# 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_sensor1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C35 H32 B2 F2 N2 S2' _chemical_formula_sum 'C35 H32 B2 F2 N2 S2' _chemical_formula_weight 604.39 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/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 17.249(4) _cell_length_b 8.0755(17) _cell_length_c 22.638(5) _cell_angle_alpha 90.00 _cell_angle_beta 103.615(14) _cell_angle_gamma 90.00 _cell_volume 3064.7(12) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description rectangular _exptl_crystal_colour red _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.310 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 354 _exptl_absorpt_coefficient_mu 0.214 _exptl_absorpt_correction_type EMPIRICAL _exptl_absorpt_correction_T_min 0.985 _exptl_absorpt_correction_T_max 0.989 _exptl_absorpt_process_details SADABS _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scan' _diffrn_detector_area_resol_mean 0.3 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 66114 _diffrn_reflns_av_R_equivalents 0.1143 _diffrn_reflns_av_sigmaI/netI 0.0888 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 1.34 _diffrn_reflns_theta_max 30.65 _reflns_number_total 9404 _reflns_number_gt 5415 _reflns_threshold_expression >2\s(I) _computing_data_collection 'Bruker kappa apex ccd' _computing_cell_refinement 'Bruker kappa apex ccd' _computing_data_reduction 'Bruker saint' _computing_structure_solution shelxs-97 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ortep-III _computing_publication_material WinGX1.80.05 _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^ > 2\s(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^)+(0.0441P)^2^+1.0376P] 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 9404 _refine_ls_number_parameters 507 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1202 _refine_ls_R_factor_gt 0.0557 _refine_ls_wR_factor_ref 0.1307 _refine_ls_wR_factor_gt 0.1074 _refine_ls_goodness_of_fit_ref 1.003 _refine_ls_restrained_S_all 1.003 _refine_ls_shift/su_max 0.006 _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 S2 S 0.46877(3) 0.55074(6) 0.36481(2) 0.02839(13) Uani 1 1 d . . . S1 S 0.27273(3) 0.30189(7) 0.42026(2) 0.02722(13) Uani 1 1 d . . . F1 F 0.10598(8) -0.27884(18) 0.53085(7) 0.0537(4) Uani 1 1 d . . . F2 F 0.16315(9) -0.18096(18) 0.62485(7) 0.0508(4) Uani 1 1 d . . . N1 N 0.24300(10) -0.2033(2) 0.55117(8) 0.0274(4) Uani 1 1 d . . . N2 N 0.13919(10) 0.0123(2) 0.54197(8) 0.0301(4) Uani 1 1 d . . . C16 C 0.34930(14) 0.6676(3) 0.28878(10) 0.0305(5) Uani 1 1 d . . . C11 C 0.39174(13) 0.1965(3) 0.50154(10) 0.0272(5) Uani 1 1 d . . . C6 C 0.18705(12) 0.1204(3) 0.51770(9) 0.0266(5) Uani 1 1 d . . . C17 C 0.43108(13) 0.6764(2) 0.30260(9) 0.0259(4) Uani 1 1 d . A . C27 C 0.44849(12) 0.9348(2) 0.23446(9) 0.0238(4) Uani 1 1 d . A . C13 C 0.36584(12) 0.3777(2) 0.41931(9) 0.0244(4) Uani 1 1 d . . . C32 C 0.44936(12) 0.9497(3) 0.17209(9) 0.0284(5) Uani 1 1 d . . . C21 C 0.73984(13) 0.6355(3) 0.30999(9) 0.0282(5) Uani 1 1 d . . . C19 C 0.60043(13) 0.5703(2) 0.27041(9) 0.0270(5) Uani 1 1 d . . . C22 C 0.71761(14) 0.7942(3) 0.32358(10) 0.0290(5) Uani 1 1 d . A . C7 C 0.14897(13) 0.2775(3) 0.51015(10) 0.0317(5) Uani 1 1 d . . . C5 C 0.26004(12) 0.0663(2) 0.50802(9) 0.0236(4) Uani 1 1 d . . . C10 C 0.31092(12) 0.1776(2) 0.48251(9) 0.0247(4) Uani 1 1 d . . . C3 C 0.35288(14) -0.1849(3) 0.51358(10) 0.0296(5) Uani 1 1 d . . . C18 C 0.57727(12) 0.7312(2) 0.28469(9) 0.0235(4) Uani 1 1 d . A . C14 C 0.37568(12) 0.4916(2) 0.37197(9) 0.0249(4) Uani 1 1 d . . . C12 C 0.42273(13) 0.3104(3) 0.46565(10) 0.0265(4) Uani 1 1 d . . . C2 C 0.35024(15) -0.3412(3) 0.53770(11) 0.0333(5) Uani 1 1 d . . . C30 C 0.37731(13) 1.2109(3) 0.16488(12) 0.0381(6) Uani 1 1 d . . . C15 C 0.31792(14) 0.5629(3) 0.32708(10) 0.0302(5) Uani 1 1 d . . . C20 C 0.68045(13) 0.5262(3) 0.28314(10) 0.0288(5) Uani 1 1 d . A . C23 C 0.63866(13) 0.8444(2) 0.31099(9) 0.0267(5) Uani 1 1 d . . . C28 C 0.41147(13) 1.0618(3) 0.26074(10) 0.0299(5) Uani 1 1 d . . . C35 C 0.48601(18) 0.8181(4) 0.14059(12) 0.0401(6) Uani 1 1 d . . . C4 C 0.28648(12) -0.0967(3) 0.52277(9) 0.0249(4) Uani 1 1 d . . . C31 C 0.41312(14) 1.0860(3) 0.13912(11) 0.0362(6) Uani 1 1 d . . . C24 C 0.54123(16) 0.4466(3) 0.23626(14) 0.0391(6) Uani 1 1 d . A . C29 C 0.37731(13) 1.1973(3) 0.22595(12) 0.0342(5) Uani 1 1 d . . . C8 C 0.07972(15) 0.2618(3) 0.52919(11) 0.0387(6) Uani 1 1 d . . . C9 C 0.07555(14) 0.0989(3) 0.54865(11) 0.0374(6) Uani 1 1 d . . . C25 C 0.82589(13) 0.5842(3) 0.32267(11) 0.0388(6) Uani 1 1 d . A 1 H24 H 0.8326 0.5019 0.2937 0.112(13) Uiso 1 1 calc R A 1 H28 H 0.8417 0.5391 0.3629 0.100(12) Uiso 1 1 calc R A 1 H29 H 0.8583 0.6789 0.3195 0.090(11) Uiso 1 1 calc R A 1 C1 C 0.28212(14) -0.3483(3) 0.56042(10) 0.0328(5) Uani 1 1 d . . . C26 C 0.62020(18) 1.0200(3) 0.32625(12) 0.0367(6) Uani 1 1 d . A . B2 B 0.48728(15) 0.7808(3) 0.27292(10) 0.0245(5) Uani 1 1 d . . . C34 C 0.3389(2) 1.3570(4) 0.1279(2) 0.0671(11) Uani 1 1 d . . . C33 C 0.4122(2) 1.0643(4) 0.32767(13) 0.0469(7) Uani 1 1 d . . . B1 B 0.16061(16) -0.1677(3) 0.56343(12) 0.0344(6) Uani 1 1 d . . . H14 H 0.7589(13) 0.877(3) 0.3403(9) 0.027(6) Uiso 1 1 d . . . H6 H 0.0384(13) 0.045(3) 0.5665(10) 0.029(6) Uiso 1 1 d . . . H13 H 0.6952(12) 0.420(3) 0.2716(9) 