Supplementary Material (ESI) for Dalton Transactions This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'George Britovsek' _publ_contact_author_address ; Department of Chemistry Imperial College of Science, Technology & Medicine Building RCS1, room 314 Frankland Road South Kensington London SW7 2AY UNITED KINGDOM ; _publ_contact_author_email G.BRITOVSEK@IMPERIAL.AC.UK _publ_section_title ; Synthesis and characterisation of luminescent fluorinated organoboron compounds ; loop_ _publ_author_name 'George Britovsek' 'Sondra Hellstrom' 'Patricia Hunt' 'Tim Jones' 'Juri Uglotti' 'A. J. P. White' #===END data_Compound_2 _database_code_depnum_ccdc_archive 'CCDC 619418' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H6 B F10 N O' _chemical_formula_weight 489.08 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 15.3409(13) _cell_length_b 7.8053(6) _cell_length_c 15.4746(14) _cell_angle_alpha 90.00 _cell_angle_beta 96.164(7) _cell_angle_gamma 90.00 _cell_volume 1842.2(3) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 2.8948 _cell_measurement_theta_max 70.9800 _exptl_crystal_description plates _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.763 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 968 _exptl_absorpt_coefficient_mu 1.605 _exptl_absorpt_correction_type 'numeric analytical' _exptl_absorpt_correction_T_min 0.62708 _exptl_absorpt_correction_T_max 0.95253 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 1.54248 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'Enhance Ultra (Cu) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'OD Xcalibur PX Ultra' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 8.2556 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16343 _diffrn_reflns_av_R_equivalents 0.0456 _diffrn_reflns_av_sigmaI/netI 0.0320 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.90 _diffrn_reflns_theta_max 71.18 _reflns_number_total 3484 _reflns_number_gt 2555 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD, Oxford Diffraction Ltd' _computing_cell_refinement 'CrysAlis RED, Oxford Diffraction Ltd' _computing_data_reduction 'CrysAlis RED, Oxford Diffraction Ltd' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0565P)^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 SHELXL _refine_ls_extinction_coef 0.00080(19) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3484 _refine_ls_number_parameters 308 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0558 _refine_ls_R_factor_gt 0.0350 _refine_ls_wR_factor_ref 0.0960 _refine_ls_wR_factor_gt 0.0855 _refine_ls_goodness_of_fit_ref 0.993 _refine_ls_restrained_S_all 0.993 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group B B 0.26769(13) 0.6492(2) 0.39846(14) 0.0339(5) Uani 1 1 d . . . N1 N 0.30568(9) 0.84515(17) 0.40733(9) 0.0327(3) Uani 1 1 d . . . C2 C 0.27081(13) 0.9970(2) 0.42142(12) 0.0394(4) Uani 1 1 d . . . H2A H 0.2115 1.0048 0.4334 0.047 Uiso 1 1 calc R . . C3 C 0.32164(14) 1.1459(2) 0.41861(13) 0.0464(5) Uani 1 1 d . . . H3A H 0.2963 1.2539 0.4293 0.056 Uiso 1 1 calc R . . C4 C 0.40689(14) 1.1386(2) 0.40082(13) 0.0467(5) Uani 1 1 d . . . H4A H 0.4400 1.2410 0.3986 0.056 Uiso 1 1 calc R . . C5 C 0.44573(12) 0.9790(2) 0.38568(12) 0.0383(4) Uani 1 1 d . . . C6 C 0.53136(13) 0.9435(3) 0.36476(14) 0.0474(5) Uani 1 1 d . . . H6A H 0.5717 1.0344 0.3599 0.057 Uiso 1 1 calc R . . C7 C 0.55592(13) 0.7777(3) 0.35154(14) 0.0495(5) Uani 1 1 d . . . H7A H 0.6136 0.7568 0.3372 0.059 Uiso 1 1 calc R . . C8 C 0.49944(12) 0.6361(2) 0.35824(13) 0.0430(5) Uani 1 1 d . . . H8A H 0.5188 0.5226 0.3490 0.052 Uiso 1 1 calc R . . C9 C 0.41653(11) 0.6668(2) 0.37837(12) 0.0349(4) Uani 1 1 d . . . O9 O 0.35098(7) 0.55579(14) 0.38826(8) 0.0377(3) Uani 1 1 d . . . C10 C 0.39108(11) 0.8369(2) 0.39075(11) 0.0322(4) Uani 1 1 d . . . C11 C 0.23181(11) 0.5856(2) 0.48811(11) 0.0326(4) Uani 1 1 d . . . C12 C 0.28368(11) 0.6083(2) 0.56661(12) 0.0356(4) Uani 1 1 d . . . F12 F 0.36071(7) 0.69423(14) 0.56796(7) 0.0466(3) Uani 1 1 d . . . C13 C 0.26381(12) 0.5452(2) 0.64516(12) 0.0393(4) Uani 1 1 d . . . F13 F 0.31887(8) 0.57007(16) 0.71757(7) 0.0553(3) Uani 1 1 d . . . C14 C 0.18712(13) 0.4548(2) 0.64851(13) 0.0428(5) Uani 1 1 d . . . F14 F 0.16694(8) 0.39257(16) 0.72470(7) 0.0590(3) Uani 1 1 d . . . C15 C 0.13262(11) 0.4287(2) 0.57355(13) 0.0405(4) Uani 1 1 d . . . F15 F 0.05875(7) 0.33956(15) 0.57609(8) 0.0577(3) Uani 1 1 d . . . C16 C 0.15600(11) 0.4922(2) 0.49554(12) 0.0361(4) Uani 1 1 d . . . F16 F 0.10113(7) 0.45319(15) 0.42471(7) 0.0505(3) Uani 1 1 d . . . C17 C 0.19916(11) 0.6400(2) 0.31056(12) 0.0337(4) Uani 1 1 d . . . C18 C 0.11981(12) 0.7274(2) 0.30423(12) 0.0370(4) Uani 1 1 d . . . F18 F 0.09862(6) 0.81763(14) 0.37401(7) 0.0459(3) Uani 1 1 d . . . C19 C 0.05950(12) 0.7295(2) 0.23184(13) 0.0434(5) Uani 1 1 d . . . F19 F -0.01546(8) 0.81752(16) 0.23162(9) 0.0627(4) Uani 1 1 d . . . C20 C 0.07691(14) 0.6394(2) 0.15928(13) 0.0469(5) Uani 1 1 d . . . F20 F 0.01966(9) 0.63948(17) 0.08756(8) 0.0707(4) Uani 1 1 d . . . C21 C 0.15434(14) 0.5510(2) 0.16127(12) 0.0458(5) Uani 1 1 d . . . F21 F 0.17327(9) 0.46344(16) 0.09071(8) 0.0661(4) Uani 1 1 d . . . C22 C 0.21334(12) 0.5520(2) 0.23516(13) 0.0395(4) Uani 1 1 d . . . F22 F 0.28687(7) 0.45961(16) 0.23069(8) 0.0578(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 B 0.0326(10) 0.0238(9) 0.0464(12) -0.0012(8) 0.0093(9) 0.0001(8) N1 0.0380(8) 0.0255(7) 0.0353(8) 0.0007(6) 0.0074(6) -0.0005(6) C2 0.0477(11) 0.0293(9) 0.0427(10) -0.0010(8) 0.0117(9) 0.0043(8) C3 0.0631(13) 0.0253(9) 0.0523(12) -0.0021(8) 0.0135(10) 0.0021(9) C4 0.0605(13) 0.0290(9) 0.0512(12) 0.0006(9) 0.0090(10) -0.0092(9) C5 0.0447(10) 0.0313(9) 0.0384(10) 0.0031(8) 0.0026(8) -0.0078(8) C6 0.0428(11) 0.0404(11) 0.0595(13) 0.0041(9) 0.0080(10) -0.0138(9) C7 