# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H30 B F2 N3 O2' _chemical_formula_weight 513.38 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' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.508(6) _cell_length_b 10.783(6) _cell_length_c 11.982(6) _cell_angle_alpha 84.890(8) _cell_angle_beta 69.760(7) _cell_angle_gamma 81.743(9) _cell_volume 1259.4(11) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.354 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 540 _exptl_absorpt_coefficient_mu 0.095 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9541 _exptl_absorpt_correction_T_max 0.9934 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9978 _diffrn_reflns_av_R_equivalents 0.0503 _diffrn_reflns_av_sigmaI/netI 0.0865 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.58 _diffrn_reflns_theta_max 27.12 _reflns_number_total 5178 _reflns_number_gt 3261 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0934P)^2^+0.2136P] 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 none _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.015(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 5178 _refine_ls_number_parameters 344 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1104 _refine_ls_R_factor_gt 0.0664 _refine_ls_wR_factor_ref 0.1851 _refine_ls_wR_factor_gt 0.1608 _refine_ls_goodness_of_fit_ref 1.017 _refine_ls_restrained_S_all 1.017 _refine_ls_shift/su_max 0.014 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group F1 F 0.71829(15) 0.81978(14) 0.02183(13) 0.0291(4) Uani 1 1 d . . . F2 F 0.87962(15) 0.93372(15) -0.10243(12) 0.0309(4) Uani 1 1 d . . . O1 O 1.2367(2) 0.6165(2) 0.21575(18) 0.0406(6) Uani 1 1 d . . . N1 N 1.2419(3) 0.4146(3) -0.3209(2) 0.0416(7) Uani 1 1 d . . . C1 C 1.1805(3) 0.4939(3) -0.2287(2) 0.0306(7) Uani 1 1 d . . . C2 C 1.0668(3) 0.5820(3) -0.2269(2) 0.0308(7) Uani 1 1 d . . . H2A H 1.0305 0.5845 -0.2895 0.037 Uiso 1 1 calc R . . C3 C 1.0073(3) 0.6643(3) -0.1366(2) 0.0270(6) Uani 1 1 d . . . H3A H 0.9298 0.7211 -0.1378 0.032 Uiso 1 1 calc R . . C4 C 1.0580(3) 0.6666(2) -0.0427(2) 0.0231(6) Uani 1 1 d . . . C5 C 1.0088(3) 0.7490(3) 0.0553(2) 0.0237(6) Uani 1 1 d . . . N6 N 0.9079(2) 0.8482(2) 0.08225(18) 0.0228(5) Uani 1 1 d . . . N7 N 0.7272(2) 1.0259(2) 0.07856(18) 0.0242(5) Uani 1 1 d . . . C8 C 0.6408(3) 1.1098(3) 0.0418(2) 0.0256(6) Uani 1 1 d . . . C9 C 0.5785(3) 1.2039(3) 0.1271(2) 0.0272(6) Uani 1 1 d . . . C10 C 0.6307(3) 1.1751(3) 0.2190(2) 0.0255(6) Uani 1 1 d . . . C11 C 0.7241(3) 1.0628(3) 0.1894(2) 0.0237(6) Uani 1 1 d . . . C12 C 0.8077(3) 0.9950(2) 0.2451(2) 0.0227(6) Uani 1 1 d . . . C13 C 0.9007(3) 0.8909(2) 0.1916(2) 0.0241(6) Uani 1 1 d . . . C14 C 0.9989(3) 0.8193(3) 0.2313(2) 0.0263(6) Uani 1 1 d . . . H14A H 1.0157 0.8284 0.3030 0.032 Uiso 1 1 calc R . . C15 