# 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_121229lt_0m _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H14 B F4 N' _chemical_formula_weight 307.09 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 1 21/c 1 ' 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 9.2845(6) _cell_length_b 8.1916(5) _cell_length_c 19.3256(12) _cell_angle_alpha 90.00 _cell_angle_beta 102.541(3) _cell_angle_gamma 90.00 _cell_volume 1434.74(16) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 6636 _cell_measurement_theta_min 2.16 _cell_measurement_theta_max 28.34 _exptl_crystal_description Lump _exptl_crystal_colour Orange _exptl_crystal_size_max 0.27 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.422 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 632 _exptl_absorpt_coefficient_mu 0.118 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8851 _exptl_absorpt_correction_T_max 0.9486 _exptl_absorpt_process_details 'SADABS V2008/1 (Bruker AXS)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 8.3333 _diffrn_reflns_number 13349 _diffrn_reflns_av_R_equivalents 0.0252 _diffrn_reflns_av_sigmaI/netI 0.0240 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.16 _diffrn_reflns_theta_max 28.34 _reflns_number_total 3556 _reflns_number_gt 2845 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker AXS, 2010)' _computing_cell_refinement 'SAINT V7.68A (Bruker AXS, 2009)' _computing_data_reduction 'SAINT V7.68A (Bruker AXS, 2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 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^)+(0.1065P)^2^+0.6685P] 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 3556 _refine_ls_number_parameters 199 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0661 _refine_ls_R_factor_gt 0.0506 _refine_ls_wR_factor_ref 0.1863 _refine_ls_wR_factor_gt 0.1587 _refine_ls_goodness_of_fit_ref 1.103 _refine_ls_restrained_S_all 1.103 _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 0.21724(14) 0.93104(17) 0.13779(7) 0.0188(3) Uani 1 1 d . . . B1 B 0.1731(2) 0.1385(2) 0.40599(10) 0.0242(4) Uani 1 1 d . . . F1 F 0.30272(13) 0.21697(15) 0.43869(7) 0.0375(3) Uani 1 1 d . . . F2 F 0.12693(16) 0.03893(15) 0.45535(7) 0.0447(4) Uani 1 1 d . . . F3 F 0.06624(14) 0.25537(16) 0.38307(8) 0.0457(4) Uani 1 1 d . . . F4 F 0.19329(19) 0.0430(2) 0.35078(7) 0.0600(5) Uani 1 1 d . . . C1 C 0.28821(17) 0.7798(2) 0.14482(8) 0.0189(3) Uani 1 1 d . . . C2 C 0.32702(18) 0.7077(2) 0.08731(9) 0.0220(4) Uani 1 1 d . . . C3 C 0.2964(2) 0.7899(2) 0.02137(9) 0.0269(4) Uani 1 1 d . . . H3A H 0.3235 0.7413 -0.0186 0.032 Uiso 1 1 calc R . . C4 C 0.2286(2) 0.9377(2) 0.01472(9) 0.0266(4) Uani 1 1 d . . . H4A H 0.2105 0.9927 -0.0296 0.032 Uiso 1 1 calc R . . C5 C 0.18488(18) 1.0104(2) 0.07301(9) 0.0224(4) Uani 1 1 d . . . C6 C 0.11046(19) 1.1616(2) 0.06753(10) 0.0279(4) Uani 1 1 d . . . H6A H 0.0884 1.2169 0.0233 0.033 Uiso 1 1 calc R . . C7 C 0.0697(2) 1.2295(2) 0.12479(11) 0.0298(4) Uani 1 1 d . . . H7A H 0.0172 1.3298 0.1205 0.036 Uiso 1 1 calc R . . C8 C 0.10679(19) 1.1484(2) 0.19018(10) 0.0270(4) Uani 1 1 d . . . H8A H 0.0817 1.1958 0.2309 0.032 Uiso 1 1 calc R . . C9 C 0.17819(18) 1.0028(2) 0.19587(9) 0.0221(4) Uani 1 1 d . . . H9A H 0.2017 0.9492 0.2405 0.027 Uiso 1 1 calc R . . C10 C 0.32069(17) 0.7025(2) 0.21644(8) 0.0183(3) Uani 1 1 d . . . C11 C 0.22169(18) 0.5922(2) 0.23505(9) 0.0232(4) Uani 1 1 d . . . H11A H 0.1315 0.5685 0.2027 0.028 Uiso 1 1 calc R . . C12 C 0.2545(2) 0.5167(2) 0.30096(9) 0.0261(4) Uani 1 1 d . . . H12A H 0.1873 0.4404 0.3133 0.031 Uiso 1 1 calc R . . C13 C 0.3851(2) 0.5523(2) 0.34885(9) 0.0238(4) Uani 1 1 d . . . H13A H 0.4077 0.4999 0.3938 0.029 Uiso 1 1 calc R . . C14 C 0.48254(19) 0.6645(2) 0.33084(9) 0.0239(4) Uani 1 1 d . . . H14A H 0.5709 0.6910 0.3640 0.029 Uiso 1 1 calc R . . C15 C 0.45163(18) 0.7387(2) 0.26457(9) 0.0220(4) Uani 1 1 d . . . H15A H 0.5197 0.8138 0.2521 0.026 Uiso 1 1 calc R . . C16 C 0.3999(2) 0.5437(2) 0.09377(9) 0.0275(4) Uani 1 1 d . . . H16A H 0.4129 0.5045 0.1427 0.041 Uiso 1 1 calc R . . H16B H 0.4964 0.5527 0.0813 0.041 Uiso 1 1 calc R . . H16C H 0.3380 0.4666 0.0616 0.041 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0182(6) 0.0166(7) 0.0205(7) 0.0021(5) 0.0015(5) -0.0020(5) B1 0.0295(9) 0.0208(9) 0.0220(9) -0.0001(7) 0.0052(7) -0.0010(7) F1 0.0312(6) 0.0329(7) 0.0463(7) 0.0008(5) 0.0037(5) -0.0035(5) F2 0.0677(9) 0.0318(7) 0.0345(7) 0.0049(5) 0.0108(6) -0.0162(6) F3 0.0307(6) 0.0383(7) 0.0651(9) 0.0166(6) 0.0039(6) 0.0032(5) F4 0.0751(11) 0.0707(11) 0.0362(8) -0.0231(7) 0.0163(7) 0.0025(8) C1 0.0184(7) 0.0177(8) 0.0197(7) 0.0021(6) 0.0019(6) -0.0020(6) C2 0.0223(8) 0.0226(8) 0.0207(8) 0.0007(6) 0.0037(6) -0.0028(6) C3 0.0318(9) 0.0299(10) 0.0190(8) -0.0006(7) 0.0057(7) -0.0050(7) C4 0.0310(9) 0.0280(9) 0.0190(8) 0.0054(6) 0.0013(6) -0.0068(7) C5 0.0216(8) 0.0214(8) 0.0219(8) 0.0052(6) -0.0003(6) -0.0044(6) C6 0.0268(8) 0.0223(9) 0.0307(9) 0.0078(7) -0.0022(7) -0.0025(7) C7 0.0262(9) 0.0203(9) 0.0389(10) 0.0026(7) -0.0021(7) 0.0022(7) C8 0.0251(8) 0.0227(9) 0.0324(9) -0.0026(7) 0.0042(7) 