0.0345(10) 0.0475(12) 0.0678(14) 0.0038(10) 0.0120(10) -0.0058(9) C8 0.0340(10) 0.0358(10) 0.0603(13) 0.0025(9) 0.0097(9) 0.0017(8) C9 0.0344(9) 0.0288(9) 0.0416(10) 0.0027(7) 0.0046(8) -0.0035(7) O9 0.0322(6) 0.0241(6) 0.0582(8) 0.0011(5) 0.0105(6) -0.0023(5) C10 0.0346(9) 0.0288(9) 0.0331(9) 0.0021(7) 0.0031(7) -0.0016(7) C11 0.0340(9) 0.0234(8) 0.0408(10) -0.0005(7) 0.0053(8) 0.0031(7) C12 0.0345(9) 0.0273(9) 0.0455(11) -0.0010(8) 0.0063(8) -0.0004(7) F12 0.0420(6) 0.0451(6) 0.0510(7) 0.0020(5) -0.0028(5) -0.0110(5) C13 0.0449(10) 0.0357(10) 0.0365(10) -0.0028(8) 0.0011(9) 0.0065(8) F13 0.0627(7) 0.0616(8) 0.0399(6) -0.0026(5) -0.0027(5) -0.0003(6) C14 0.0533(12) 0.0360(10) 0.0416(11) 0.0047(8) 0.0160(9) 0.0075(9) F14 0.0714(8) 0.0637(8) 0.0449(7) 0.0106(6) 0.0197(6) 0.0003(6) C15 0.0359(10) 0.0357(10) 0.0520(12) 0.0042(8) 0.0146(9) -0.0013(8) F15 0.0456(6) 0.0622(8) 0.0676(8) 0.0114(6) 0.0166(6) -0.0143(6) C16 0.0344(9) 0.0331(9) 0.0405(10) -0.0009(8) 0.0020(8) -0.0003(8) F16 0.0442(6) 0.0570(7) 0.0492(7) 0.0044(5) -0.0002(5) -0.0182(5) C17 0.0350(9) 0.0274(9) 0.0405(10) 0.0006(7) 0.0119(8) -0.0038(7) C18 0.0400(10) 0.0339(9) 0.0383(10) -0.0003(8) 0.0097(8) 0.0004(8) F18 0.0417(6) 0.0494(7) 0.0476(7) -0.0063(5) 0.0100(5) 0.0106(5) C19 0.0399(10) 0.0405(10) 0.0496(12) 0.0073(9) 0.0038(9) 0.0033(9) F19 0.0517(7) 0.0661(8) 0.0672(8) 0.0052(6) -0.0069(6) 0.0164(6) C20 0.0573(12) 0.0418(11) 0.0400(11) 0.0051(9) -0.0012(9) -0.0087(10) F20 0.0857(9) 0.0708(9) 0.0502(8) 0.0029(6) -0.0174(7) -0.0059(7) C21 0.0639(13) 0.0391(11) 0.0365(11) -0.0056(8) 0.0145(10) -0.0125(10) F21 0.0915(9) 0.0644(8) 0.0449(7) -0.0185(6) 0.0188(7) -0.0098(7) C22 0.0414(10) 0.0327(9) 0.0467(11) -0.0038(8) 0.0159(9) -0.0025(8) F22 0.0493(7) 0.0613(7) 0.0651(8) -0.0220(6) 0.0169(6) 0.0075(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag B O9 1.494(2) . ? B C11 1.624(3) . ? B C17 1.629(3) . ? B N1 1.637(2) . ? N1 C2 1.328(2) . ? N1 C10 1.363(2) . ? C2 C3 1.403(3) . ? C3 C4 1.366(3) . ? C4 C5 1.411(3) . ? C5 C10 1.398(2) . ? C5 C6 1.414(3) . ? C6 C7 1.369(3) . ? C7 C8 1.415(3) . ? C8 C9 1.363(2) . ? C9 O9 1.349(2) . ? C9 C10 1.402(2) . ? C11 C16 1.388(2) . ? C11 C12 1.390(2) . ? C12 F12 1.357(2) . ? C12 C13 1.375(3) . ? C13 F13 1.343(2) . ? C13 C14 1.378(3) . ? C14 F14 1.342(2) . ? C14 C15 1.370(3) . ? C15 F15 1.334(2) . ? C15 C16 1.387(3) . ? C16 F16 1.343(2) . ? C17 C18 1.390(2) . ? C17 C22 1.391(3) . ? C18 F18 1.358(2) . ? C18 C19 1.374(3) . ? C19 F19 1.339(2) . ? C19 C20 1.375(3) . ? C20 F20 1.339(2) . ? C20 C21 1.371(3) . ? C21 F21 1.346(2) . ? C21 C22 1.380(3) . ? C22 F22 1.347(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 O9 B C11 108.26(14) . . ? O9 B C17 111.90(15) . . ? C11 B C17 116.89(15) . . ? O9 B N1 99.43(13) . . ? C11 B N1 111.35(14) . . ? C17 B N1 107.64(14) . . ? C2 N1 C10 119.04(15) . . ? C2 N1 B 134.55(15) . . ? C10 N1 B 106.28(13) . . ? N1 C2 C3 119.95(17) . . ? C4 C3 C2 121.27(17) . . ? C3 C4 C5 120.04(17) . . ? C10 C5 C4 115.14(17) . . ? C10 C5 C6 115.78(16) . . ? C4 C5 C6 129.07(18) . . ? C7 C6 C5 119.78(17) . . ? C6 C7 C8 123.16(18) . . ? C9 C8 C7 118.20(17) . . ? O9 C9 C8 129.65(16) . . ? O9 C9 C10 111.76(15) . . ? C8 C9 C10 118.58(16) . . ? C9 O9 B 110.80(13) . . ? N1 C10 C5 124.55(15) . . ? N1 C10 C9 110.97(14) . . ? C5 C10 C9 124.48(16) . . ? C16 C11 C12 113.62(16) . . ? C16 C11 B 126.53(16) . . ? C12 C11 B 119.52(15) . . ? F12 C12 C13 116.01(16) . . ? F12 C12 C11 119.48(16) . . ? C13 C12 C11 124.49(16) . . ? F13 C13 C12 120.43(17) . . ? F13 C13 C14 120.39(17) . . ? C12 C13 C14 119.18(17) . . ? F14 C14 C15 120.86(17) . . ? F14 C14 C13 119.80(18) . . ? C15 C14 C13 119.34(17) . . ? F15 C15 C14 119.70(17) . . ? F15 C15 C16 120.78(17) . . ? C14 C15 C16 119.50(16) . . ? F16 C16 C15 115.54(15) . . ? F16 C16 C11 120.59(16) . . ? C15 C16 C11 123.84(17) . . ? C18 C17 C22 113.45(17) . . ? C18 C17 B 121.29(15) . . ? C22 C17 B 125.23(16) . . ? F18 C18 C19 116.38(16) . . ? F18 C18 C17 118.77(16) . . ? C19 C18 C17 124.85(17) . . ? F19 C19 C18 120.73(18) . . ? F19 C19 C20 120.15(18) . . ? C18 C19 C20 119.11(18) . . ? F20 C20 C21 120.54(19) . . ? F20 C20 C19 120.59(19) . . ? C21 C20 C19 118.87(18) . . ? F21 C21 C20 119.95(19) . . ? F21 C21 C22 119.69(19) . . ? C20 C21 C22 120.36(18) . . ? F22 C22 C21 115.65(17) . . ? F22 C22 C17 120.98(17) . . ? C21 C22 C17 123.36(17) . . ? _diffrn_measured_fraction_theta_max 0.976 _diffrn_reflns_theta_full 71.18 _diffrn_measured_fraction_theta_full 0.976 _refine_diff_density_max 0.175 _refine_diff_density_min -0.197 _refine_diff_density_rms 0.040 data_Compound_1 _database_code_depnum_ccdc_archive 'CCDC 632949' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C27.50 H8 B Cl F15 N O' _chemical_formula_weight 699.61 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.3639 0.7018 '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 26.9700(11) _cell_length_b 10.5284(4) _cell_length_c 37.9995(14) _cell_angle_alpha 90.00 _cell_angle_beta 104.723(3) _cell_angle_gamma 90.00 _cell_volume 10435.7(7) _cell_formula_units_Z 16 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 2.5632 _cell_measurement_theta_max 71.0242 _exptl_crystal_description plates _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.781 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 5520 _exptl_absorpt_coefficient_mu 2.561 _exptl_absorpt_correction_type 'numeric analytical' _exptl_absorpt_correction_T_min 0.70990 _exptl_absorpt_correction_T_max 0.84410 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 1.54248 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'Enhance Ultra (Cu) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'OD Xcalibur PX Ultra' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 8.2556 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 