C 1.0681(3) 0.7316(3) 0.1452(2) 0.0260(6) Uani 1 1 d . . . C16 C 1.1797(3) 0.6368(3) 0.1430(2) 0.0286(6) Uani 1 1 d . . . O17 O 1.22710(18) 0.56303(18) 0.04509(16) 0.0298(5) Uani 1 1 d . . . C18 C 1.1677(3) 0.5753(3) -0.0438(2) 0.0246(6) Uani 1 1 d . . . C19 C 1.2280(3) 0.4911(3) -0.1324(2) 0.0280(6) Uani 1 1 d . . . H19A H 1.3019 0.4309 -0.1283 0.034 Uiso 1 1 calc R . . C20 C 1.2281(4) 0.4525(4) -0.4446(4) 0.0727(13) Uani 1 1 d . . . H20A H 1.1977 0.5435 -0.4487 0.087 Uiso 1 1 calc R . . H20B H 1.3181 0.4351 -0.5076 0.087 Uiso 1 1 calc R . . C21 C 1.1315(4) 0.3835(4) -0.4641(4) 0.0736(13) Uani 1 1 d . . . H21A H 1.1237 0.4082 -0.5424 0.110 Uiso 1 1 calc R . . H21B H 1.0422 0.4017 -0.4022 0.110 Uiso 1 1 calc R . . H21C H 1.1624 0.2935 -0.4610 0.110 Uiso 1 1 calc R . . C22 C 1.3522(3) 0.3169(3) -0.3173(3) 0.0367(7) Uani 1 1 d . . . H22A H 1.3551 0.2486 -0.3686 0.044 Uiso 1 1 calc R . . H22B H 1.3318 0.2812 -0.2348 0.044 Uiso 1 1 calc R . . C23 C 1.4909(3) 0.3625(3) -0.3578(3) 0.0470(9) Uani 1 1 d . . . H23A H 1.5599 0.2926 -0.3530 0.070 Uiso 1 1 calc R . . H23B H 1.4898 0.4288 -0.3064 0.070 Uiso 1 1 calc R . . H23C H 1.5132 0.3958 -0.4402 0.070 Uiso 1 1 calc R . . C24 C 0.6184(3) 1.1036(3) -0.0742(2) 0.0297(6) Uani 1 1 d . . . H24A H 0.6735 1.0293 -0.1154 0.045 Uiso 1 1 calc R . . H24B H 0.6455 1.1791 -0.1238 0.045 Uiso 1 1 calc R . . H24C H 0.5215 1.0983 -0.0594 0.045 Uiso 1 1 calc R . . C25 C 0.4714(3) 1.3103(3) 0.1204(2) 0.0335(7) Uani 1 1 d . . . H25A H 0.4691 1.3202 0.0382 0.040 Uiso 1 1 calc R . . H25B H 0.4964 1.3891 0.1392 0.040 Uiso 1 1 calc R . . C26 C 0.3300(3) 1.2887(3) 0.2063(3) 0.0382(8) Uani 1 1 d . . . H26A H 0.2635 1.3598 0.1990 0.057 Uiso 1 1 calc R . . H26B H 0.3313 1.2808 0.2880 0.057 Uiso 1 1 calc R . . H26C H 0.3042 1.2116 0.1871 0.057 Uiso 1 1 calc R . . C27 C 0.5974(3) 1.2523(3) 0.3257(2) 0.0311(7) Uani 1 1 d . . . H27A H 0.5294 1.3236 0.3224 0.047 Uiso 1 1 calc R . . H27B H 0.6805 1.2831 0.3262 0.047 Uiso 1 1 calc R . . H27C H 0.5605 1.2005 0.3983 0.047 Uiso 1 1 calc R . . C28 C 0.8023(3) 1.0277(2) 0.3658(2) 0.0245(6) Uani 1 1 d . . . C29 C 0.6979(3) 0.9936(3) 0.4668(2) 0.0349(7) Uani 1 1 d . . . H29A H 0.6311 0.9470 0.4597 0.042 Uiso 1 1 calc R . . C30 C 0.6903(3) 1.0272(3) 0.5784(3) 0.0416(8) Uani 1 1 d . . . H30A H 0.6193 1.0025 0.6475 0.050 Uiso 1 1 calc R . . C31 C 0.7862(3) 1.0968(3) 0.5887(3) 0.0423(8) Uani 1 1 d . . . H31A H 0.7804 1.1212 0.6648 0.051 Uiso 1 1 calc R . . C32 C 0.8903(3) 1.1306(3) 0.4883(3) 0.0421(8) Uani 1 1 d . . . H32A H 0.9559 1.1787 0.4954 0.050 Uiso 1 1 calc R . . C33 C 0.8998(3) 1.0951(3) 0.3774(2) 0.0314(7) Uani 1 1 d . . . H33A H 0.9732 1.1170 0.3090 0.038 Uiso 1 1 calc R . . B1 B 0.8087(3) 0.9043(3) 0.0157(3) 0.0230(7) 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 F1 0.0321(9) 