0.0011(7) C9 0.0226(8) 0.0206(8) 0.0227(8) 0.0001(6) 0.0038(6) -0.0017(6) C10 0.0206(7) 0.0164(7) 0.0177(7) 0.0004(6) 0.0035(6) 0.0022(6) C11 0.0227(8) 0.0228(9) 0.0237(8) 0.0009(6) 0.0042(6) -0.0038(6) C12 0.0295(9) 0.0241(9) 0.0270(9) 0.0041(7) 0.0115(7) -0.0024(7) C13 0.0328(9) 0.0208(8) 0.0188(7) 0.0042(6) 0.0075(6) 0.0071(7) C14 0.0240(8) 0.0220(9) 0.0231(8) 0.0009(6) -0.0004(6) 0.0040(6) C15 0.0207(8) 0.0198(8) 0.0244(8) 0.0025(6) 0.0028(6) -0.0008(6) C16 0.0333(9) 0.0251(9) 0.0250(9) -0.0020(7) 0.0085(7) 0.0030(7) _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 C9 1.383(2) . ? N1 C5 1.385(2) . ? N1 C1 1.396(2) . ? B1 F4 1.368(2) . ? B1 F3 1.381(2) . ? B1 F1 1.390(2) . ? B1 F2 1.391(2) . ? C1 C2 1.374(2) . ? C1 C10 1.492(2) . ? C2 C3 1.414(2) . ? C2 C16 1.497(2) . ? C3 C4 1.358(3) . ? C3 H3A 0.9500 . ? C4 C5 1.410(3) . ? C4 H4A 0.9500 . ? C5 C6 1.411(2) . ? C6 C7 1.363(3) . ? C6 H6A 0.9500 . ? C7 C8 1.403(3) . ? C7 H7A 0.9500 . ? C8 C9 1.357(2) . ? C8 H8A 0.9500 . ? C9 H9A 0.9500 . ? C10 C11 1.391(2) . ? C10 C15 1.393(2) . ? C11 C12 1.389(2) . ? C11 H11A 0.9500 . ? C12 C13 1.387(3) . ? C12 H12A 0.9500 . ? C13 C14 1.386(3) . ? C13 H13A 0.9500 . ? C14 C15 1.390(2) . ? C14 H14A 0.9500 . ? C15 H15A 0.9500 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C9 N1 C5 119.38(14) . . ? C9 N1 C1 119.96(14) . . ? C5 N1 C1 120.66(14) . . ? F4 B1 F3 110.92(16) . . ? F4 B1 F1 111.53(16) . . ? F3 B1 F1 108.42(16) . . ? F4 B1 F2 108.33(16) . . ? F3 B1 F2 108.65(16) . . ? F1 B1 F2 108.94(15) . . ? C2 C1 N1 120.25(15) . . ? C2 C1 C10 122.17(15) . . ? N1 C1 C10 117.58(14) . . ? C1 C2 C3 119.19(16) . . ? C1 C2 C16 120.74(15) . . ? C3 C2 C16 120.06(15) . . ? C4 C3 C2 120.53(16) . . ? C4 C3 H3A 119.7 . . ? C2 C3 H3A 119.7 . . ? C3 C4 C5 120.61(16) . . ? C3 C4 H4A 119.7 . . ? C5 C4 H4A 119.7 . . ? N1 C5 C4 118.72(16) . . ? N1 C5 C6 119.13(16) . . ? C4 C5 C6 122.15(16) . . ? C7 C6 C5 120.98(16) . . ? C7 C6 H6A 119.5 . . ? C5 C6 H6A 119.5 . . ? C6 C7 C8 118.75(17) . . ? C6 C7 H7A 120.6 . . ? C8 C7 H7A 120.6 . . ? C9 C8 C7 120.60(17) . . ? C9 C8 H8A 119.7 . . ? C7 C8 H8A 119.7 . . ? C8 C9 N1 121.13(16) . . ? C8 C9 H9A 119.4 . . ? N1 C9 H9A 119.4 . . ? C11 C10 C15 119.71(15) . . ? C11 C10 C1 120.26(14) . . ? C15 C10 C1 120.02(14) . . ? C12 C11 C10 120.04(16) . . ? C12 C11 H11A 120.0 . . ? C10 C11 H11A 120.0 . . ? C13 C12 C11 120.30(16) . . ? C13 C12 H12A 119.9 . . ? C11 C12 H12A 119.9 . . ? C14 C13 C12 119.68(16) . . ? C14 C13 H13A 120.2 . . ? C12 C13 H13A 120.2 . . ? C13 C14 C15 120.38(16) . . ? C13 C14 H14A 119.8 . . ? C15 C14 H14A 119.8 . . ? C14 C15 C10 119.87(15) . . ? C14 C15 H15A 120.1 . . ? C10 C15 H15A 120.1 . . ? C2 C16 H16A 109.5 . . ? C2 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C2 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 28.34 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.630 _refine_diff_density_min -0.420 _refine_diff_density_rms 0.119 _database_code_depnum_ccdc_archive 'CCDC 948578' ####################################################################### # # 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_121217lt_0m _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C34 H32 B2 F8 N2' _chemical_formula_weight 642.24 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' _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 7.2675(3) _cell_length_b 7.9484(4) _cell_length_c 27.5441(13) _cell_angle_alpha 82.921(2) _cell_angle_beta 83.610(2) _cell_angle_gamma 74.824(2) _cell_volume 1518.70(12) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5807 _cell_measurement_theta_min 2.99 _cell_measurement_theta_max 27.18 _exptl_crystal_description Lump _exptl_crystal_colour ? _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.404 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 664 _exptl_absorpt_coefficient_mu 0.115 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8867 _exptl_absorpt_correction_T_max 0.9422 _exptl_absorpt_process_details 'SADABS V2008/1 (Bruker AXS)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 8.3333 _diffrn_reflns_number 24864 _diffrn_reflns_av_R_equivalents 0.0291 _diffrn_reflns_av_sigmaI/netI 0.0400 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -35 _diffrn_reflns_limit_l_max 36 _diffrn_reflns_theta_min 0.75 _diffrn_reflns_theta_max 28.34 _reflns_number_total 7473 _reflns_number_gt 5285 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0784P)^2^+0.1253P] 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 7473 _refine_ls_number_parameters 417 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0708 _refine_ls_R_factor_gt 0.0443 _refine_ls_wR_factor_ref 0.1471 _refine_ls_wR_factor_gt 0.1210 _refine_ls_goodness_of_fit_ref 1.090 _refine_ls_restrained_S_all 1.090 _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 F1 F 0.13562(14) 0.35908(13) 0.42354(4) 0.0324(3) Uani 1 1 d . . . F2 F 0.06241(19) 0.23874(17) 0.36031(4) 0.0538(4) Uani 1 1 d . . . F3 F 0.13450(15) 0.07207(13) 0.43128(4) 0.0363(3) Uani 1 1 d . . . F4 F 0.36723(15) 0.16408(15) 0.38282(4) 0.0412(3) Uani 1 1 d . . . F5 