47810 _diffrn_reflns_av_R_equivalents 0.0325 _diffrn_reflns_av_sigmaI/netI 0.0242 _diffrn_reflns_limit_h_min -32 _diffrn_reflns_limit_h_max 33 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -45 _diffrn_reflns_limit_l_max 45 _diffrn_reflns_theta_min 3.39 _diffrn_reflns_theta_max 71.21 _reflns_number_total 9862 _reflns_number_gt 8016 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD, Oxford Diffraction Ltd' _computing_cell_refinement 'CrysAlis RED, Oxford Diffraction Ltd' _computing_data_reduction 'CrysAlis RED, Oxford Diffraction Ltd' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0452P)^2^+33.2843P] 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 SHELXL _refine_ls_extinction_coef 0.000091(11) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 9862 _refine_ls_number_parameters 860 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0643 _refine_ls_R_factor_gt 0.0514 _refine_ls_wR_factor_ref 0.1365 _refine_ls_wR_factor_gt 0.1298 _refine_ls_goodness_of_fit_ref 1.111 _refine_ls_restrained_S_all 1.111 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group B B 0.14475(13) 0.1866(3) 0.01230(9) 0.0309(7) Uani 1 1 d . . . O1 O 0.16967(8) 0.1259(2) -0.01481(5) 0.0327(5) Uani 1 1 d . . . N1 N 0.22357(10) -0.0568(3) -0.03346(7) 0.0363(6) Uani 1 1 d D . . H1 H 0.2336(13) -0.013(3) -0.0126(5) 0.045(10) Uiso 1 1 d D . . C1 C 0.25458(14) -0.1482(3) -0.03944(10) 0.0428(8) Uani 1 1 d . . . H1A H 0.2873 -0.1603 -0.0231 0.051 Uiso 1 1 calc R . . C2 C 0.23851(15) -0.2256(3) -0.06976(11) 0.0487(9) Uani 1 1 d . . . H2A H 0.2602 -0.2909 -0.0745 0.058 Uiso 1 1 calc R . . C3 C 0.19102(14) -0.2067(3) -0.09281(10) 0.0475(9) Uani 1 1 d . . . H3A H 0.1800 -0.2603 -0.1135 0.057 Uiso 1 1 calc R . . C4 C 0.15823(13) -0.1103(3) -0.08667(9) 0.0413(8) Uani 1 1 d . . . C5 C 0.10819(14) -0.0865(4) -0.10846(10) 0.0495(9) Uani 1 1 d . . . H5A H 0.0946 -0.1361 -0.1296 0.059 Uiso 1 1 calc R . . C6 C 0.07957(14) 0.0081(4) -0.09896(10) 0.0503(9) Uani 1 1 d . . . H6A H 0.0462 0.0237 -0.1139 0.060 Uiso 1 1 calc R . . C7 C 0.09795(13) 0.0838(4) -0.06751(9) 0.0426(8) Uani 1 1 d . . . H7A H 0.0767 0.1485 -0.0618 0.051 Uiso 1 1 calc R . . C8 C 0.14603(12) 0.0646(3) -0.04527(8) 0.0328(7) Uani 1 1 d . . . C9 C 0.17636(12) -0.0337(3) -0.05546(8) 0.0343(7) Uani 1 1 d . . . C10 C 0.11315(11) 0.3134(3) -0.00714(8) 0.0320(6) Uani 1 1 d . . . C11 C 0.06044(11) 0.3342(3) -0.01604(8) 0.0345(7) Uani 1 1 d . . . F11 F 0.02828(7) 0.24290(19) -0.01045(5) 0.0446(5) Uani 1 1 d . . . C12 C 0.03770(12) 0.4459(3) -0.03157(9) 0.0400(8) Uani 1 1 d . . . F12 F -0.01370(7) 0.4589(2) -0.03912(6) 0.0539(5) Uani 1 1 d . . . C13 C 0.06681(14) 0.5429(3) -0.03916(9) 0.0430(8) Uani 1 1 d . . . F13 F 0.04516(9) 0.6512(2) -0.05429(6) 0.0615(6) Uani 1 1 d . . . C14 C 0.11923(14) 0.5265(3) -0.03176(9) 0.0418(8) Uani 1 1 d . . . F14 F 0.14908(9) 0.6202(2) -0.03949(6) 0.0572(6) Uani 1 1 d . . . C15 C 0.14028(11) 0.4138(3) -0.01674(8) 0.0333(7) Uani 1 1 d . . . F15 F 0.19226(7) 0.40483(18) -0.01049(5) 0.0416(4) Uani 1 1 d . . . C16 C 0.19434(11) 0.2230(3) 0.04686(8) 0.0295(6) Uani 1 1 d . . . C17 C 0.20203(11) 0.3344(3) 0.06729(8) 0.0328(7) Uani 1 1 d . . . F17 F 0.16718(7) 0.42982(18) 0.05978(5) 0.0415(4) Uani 1 1 d . . . C18 C 0.24473(12) 0.3580(3) 0.09584(8) 0.0337(7) Uani 1 1 d . . . F18 F 0.24913(8) 0.46836(18) 0.11438(5) 0.0475(5) Uani 1 1 d . . . C19 C 0.28276(12) 0.2694(3) 0.10503(8) 0.0389(7) Uani 1 1 d . . . F19 F 0.32481(7) 0.2917(2) 0.13240(5) 0.0538(5) Uani 1 1 d . . . C20 C 0.27724(12) 0.1567(3) 0.08630(8) 0.0362(7) Uani 1 1 d . . . F20 F 0.31365(8) 0.0660(2) 0.09510(6) 0.0525(5) Uani 1 1 d . . . C21 C 0.23356(11) 0.1361(3) 0.05902(8) 0.0317(6) Uani 1 1 d . . . F21 F 0.23043(7) 0.01784(17) 0.04374(5) 0.0388(4) Uani 1 1 d . . . C22 C 0.11109(11) 0.0846(3) 0.03004(8) 0.0335(7) Uani 1 1 d . . . C23 C 0.08426(12) 0.1289(3) 0.05458(9) 0.0376(7) Uani 1 1 d . . . F23 F 0.08337(7) 0.25477(19) 0.06108(5) 0.0453(5) Uani 1 1 d . . . C24 C 0.05864(13) 0.0514(4) 0.07328(9) 0.0446(8) Uani 1 1 d . . . F24 F 0.03334(9) 0.1019(3) 0.09626(6) 0.0675(7) Uani 1 1 d . . . C25 C 0.05988(13) -0.0779(4) 0.06887(10) 0.0475(9) Uani 1 1 d . . . F25 F 0.03575(9) -0.1550(2) 0.08759(6) 0.0669(7) Uani 1 1 d . . . C26 C 0.08683(13) -0.1280(3) 0.04608(9) 0.0429(8) Uani 1 1 d . . . F26 F 0.09019(9) -0.2546(2) 0.04231(6) 0.0581(6) Uani 1 1 d . . . C27 C 0.11172(12) -0.0466(3) 0.02745(8) 0.0357(7) Uani 1 1 d . . . F27 F 0.13833(8) -0.10682(18) 0.00642(5) 0.0461(5) Uani 1 1 d . . . B' B 0.34927(13) 0.9691(3) 0.21742(9) 0.0295(7) Uani 1 1 d . . . O1' O 0.35098(8) 1.0063(2) 0.25558(5) 0.0337(5) Uani 1 1 d . . . N1' N 0.33095(9) 1.0886(2) 0.31463(7) 0.0330(6) Uani 1 1 d D . . H1' H 0.3100(11) 1.099(3) 0.2923(4) 0.042(10) Uiso 1 1 d D . . C1' C 0.31636(13) 1.1360(3) 0.34294(9) 0.0420(8) Uani 1 1 d . . . H1'A H 0.2851 1.1816 0.3393 0.050 Uiso 1 1 calc R . . C2' C 0.34717(13) 1.1181(4) 0.37774(9) 0.0458(8) Uani 1 1 d . . . H2'A H 0.3373 1.1521 0.3981 0.055 Uiso 1 1 calc R . . C3' C 0.39158(13) 1.0519(4) 0.38265(9) 0.0436(8) Uani 1 1 d . . . H3'A H 0.4123 1.0388 0.4066 0.052 Uiso 1 1 calc R . . C4' C 0.40761(12) 1.0022(3) 0.35302(8) 0.0370(7) Uani 1 1 d . . . C5' C 0.45366(12) 0.9345(4) 0.35582(9) 0.0443(8) Uani 1 1 d . . . H5'A H 0.4758 0.9159 0.3790 0.053 Uiso 1 1 calc R . . C6' C 0.46577(12) 0.8962(4) 0.32470(10) 0.0446(8) Uani 1 1 d . . . H6'A H 0.4971 0.8524 0.3267 0.054 Uiso 1 1 calc R . . C7' C 0.43362(12) 0.9191(3) 0.28973(9) 0.0402(8) Uani 1 1 d . . . H7'A H 0.4440 0.8930 0.2688 0.048 Uiso 1 1 calc R . . C8' C 0.38718(11) 0.9792(3) 0.28585(8) 0.0319(6) Uani 1 1 d . . . C9' C 0.37533(11) 1.0226(3) 0.31803(8) 0.0296(6) Uani 1 1 d . . . C10' C 0.35427(11) 0.8122(3) 0.21626(8) 0.0310(6) Uani 1 1 d . . . C11' C 0.39588(12) 0.7446(3) 0.21078(9) 