0.024(6) Uiso 1 1 d . . . H9 H 0.2647(15) 0.548(3) 0.3246(11) 0.044(7) Uiso 1 1 d . . . H17 H 0.5820(14) 1.068(3) 0.2920(11) 0.038(7) Uiso 1 1 d . . . H11 H 0.3512(14) 1.285(3) 0.2460(11) 0.042(7) Uiso 1 1 d . . . H10 H 0.3168(14) 0.731(3) 0.2572(10) 0.036(6) Uiso 1 1 d . . . H21 H 0.4376(16) 0.972(4) 0.3512(12) 0.054(8) Uiso 1 1 d . . . H8 H 0.4786(14) 0.339(3) 0.4740(10) 0.033(6) Uiso 1 1 d . . . H12 H 0.4152(13) 1.087(3) 0.0987(11) 0.031(6) Uiso 1 1 d . . . H1 H 0.2610(13) -0.435(3) 0.5786(10) 0.034(6) Uiso 1 1 d . . . H7 H 0.4242(14) 0.138(3) 0.5358(11) 0.034(6) Uiso 1 1 d . . . H4 H 0.1687(14) 0.373(3) 0.4964(11) 0.040(7) Uiso 1 1 d . . . H23 H 0.4871(19) 0.482(3) 0.2271(13) 0.063(9) Uiso 1 1 d . . . H5 H 0.0417(15) 0.346(3) 0.5300(11) 0.046(7) Uiso 1 1 d . . . H15 H 0.5949(15) 1.025(3) 0.3594(12) 0.048(8) Uiso 1 1 d . . . H18 H 0.4952(16) 0.856(3) 0.1019(13) 0.056(8) Uiso 1 1 d . . . H2 H 0.3850(14) -0.428(3) 0.5378(11) 0.038(7) Uiso 1 1 d . . . H16 H 0.6670(17) 1.087(3) 0.3361(12) 0.057(8) Uiso 1 1 d . . . H3 H 0.3912(14) -0.140(3) 0.4915(10) 0.037(6) Uiso 1 1 d . . . H20 H 0.5345(17) 0.783(3) 0.1654(13) 0.051(8) Uiso 1 1 d . . . H19 H 0.4518(18) 0.723(4) 0.1306(13) 0.061(9) Uiso 1 1 d . . . H22 H 0.359(2) 1.067(4) 0.3345(15) 0.084(11) Uiso 1 1 d . . . H31 H 0.288(2) 1.340(4) 0.1113(15) 0.073(10) Uiso 1 1 d . . . H30 H 0.337(3) 1.443(5) 0.152(2) 0.121(18) Uiso 1 1 d . . . H25 H 0.439(2) 1.160(5) 0.3487(17) 0.102(13) Uiso 1 1 d . . . H27 H 0.541(2) 0.349(5) 0.2574(17) 0.093(12) Uiso 1 1 d . . . H32 H 0.369(3) 1.389(6) 0.097(2) 0.141(18) Uiso 1 1 d . . . H26 H 0.554(2) 0.410(5) 0.1998(18) 0.107(13) 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 S2 0.0256(3) 0.0276(3) 0.0311(3) 0.0080(2) 0.0050(2) -0.0007(2) S1 0.0237(3) 0.0309(3) 0.0268(3) 0.0058(2) 0.0055(2) 0.0012(2) F1 0.0319(8) 0.0484(9) 0.0785(11) -0.0135(8) 0.0085(8) -0.0181(7) F2 0.0576(10) 0.0580(9) 0.0452(9) 0.0111(7) 0.0287(8) -0.0042(8) N1 0.0244(9) 0.0309(9) 0.0258(9) 0.0003(8) 0.0040(7) -0.0081(8) N2 0.0210(9) 0.0420(11) 0.0277(10) -0.0038(8) 0.0068(8) -0.0049(8) C16 0.0307(12) 0.0290(11) 0.0321(12) 0.0088(10) 0.0081(10) 0.0078(10) C11 0.0238(11) 0.0284(11) 0.0289(11) 0.0045(9) 0.0050(9) 0.0014(9) C6 0.0222(11) 0.0355(12) 0.0215(10) -0.0021(9) 0.0039(9) -0.0019(9) C17 0.0293(12) 0.0215(10) 0.0270(11) 0.0031(8) 0.0069(9) 0.0034(9) C27 0.0245(11) 0.0212(10) 0.0256(11) 0.0016(8) 0.0055(8) -0.0048(8) C13 0.0252(11) 0.0221(10) 0.0275(11) -0.0017(8) 0.0095(9) 0.0002(8) C32 0.0238(11) 0.0343(12) 0.0253(11) 0.0018(9) 0.0022(9) -0.0093(9) C21 0.0279(12) 0.0348(12) 0.0226(11) 0.0056(9) 0.0076(9) -0.0035(9) C19 0.0288(12) 0.0228(10) 0.0299(11) -0.0001(9) 