F 0.34946(19) 0.93585(16) 0.07575(5) 0.0534(3) Uani 1 1 d . . . F6 F 0.41262(15) 0.64727(14) 0.10157(4) 0.0393(3) Uani 1 1 d . . . F7 F 0.10749(15) 0.80773(18) 0.09779(4) 0.0489(3) Uani 1 1 d . . . F8 F 0.28703(19) 0.84548(16) 0.15569(4) 0.0506(3) Uani 1 1 d . . . N1 N 1.00672(18) 0.30107(16) 0.07322(5) 0.0187(3) Uani 1 1 d . . . N2 N 0.46178(17) 0.72625(16) 0.43499(5) 0.0184(3) Uani 1 1 d . . . C1 C 1.2689(2) 0.3385(2) -0.00698(6) 0.0248(4) Uani 1 1 d . . . H1 H 1.3615 0.3476 -0.0337 0.030 Uiso 1 1 calc R . . C2 C 1.1228(2) 0.2654(2) -0.01134(6) 0.0228(3) Uani 1 1 d . . . H2 H 1.1108 0.2272 -0.0419 0.027 Uiso 1 1 calc R . . C3 C 0.9886(2) 0.2453(2) 0.02871(6) 0.0201(3) Uani 1 1 d . . . C4 C 0.8786(2) 0.2795(2) 0.11414(6) 0.0195(3) Uani 1 1 d . . . C5 C 0.9120(2) 0.3357(2) 0.16112(6) 0.0211(3) Uani 1 1 d . . . C6 C 0.7962(2) 0.4899(2) 0.17803(6) 0.0269(4) Uani 1 1 d . . . H6 H 0.7001 0.5629 0.1587 0.032 Uiso 1 1 calc R . . C7 C 0.8222(3) 0.5363(2) 0.22327(6) 0.0304(4) Uani 1 1 d . . . H7 H 0.7436 0.6415 0.2349 0.037 Uiso 1 1 calc R . . C8 C 0.9616(2) 0.4303(2) 0.25157(6) 0.0269(4) Uani 1 1 d . . . H8 H 0.9772 0.4618 0.2827 0.032 Uiso 1 1 calc R . . C9 C 0.7314(2) 0.2056(2) 0.10983(6) 0.0219(3) Uani 1 1 d . . . C10 C 0.7112(2) 0.1508(2) 0.06430(6) 0.0230(3) Uani 1 1 d . . . H10 H 0.6097 0.0990 0.0613 0.028 Uiso 1 1 calc R . . C11 C 0.8357(2) 0.1716(2) 0.02483(6) 0.0216(3) Uani 1 1 d . . . H11 H 0.8192 0.1359 -0.0057 0.026 Uiso 1 1 calc R . . C12 C 0.5978(2) 0.1703(2) 0.15345(6) 0.0287(4) Uani 1 1 d . . . H12A H 0.4685 0.1852 0.1427 0.034 Uiso 1 1 calc R . . H12B H 0.5886 0.2559 0.1774 0.034 Uiso 1 1 calc R . . C13 C 0.6677(3) -0.0133(3) 0.17784(7) 0.0408(5) Uani 1 1 d . . . H13A H 0.6746 -0.0982 0.1543 0.061 Uiso 1 1 calc R . . H13B H 0.5788 -0.0332 0.2061 0.061 Uiso 1 1 calc R . . H13C H 0.7950 -0.0276 0.1889 0.061 Uiso 1 1 calc R . . C14 C 1.0782(2) 0.2786(2) 0.23450(6) 0.0257(4) Uani 1 1 d . . . H14 H 1.1752 0.2069 0.2538 0.031 Uiso 1 1 calc R . . C15 C 1.0546(2) 0.2305(2) 0.18936(6) 0.0229(3) Uani 1 1 d . . . H15 H 1.1352 0.1263 0.1777 0.028 Uiso 1 1 calc R . . C16 C 1.1516(2) 0.3819(2) 0.07665(6) 0.0213(3) Uani 1 1 d . . . H16 H 1.1610 0.4252 0.1067 0.026 Uiso 1 1 calc R . . C17 C 1.2795(2) 0.4002(2) 0.03820(6) 0.0235(3) Uani 1 1 d . . . H17 H 1.3780 0.4555 0.0416 0.028 Uiso 1 1 calc R . . C18 C 0.2771(2) 0.6885(2) 0.52842(6) 0.0250(4) Uani 1 1 d . . . H18 H 0.2133 0.6754 0.5602 0.030 Uiso 1 1 calc R . . C19 C 0.4402(2) 0.7452(2) 0.52220(6) 0.0228(3) Uani 1 1 d . . . H19 H 0.4910 0.7704 0.5500 0.027 Uiso 1 1 calc R . . C20 C 0.5352(2) 0.7671(2) 0.47516(6) 0.0195(3) Uani 1 1 d . . . C21 C 0.5552(2) 0.7425(2) 0.38769(6) 0.0190(3) Uani 1 1 d . . . C22 C 0.4685(2) 0.6976(2) 0.34609(6) 0.0207(3) Uani 1 1 d . . . C23 C 0.3716(2) 0.8314(2) 0.31381(6) 0.0220(3) Uani 1 1 d . . . H23 H 0.3517 0.9502 0.3199 0.026 Uiso 1 1 calc R . . C24 C 0.3041(2) 0.7912(2) 0.27266(6) 0.0247(4) Uani 1 1 d . . . H24 H 0.2397 0.8828 0.2503 0.030 Uiso 1 1 calc R . . C25 C 0.3298(2) 0.6190(2) 0.26388(6) 0.0279(4) Uani 1 1 d . . . H25 H 0.2852 0.5922 0.2353 0.033 Uiso 1 1 calc R . . C26 C 0.2050(2) 0.6500(2) 0.48717(6) 0.0238(4) Uani 1 1 d . . . H26 H 0.0912 0.6104 0.4910 0.029 Uiso 1 1 calc R . . C27 C 0.2960(2) 0.6685(2) 0.44187(6) 0.0211(3) Uani 1 1 d . . . H27 H 0.2450 0.6414 0.4144 0.025 Uiso 1 1 calc R . . C28 C 0.7005(2) 0.8289(2) 0.46784(6) 0.0223(3) Uani 1 1 d . . . H28 H 0.7511 0.8586 0.4950 0.027 Uiso 1 1 calc R . . C29 C 0.7892(2) 0.8469(2) 0.42210(6) 0.0224(3) Uani 1 1 d . . . H29 H 0.9002 0.8908 0.4175 0.027 Uiso 1 1 calc R . . C30 C 0.7181(2) 0.8011(2) 0.38143(6) 0.0209(3) Uani 1 1 d . . . C31 C 0.8232(2) 0.8222(2) 0.33162(6) 0.0269(4) Uani 1 1 d . . . H31A H 0.7799 0.7568 0.3087 0.032 Uiso 1 1 calc R . . H31B H 0.9619 0.7712 0.3342 0.032 Uiso 1 1 calc R . . C32 C 0.7902(3) 1.0133(3) 0.31104(7) 0.0359(4) Uani 1 1 d . . . H32A H 0.6533 1.0638 0.3079 0.054 Uiso 1 1 calc R . . H32B H 0.8606 1.0212 0.2787 0.054 Uiso 1 1 calc R . . H32C H 0.8356 1.0781 0.3333 0.054 Uiso 1 1 calc R . . C33 C 0.4925(3) 0.5242(2) 0.33740(6) 0.0292(4) Uani 1 1 d . . . H33 H 0.5584 0.4320 0.3593 0.035 Uiso 1 1 calc R . . C34 C 0.4205(3) 0.4859(2) 0.29674(7) 0.0330(4) Uani 1 1 d . . . H34 H 0.4336 0.3673 0.2915 0.040 Uiso 1 1 calc R . . B1 B 0.1745(3) 0.2096(3) 0.39873(7) 0.0243(4) Uani 1 1 d . . . B2 B 0.2888(3) 0.8095(3) 0.10803(7) 0.0250(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 F1 0.0343(6) 0.0273(5) 0.0374(6) -0.0112(5) 0.0048(4) -0.0104(4) F2 0.0699(9) 0.0584(8) 0.0402(7) 0.0014(6) -0.0325(6) -0.0202(7) F3 0.0426(6) 0.0283(6) 0.0382(6) 0.0022(5) -0.0003(5) -0.0132(5) F4 0.0343(6) 0.0412(7) 0.0490(7) -0.0176(5) 0.0126(5) -0.0118(5) F5 0.0679(9) 0.0452(8) 0.0519(8) 0.0146(6) -0.0143(6) -0.0277(6) F6 0.0430(6) 0.0343(6) 0.0366(6) -0.0108(5) -0.0005(5) -0.0002(5) F7 0.0297(6) 0.0780(9) 0.0391(7) -0.0066(6) -0.0069(5) -0.0119(6) F8 0.0717(9) 0.0481(7) 0.0275(6) -0.0182(5) -0.0167(5) 0.0047(6) N1 0.0204(6) 0.0164(6) 0.0184(7) -0.0012(5) -0.0027(5) -0.0030(5) N2 0.0180(6) 0.0174(7) 