0.0356(7) Uani 1 1 d . . . F11' F 0.43894(7) 0.80545(18) 0.20775(5) 0.0438(5) Uani 1 1 d . . . C12' C 0.39799(13) 0.6140(3) 0.20859(10) 0.0427(8) Uani 1 1 d . . . F12' F 0.43978(9) 0.5572(2) 0.20267(7) 0.0643(6) Uani 1 1 d . . . C13' C 0.35715(14) 0.5423(3) 0.21269(10) 0.0468(9) Uani 1 1 d . . . F13' F 0.35818(10) 0.41535(19) 0.21021(7) 0.0688(7) Uani 1 1 d . . . C14' C 0.31582(13) 0.6035(3) 0.21971(9) 0.0422(8) Uani 1 1 d . . . F14' F 0.27569(8) 0.5358(2) 0.22474(7) 0.0617(6) Uani 1 1 d . . . C15' C 0.31514(11) 0.7343(3) 0.22130(8) 0.0353(7) Uani 1 1 d . . . F15' F 0.27207(7) 0.78643(19) 0.22753(5) 0.0447(5) Uani 1 1 d . . . C16' C 0.29275(11) 1.0233(3) 0.19336(7) 0.0286(6) Uani 1 1 d . . . C17' C 0.26040(11) 0.9643(3) 0.16345(8) 0.0305(6) Uani 1 1 d . . . F17' F 0.27194(7) 0.84730(17) 0.15230(5) 0.0368(4) Uani 1 1 d . . . C18' C 0.21525(11) 1.0155(3) 0.14278(8) 0.0346(7) Uani 1 1 d . . . F18' F 0.18615(7) 0.94986(19) 0.11429(5) 0.0464(5) Uani 1 1 d . . . C19' C 0.19912(11) 1.1322(3) 0.15161(9) 0.0374(7) Uani 1 1 d . . . F19' F 0.15525(7) 1.1842(2) 0.13213(6) 0.0525(5) Uani 1 1 d . . . C20' C 0.22931(12) 1.1960(3) 0.18090(9) 0.0363(7) Uani 1 1 d . . . F20' F 0.21486(8) 1.31145(19) 0.18974(6) 0.0528(5) Uani 1 1 d . . . C21' C 0.27440(11) 1.1420(3) 0.20072(8) 0.0327(7) Uani 1 1 d . . . F21' F 0.30214(7) 1.21264(17) 0.22866(5) 0.0428(5) Uani 1 1 d . . . C22' C 0.39123(11) 1.0457(3) 0.20012(8) 0.0283(6) Uani 1 1 d . . . C23' C 0.39618(11) 1.0151(3) 0.16546(8) 0.0298(6) Uani 1 1 d . . . F23' F 0.37027(7) 0.91353(17) 0.14799(5) 0.0372(4) Uani 1 1 d . . . C24' C 0.42625(11) 1.0796(3) 0.14728(8) 0.0352(7) Uani 1 1 d . . . F24' F 0.42885(7) 1.0430(2) 0.11390(5) 0.0487(5) Uani 1 1 d . . . C25' C 0.45417(12) 1.1827(3) 0.16375(9) 0.0384(7) Uani 1 1 d . . . F25' F 0.48453(8) 1.2462(2) 0.14666(6) 0.0541(5) Uani 1 1 d . . . C26' C 0.45131(11) 1.2180(3) 0.19780(9) 0.0351(7) Uani 1 1 d . . . F26' F 0.47815(7) 1.31918(18) 0.21385(6) 0.0489(5) Uani 1 1 d . . . C27' C 0.42024(11) 1.1502(3) 0.21531(8) 0.0317(6) Uani 1 1 d . . . F27' F 0.41976(7) 1.19248(18) 0.24892(5) 0.0428(4) Uani 1 1 d . . . C30 C 0.4217(3) 0.4319(7) 0.3073(2) 0.0674(19) Uani 0.785(4) 1 d P A 1 H30A H 0.4408 0.3956 0.3309 0.081 Uiso 0.785(4) 1 calc PR A 1 H30B H 0.4348 0.3932 0.2877 0.081 Uiso 0.785(4) 1 calc PR A 1 Cl1 Cl 0.35377(6) 0.40223(14) 0.29973(5) 0.0716(6) Uani 0.785(4) 1 d P A 1 Cl2 Cl 0.42929(12) 0.6007(2) 0.30740(6) 0.0992(8) Uani 0.785(4) 1 d P A 1 C30' C 0.402(2) 0.422(6) 0.3000(16) 0.16(3) Uiso 0.215(4) 1 d P A 2 H30C H 0.3721 0.4489 0.2804 0.186 Uiso 0.215(4) 1 calc PR A 2 H30D H 0.4216 0.3575 0.2901 0.186 Uiso 0.215(4) 1 calc PR A 2 Cl1' Cl 0.3866(3) 0.3747(8) 0.3289(2) 0.106(3) Uiso 0.215(4) 1 d P A 2 Cl2' Cl 0.4419(4) 0.5560(10) 0.3179(3) 0.095(3) Uiso 0.215(4) 1 d P A 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 B 0.0266(16) 0.0361(19) 0.0309(17) -0.0034(14) 0.0089(13) -0.0014(14) O1 0.0347(11) 0.0357(11) 0.0280(10) -0.0056(9) 0.0084(9) 0.0000(9) N1 0.0401(15) 0.0341(14) 0.0366(15) -0.0045(12) 0.0131(12) -0.0019(12) C1 0.0474(19) 0.0339(17) 0.052(2) -0.0024(15) 0.0210(16) 0.0006(15) C2 0.057(2) 0.0344(18) 0.064(2) -0.0107(17) 0.0325(19) -0.0070(16) C3 0.056(2) 0.044(2) 0.050(2) -0.0139(16) 0.0277(18) -0.0187(17) C4 0.0431(18) 0.0461(19) 0.0394(18) -0.0099(15) 0.0192(15) -0.0172(15) C5 0.050(2) 0.063(2) 0.0377(18) -0.0178(17) 0.0146(16) -0.0174(18) C6 0.0420(19) 0.068(3) 0.0373(18) -0.0109(17) 0.0039(15) -0.0103(18) C7 0.0399(18) 0.052(2) 0.0360(17) -0.0067(15) 0.0094(14) -0.0014(15) C8 0.0348(16) 0.0348(16) 0.0305(15) -0.0030(13) 0.0115(13) -0.0065(13) C9 0.0365(16) 0.0355(17) 0.0336(16) -0.0023(13) 0.0139(13) -0.0070(13) C10 0.0315(15) 0.0396(17) 0.0255(14) -0.0036(12) 0.0084(12) 0.0005(13) C11 0.0305(15) 0.0456(18) 0.0271(15) -0.0024(13) 0.0069(12) -0.0020(14) F11 0.0290(9) 0.0555(12) 0.0461(11) 0.0031(9) 0.0037(8) -0.0060(8) C12 0.0329(16) 0.052(2) 0.0319(16) -0.0041(15) 0.0028(13) 0.0089(15) F12 0.0356(10) 0.0706(14) 0.0492(12) -0.0016(10) -0.0005(9) 0.0142(10) C13 0.051(2) 0.0412(19) 0.0332(17) 0.0030(14) 0.0038(15) 0.0133(16) F13 0.0691(15) 0.0502(13) 0.0588(13) 0.0136(11) 0.0045(11) 0.0180(11) C14 0.050(2) 0.0396(18) 0.0356(17) 0.0035(14) 0.0102(15) -0.0063(15) F14 0.0643(14) 0.0480(12) 0.0599(13) 0.0174(10) 0.0168(11) -0.0045(10) C15 0.0316(16) 0.0417(18) 0.0266(15) -0.0007(13) 0.0071(12) 0.0001(13) F15 0.0327(9) 0.0490(11) 0.0450(10) 0.0037(9) 0.0132(8) -0.0042(8) C16 0.0283(14) 0.0361(16) 0.0246(14) -0.0003(12) 0.0077(11) -0.0018(12) C17 0.0312(15) 0.0367(17) 0.0307(15) -0.0009(13) 0.0082(12) -0.0004(13) F17 0.0415(10) 0.0404(10) 0.0397(10) -0.0080(8) 0.0054(8) 0.0056(8) C18 0.0389(17) 0.0340(16) 0.0293(15) -0.0052(13) 0.0109(13) -0.0090(13) F18 0.0511(11) 0.0419(11) 0.0452(11) -0.0120(9) 0.0046(9) -0.0081(9) C19 0.0289(16) 0.054(2) 0.0313(16) 0.0019(15) 0.0025(13) -0.0073(14) F19 0.0411(11) 0.0688(14) 0.0411(11) -0.0045(10) -0.0085(9) -0.0067(10) C20 0.0320(16) 0.0424(18) 0.0332(16) 0.0060(14) 0.0067(13) 0.0061(14) F20 0.0429(11) 0.0587(13) 0.0494(12) 0.0053(10) -0.0002(9) 0.0163(10) C21 0.0333(16) 0.0321(16) 0.0324(15) 0.0006(12) 0.0134(13) -0.0024(12) F21 0.0428(10) 0.0341(10) 0.0389(10) -0.0002(8) 0.0095(8) 0.0035(8) C22 0.0289(15) 0.0412(18) 0.0291(15) -0.0007(13) 0.0048(12) -0.0048(13) C23 0.0305(16) 0.0462(19) 0.0358(17) -0.0014(14) 0.0077(13) -0.0051(14) F23 0.0444(11) 0.0536(12) 0.0406(10) -0.0046(9) 0.0159(8) -0.0005(9) C24 0.0354(17) 0.067(2) 0.0333(17) 0.0003(16) 0.0132(14) -0.0077(16) F24 0.0638(14) 0.0930(18) 0.0594(14) -0.0051(13) 0.0407(12) -0.0115(13) C25 0.0396(19) 0.060(2) 0.0417(19) 0.0113(17) 0.0089(15) -0.0179(17) F25 0.0639(14) 0.0811(17) 0.0614(14) 0.0208(12) 0.0264(12) -0.0237(12) C26 0.0406(18) 0.044(2) 0.0395(18) 0.0065(15) 0.0011(15) -0.0116(15) F26 