0.0283(9) 0.0313(8) -0.0043(7) -0.0164(7) -0.0015(7) F2 0.0369(9) 0.0335(9) 0.0177(7) -0.0020(6) -0.0056(6) 0.0016(7) O1 0.0496(13) 0.0397(13) 0.0411(12) -0.0093(10) -0.0302(10) 0.0092(10) N1 0.0461(15) 0.0472(17) 0.0317(14) -0.0216(12) -0.0159(12) 0.0130(13) C1 0.0317(15) 0.0301(16) 0.0284(15) -0.0097(12) -0.0067(12) -0.0014(12) C2 0.0359(16) 0.0337(17) 0.0233(14) -0.0053(12) -0.0122(12) 0.0021(13) C3 0.0280(14) 0.0277(15) 0.0245(14) -0.0039(11) -0.0084(11) -0.0001(12) C4 0.0274(14) 0.0228(14) 0.0200(13) -0.0024(10) -0.0085(10) -0.0033(11) C5 0.0234(13) 0.0230(14) 0.0244(13) 0.0001(11) -0.0079(10) -0.0031(11) N6 0.0258(11) 0.0224(12) 0.0197(11) -0.0046(9) -0.0069(9) -0.0007(9) N7 0.0281(12) 0.0259(13) 0.0196(11) -0.0038(9) -0.0095(9) -0.0010(10) C8 0.0250(13) 0.0268(15) 0.0245(13) -0.0008(11) -0.0083(11) -0.0023(12) C9 0.0312(14) 0.0229(15) 0.0261(14) -0.0012(11) -0.0087(11) -0.0014(12) C10 0.0280(14) 0.0223(14) 0.0240(13) -0.0019(11) -0.0061(11) -0.0017(11) C11 0.0243(13) 0.0250(15) 0.0211(13) -0.0035(11) -0.0060(10) -0.0029(11) C12 0.0262(13) 0.0220(14) 0.0207(13) -0.0037(11) -0.0074(10) -0.0050(11) C13 0.0284(14) 0.0244(15) 0.0204(13) -0.0041(11) -0.0087(11) -0.0034(12) C14 0.0316(14) 0.0262(15) 0.0242(13) -0.0047(11) -0.0123(11) -0.0044(12) C15 0.0303(14) 0.0239(15) 0.0261(14) -0.0009(11) -0.0130(11) -0.0020(12) C16 0.0328(15) 0.0244(15) 0.0306(15) -0.0067(12) -0.0127(12) -0.0014(12) O17 0.0316(10) 0.0309(11) 0.0291(10) -0.0050(8) -0.0153(8) 0.0049(9) C18 0.0274(14) 0.0236(15) 0.0225(13) 0.0006(11) -0.0088(11) -0.0025(11) C19 0.0274(14) 0.0244(15) 0.0288(14) -0.0042(11) -0.0065(11) 0.0020(12) C20 0.055(2) 0.070(3) 0.089(3) -0.057(3) -0.017(2) 0.018(2) C21 0.070(3) 0.056(3) 0.083(3) 0.000(2) -0.011(2) -0.007(2) C22 0.0426(17) 0.0271(16) 0.0367(16) -0.0123(13) -0.0097(14) 0.0051(14) C23 0.0450(19) 0.044(2) 0.047(2) -0.0100(16) -0.0088(15) 0.0003(16) C24 0.0351(15) 0.0315(16) 0.0234(13) -0.0001(12) -0.0125(12) -0.0007(13) C25 0.0397(16) 0.0315(17) 0.0296(15) -0.0037(12) -0.0152(13) 0.0052(13) C26 0.0375(17) 0.0388(18) 0.0392(17) -0.0074(14) -0.0171(14) 0.0067(14) C27 0.0396(16) 0.0264(15) 0.0280(15) -0.0077(12) -0.0137(12) 0.0032(13) C28 0.0323(15) 0.0204(14) 0.0218(13) -0.0043(11) -0.0123(11) 0.0040(11) C29 0.0425(17) 0.0339(17) 0.0262(15) -0.0043(12) -0.0071(13) -0.0074(14) C30 0.0472(19) 0.047(2) 0.0220(15) -0.0022(13) -0.0019(13) -0.0018(16) C31 0.0471(19) 0.064(2) 0.0195(14) -0.0124(14) -0.0159(13) 0.0010(17) C32 0.0408(18) 0.056(2) 0.0343(17) -0.0126(15) -0.0163(14) -0.0074(15) C33 0.0336(15) 0.0416(18) 0.0205(13) -0.0041(12) -0.0104(11) -0.0044(13) B1 0.0233(15) 0.0231(16) 0.0221(15) -0.0008(12) -0.0071(12) -0.0029(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 F1 B1 1.387(3) . ? F2 B1 1.385(3) . ? O1 C16 1.207(3) . ? N1 C1 1.372(3) . ? N1 