0.0192(7) -0.0013(5) -0.0029(5) -0.0030(5) C1 0.0248(8) 0.0222(8) 0.0242(8) -0.0002(7) 0.0027(6) -0.0031(7) C2 0.0287(8) 0.0173(8) 0.0197(8) -0.0021(6) -0.0027(6) -0.0008(6) C3 0.0241(8) 0.0160(8) 0.0186(8) -0.0012(6) -0.0040(6) -0.0015(6) C4 0.0207(7) 0.0164(7) 0.0191(8) -0.0010(6) -0.0024(6) -0.0009(6) C5 0.0235(8) 0.0217(8) 0.0184(8) -0.0019(6) -0.0007(6) -0.0068(6) C6 0.0283(9) 0.0258(9) 0.0242(9) -0.0043(7) -0.0045(7) -0.0007(7) C7 0.0348(10) 0.0284(9) 0.0261(9) -0.0082(7) -0.0019(7) -0.0023(7) C8 0.0326(9) 0.0302(9) 0.0203(8) -0.0036(7) -0.0024(7) -0.0113(7) C9 0.0211(8) 0.0189(8) 0.0244(8) -0.0013(6) -0.0023(6) -0.0031(6) C10 0.0220(8) 0.0187(8) 0.0285(9) -0.0013(7) -0.0057(6) -0.0044(6) C11 0.0249(8) 0.0169(8) 0.0224(8) -0.0022(6) -0.0073(6) -0.0020(6) C12 0.0262(9) 0.0342(10) 0.0274(9) -0.0044(8) 0.0029(7) -0.0120(7) C13 0.0433(11) 0.0463(12) 0.0327(11) 0.0082(9) 0.0010(8) -0.0187(10) C14 0.0276(8) 0.0256(9) 0.0239(9) 0.0022(7) -0.0060(7) -0.0073(7) C15 0.0234(8) 0.0219(8) 0.0220(8) -0.0011(7) -0.0028(6) -0.0033(6) C16 0.0228(8) 0.0176(8) 0.0237(8) -0.0018(6) -0.0059(6) -0.0038(6) C17 0.0224(8) 0.0207(8) 0.0271(9) 0.0014(7) -0.0032(6) -0.0058(6) C18 0.0231(8) 0.0241(9) 0.0227(8) 0.0009(7) 0.0012(6) 0.0006(6) C19 0.0241(8) 0.0224(8) 0.0192(8) -0.0025(6) -0.0034(6) -0.0005(6) C20 0.0207(7) 0.0170(8) 0.0198(8) -0.0029(6) -0.0041(6) -0.0015(6) C21 0.0207(7) 0.0168(8) 0.0187(8) -0.0020(6) -0.0021(6) -0.0029(6) C22 0.0204(7) 0.0234(8) 0.0195(8) -0.0019(6) -0.0005(6) -0.0079(6) C23 0.0216(8) 0.0239(8) 0.0207(8) -0.0036(7) 0.0005(6) -0.0063(6) C24 0.0232(8) 0.0299(9) 0.0206(8) -0.0011(7) -0.0022(6) -0.0065(7) C25 0.0296(9) 0.0368(10) 0.0219(9) -0.0065(7) -0.0024(7) -0.0149(8) C26 0.0198(8) 0.0215(8) 0.0283(9) 0.0010(7) -0.0017(6) -0.0035(6) C27 0.0188(7) 0.0187(8) 0.0257(8) 0.0006(6) -0.0050(6) -0.0045(6) C28 0.0208(8) 0.0216(8) 0.0242(8) -0.0046(7) -0.0052(6) -0.0021(6) C29 0.0189(7) 0.0220(8) 0.0266(9) -0.0026(7) -0.0039(6) -0.0048(6) C30 0.0195(7) 0.0188(8) 0.0238(8) -0.0035(6) -0.0016(6) -0.0030(6) C31 0.0243(8) 0.0339(10) 0.0239(9) -0.0076(7) 0.0037(6) -0.0101(7) C32 0.0410(11) 0.0400(11) 0.0292(10) -0.0009(8) 0.0060(8) -0.0192(9) C33 0.0400(10) 0.0230(9) 0.0256(9) -0.0002(7) -0.0083(7) -0.0084(7) C34 0.0470(11) 0.0252(9) 0.0313(10) -0.0064(8) -0.0069(8) -0.0136(8) B1 0.0281(9) 0.0251(10) 0.0213(9) -0.0037(8) -0.0020(7) -0.0087(8) B2 0.0290(10) 0.0259(10) 0.0204(9) -0.0058(8) -0.0051(7) -0.0046(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 F1 B1 1.393(2) . ? F2 B1 1.367(2) . ? F3 B1 1.396(2) . ? F4 B1 1.387(2) . ? F5 B2 1.385(2) . ? F6 B2 1.385(2) . ? F7 B2 1.382(2) . ? F8 B2 1.375(2) . ? N1 C3 1.385(2) . ? N1 C16 1.386(2) . ? N1 C4 1.4029(19) . ? N2 C27 1.3839(19) . ? N2 C20 1.3875(19) . ? N2 C21 1.4080(19) . ? C1 C2 1.359(2) . ? C1 C17 1.410(2) . ? C1 H1 0.9500 . ? C2 C3 1.412(2) . ? C2 H2 0.9500 . ? C3 C11 1.405(2) . ? C4 C9 1.371(2) . ? C4 C5 1.483(2) . ? C5 C6 1.393(2) . ? C5 C15 1.394(2) . ? C6 C7 1.388(2) . ? C6 H6 0.9500 . ? C7 C8 1.382(3) . ? C7 H7 0.9500 . ? C8 C14 1.382(2) . ? C8 H8 0.9500 . ? C9 C10 1.412(2) . ? C9 C12 1.505(2) . ? C10 C11 1.357(2) . ? C10 H10 0.9500 . ? C11 H11 0.9500 . ? C12 C13 1.512(3) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 C15 1.386(2) . ? C14 H14 0.9500 . ? C15 H15 0.9500 . ? C16 C17 1.350(2) . ? C16 H16 0.9500 . ? C17 H17 0.9500 . ? C18 C19 1.361(2) . ? C18 C26 1.401(2) . ? C18 H18 0.9500 . ? C19 C20 1.413(2) . ? C19 H19 0.9500 . ? C20 C28 1.398(2) . ? C21 C30 1.368(2) . ? C21 C22 1.489(2) . ? C22 C23 1.390(2) . ? C22 C33 1.390(2) . ? C23 C24 1.387(2) . ? C23 H23 0.9500 . ? C24 C25 1.380(2) . ? C24 H24 0.9500 . ? C25 C34 1.380(3) . ? C25 H25 0.9500 . ? C26 C27 1.356(2) . ? C26 H26 0.9500 . ? C27 H27 0.9500 . ? C28 C29 1.359(2) . ? C28 H28 0.9500 . ? C29 C30 1.408(2) . ? C29 H29 0.9500 . ? C30 C31 1.507(2) . ? C31 C32 1.521(3) . ? C31 H31A 0.9900 . ? C31 H31B 0.9900 . ? C32 H32A 0.9800 . ? C32 H32B 0.9800 . ? C32 H32C 0.9800 . ? C33 C34 1.385(2) . ? C33 H33 0.9500 . ? C34 H34 0.9500 . ? 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 C16 119.01(13) . . ? C3 N1 C4 120.79(13) . . ? C16 N1 C4 120.19(13) . . ? C27 N2 C20 119.36(13) . . ? C27 N2 C21 120.20(13) . . ? C20 N2 C21 120.44(12) . . ? C2 C1 C17 118.34(15) . . ? C2 C1 H1 120.8 . . ? C17 C1 H1 120.8 . . ? C1 C2 C3 121.23(15) . . ? C1 C2 H2 119.4 . . ? C3 C2 H2 119.4 . . ? N1 C3 C11 118.70(14) . . ? N1 C3 C2 119.20(14) . . ? C11 C3 C2 122.09(15) . . ? C9 C4 N1 119.70(14) . . ? C9 C4 C5 122.57(14) . . ? N1 C4 C5 117.71(13) . . ? C6 C5 C15 119.86(15) . . ? C6 C5 C4 120.16(14) . . ? C15 C5 C4 119.94(14) . . ? C7 C6 C5 119.63(16) . . ? C7 C6 H6 120.2 . . ? C5 C6 H6 120.2 . . ? C8 C7 C6 120.41(16) . . ? C8 C7 H7 119.8 . . ? C6 C7 H7 119.8 . . ? C14 C8 C7 119.98(16) . . ? C14 C8 H8 120.0 . . ? C7 C8 H8 120.0 . . ? C4 C9 C10 119.57(14) . . ? C4 C9 C12 121.44(15) . . ? C10 C9 C12 118.86(14) . . ? C11 C10 C9 120.53(15) . . ? C11 C10 H10 119.7 . . ? C9 C10 H10 119.7 . . ? C10 C11 C3 120.67(15) . . ? C10 C11 H11 119.7 . . ? C3 C11 H11 119.7 . . ? C9 C12 C13 110.94(14) . . ? C9 C12 H12A 109.5 . . ? C13 C12 H12A 109.5 . . ? C9 C12 H12B 109.5 . . ? C13 C12 H12B 109.5 . . ? H12A C12 H12B 108.0 . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C8 C14 C15 120.37(15) . . ? C8 C14 H14 119.8 . . ? C15 C14 H14 119.8 . . ? C14 C15 C5 119.74(15) . . ? C14 C15 H15 120.1 . . ? C5 C15 H15 120.1 . . ? C17 C16 N1 121.35(15) . . ? C17 C16 H16 119.3 . . ? N1 C16 H16 119.3 . . ? C16 C17 C1 120.77(15) . . ? C16 C17 H17 119.6 . . ? C1 C17 H17 119.6 . . ? C19 C18 C26 118.78(15) . . ? C19 C18 H18 120.6 . . ? C26 C18 H18 120.6 . . ? C18 C19 C20 121.19(15) . . ? C18 C19 H19 119.4 . . ? C20 C19 H19 119.4 . . ? N2 C20 C28 119.10(14) . . ? N2 C20 C19 118.82(14) . . ? C28 C20 C19 122.09(14) . . ? C30 C21 N2 119.51(14) . . ? C30 C21 C22 122.65(14) . . ? N2 C21 C22 117.83(13) . . ? C23 C22 C33 119.54(15) . . ? C23 C22 C21 119.33(14) . . ? C33 C22 C21 121.02(14) . . ? C24 C23 C22 119.84(15) . . ? C24 C23 H23 120.1 . . ? C22 C23 H23 120.1 . . ? C25 C24 C23 120.48(16) . . ? C25 C24 H24 119.8 . . ? C23 C24 H24 119.8 . . ? C34 C25 C24 119.71(16) . . ? C34 C25 H25 120.1 . . ? C24 C25 H25 120.1 . . ? C27 C26 C18 120.66(15) . . ? C27 C26 H26 119.7 . . ? C18 C26 H26 119.7 . . ? C26 C27 N2 121.19(15) . . ? C26 C27 H27 119.4 . . ? N2 C27 H27 119.4 . . ? C29 C28 C20 120.49(15) . . ? C29 C28 H28 119.8 . . ? C20 C28 H28 119.8 . . ? C28 C29 C30 120.59(15) . . ? C28 C29 H29 119.7 . . ? C30 C29 H29 119.7 . . ? C21 C30 C29 119.84(14) . . ? C21 C30 C31 121.80(14) . . ? C29 C30 C31 118.34(14) . . ? C30 C31 C32 112.10(14) . . ? C30 C31 H31A 109.2 . . ? C32 C31 H31A 109.2 . . ? C30 C31 H31B 109.2 . . ? C32 C31 H31B 109.2 . . ? H31A C31 H31B 107.9 . . ? 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 C22 119.98(16) . . ? C34 C33 H33 120.0 . . ? C22 C33 H33 120.0 . . ? C25 C34 C33 120.39(16) . . ? C25 C34 H34 119.8 . . ? C33 C34 H34 119.8 . . ? F2 B1 F4 111.32(15) . . ? F2 B1 F1 110.03(15) . . ? F4 B1 F1 109.24(14) . . ? F2 B1 F3 109.24(15) . . ? F4 B1 F3 108.20(15) . . ? F1 B1 F3 108.74(14) . . ? F8 B2 F7 110.34(15) . . ? F8 B2 F5 110.26(15) . . ? F7 B2 F5 108.56(15) . . ? F8 B2 F6 109.16(15) . . ? F7 B2 F6 109.31(15) . . ? F5 B2 F6 109.19(15) . . ? _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 28.34 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 0.334 _refine_diff_density_min -0.352 _refine_diff_density_rms 0.087 _database_code_depnum_ccdc_archive 'CCDC 948579' ####################################################################### # # 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_130111lt_0m _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C36 H32 B2 F8 N2 O4' _chemical_formula_weight 730.26 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' 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' _symmetry_cell_setting ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.5920(2) _cell_length_b 11.1165(2) _cell_length_c 14.8645(3) _cell_angle_alpha 89.8660(10) _cell_angle_beta 69.4220(10) _cell_angle_gamma 88.0730(10) _cell_volume 1637.55(5) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9961 _cell_measurement_theta_min 1.46 _cell_measurement_theta_max 28.36 _exptl_crystal_description Lump _exptl_crystal_colour black _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.481 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 752 _exptl_absorpt_coefficient_mu 0.126 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8900 _exptl_absorpt_correction_T_max 0.9486 _exptl_absorpt_process_details 'SADABS V2008/1 (Bruker AXS)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 8.3333 _diffrn_reflns_number 29457 _diffrn_reflns_av_R_equivalents 0.0356 _diffrn_reflns_av_sigmaI/netI 0.0394 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.46 _diffrn_reflns_theta_max 28.36 _reflns_number_total 8105 _reflns_number_gt 5910 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker AXS, 2010)' _computing_cell_refinement 'SAINT V7.68A (Bruker AXS, 2009)' _computing_data_reduction 'SAINT V7.68A (Bruker AXS, 2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 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^)+(0.1246P)^2^+0.1161P] 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 8105 _refine_ls_number_parameters 483 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0783 _refine_ls_R_factor_gt 0.0514 _refine_ls_wR_factor_ref 0.1990 _refine_ls_wR_factor_gt 0.1578 _refine_ls_goodness_of_fit_ref 1.103 _refine_ls_restrained_S_all 1.103 _refine_ls_shift/su_max 0.003 _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 0.12545(16) 0.38917(14) 0.40063(11) 0.0172(3) Uani 1 1 d . . . N2 N 0.48913(16) -0.09661(14) 0.11833(11) 0.0190(3) Uani 1 1 d . . . O1 O 0.33218(14) 0.45287(13) 0.51598(10) 0.0244(3) Uani 1 1 d . . . O2 O 0.42163(14) 0.34543(12) 0.37756(10) 0.0237(3) Uani 1 1 d . . . O3 O 0.79291(15) -0.00759(13) -0.01616(10) 0.0260(3) Uani 1 1 d . . . O4 O 0.77825(13) -0.12267(12) 0.11203(10) 0.0215(3) Uani 1 1 d . . . B1 B 0.2157(2) 0.3969(2) 0.12077(17) 0.0241(5) Uani 1 1 d . . . B2 B 0.8782(2) 0.91245(19) 0.37467(17) 0.0224(5) Uani 1 1 d . . . F1 F 0.2037(2) 0.3354(2) 0.04130(18) 0.0498(7) Uani 0.705(3) 1 d P . . F1' F 0.1949(6) 0.2844(6) 0.0984(5) 0.0498(7) Uani 0.295(3) 1 d P . . F2 F 0.3426(3) 0.4394(2) 0.0924(3) 0.0732(12) Uani 0.761(6) 1 d P . . F2' F 0.3128(8) 0.4392(8) 0.0468(11) 0.0732(12) Uani 0.239(6) 1 d P . . F3 F 0.11599(13) 0.48829(12) 0.14414(10) 0.0351(5) Uani 0.999(5) 1 d P . . F4 F 0.1814(3) 0.3160(2) 0.19470(16) 0.0535(7) Uani 0.669(3) 1 d P . . F4' F 0.2615(5) 0.3879(5) 0.1999(3) 0.0535(7) Uani 0.331(3) 1 d P . . F5 F 1.01548(13) 0.91636(11) 0.35817(10) 0.0353(3) Uani 1 1 d . . . F6 F 0.84907(19) 0.97746(13) 0.30400(12) 0.0481(7) Uani 0.930(6) 1 d P . . F7 F 0.80766(14) 0.96553(12) 0.46297(10) 0.0388(4) Uani 1 1 d . . . F8 F 0.84131(14) 0.79421(11) 0.37403(10) 0.0345(3) Uani 1 1 d . . . C1 C 0.22678(19) 0.46743(16) 0.39965(13) 0.0176(4) Uani 1 1 d . . . C2 C 0.22292(19) 0.58484(16) 0.37229(13) 0.0176(4) Uani 1 1 d . . . C3 C 0.10714(19) 0.62925(17) 0.35359(14) 0.0195(4) Uani 1 1 d . . . H3A H 0.0999 0.7117 0.3386 0.023 Uiso 1 1 calc R . . C4 C 0.0068(2) 0.55439(17) 0.35701(14) 0.0193(4) Uani 1 1 d . . . H4A H -0.0707 0.5855 0.3455 0.023 Uiso 1 1 calc R . . C5 C 0.01611(19) 0.43145(16) 0.37741(13) 0.0176(4) Uani 1 1 d . . . C6 C -0.0811(2) 0.34941(17) 0.37410(14) 0.0222(4) Uani 1 1 d . . . H6A H -0.1569 0.3778 0.3592 0.027 Uiso 1 1 calc R . . C7 C -0.0682(2) 0.23067(18) 0.39184(15) 0.0235(4) Uani 1 1 d . . . H7A H -0.1316 0.1755 0.3861 0.028 Uiso 1 1 calc R . . C8 C 0.0406(2) 0.19096(17) 0.41878(14) 0.0227(4) Uani 1 1 d . . . H8A H 0.0489 0.1087 0.4339 0.027 Uiso 1 1 calc R . . C9 C 0.1336(2) 0.26876(17) 0.42340(14) 0.0207(4) Uani 1 1 d . . . H9A H 0.2059 0.2404 0.4426 0.025 Uiso 1 1 calc R . . C10 C 0.33313(19) 0.42085(16) 0.43861(14) 0.0189(4) Uani 1 1 d . . . C11 C 0.5338(2) 0.29629(18) 0.40485(17) 0.0268(5) Uani 1 1 d . . . H11A H 0.5301 0.3325 0.4665 0.032 Uiso 1 1 calc R . . H11B H 0.6212 0.3152 0.3550 0.032 Uiso 1 1 calc R . . C12 C 0.5208(2) 0.16245(19) 0.41461(16) 0.0260(4) Uani 1 1 d . . . H12A H 0.5946 0.1280 0.4329 0.039 Uiso 1 1 calc R . . H12B H 0.5250 0.1274 0.3531 0.039 Uiso 1 1 calc R . . H12C H 0.4342 0.1446 0.4642 0.039 Uiso 1 1 calc R . . C13 C 0.33621(19) 0.66602(17) 0.36003(14) 0.0194(4) Uani 1 1 d . . . C14 C 0.4703(2) 0.62521(18) 0.31809(14) 0.0229(4) Uani 1 1 d . . . H14A H 0.4904 0.5434 0.2985 0.027 Uiso 1 1 calc R . . C15 C 0.5744(2) 0.7037(2) 0.30489(15) 0.0276(5) Uani 1 1 d . . . H15A H 0.6655 0.6748 0.2774 0.033 Uiso 1 1 calc R . . C16 C 0.5464(2) 0.82388(19) 0.33160(15) 0.0265(5) Uani 1 1 d . . . H16A H 0.6180 0.8773 0.3223 0.032 Uiso 1 1 calc R . . C17 C 0.4133(2) 0.86562(18) 0.37194(15) 0.0247(4) Uani 1 1 d . . . H17A H 0.3938 0.9480 0.3901 0.030 Uiso 1 1 calc R . . C18 C 0.3084(2) 0.78780(17) 0.38598(14) 0.0215(4) Uani 1 1 d . . . H18A H 0.2175 0.8172 0.4132 0.026 Uiso 1 1 calc R . . C19 C 0.58450(19) -0.01117(17) 0.11451(14) 0.0191(4) Uani 1 1 d . . . C20 C 0.5456(2) 0.10304(17) 0.15094(14) 0.0207(4) Uani 1 1 d . . . C21 C 0.4050(2) 0.13324(19) 0.19096(15) 0.0249(4) Uani 1 1 d . . . H21A H 0.3756 0.2122 0.2154 0.030 Uiso 1 1 calc R . . C22 C 0.3127(2) 0.04982(19) 0.19443(15) 0.0251(4) Uani 1 1 d . . . H22A H 0.2193 0.0714 0.2214 0.030 Uiso 1 1 calc R . . C23 C 0.35249(19) -0.06804(18) 0.15897(14) 0.0214(4) Uani 1 1 d . . . C24 C 0.2594(2) -0.15641(19) 0.16239(14) 0.0239(4) Uani 1 1 d . . . H24A H 0.1656 -0.1366 0.1896 0.029 Uiso 1 1 calc R . . C25 C 0.3005(2) -0.27010(19) 0.12759(15) 0.0245(4) Uani 1 1 d . . . H25A H 0.2367 -0.3298 0.1316 0.029 Uiso 1 1 calc R . . C26 C 0.4400(2) -0.29652(18) 0.08562(15) 0.0243(4) Uani 1 1 d . . . H26A H 0.4707 -0.3749 0.0605 0.029 Uiso 1 1 calc R . . C27 C 0.5311(2) -0.21157(18) 0.08061(14) 0.0222(4) Uani 1 1 d . . . H27A H 0.6247 -0.2308 0.0510 0.027 Uiso 1 1 calc R . . C28 C 0.7315(2) -0.04688(16) 0.06160(14) 0.0192(4) Uani 1 1 d . . . C29 C 0.9211(2) -0.16102(19) 0.06682(16) 0.0268(5) Uani 1 1 d . . . H29A H 0.9799 -0.0971 0.0739 0.032 Uiso 1 1 calc R . . H29B H 0.9428 -0.1774 -0.0025 0.032 Uiso 1 1 calc R . . C30 C 0.9427(2) -0.2731(2) 0.11646(19) 0.0344(5) Uani 1 1 d . . . H30A H 1.0373 -0.3010 0.0883 0.052 Uiso 1 1 calc R . . H30B H 0.8844 -0.3357 0.1086 0.052 Uiso 1 1 calc R . . H30C H 0.9206 -0.2558 0.1850 0.052 Uiso 1 1 calc R . . C31 C 0.6454(2) 0.19483(18) 0.14902(14) 0.0216(4) Uani 1 1 d . . . C32 C 0.7606(2) 0.16538(18) 0.17131(14) 0.0224(4) Uani 1 1 d . . . H32A H 0.7757 0.0855 0.1890 0.027 Uiso 1 1 calc R . . C33 C 0.8530(2) 0.2534(2) 0.16747(15) 0.0271(5) Uani 1 1 d . . . H33A H 0.9310 0.2333 0.1826 0.033 Uiso 1 1 calc R . . C34 C 0.8316(2) 0.3700(2) 0.14167(17) 0.0307(5) Uani 1 1 d . . . H34A H 0.8961 0.4292 0.1373 0.037 Uiso 1 1 calc R . . C35 C 0.7160(2) 0.4001(2) 0.12223(16) 0.0305(5) Uani 1 1 d . . . H35A H 0.7004 0.4805 0.1059 0.037 Uiso 1 1 calc R . . C36 C 0.6230(2) 0.31383(19) 0.12636(15) 0.0264(4) Uani 1 1 d . . . H36A H 0.5434 0.3356 0.1137 0.032 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0182(8) 0.0156(7) 0.0183(8) -0.0004(6) -0.0070(6) -0.0014(6) N2 0.0192(8) 0.0213(8) 