0.0636(14) 0.0443(12) 0.0631(14) 0.0125(10) 0.0099(11) -0.0144(10) C27 0.0340(16) 0.0403(18) 0.0312(16) 0.0012(13) 0.0054(13) -0.0044(13) F27 0.0550(12) 0.0374(10) 0.0504(11) -0.0014(9) 0.0214(9) -0.0035(9) B' 0.0278(16) 0.0344(18) 0.0265(16) -0.0038(14) 0.0075(13) -0.0016(14) O1' 0.0311(11) 0.0430(12) 0.0258(10) -0.0024(9) 0.0049(8) 0.0045(9) N1' 0.0315(13) 0.0372(14) 0.0290(13) -0.0033(11) 0.0055(11) 0.0034(11) C1' 0.0399(18) 0.050(2) 0.0378(18) -0.0047(15) 0.0137(14) 0.0089(15) C2' 0.0454(19) 0.061(2) 0.0324(17) -0.0081(16) 0.0127(15) 0.0007(17) C3' 0.0395(18) 0.061(2) 0.0279(16) -0.0013(15) 0.0048(13) -0.0024(16) C4' 0.0308(16) 0.0470(19) 0.0319(16) -0.0001(14) 0.0059(13) -0.0045(14) C5' 0.0301(16) 0.061(2) 0.0370(18) 0.0016(16) -0.0005(14) 0.0053(15) C6' 0.0269(16) 0.057(2) 0.048(2) -0.0055(17) 0.0060(14) 0.0056(15) C7' 0.0316(16) 0.052(2) 0.0388(18) -0.0075(15) 0.0117(14) 0.0013(14) C8' 0.0285(15) 0.0372(17) 0.0285(15) -0.0017(13) 0.0046(12) -0.0040(12) C9' 0.0261(14) 0.0314(15) 0.0308(15) -0.0011(12) 0.0063(12) -0.0035(12) C10' 0.0312(15) 0.0358(16) 0.0257(14) 0.0002(12) 0.0069(12) -0.0021(12) C11' 0.0357(16) 0.0360(17) 0.0370(17) 0.0068(13) 0.0129(13) -0.0006(13) F11' 0.0366(10) 0.0391(10) 0.0620(12) 0.0076(9) 0.0240(9) 0.0025(8) C12' 0.0456(19) 0.0362(18) 0.049(2) 0.0042(15) 0.0162(16) 0.0083(15) F12' 0.0671(15) 0.0461(12) 0.0888(17) 0.0087(12) 0.0367(13) 0.0226(11) C13' 0.054(2) 0.0286(17) 0.051(2) 0.0051(15) 0.0010(17) -0.0001(15) F13' 0.0761(16) 0.0294(11) 0.0962(19) 0.0096(11) 0.0135(14) 0.0008(10) C14' 0.0356(17) 0.0404(19) 0.0472(19) 0.0108(15) 0.0044(14) -0.0080(14) F14' 0.0420(11) 0.0490(12) 0.0876(17) 0.0243(12) 0.0043(11) -0.0145(9) C15' 0.0308(16) 0.0412(18) 0.0318(16) 0.0047(13) 0.0042(12) -0.0011(13) F15' 0.0320(9) 0.0523(12) 0.0529(11) 0.0091(9) 0.0166(8) -0.0001(8) C16' 0.0291(14) 0.0339(16) 0.0249(14) 0.0004(12) 0.0109(11) -0.0014(12) C17' 0.0325(15) 0.0312(16) 0.0292(15) -0.0013(12) 0.0101(12) -0.0027(12) F17' 0.0388(10) 0.0368(10) 0.0347(9) -0.0075(8) 0.0091(8) -0.0022(8) C18' 0.0313(15) 0.0451(18) 0.0260(15) -0.0004(13) 0.0049(12) -0.0060(13) F18' 0.0408(10) 0.0573(12) 0.0349(10) -0.0076(9) -0.0018(8) -0.0055(9) C19' 0.0275(15) 0.0458(19) 0.0364(17) 0.0095(14) 0.0037(13) 0.0044(13) F19' 0.0379(10) 0.0633(14) 0.0492(12) 0.0073(10) -0.0017(9) 0.0125(9) C20' 0.0368(17) 0.0326(16) 0.0413(18) 0.0012(14) 0.0131(14) 0.0030(13) F20' 0.0511(12) 0.0409(11) 0.0615(13) -0.0052(10) 0.0052(10) 0.0141(9) C21' 0.0321(15) 0.0364(17) 0.0293(15) -0.0036(13) 0.0072(12) -0.0033(13) F21' 0.0409(10) 0.0377(10) 0.0446(11) -0.0110(8) 0.0011(8) 0.0002(8) C22' 0.0257(14) 0.0312(15) 0.0269(14) -0.0021(12) 0.0046(11) 0.0001(12) C23' 0.0272(14) 0.0295(15) 0.0310(15) -0.0027(12) 0.0043(12) -0.0018(12) F23' 0.0418(10) 0.0388(10) 0.0312(9) -0.0076(7) 0.0095(8) -0.0094(8) C24' 0.0304(15) 0.0457(19) 0.0296(15) 0.0022(13) 0.0076(12) -0.0009(14) F24' 0.0468(11) 0.0719(14) 0.0306(9) -0.0007(9) 0.0156(8) -0.0081(10) C25' 0.0299(16) 0.0407(18) 0.0430(18) 0.0111(15) 0.0063(13) -0.0046(13) F25' 0.0488(12) 0.0607(13) 0.0545(12) 0.0138(10) 0.0166(10) -0.0179(10) C26' 0.0269(15) 0.0314(16) 0.0430(18) -0.0004(13) 0.0015(13) -0.0038(12) F26' 0.0421(11) 0.0362(10) 0.0640(13) -0.0051(9) 0.0055(9) -0.0144(8) C27' 0.0304(15) 0.0330(16) 0.0303(15) -0.0047(12) 0.0051(12) 0.0019(12) F27' 0.0466(11) 0.0435(11) 0.0384(10) -0.0146(8) 0.0111(8) -0.0094(8) C30 0.054(4) 0.064(4) 0.082(5) -0.002(3) 0.012(3) 0.021(3) Cl1 0.0709(10) 0.0647(9) 0.0917(12) -0.0027(7) 0.0433(9) -0.0043(7) Cl2 0.144(2) 0.0775(14) 0.0720(12) -0.0010(10) 0.0205(13) -0.0411(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag B O1 1.508(4) . ? B C10 1.654(5) . ? B C22 1.656(5) . ? B C16 1.664(4) . ? O1 C8 1.337(4) . ? N1 C1 1.331(4) . ? N1 C9 1.356(4) . ? C1 C2 1.388(5) . ? C2 C3 1.370(6) . ? C3 C4 1.405(5) . ? C4 C9 1.414(4) . ? C4 C5 1.415(5) . ? C5 C6 1.363(5) . ? C6 C7 1.417(5) . ? C7 C8 1.371(5) . ? C8 C9 1.432(4) . ? C10 C15 1.386(4) . ? C10 C11 1.392(4) . ? C11 F11 1.347(4) . ? C11 C12 1.387(5) . ? C12 F12 1.350(4) . ? C12 C13 1.363(5) . ? C13 F13 1.342(4) . ? C13 C14 1.380(5) . ? C14 F14 1.352(4) . ? C14 C15 1.376(5) . ? C15 F15 1.364(3) . ? C16 C21 1.386(4) . ? C16 C17 1.393(4) . ? C17 F17 1.355(4) . ? C17 C18 1.389(4) . ? C18 F18 1.348(3) . ? C18 C19 1.365(5) . ? C19 F19 1.350(3) . ? C19 C20 1.372(5) . ? C20 F20 1.350(4) . ? C20 C21 1.374(4) . ? C21 F21 1.368(3) . ? C22 C27 1.386(5) . ? C22 C23 1.398(4) . ? C23 F23 1.350(4) . ? C23 C24 1.377(5) . ? C24 F24 1.347(4) . ? C24 C25 1.373(5) . ? C25 F25 1.351(4) . ? C25 C26 1.370(5) . ? C26 F26 1.346(4) . ? C26 C27 1.388(5) . ? C27 F27 1.359(4) . ? B' O1' 1.491(4) . ? B' C22' 1.655(4) . ? B' C10' 1.659(5) . ? B' C16' 1.666(4) . ? O1' C8' 1.337(3) . ? N1' C1' 1.333(4) . ? N1' C9' 1.361(4) . ? C1' C2' 1.384(5) . ? C2' C3' 1.358(5) . ? C3' C4' 1.405(5) . ? C4' C9' 1.409(4) . ? C4' C5' 1.412(5) . ? C5' C6' 1.365(5) . ? C6' C7' 1.411(5) . ? C7' C8' 1.377(4) . ? C8' C9' 1.416(4) . ? C10' C15' 1.387(4) . ? C10' C11' 1.388(4) . ? C11' F11' 1.357(4) . ? C11' C12' 1.379(5) . ? C12' F12' 1.344(4) . ? C12' C13' 1.377(5) . ? C13' F13' 1.340(4) . ? C13' C14' 1.371(5) . ? C14' F14' 1.349(4) . ? C14' C15' 1.379(5) . ? C15' F15' 1.359(4) . ? C16' C17' 1.391(4) . ? C16' C21' 1.398(4) . ? C17' F17' 1.364(3) . ? C17' C18' 1.380(4) . ? C18' F18' 1.354(3) . ? C18' C19' 1.373(5) . ? C19' F19' 1.343(3) . ? C19' C20' 1.375(5) . ? C20' F20' 1.345(4) . ? C20' C21' 1.379(4) . ? C21' F21' 1.355(3) . ? C22' C27' 1.388(4) . ? C22' C23' 1.395(4) . ? C23' F23' 1.355(3) . ? C23' C24' 1.371(4) . ? C24' F24' 1.344(4) . ? C24' C25' 1.378(5) . ? C25' F25' 1.344(4) . ? C25' C26' 1.367(5) . ? C26' F26' 1.344(3) . ? C26' C27' 1.392(4) . ? C27' F27' 1.356(3) . ? C30 Cl2 1.788(8) . ? C30 Cl1 1.809(8) . ? C30' Cl1' 