C22 1.460(4) . ? N1 C20 1.552(5) . ? C1 C19 1.404(4) . ? C1 C2 1.410(4) . ? C2 C3 1.376(4) . ? C3 C4 1.405(4) . ? C4 C18 1.401(4) . ? C4 C5 1.438(4) . ? C5 N6 1.368(3) . ? C5 C15 1.407(4) . ? N6 C13 1.401(3) . ? N6 B1 1.549(4) . ? N7 C8 1.344(3) . ? N7 C11 1.408(3) . ? N7 B1 1.558(4) . ? C8 C9 1.426(4) . ? C8 C24 1.496(4) . ? C9 C10 1.386(4) . ? C9 C25 1.505(4) . ? C10 C11 1.432(4) . ? C10 C27 1.498(4) . ? C11 C12 1.374(4) . ? C12 C13 1.417(4) . ? C12 C28 1.499(4) . ? C13 C14 1.390(4) . ? C14 C15 1.395(4) . ? C15 C16 1.435(4) . ? C16 O17 1.380(3) . ? O17 C18 1.397(3) . ? C18 C19 1.377(4) . ? C20 C21 1.432(6) . ? C22 C23 1.509(5) . ? C25 C26 1.523(4) . ? C28 C33 1.389(4) . ? C28 C29 1.386(4) . ? C29 C30 1.390(4) . ? C30 C31 1.383(5) . ? C31 C32 1.380(4) . ? C32 C33 1.381(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 C22 120.9(2) . . ? C1 N1 C20 119.5(3) . . ? C22 N1 C20 117.0(2) . . ? N1 C1 C19 121.6(3) . . ? N1 C1 C2 121.3(3) . . ? C19 C1 C2 117.1(2) . . ? C3 C2 C1 121.6(3) . . ? C2 C3 C4 121.8(2) . . ? C18 C4 C3 115.6(2) . . ? C18 C4 C5 116.5(2) . . ? C3 C4 C5 127.9(2) . . ? N6 C5 C15 108.7(2) . . ? N6 C5 C4 131.8(2) . . ? C15 C5 C4 119.5(2) . . ? C5 N6 C13 107.1(2) . . ? C5 N6 B1 129.9(2) . . ? C13 N6 B1 122.9(2) . . ? C8 N7 C11 107.6(2) . . ? C8 N7 B1 126.7(2) . . ? C11 N7 B1 125.5(2) . . ? N7 C8 C9 110.3(2) . . ? N7 C8 C24 123.4(2) . . ? C9 C8 C24 126.3(2) . . ? C10 C9 C8 107.0(2) . . ? C10 C9 C25 126.8(2) . . ? C8 C9 C25 126.1(2) . . ? C9 C10 C11 107.0(2) . . ? C9 C10 C27 125.2(2) . . ? C11 C10 C27 127.8(2) . . ? C12 C11 N7 119.5(2) . . ? C12 C11 C10 132.3(2) . . ? N7 C11 C10 108.1(2) . . ? C11 C12 C13 121.4(2) . . ? C11 C12 C28 121.1(2) . . ? C13 C12 C28 117.6(2) . . ? C14 C13 N6 109.5(2) . . ? C14 C13 C12 128.4(2) . . ? N6 C13 C12 122.0(2) . . ? C13 C14 C15 106.5(2) . . ? C14 C15 C5 108.1(2) . . ? C14 C15 C16 128.7(2) . . ? C5 C15 C16 123.1(3) . . ? O1 C16 O17 117.4(2) . . ? O1 C16 C15 127.2(3) . . ? O17 C16 C15 115.4(2) . . ? C16 O17 C18 122.8(2) . . ? C19 C18 O17 113.8(2) . . ? C19 C18 C4 123.6(2) . . ? O17 C18 C4 122.6(2) . . ? C18 C19 C1 120.1(2) . . ? C21 C20 N1 110.2(4) . . ? N1 C22 C23 113.7(3) . . ? C9 C25 C26 112.1(2) . . ? C33 C28 C29 119.3(2) . . ? C33 C28 C12 120.4(2) . . ? C29 C28 C12 120.3(3) . . ? C28 C29 C30 120.4(3) . . ? C31 C30 C29 119.9(3) . . ? C32 C31 C30 119.8(3) . . ? C31 C32 C33 120.5(3) . . ? C32 C33 C28 120.1(3) . . ? F2 B1 F1 109.5(2) . . ? F2 B1 N6 110.9(2) . . ? F1 B1 N6 110.1(2) . . ? F2 B1 N7 109.4(2) . . ? F1 B1 N7 109.3(2) . . ? N6 B1 N7 107.5(2) . . ? _diffrn_measured_fraction_theta_max 0.929 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.953 _refine_diff_density_max 1.049 _refine_diff_density_min -0.557 _refine_diff_density_rms 0.060 _database_code_depnum_ccdc_archive 'CCDC 956947'