0.0176(8) -0.0002(6) -0.0082(6) 0.0021(6) O1 0.0261(8) 0.0260(7) 0.0233(7) -0.0017(6) -0.0117(6) 0.0015(6) O2 0.0209(7) 0.0238(7) 0.0290(8) -0.0067(6) -0.0125(6) 0.0053(6) O3 0.0281(8) 0.0274(7) 0.0214(7) 0.0036(6) -0.0074(6) -0.0005(6) O4 0.0177(7) 0.0226(7) 0.0229(7) 0.0041(5) -0.0060(6) 0.0026(5) B1 0.0245(12) 0.0232(11) 0.0219(11) -0.0024(9) -0.0047(9) 0.0007(9) B2 0.0247(12) 0.0165(10) 0.0298(12) 0.0000(9) -0.0145(10) 0.0003(8) F1 0.0413(11) 0.0636(16) 0.0489(15) -0.0303(12) -0.0228(11) 0.0160(10) F1' 0.0413(11) 0.0636(16) 0.0489(15) -0.0303(12) -0.0228(11) 0.0160(10) F2 0.0198(11) 0.0372(10) 0.161(3) -0.0264(15) -0.0290(13) 0.0008(8) F2' 0.0198(11) 0.0372(10) 0.161(3) -0.0264(15) -0.0290(13) 0.0008(8) F3 0.0320(8) 0.0336(8) 0.0416(9) -0.0055(6) -0.0161(6) 0.0106(6) F4 0.0517(15) 0.0514(14) 0.0381(11) 0.0166(11) 0.0054(11) 0.0289(10) F4' 0.0517(15) 0.0514(14) 0.0381(11) 0.0166(11) 0.0054(11) 0.0289(10) F5 0.0249(7) 0.0271(7) 0.0488(8) -0.0042(6) -0.0068(6) -0.0004(5) F6 0.0821(14) 0.0277(8) 0.0572(12) 0.0133(7) -0.0525(10) -0.0084(8) F7 0.0321(8) 0.0301(7) 0.0442(8) -0.0056(6) -0.0014(6) 0.0051(6) F8 0.0409(8) 0.0180(6) 0.0534(9) 0.0016(6) -0.0274(7) -0.0034(5) C1 0.0162(9) 0.0180(9) 0.0180(9) -0.0019(7) -0.0051(7) -0.0011(7) C2 0.0198(9) 0.0156(8) 0.0170(9) -0.0009(7) -0.0060(7) -0.0006(7) C3 0.0200(9) 0.0168(9) 0.0209(9) 0.0006(7) -0.0064(8) -0.0006(7) C4 0.0192(9) 0.0199(9) 0.0192(9) -0.0006(7) -0.0071(7) 0.0008(7) C5 0.0172(9) 0.0186(9) 0.0167(9) -0.0015(7) -0.0054(7) -0.0010(7) C6 0.0201(10) 0.0227(10) 0.0245(10) -0.0020(8) -0.0086(8) -0.0024(8) C7 0.0242(10) 0.0212(9) 0.0251(10) -0.0022(8) -0.0082(8) -0.0066(8) C8 0.0277(11) 0.0176(9) 0.0223(10) -0.0004(7) -0.0081(8) -0.0029(8) C9 0.0248(10) 0.0170(9) 0.0207(10) 0.0010(7) -0.0084(8) 0.0003(7) C10 0.0180(9) 0.0147(8) 0.0238(10) 0.0022(7) -0.0069(8) -0.0027(7) C11 0.0199(10) 0.0239(10) 0.0415(13) -0.0056(9) -0.0172(9) 0.0036(8) C12 0.0272(11) 0.0251(10) 0.0277(11) 0.0010(8) -0.0124(9) -0.0001(8) C13 0.0204(10) 0.0204(9) 0.0179(9) 0.0036(7) -0.0072(7) -0.0032(7) C14 0.0218(10) 0.0225(9) 0.0232(10) 0.0022(8) -0.0062(8) -0.0021(8) C15 0.0189(10) 0.0360(12) 0.0251(11) 0.0055(9) -0.0042(8) -0.0048(8) C16 0.0277(11) 0.0293(11) 0.0262(11) 0.0083(8) -0.0132(9) -0.0129(9) C17 0.0300(11) 0.0218(9) 0.0253(10) 0.0023(8) -0.0129(9) -0.0072(8) C18 0.0221(10) 0.0203(9) 0.0221(10) 0.0026(7) -0.0078(8) -0.0036(7) C19 0.0206(9) 0.0209(9) 0.0189(9) 0.0011(7) -0.0108(8) 0.0012(7) C20 0.0234(10) 0.0210(9) 0.0215(10) -0.0013(7) -0.0129(8) 0.0029(7) C21 0.0248(10) 0.0244(10) 0.0280(11) -0.0055(8) -0.0128(8) 0.0058(8) C22 0.0199(10) 0.0284(10) 0.0283(11) -0.0047(8) -0.0109(8) 0.0062(8) C23 0.0189(10) 0.0283(10) 0.0186(9) 0.0012(8) -0.0088(8) 0.0013(8) C24 0.0206(10) 0.0311(11) 0.0204(10) 0.0027(8) -0.0079(8) -0.0006(8) C25 0.0267(11) 0.0262(10) 0.0241(10) 0.0053(8) -0.0130(8) -0.0050(8) C26 0.0298(11) 0.0213(9) 0.0238(10) 0.0002(8) -0.0123(8) 0.0002(8) C27 0.0235(10) 0.0218(9) 0.0223(10) -0.0020(7) -0.0097(8) 0.0035(7) C28 0.0216(10) 0.0167(8) 0.0208(10) -0.0009(7) -0.0095(8) -0.0005(7) C29 0.0159(10) 0.0276(10) 0.0342(12) 0.0018(9) -0.0059(8) 0.0033(8) C30 0.0255(11) 0.0320(12) 0.0458(14) 0.0053(10) -0.0134(10) 0.0064(9) C31 0.0238(10) 0.0219(9) 0.0201(9) -0.0036(7) -0.0090(8) 0.0018(7) C32 0.0239(10) 0.0235(9) 0.0210(10) -0.0046(7) -0.0098(8) 0.0045(8) C33 0.0250(11) 0.0330(11) 0.0244(10) -0.0060(8) -0.0101(8) 0.0004(8) C34 0.0304(12) 0.0275(11) 0.0319(12) -0.0045(9) -0.0079(9) -0.0050(9) C35 0.0392(13) 0.0235(10) 0.0293(11) -0.0007(8) -0.0128(10) 0.0003(9) C36 0.0303(11) 0.0250(10) 0.0268(11) -0.0040(8) -0.0143(9) 0.0038(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 N1 C9 1.387(2) . ? N1 C5 1.388(2) . ? N1 C1 1.400(2) . ? N2 C23 1.384(2) . ? N2 C27 1.391(2) . ? N2 C19 1.396(2) . ? O1 C10 1.201(2) . ? O2 C10 1.326(2) . ? O2 C11 1.472(2) . ? O3 C28 1.199(2) . ? O4 C28 1.322(2) . ? O4 C29 1.472(2) . ? B1 F2' 1.312(12) . ? B1 F1' 1.340(6) . ? B1 F2 1.360(4) . ? B1 F4 1.372(3) . ? B1 F3 1.393(3) . ? B1 F1 1.412(3) . ? B1 F4' 1.424(6) . ? B2 F7 1.383(3) . ? B2 F8 1.385(2) . ? B2 F5 1.389(3) . ? B2 F6 1.389(3) . ? F1 F1' 0.998(7) . ? F1 F2' 1.681(9) . ? F1' F4 1.432(6) . ? F2 F2' 0.843(13) . ? F2 F4' 1.638(6) . ? F4 F4' 1.206(6) . ? C1 C2 1.370(3) . ? C1 C10 1.513(3) . ? C2 C3 1.422(3) . ? C2 C13 1.485(2) . ? C3 C4 1.359(3) . ? C3 H3A 0.9500 . ? C4 C5 1.407(3) . ? C4 H4A 0.9500 . ? C5 C6 1.412(3) . ? C6 C7 1.357(3) . ? C6 H6A 0.9500 . ? C7 C8 1.404(3) . ? C7 H7A 0.9500 . ? C8 C9 1.352(3) . ? C8 H8A 0.9500 . ? C9 H9A 0.9500 . ? C11 C12 1.501(3) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 C14 1.395(3) . ? C13 C18 1.401(3) . ? C14 C15 1.389(3) . ? C14 H14A 0.9500 . ? C15 C16 1.387(3) . ? C15 H15A 0.9500 . ? C16 C17 1.388(3) . ? C16 H16A 0.9500 . ? C17 C18 1.388(3) . ? C17 H17A 0.9500 . ? C18 H18A 0.9500 . ? C19 C20 1.373(3) . ? C19 C28 1.517(3) . ? C20 C21 1.425(3) . ? C20 C31 1.487(3) . ? C21 C22 1.357(3) . ? C21 H21A 0.9500 . ? C22 C23 1.408(3) . ? C22 H22A 0.9500 . ? C23 C24 1.403(3) . ? C24 C25 1.365(3) . ? C24 H24A 0.9500 . ? C25 C26 1.408(3) . ? C25 H25A 0.9500 . ? C26 C27 1.356(3) . ? C26 H26A 0.9500 . ? C27 H27A 0.9500 . ? C29 C30 1.498(3) . ? C29 H29A 0.9900 . ? C29 H29B 0.9900 . ? C30 H30A 0.9800 . ? C30 H30B 0.9800 . ? C30 H30C 0.9800 . ? C31 C36 1.397(3) . ? C31 C32 1.401(3) . ? C32 C33 1.394(3) . ? C32 H32A 0.9500 . ? C33 C34 1.385(3) . ? C33 H33A 0.9500 . ? C34 C35 1.384(3) . ? C34 H34A 0.9500 . ? C35 C36 1.383(3) . ? C35 H35A 0.9500 . ? C36 H36A 0.9500 . ? 