1.37(6) . ? C30' Cl2' 1.80(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 O1 B C10 107.8(2) . . ? O1 B C22 112.9(3) . . ? C10 B C22 115.6(2) . . ? O1 B C16 103.2(2) . . ? C10 B C16 112.7(3) . . ? C22 B C16 104.0(2) . . ? C8 O1 B 126.8(2) . . ? C1 N1 C9 123.8(3) . . ? N1 C1 C2 119.2(3) . . ? C3 C2 C1 119.3(3) . . ? C2 C3 C4 121.6(3) . . ? C3 C4 C9 116.9(3) . . ? C3 C4 C5 125.3(3) . . ? C9 C4 C5 117.7(3) . . ? C6 C5 C4 119.6(3) . . ? C5 C6 C7 122.3(3) . . ? C8 C7 C6 120.7(3) . . ? O1 C8 C7 129.1(3) . . ? O1 C8 C9 113.8(3) . . ? C7 C8 C9 117.1(3) . . ? N1 C9 C4 119.0(3) . . ? N1 C9 C8 118.3(3) . . ? C4 C9 C8 122.6(3) . . ? C15 C10 C11 113.0(3) . . ? C15 C10 B 119.1(3) . . ? C11 C10 B 127.9(3) . . ? F11 C11 C12 116.1(3) . . ? F11 C11 C10 120.5(3) . . ? C12 C11 C10 123.4(3) . . ? F12 C12 C13 119.6(3) . . ? F12 C12 C11 119.7(3) . . ? C13 C12 C11 120.6(3) . . ? F13 C13 C12 121.1(3) . . ? F13 C13 C14 120.4(3) . . ? C12 C13 C14 118.6(3) . . ? F14 C14 C15 120.9(3) . . ? F14 C14 C13 120.0(3) . . ? C15 C14 C13 119.1(3) . . ? F15 C15 C14 115.4(3) . . ? F15 C15 C10 119.3(3) . . ? C14 C15 C10 125.3(3) . . ? C21 C16 C17 112.2(3) . . ? C21 C16 B 120.2(3) . . ? C17 C16 B 127.6(3) . . ? F17 C17 C18 115.1(3) . . ? F17 C17 C16 120.6(3) . . ? C18 C17 C16 124.2(3) . . ? F18 C18 C19 119.6(3) . . ? F18 C18 C17 120.5(3) . . ? C19 C18 C17 119.8(3) . . ? F19 C19 C18 120.5(3) . . ? F19 C19 C20 120.6(3) . . ? C18 C19 C20 118.9(3) . . ? F20 C20 C19 120.5(3) . . ? F20 C20 C21 120.3(3) . . ? C19 C20 C21 119.2(3) . . ? F21 C21 C20 114.4(3) . . ? F21 C21 C16 120.0(3) . . ? C20 C21 C16 125.6(3) . . ? C27 C22 C23 113.4(3) . . ? C27 C22 B 126.9(3) . . ? C23 C22 B 119.1(3) . . ? F23 C23 C24 116.9(3) . . ? F23 C23 C22 119.0(3) . . ? C24 C23 C22 124.0(3) . . ? F24 C24 C25 120.1(3) . . ? F24 C24 C23 120.3(3) . . ? C25 C24 C23 119.6(3) . . ? F25 C25 C26 120.3(4) . . ? F25 C25 C24 120.2(3) . . ? C26 C25 C24 119.5(3) . . ? F26 C26 C25 120.6(3) . . ? F26 C26 C27 120.2(3) . . ? C25 C26 C27 119.2(3) . . ? F27 C27 C22 121.6(3) . . ? F27 C27 C26 114.1(3) . . ? C22 C27 C26 124.3(3) . . ? O1' B' C22' 113.8(2) . . ? O1' B' C10' 107.7(2) . . ? C22' B' C10' 113.9(2) . . ? O1' B' C16' 104.0(2) . . ? C22' B' C16' 103.8(2) . . ? C10' B' C16' 113.3(2) . . ? C8' O1' B' 128.0(2) . . ? C1' N1' C9' 123.2(3) . . ? N1' C1' C2' 119.5(3) . . ? C3' C2' C1' 119.7(3) . . ? C2' C3' C4' 121.4(3) . . ? C3' C4' C9' 117.2(3) . . ? C3' C4' C5' 124.8(3) . . ? C9' C4' C5' 118.0(3) . . ? C6' C5' C4' 118.9(3) . . ? C5' C6' C7' 122.7(3) . . ? C8' C7' C6' 120.2(3) . . ? O1' C8' C7' 129.5(3) . . ? O1' C8' C9' 113.5(3) . . ? C7' C8' C9' 117.0(3) . . ? N1' C9' C4' 119.0(3) . . ? N1' C9' C8' 118.0(3) . . ? C4' C9' C8' 123.0(3) . . ? C15' C10' C11' 113.0(3) . . ? C15' C10' B' 121.0(3) . . ? C11' C10' B' 126.1(3) . . ? F11' C11' C12' 114.6(3) . . ? F11' C11' C10' 120.8(3) . . ? C12' C11' C10' 124.6(3) . . ? F12' C12' C13' 120.2(3) . . ? F12' C12' C11' 120.2(3) . . ? C13' C12' C11' 119.6(3) . . ? F13' C13' C14' 121.0(3) . . ? F13' C13' C12' 120.5(3) . . ? C14' C13' C12' 118.5(3) . . ? F14' C14' C13' 120.0(3) . . ? F14' C14' C15' 120.1(3) . . ? C13' C14' C15' 119.9(3) . . ? F15' C15' C14' 115.6(3) . . ? F15' C15' C10' 120.0(3) . . ? C14' C15' C10' 124.4(3) . . ? C17' C16' C21' 112.5(3) . . ? C17' C16' B' 126.3(3) . . ? C21' C16' B' 121.2(3) . . ? F17' C17' C18' 114.5(3) . . ? F17' C17' C16' 120.8(3) . . ? C18' C17' C16' 124.7(3) . . ? F18' C18' C19' 119.8(3) . . ? F18' C18' C17' 120.2(3) . . ? C19' C18' C17' 120.0(3) . . ? F19' C19' C18' 121.3(3) . . ? F19' C19' C20' 120.3(3) . . ? C18' C19' C20' 118.4(3) . . ? F20' C20' C19' 119.6(3) . . ? F20' C20' C21' 120.5(3) . . ? C19' C20' C21' 120.0(3) . . ? F21' C21' C20' 115.9(3) . . ? F21' C21' C16' 119.6(3) . . ? C20' C21' C16' 124.5(3) . . ? C27' C22' C23' 113.3(3) . . ? C27' C22' B' 126.2(3) . . ? C23' C22' B' 120.1(2) . . ? F23' C23' C24' 116.2(3) . . ? F23' C23' C22' 118.9(3) . . ? C24' C23' C22' 124.9(3) . . ? F24' C24' C23' 120.9(3) . . ? F24' C24' C25' 120.0(3) . . ? C23' C24' C25' 119.1(3) . . ? F25' C25' C26' 120.7(3) . . ? F25' C25' C24' 120.1(3) . . ? C26' C25' C24' 119.2(3) . . ? F26' C26' C25' 119.4(3) . . ? F26' C26' C27' 120.6(3) . . ? C25' C26' C27' 120.0(3) . . ? F27' C27' C22' 120.8(3) . . ? F27' C27' C26' 115.7(3) . . ? C22' C27' C26' 123.5(3) . . ? Cl2 C30 Cl1 106.4(3) . . ? Cl1' C30' Cl2' 105(4) . . ? _diffrn_measured_fraction_theta_max 0.976 _diffrn_reflns_theta_full 71.21 _diffrn_measured_fraction_theta_full 0.976 _refine_diff_density_max 0.601 _refine_diff_density_min -0.493 _refine_diff_density_rms 0.057 #===END data_Compound_4 _database_code_depnum_ccdc_archive 'CCDC 632950' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H12 B2 F10 N2 O3' _chemical_formula_weight 660.04 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.0303(8) _cell_length_b 12.2898(12) _cell_length_c 13.6929(15) _cell_angle_alpha 86.956(8) _cell_angle_beta 89.875(9) _cell_angle_gamma 85.670(8) _cell_volume 1345.6(2) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 3.6089 _cell_measurement_theta_max 70.8672 _exptl_crystal_description 'thin plates' _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.06 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.629 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 660 _exptl_absorpt_coefficient_mu 1.342 _exptl_absorpt_correction_type 'numeric analytical' _exptl_absorpt_correction_T_min 0.93743 _exptl_absorpt_correction_T_max 0.98947 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 1.54248 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'Enhance Ultra (Cu) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'OD Xcalibur PX Ultra' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 8.2556 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12680 _diffrn_reflns_av_R_equivalents 0.0459 _diffrn_reflns_av_sigmaI/netI 0.0548 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.61 _diffrn_reflns_theta_max 71.07 _reflns_number_total 4983 _reflns_number_gt 3342 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD, Oxford Diffraction Ltd' _computing_cell_refinement 'CrysAlis RED, Oxford Diffraction Ltd' _computing_data_reduction 'CrysAlis RED, Oxford Diffraction Ltd' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0513P)^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 4983 _refine_ls_number_parameters 424 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0914 _refine_ls_R_factor_gt 0.0498 _refine_ls_wR_factor_ref 0.1169 _refine_ls_wR_factor_gt 0.0993 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_restrained_S_all 1.046 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group B1 B 0.7185(4) 0.7325(2) 0.3331(2) 0.0295(7) Uani 1 1 d . . . B2 B 0.7434(4) 0.7418(2) 0.1493(2) 0.0285(7) Uani 1 1 d . . . O1 O 0.8164(2) 0.62291(13) 0.34253(13) 0.0311(4) Uani 1 1 d . . . O2 O 0.6245(2) 0.65327(13) 0.13647(13) 0.0312(4) Uani 1 1 d . . . O3 O 0.7334(2) 0.78688(13) 0.24085(12) 0.0299(4) Uani 1 1 d . . . N1 N 0.5299(3) 0.69112(16) 0.35138(15) 0.0269(5) Uani 1 1 d . . . N2 N 0.9207(3) 0.66639(16) 0.13710(15) 0.0270(5) Uani 1 1 d . . . C1 C 0.3783(3) 0.7426(2) 0.35245(19) 0.0318(6) Uani 1 1 d . . . H1A H 0.3655 0.8199 0.3426 0.038 Uiso 1 1 calc R . . C2 C 0.2377(4) 0.6836(2) 0.3680(2) 0.0393(7) Uani 1 1 d . . . H2A H 0.1302 0.7213 0.3704 0.047 Uiso 1 1 calc R . . C3 C 0.2534(4) 0.5716(2) 0.3798(2) 0.0419(7) Uani 1 1 d . . . H3A H 0.1568 0.5324 0.3902 0.050 Uiso 1 1 calc R . . C4 C 0.4120(4) 0.5146(2) 0.37649(19) 0.0352(6) Uani 1 1 d . . . C5 C 0.4563(4) 0.4003(2) 0.3833(2) 0.0478(8) Uani 1 1 d . . . H5A H 0.3721 0.3504 0.3922 0.057 Uiso 1 1 calc R . . C6 C 0.6191(5) 0.3624(2) 0.3770(2) 0.0467(8) Uani 1 1 d . . . H6A H 0.6448 0.2856 0.3813 0.056 Uiso 1 1 calc R . . C7 C 0.7534(4) 0.4310(2) 0.3644(2) 0.0394(7) Uani 1 1 d . . . H7A H 0.8658 0.4012 0.3608 0.047 Uiso 1 1 calc R . . C8 C 0.7142(3) 0.5414(2) 0.35770(19) 0.0306(6) Uani 1 1 d . . . C9 C 0.5461(3) 0.5806(2) 0.36347(18) 0.0292(6) Uani 1 1 d . . . C10 C 0.7600(3) 0.81165(19) 0.42132(19) 0.0286(6) Uani 1 1 d . . . C11 C 0.7018(3) 0.9210(2) 0.4174(2) 0.0332(6) Uani 1 1 d . . . F11 F 0.6006(2) 0.96229(12) 0.34390(12) 0.0493(5) Uani 1 1 d . . . C12 C 0.7369(4) 0.9929(2) 0.4875(2) 0.0374(7) Uani 1 1 d . . . F12 F 0.6762(2) 1.09873(12) 0.47876(13) 0.0553(5) Uani 1 1 d . . . C13 C 0.8320(4) 0.9570(2) 0.5672(2) 0.0408(7) Uani 1 1 d . . . F13 F 0.8678(2) 1.02629(14) 0.63583(14) 0.0609(5) Uani 1 1 d . . . C14 C 0.8911(4) 0.8492(2) 0.5758(2) 0.0395(7) Uani 1 1 d . . . F14 F 0.9844(2) 0.81165(15) 0.65406(14) 0.0633(6) Uani 1 1 d . . . C15 C 0.8540(3) 0.7800(2) 0.5042(2) 0.0318(6) Uani 1 1 d . . . F15 F 0.9162(2) 0.67423(12) 0.51947(12) 0.0435(4) Uani 1 1 d . . . C16 C 1.0791(3) 0.6883(2) 0.14054(19) 0.0325(6) Uani 1 1 d . . . H16A H 1.1071 0.7613 0.1468 0.039 Uiso 1 1 calc R . . C17 C 1.2065(4) 0.6037(2) 0.1351(2) 0.0400(7) Uani 1 1 d . . . H17A H 1.3202 0.6202 0.1360 0.048 Uiso 1 1 calc R . . C18 C 1.1676(4) 0.4974(2) 0.1283(2) 0.0410(7) Uani 1 1 d . . . H18A H 1.2544 0.4406 0.1263 0.049 Uiso 1 1 calc R . . C19 C 0.9999(3) 0.4721(2) 0.1242(2) 0.0349(6) Uani 1 1 d . . . C20 C 0.9337(4) 0.3686(2) 0.1168(2) 0.0412(7) Uani 1 1 d . . . H20A H 1.0064 0.3042 0.1144 0.049 Uiso 1 1 calc R . . C21 C 0.7644(4) 0.3629(2) 0.1132(2) 0.0428(7) Uani 1 1 d . . . H21A H 0.7224 0.2933 0.1080 0.051 Uiso 1 1 calc R . . C22 C 0.6485(4) 0.4550(2) 0.1169(2) 0.0377(7) Uani 1 1 d . . . H22A H 0.5319 0.4475 0.1129 0.045 Uiso 1 1 calc R . . C23 C 0.7084(3) 0.5555(2) 0.12616(19) 0.0302(6) Uani 1 1 d . . . C24 C 0.8815(3) 0.56174(19) 0.12786(18) 0.0277(6) Uani 1 1 d . . . C25 C 0.7275(3) 0.83607(19) 0.06049(19) 0.0296(6) Uani 1 1 d . . . C26 C 0.6575(4) 0.8248(2) -0.0301(2) 0.0391(7) Uani 1 1 d . . . F26 F 0.6001(3) 0.72746(14) -0.05153(14) 0.0665(6) Uani 1 1 d . . . C27 C 0.6397(4) 0.9056(3) -0.1035(2) 0.0502(8) Uani 1 1 d . . . F27 F 0.5692(4) 0.88755(19) -0.18935(16) 0.0974(9) Uani 1 1 d . . . C28 C 0.6969(4) 1.0057(2) -0.0884(2) 0.0462(8) Uani 1 1 d . . . F28 F 0.6813(3) 1.08684(15) -0.15899(15) 0.0686(6) Uani 1 1 d . . . C29 C 0.7699(4) 1.0220(2) -0.0011(2) 0.0429(7) Uani 1 1 d . . . F29 F 0.8308(3) 1.12001(13) 0.01333(14) 0.0692(6) Uani 1 1 d . . . C30 C 0.7862(4) 0.9387(2) 0.0700(2) 0.0379(7) Uani 1 1 d . . . F30 F 0.8708(3) 0.95965(15) 0.15139(13) 0.0679(6) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 B1 0.0304(17) 0.0233(14) 0.0349(17) -0.0004(13) 0.0018(13) -0.0020(12) B2 0.0248(16) 0.0253(14) 0.0357(17) -0.0027(13) 0.0018(13) -0.0039(12) O1 0.0284(10) 0.0274(9) 0.0372(11) -0.0023(8) -0.0005(8) 0.0006(7) O2 0.0257(10) 0.0265(9) 0.0418(11) -0.0036(8) 0.0029(8) -0.0027(7) O3 0.0363(11) 0.0245(9) 0.0292(10) -0.0034(7) 0.0051(8) -0.0030(7) N1 0.0318(12) 0.0261(11) 0.0225(11) -0.0015(9) 0.0005(9) 0.0007(9) N2 0.0273(12) 0.0274(11) 0.0266(12) -0.0010(9) 0.0019(9) -0.0047(9) C1 0.0347(16) 0.0350(14) 0.0255(14) -0.0034(11) 0.0009(11) -0.0002(12) C2 0.0288(16) 0.0572(19) 0.0319(16) -0.0043(14) 0.0005(12) -0.0013(13) C3 0.0373(18) 0.0577(19) 0.0332(16) -0.0028(14) 0.0026(13) -0.0190(14) C4 0.0432(17) 0.0371(15) 0.0266(15) 0.0010(12) -0.0007(12) -0.0135(13) C5 0.067(2) 0.0351(16) 0.0435(19) 0.0021(14) 0.0025(16) -0.0222(16) C6 0.076(3) 0.0254(14) 0.0377(18) 0.0055(13) -0.0048(16) -0.0056(15) C7 0.0527(19) 0.0274(14) 0.0370(17) -0.0009(12) -0.0055(14) 0.0044(13) C8 0.0375(16) 0.0263(13) 0.0279(14) 0.0004(11) -0.0018(12) -0.0026(12) C9 0.0360(15) 0.0261(13) 0.0255(14) 0.0010(11) -0.0004(11) -0.0034(11) C10 0.0254(14) 0.0279(13) 0.0325(15) -0.0015(11) 0.0060(11) -0.0012(11) C11 