0.0077(9) -0.0031(9) C22 0.0309(12) 0.0312(12) 0.0233(11) 0.0018(9) 0.0031(9) -0.0086(10) C7 0.0275(12) 0.0395(13) 0.0268(12) -0.0013(10) 0.0036(10) 0.0024(10) C5 0.0218(10) 0.0283(10) 0.0196(10) -0.0010(8) 0.0026(8) -0.0021(9) C10 0.0245(11) 0.0258(10) 0.0245(10) 0.0020(8) 0.0069(9) 0.0022(9) C3 0.0298(12) 0.0303(11) 0.0294(12) 0.0004(9) 0.0084(10) -0.0012(10) C18 0.0294(11) 0.0206(10) 0.0204(10) 0.0016(8) 0.0057(9) -0.0014(8) C14 0.0256(11) 0.0225(10) 0.0277(11) 0.0012(8) 0.0088(9) 0.0037(8) C12 0.0223(11) 0.0282(11) 0.0289(11) 0.0018(9) 0.0057(9) -0.0011(9) C2 0.0353(13) 0.0278(12) 0.0349(13) -0.0009(10) 0.0042(11) 0.0021(10) C30 0.0248(12) 0.0310(12) 0.0496(15) 0.0157(11) -0.0093(11) -0.0083(10) C15 0.0233(11) 0.0314(11) 0.0381(13) 0.0085(10) 0.0116(10) 0.0059(10) C20 0.0302(12) 0.0261(11) 0.0320(12) 0.0011(9) 0.0113(10) 0.0015(10) C23 0.0348(12) 0.0244(10) 0.0203(10) 0.0021(8) 0.0052(9) -0.0046(9) C28 0.0307(12) 0.0241(10) 0.0354(12) 0.0012(9) 0.0088(10) -0.0010(9) C35 0.0409(16) 0.0543(17) 0.0254(13) -0.0045(12) 0.0083(12) -0.0028(14) C4 0.0226(11) 0.0289(11) 0.0226(10) 0.0002(8) 0.0043(8) -0.0045(9) C31 0.0316(13) 0.0451(14) 0.0269(12) 0.0106(11) -0.0031(10) -0.0140(11) C24 0.0294(14) 0.0279(13) 0.0581(18) -0.0137(12) 0.0064(12) -0.0025(11) C29 0.0233(11) 0.0215(10) 0.0555(16) 0.0027(11) 0.0045(11) -0.0005(9) C8 0.0281(13) 0.0532(16) 0.0344(13) -0.0060(11) 0.0066(11) 0.0087(12) C9 0.0241(12) 0.0562(16) 0.0332(13) -0.0074(11) 0.0096(10) -0.0052(11) C25 0.0265(13) 0.0511(15) 0.0382(14) 0.0010(12) 0.0064(11) -0.0021(11) C1 0.0368(14) 0.0284(12) 0.0313(12) 0.0019(10) 0.0038(10) -0.0078(10) C26 0.0450(16) 0.0277(12) 0.0331(14) -0.0056(10) 0.0007(12) -0.0040(11) B2 0.0325(13) 0.0199(11) 0.0202(11) -0.0040(9) 0.0044(10) -0.0012(10) C34 0.054(2) 0.0461(18) 0.080(3) 0.0316(18) -0.026(2) -0.0035(16) C33 0.072(2) 0.0326(14) 0.0418(16) -0.0016(12) 0.0258(15) 0.0116(15) B1 0.0293(14) 0.0403(15) 0.0360(15) -0.0029(12) 0.0121(12) -0.0123(12) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 S2 C14 1.719(2) . ? S2 C17 1.733(2) . ? S1 C13 1.724(2) . ? S1 C10 1.729(2) . ? F1 B1 1.382(3) . ? F2 B1 1.385(3) . ? N1 C1 1.343(3) . ? N1 C4 1.394(3) . ? N1 B1 1.538(3) . ? N2 C9 1.340(3) . ? N2 C6 1.399(3) . ? N2 B1 1.549(3) . ? C16 C17 1.373(3) . ? C16 C15 1.407(3) . ? C11 C10 1.367(3) . ? C11 C12 1.413(3) . ? C6 C5 1.398(3) . ? C6 C7 1.420(3) . ? C17 B2 1.552(3) . ? C27 C28 1.412(3) . ? C27 C32 1.421(3) . ? C27 B2 1.574(3) . ? C13 C12 1.369(3) . ? C13 C14 1.452(3) . ? C32 C31 1.393(3) . ? C32 C35 1.500(3) . ? C21 C20 1.380(3) . ? C21 C22 1.393(3) . ? C21 C25 1.502(3) . ? C19 C20 1.388(3) . ? C19 C18 1.419(3) . ? C19 C24 