) 0.0034(7) 0.0439(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag F2 B 1.395(4) . ? F1 B 1.380(3) . ? N2 C5 1.343(4) . ? N2 C9 1.389(4) . ? N2 B 1.551(4) . ? C8 C9 1.391(4) . ? C8 C10 1.400(4) . ? C8 C11 1.493(4) . ? N1 C3 1.342(4) . ? N1 C10 1.401(4) . ? N1 B 1.541(4) . ? N3 O1 1.217(4) . ? N3 O2 1.220(4) . ? N3 C14 1.467(4) . ? C15 C14 1.371(4) . ? C15 C16 1.381(4) . ? C15 H15 0.9300 . ? C11 C16 1.382(4) . ? C11 C12 1.388(4) . ? C10 C1 1.428(4) . ? C14 C13 1.380(4) . ? C9 C7 1.429(4) . ? C7 C6 1.387(4) . ? C7 C17 1.500(4) . ? C1 C2 1.380(4) . ? C1 C19 1.488(5) . ? C16 H16 0.9300 . ? C13 C12 1.372(4) . ? C13 H13 0.9300 . ? C3 C2 1.406(5) . ? C3 C4 1.492(5) . ? C5 C6 1.393(5) . ? C5 C18 1.498(5) . ? C12 H12 0.9300 . ? C19 H19A 0.9600 . ? C19 H19C 0.9600 . ? C19 H19B 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C17 H17A 0.9600 . ? C18 H18A 0.9600 . ? C18 H18C 0.9600 . ? C18 H18B 0.9600 . ? C2 H2 0.9300 . ? C6 H6 0.9300 . ? C4 H4B 0.9600 . ? C4 H4C 0.9600 . ? C4 H4A 0.9600 . ? Cl C20 1.715(5) . ? C20 Cl1 1.737(5) . ? C20 H20 0.95(6) . ? C20 H20A 0.96(6) . ? 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 C5 N2 C9 108.7(2) . . ? C5 N2 B 125.9(3) . . ? C9 N2 B 125.3(2) . . ? C9 C8 C10 121.6(2) . . ? C9 C8 C11 119.8(2) . . ? C10 C8 C11 118.6(2) . . ? C3 N1 C10 108.2(2) . . ? C3 N1 B 126.8(2) . . ? C10 N1 B 124.9(2) . . ? O1 N3 O2 122.9(3) . . ? O1 N3 C14 118.7(3) . . ? O2 N3 C14 118.4(3) . . ? C14 C15 C16 118.4(2) . . ? C14 C15 H15 120.8 . . ? C16 C15 H15 120.8 . . ? C16 C11 C12 119.5(3) . . ? C16 C11 C8 121.5(2) . . ? C12 C11 C8 119.0(2) . . ? C8 C10 N1 120.0(2) . . ? C8 C10 C1 131.9(3) . . ? N1 C10 C1 107.9(2) . . ? C15 C14 C13 122.4(3) . . ? C15 C14 N3 118.9(2) . . ? C13 C14 N3 118.7(3) . . ? N2 C9 C8 120.4(2) . . ? N2 C9 C7 107.7(2) . . ? C8 C9 C7 132.0(3) . . ? C6 C7 C9 105.9(3) . . ? C6 C7 C17 124.7(3) . . ? C9 C7 C17 129.4(3) . . ? C2 C1 C10 106.1(3) . . ? C2 C1 C19 124.1(3) . . ? C10 C1 C19 129.8(3) . . ? C15 C16 C11 120.6(3) . . ? C15 C16 H16 119.7 . . ? C11 C16 H16 119.7 . . ? C12 C13 C14 118.4(3) . . ? C12 C13 H13 120.8 . . ? C14 C13 H13 120.8 . . ? N1 C3 C2 109.3(3) . . ? N1 C3 C4 123.7(3) . . ? C2 C3 C4 127.0(3) . . ? N2 C5 C6 109.2(3) . . ? N2 C5 C18 123.3(3) . . ? C6 C5 C18 127.5(3) . . ? C13 C12 C11 120.6(2) . . ? C13 C12 H12 119.7 . . ? C11 C12 H12 119.7 . . ? F1 B F2 109.4(2) . . ? F1 B N1 110.8(2) . . ? F2 B N1 109.7(2) . . ? F1 B N2 110.7(2) . . ? F2 B N2 109.4(2) . . ? N1 B N2 106.9(2) . . ? C1 C19 H19A 109.5 . . ? C1 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? C1 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? H19C C19 H19B 109.5 . . ? C7 C17 H17B 109.5 . . ? C7 C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C7 C17 H17A 109.5 . . ? H17B C17 H17A 109.5 . . ? H17C C17 H17A 109.5 . . ? C5 C18 H18A 109.5 . . ? C5 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? C5 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? H18C C18 H18B 109.5 . . ? C1 C2 C3 108.5(3) . . ? C1 C2 H2 125.8 . . ? C3 C2 H2 125.8 . . ? C7 C6 C5 108.5(3) . . ? C7 C6 H6 125.7 . . ? C5 C6 H6 125.7 . . ? C3 C4 H4B 109.5 . . ? C3 C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C3 C4 H4A 109.5 . . ? H4B C4 H4A 109.5 . . ? H4C C4 H4A 109.5 . . ? Cl C20 Cl1 112.8(2) . . ? Cl C20 H20 115(3) . . ? Cl1 C20 H20 112(3) . . ? Cl C20 H20A 112(4) . . ? Cl1 C20 H20A 99(4) . . ? H20 C20 H20A 104(4) . . ? _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 63.98 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 0.327 _refine_diff_density_min -0.632 _refine_diff_density_rms 0.128