0.0360(16) 0.0300(14) 0.0328(15) 0.0002(12) -0.0013(12) 0.0013(12) F11 0.0713(12) 0.0341(8) 0.0398(10) -0.0043(7) -0.0139(9) 0.0152(8) C12 0.0463(18) 0.0246(14) 0.0409(17) -0.0069(12) 0.0024(14) 0.0028(12) F12 0.0829(14) 0.0278(8) 0.0543(11) -0.0097(8) -0.0042(10) 0.0074(8) C13 0.0447(18) 0.0392(16) 0.0404(18) -0.0161(14) -0.0018(14) -0.0053(13) F13 0.0707(13) 0.0545(11) 0.0594(12) -0.0296(9) -0.0142(10) 0.0006(9) C14 0.0367(17) 0.0466(17) 0.0343(16) -0.0043(13) -0.0078(13) 0.0045(13) F14 0.0714(14) 0.0647(12) 0.0519(12) -0.0148(9) -0.0294(10) 0.0164(10) C15 0.0325(15) 0.0254(13) 0.0368(16) -0.0001(12) 0.0028(12) 0.0006(11) F15 0.0520(10) 0.0338(8) 0.0426(10) 0.0008(7) -0.0082(8) 0.0091(7) C16 0.0308(16) 0.0369(15) 0.0307(15) -0.0009(12) 0.0012(12) -0.0085(12) C17 0.0274(16) 0.0514(18) 0.0415(17) -0.0028(14) 0.0011(13) -0.0046(13) C18 0.0325(16) 0.0447(17) 0.0448(18) -0.0047(14) 0.0002(13) 0.0047(13) C19 0.0344(16) 0.0368(15) 0.0337(16) -0.0068(12) 0.0024(12) -0.0012(12) C20 0.0452(19) 0.0303(15) 0.0474(18) -0.0084(13) 0.0004(14) 0.0069(13) C21 0.051(2) 0.0277(14) 0.0510(19) -0.0112(13) 0.0016(15) -0.0061(13) C22 0.0329(16) 0.0334(15) 0.0484(18) -0.0088(13) 0.0019(13) -0.0077(12) C23 0.0320(15) 0.0282(14) 0.0308(15) -0.0029(11) 0.0009(12) -0.0028(11) C24 0.0291(14) 0.0276(13) 0.0269(14) -0.0038(11) 0.0021(11) -0.0035(11) C25 0.0294(15) 0.0269(13) 0.0326(15) -0.0016(11) 0.0029(12) -0.0026(11) C26 0.0471(18) 0.0301(14) 0.0405(17) -0.0013(13) -0.0093(14) -0.0057(13) F26 0.1049(17) 0.0447(10) 0.0531(12) -0.0016(9) -0.0289(11) -0.0271(10) C27 0.060(2) 0.0504(19) 0.0393(19) 0.0063(15) -0.0174(16) -0.0068(16) F27 0.144(2) 0.0899(16) 0.0598(14) 0.0236(12) -0.0610(15) -0.0385(15) C28 0.053(2) 0.0359(16) 0.047(2) 0.0143(14) 0.0014(16) 0.0027(14) F28 0.0838(15) 0.0555(11) 0.0632(13) 0.0280(10) -0.0089(11) -0.0049(10) C29 0.059(2) 0.0265(14) 0.0443(18) 0.0014(13) 0.0104(15) -0.0098(13) F29 0.1149(18) 0.0353(9) 0.0604(13) 0.0032(9) 0.0109(12) -0.0290(10) C30 0.0508(18) 0.0353(15) 0.0288(15) -0.0028(12) 0.0005(13) -0.0100(13) F30 0.1132(17) 0.0560(11) 0.0407(11) 0.0029(9) -0.0117(11) -0.0500(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag B1 O3 1.406(4) . ? B1 O1 1.507(3) . ? B1 C10 1.641(4) . ? B1 N1 1.648(4) . ? B2 O3 1.397(3) . ? B2 O2 1.518(3) . ? B2 C25 1.633(4) . ? B2 N2 1.652(4) . ? O1 C8 1.350(3) . ? O2 C23 1.347(3) . ? N1 C1 1.329(3) . ? N1 C9 1.356(3) . ? N2 C16 1.321(3) . ? N2 C24 1.359(3) . ? C1 C2 1.398(4) . ? C2 C3 1.374(4) . ? C3 C4 1.408(4) . ? C4 C9 1.402(4) . ? C4 C5 1.421(4) . ? C5 C6 1.358(5) . ? C6 C7 1.422(4) . ? C7 C8 1.368(4) . ? C8 C9 1.402(4) . ? C10 C15 1.386(4) . ? C10 C11 1.387(4) . ? C11 F11 1.349(3) . ? C11 C12 1.381(4) . ? C12 F12 1.354(3) . ? C12 C13 1.368(4) . ? C13 F13 1.346(3) . ? C13 C14 1.372(4) . ? C14 F14 1.350(3) . ? C14 C15 1.379(4) . ? C15 F15 1.362(3) . ? C16 C17 1.407(4) . ? C17 C18 1.374(4) . ? C18 C19 1.406(4) . ? C19 C24 1.403(4) . ? C19 C20 1.423(4) . ? C20 C21 1.368(4) . ? C21 C22 1.413(4) . ? C22 C23 1.371(4) . ? C23 C24 1.398(4) . ? C25 C26 1.381(4) . ? C25 C30 1.391(4) . ? C26 F26 1.361(3) . ? C26 C27 1.374(4) . ? C27 F27 1.343(4) . ? C27 C28 1.370(4) . ? C28 F28 1.350(3) . ? C28 C29 1.364(4) . ? C29 F29 1.358(3) . ? C29 C30 1.374(4) . ? C30 F30 1.353(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O3 B1 O1 113.6(2) . . ? O3 B1 C10 111.2(2) . . ? O1 B1 C10 112.5(2) . . ? O3 B1 N1 112.1(2) . . ? O1 B1 N1 98.57(18) . . ? C10 B1 N1 108.2(2) . . ? O3 B2 O2 113.9(2) . . ? O3 B2 C25 111.7(2) . . ? O2 B2 C25 112.2(2) . . ? O3 B2 N2 111.2(2) . . ? O2 B2 N2 98.10(18) . . ? C25 B2 N2 108.9(2) . . ? C8 O1 B1 111.1(2) . . ? C23 O2 B2 111.21(19) . . ? B2 O3 B1 128.2(2) . . ? C1 N1 C9 119.2(2) . . ? C1 N1 B1 133.5(2) . . ? C9 N1 B1 107.3(2) . . ? C16 N2 C24 119.6(2) . . ? C16 N2 B2 133.0(2) . . ? C24 N2 B2 107.26(19) . . ? N1 C1 C2 120.3(2) . . ? C3 C2 C1 120.7(3) . . ? C2 C3 C4 120.3(3) . . ? C9 C4 C3 115.1(2) . . ? C9 C4 C5 115.2(3) . . ? C3 C4 C5 129.7(3) . . ? C6 C5 C4 120.0(3) . . ? C5 C6 C7 123.9(3) . . ? C8 C7 C6 117.3(3) . . ? O1 C8 C7 129.0(3) . . ? O1 C8 C9 112.2(2) . . ? C7 C8 C9 118.8(2) . . ? N1 C9 C4 124.4(2) . . ? N1 C9 C8 110.8(2) . . ? C4 C9 C8 124.8(2) . . ? C15 C10 C11 113.4(2) . . ? C15 C10 B1 125.7(2) . . ? C11 C10 B1 120.9(2) . . ? F11 C11 C12 115.9(2) . . ? F11 C11 C10 120.3(2) . . ? C12 C11 C10 123.8(3) . . ? F12 C12 C13 119.3(2) . . ? F12 C12 C11 120.6(3) . . ? C13 C12 C11 120.0(2) . . ? F13 C13 C12 120.7(3) . . ? F13 C13 C14 120.6(3) . . ? C12 C13 C14 118.7(2) . . ? F14 C14 C13 119.9(3) . . ? F14 C14 C15 120.5(2) . . ? C13 C14 C15 119.5(3) . . ? F15 C15 C14 115.4(2) . . ? F15 C15 C10 120.3(2) . . ? C14 C15 C10 124.4(2) . . ? N2 C16 C17 120.2(2) . . ? C18 C17 C16 120.4(3) . . ? C17 C18 C19 120.4(3) . . ? C24 C19 C18 115.3(2) . . ? C24 C19 C20 115.6(2) . . ? C18 C19 C20 129.2(3) . . ? C21 C20 C19 119.3(3) . . ? C20 C21 C22 123.6(2) . . ? C23 C22 C21 118.4(3) . . ? O2 C23 C22 129.5(2) . . ? O2 C23 C24 112.4(2) . . ? C22 C23 C24 118.1(2) . . ? N2 C24 C23 110.9(2) . . ? N2 C24 C19 124.1(2) . . ? C23 C24 C19 125.0(2) . . ? C26 C25 C30 112.8(2) . . ? C26 C25 B2 125.4(2) . . ? C30 C25 B2 121.8(2) . . ? F26 C26 C27 115.4(3) . . ? F26 C26 C25 119.5(2) . . ? C27 C26 C25 125.1(2) . . ? F27 C27 C28 119.9(3) . . ? F27 C27 C26 121.1(3) . . ? C28 C27 C26 119.1(3) . . ? F28 C28 C29 120.5(3) . . ? F28 C28 C27 120.5(3) . . ? C29 C28 C27 119.0(3) . . ? F29 C29 C28 119.3(3) . . ? F29 C29 C30 120.7(3) . . ? C28 C29 C30 120.0(2) . . ? F30 C30 C29 115.9(2) . . ? F30 C30 C25 120.0(2) . . ? C29 C30 C25 124.0(3) . . ? _diffrn_measured_fraction_theta_max 0.960 _diffrn_reflns_theta_full 71.07 _diffrn_measured_fraction_theta_full 0.960 _refine_diff_density_max 0.296 _refine_diff_density_min -0.282 _refine_diff_density_rms 0.043 #===END