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 C9 N1 C5 119.22(16) . . ? C9 N1 C1 120.79(16) . . ? C5 N1 C1 119.98(15) . . ? C23 N2 C27 119.35(17) . . ? C23 N2 C19 120.65(16) . . ? C27 N2 C19 120.00(16) . . ? C10 O2 C11 117.71(15) . . ? C28 O4 C29 115.47(15) . . ? F2' B1 F1' 107.4(5) . . ? F2' B1 F2 36.7(5) . . ? F1' B1 F2 120.7(3) . . ? F2' B1 F4 146.4(5) . . ? F1' B1 F4 63.7(3) . . ? F2 B1 F4 117.0(3) . . ? F2' B1 F3 103.9(4) . . ? F1' B1 F3 123.2(3) . . ? F2 B1 F3 112.9(2) . . ? F4 B1 F3 107.61(19) . . ? F2' B1 F1 76.1(6) . . ? F1' B1 F1 42.4(3) . . ? F2 B1 F1 107.2(3) . . ? F4 B1 F1 105.7(2) . . ? F3 B1 F1 105.7(2) . . ? F2' B1 F4' 108.7(7) . . ? F1' B1 F4' 106.6(4) . . ? F2 B1 F4' 72.0(3) . . ? F4 B1 F4' 51.1(3) . . ? F3 B1 F4' 106.4(2) . . ? F1 B1 F4' 145.1(3) . . ? F7 B2 F8 109.91(18) . . ? F7 B2 F5 108.83(17) . . ? F8 B2 F5 110.02(17) . . ? F7 B2 F6 108.56(18) . . ? F8 B2 F6 110.27(17) . . ? F5 B2 F6 109.23(19) . . ? F1' F1 B1 64.9(4) . . ? F1' F1 F2' 102.9(6) . . ? B1 F1 F2' 49.3(5) . . ? F1 F1' B1 72.6(5) . . ? F1 F1' F4 131.1(6) . . ? B1 F1' F4 59.2(3) . . ? F2' F2 B1 68.6(7) . . ? F2' F2 F4' 124.2(8) . . ? B1 F2 F4' 55.8(3) . . ? F2 F2' B1 74.7(11) . . ? F2 F2' F1 120.6(11) . . ? B1 F2' F1 54.6(3) . . ? F4' F4 B1 66.7(3) . . ? F4' F4 F1' 114.0(4) . . ? B1 F4 F1' 57.0(3) . . ? F4 F4' B1 62.3(3) . . ? F4 F4' F2 109.0(4) . . ? B1 F4' F2 52.2(2) . . ? C2 C1 N1 121.05(17) . . ? C2 C1 C10 121.22(16) . . ? N1 C1 C10 117.49(16) . . ? C1 C2 C3 118.55(17) . . ? C1 C2 C13 122.20(17) . . ? C3 C2 C13 119.24(16) . . ? C4 C3 C2 120.39(17) . . ? C4 C3 H3A 119.8 . . ? C2 C3 H3A 119.8 . . ? C3 C4 C5 120.90(18) . . ? C3 C4 H4A 119.5 . . ? C5 C4 H4A 119.5 . . ? N1 C5 C4 118.80(16) . . ? N1 C5 C6 118.86(17) . . ? C4 C5 C6 122.34(18) . . ? C7 C6 C5 121.23(19) . . ? C7 C6 H6A 119.4 . . ? C5 C6 H6A 119.4 . . ? C6 C7 C8 118.77(18) . . ? C6 C7 H7A 120.6 . . ? C8 C7 H7A 120.6 . . ? C9 C8 C7 120.62(18) . . ? C9 C8 H8A 119.7 . . ? C7 C8 H8A 119.7 . . ? C8 C9 N1 121.17(18) . . ? C8 C9 H9A 119.4 . . ? N1 C9 H9A 119.4 . . ? O1 C10 O2 127.11(18) . . ? O1 C10 C1 121.00(17) . . ? O2 C10 C1 111.89(16) . . ? O2 C11 C12 108.21(16) . . ? O2 C11 H11A 110.1 . . ? C12 C11 H11A 110.1 . . ? O2 C11 H11B 110.1 . . ? C12 C11 H11B 110.1 . . ? H11A C11 H11B 108.4 . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C14 C13 C18 119.05(18) . . ? C14 C13 C2 121.34(17) . . ? C18 C13 C2 119.51(17) . . ? C15 C14 C13 120.30(19) . . ? C15 C14 H14A 119.9 . . ? C13 C14 H14A 119.9 . . ? C16 C15 C14 120.4(2) . . ? C16 C15 H15A 119.8 . . ? C14 C15 H15A 119.8 . . ? C15 C16 C17 119.61(18) . . ? C15 C16 H16A 120.2 . . ? C17 C16 H16A 120.2 . . ? C16 C17 C18 120.42(19) . . ? C16 C17 H17A 119.8 . . ? C18 C17 H17A 119.8 . . ? C17 C18 C13 120.16(19) . . ? C17 C18 H18A 119.9 . . ? C13 C18 H18A 119.9 . . ? C20 C19 N2 121.09(17) . . ? C20 C19 C28 121.62(17) . . ? N2 C19 C28 117.11(16) . . ? C19 C20 C21 118.26(18) . . ? C19 C20 C31 121.98(18) . . ? C21 C20 C31 119.75(17) . . ? C22 C21 C20 120.37(18) . . ? C22 C21 H21A 119.8 . . ? C20 C21 H21A 119.8 . . ? C21 C22 C23 121.41(18) . . ? C21 C22 H22A 119.3 . . ? C23 C22 H22A 119.3 . . ? N2 C23 C24 119.15(18) . . ? N2 C23 C22 118.19(18) . . ? C24 C23 C22 122.65(18) . . ? C25 C24 C23 121.57(19) . . ? C25 C24 H24A 119.2 . . ? C23 C24 H24A 119.2 . . ? C24 C25 C26 118.18(19) . . ? C24 C25 H25A 120.9 . . ? C26 C25 H25A 120.9 . . ? C27 C26 C25 120.91(19) . . ? C27 C26 H26A 119.5 . . ? C25 C26 H26A 119.5 . . ? C26 C27 N2 120.81(18) . . ? C26 C27 H27A 119.6 . . ? N2 C27 H27A 119.6 . . ? O3 C28 O4 126.86(18) . . ? O3 C28 C19 121.49(18) . . ? O4 C28 C19 111.64(16) . . ? O4 C29 C30 107.27(17) . . ? O4 C29 H29A 110.3 . . ? C30 C29 H29A 110.3 . . ? O4 C29 H29B 110.3 . . ? C30 C29 H29B 110.3 . . ? H29A C29 H29B 108.5 . . ? C29 C30 H30A 109.5 . . ? C29 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? C29 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? C36 C31 C32 118.98(18) . . ? C36 C31 C20 119.50(18) . . ? C32 C31 C20 121.50(18) . . ? C33 C32 C31 119.93(19) . . ? C33 C32 H32A 120.0 . . ? C31 C32 H32A 120.0 . . ? C34 C33 C32 120.4(2) . . ? C34 C33 H33A 119.8 . . ? C32 C33 H33A 119.8 . . ? C35 C34 C33 119.8(2) . . ? C35 C34 H34A 120.1 . . ? C33 C34 H34A 120.1 . . ? C36 C35 C34 120.4(2) . . ? C36 C35 H35A 119.8 . . ? C34 C35 H35A 119.8 . . ? C35 C36 C31 120.4(2) . . ? C35 C36 H36A 119.8 . . ? C31 C36 H36A 119.8 . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 28.36 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.791 _refine_diff_density_min -0.656 _refine_diff_density_rms 0.122 _database_code_depnum_ccdc_archive 'CCDC 948580'