1.505(3) . ? C22 C23 1.385(3) . ? C7 C8 1.368(3) . ? C5 C4 1.407(3) . ? C5 C10 1.466(3) . ? C3 C2 1.380(3) . ? C3 C4 1.405(3) . ? C18 C23 1.419(3) . ? C18 B2 1.564(3) . ? C14 C15 1.371(3) . ? C2 C1 1.390(3) . ? C30 C31 1.381(4) . ? C30 C29 1.387(3) . ? C30 C34 1.508(4) . ? C23 C26 1.511(3) . ? C28 C29 1.395(3) . ? C28 C33 1.512(3) . ? C8 C9 1.395(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 C14 S2 C17 93.40(10) . . ? C13 S1 C10 92.24(10) . . ? C1 N1 C4 107.78(18) . . ? C1 N1 B1 125.91(18) . . ? C4 N1 B1 126.01(18) . . ? C9 N2 C6 107.08(19) . . ? C9 N2 B1 126.53(19) . . ? C6 N2 B1 126.08(18) . . ? C17 C16 C15 114.5(2) . . ? C10 C11 C12 112.8(2) . . ? C5 C6 N2 120.20(19) . . ? C5 C6 C7 131.9(2) . . ? N2 C6 C7 107.79(18) . . ? C16 C17 B2 129.96(19) . . ? C16 C17 S2 108.88(15) . . ? B2 C17 S2 121.12(16) . . ? C28 C27 C32 117.96(19) . . ? C28 C27 B2 121.09(18) . . ? C32 C27 B2 120.95(18) . . ? C12 C13 C14 129.04(19) . . ? C12 C13 S1 110.56(15) . . ? C14 C13 S1 120.35(16) . . ? C31 C32 C27 119.4(2) . . ? C31 C32 C35 119.4(2) . . ? C27 C32 C35 121.1(2) . . ? C20 C21 C22 118.1(2) . . ? C20 C21 C25 120.4(2) . . ? C22 C21 C25 121.5(2) . . ? C20 C19 C18 120.47(19) . . ? C20 C19 C24 117.2(2) . . ? C18 C19 C24 122.1(2) . . ? C23 C22 C21 122.2(2) . . ? C8 C7 C6 107.0(2) . . ? C6 C5 C4 120.58(19) . . ? C6 C5 C10 120.98(18) . . ? C4 C5 C10 118.44(18) . . ? C11 C10 C5 127.20(19) . . ? C11 C10 S1 110.89(15) . . ? C5 C10 S1 121.89(15) . . ? C2 C3 C4 107.5(2) . . ? C19 C18 C23 117.58(19) . . ? C19 C18 B2 121.15(18) . . ? C23 C18 B2 121.26(18) . . ? C15 C14 C13 128.48(19) . . ? C15 C14 S2 110.19(16) . . ? C13 C14 S2 121.31(16) . . ? C13 C12 C11 113.5(2) . . ? C3 C2 C1 107.1(2) . . ? C31 C30 C29 117.9(2) . . ? C31 C30 C34 121.2(3) . . ? C29 C30 C34 120.8(3) . . ? C14 C15 C16 113.0(2) . . ? C21 C20 C19 121.7(2) . . ? C22 C23 C18 119.88(19) . . ? C22 C23 C26 118.5(2) . . ? C18 C23 C26 121.6(2) . . ? C29 C28 C27 120.3(2) . . ? C29 C28 C33 117.3(2) . . ? C27 C28 C33 122.3(2) . . ? N1 C4 C3 107.51(18) . . ? N1 C4 C5 120.50(18) . . ? C3 C4 C5 131.99(19) . . ? C30 C31 C32 122.6(2) . . ? C30 C29 C28 121.7(2) . . ? C7 C8 C9 107.5(2) . . ? N2 C9 C8 110.6(2) . . ? N1 C1 C2 110.1(2) . . ? C17 B2 C18 118.88(18) . . ? C17 B2 C27 116.19(19) . . ? C18 B2 C27 124.90(19) . . ? F1 B1 F2 110.00(19) . . ? F1 B1 N1 109.0(2) . . ? F2 B1 N1 110.8(2) . . ? F1 B1 N2 111.1(2) . . ? F2 B1 N2 109.7(2) . . ? N1 B1 N2 106.33(17) . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 30.65 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.322 _refine_diff_density_min -0.332 _refine_diff_density_rms 0.063 _database_code_depnum_ccdc_archive 'CCDC 934685'