# Electronic Supplementary Material (ESI) for RSC Advances # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # 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_120305c_0m _database_code_depnum_ccdc_archive 'CCDC 881436' #TrackingRef 'Name-1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H18 B2 F4 N4' _chemical_formula_weight 412.00 _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 Triclinic _symmetry_space_group_name_H-M P-1 _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.7199(12) _cell_length_b 7.7402(12) _cell_length_c 16.691(3) _cell_angle_alpha 102.954(2) _cell_angle_beta 93.559(2) _cell_angle_gamma 92.333(2) _cell_volume 968.6(3) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3744 _cell_measurement_theta_min 2.51 _cell_measurement_theta_max 27.39 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.413 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 424 _exptl_absorpt_coefficient_mu 0.111 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9835 _exptl_absorpt_correction_T_max 0.9868 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8349 _diffrn_reflns_av_R_equivalents 0.0199 _diffrn_reflns_av_sigmaI/netI 0.0287 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.51 _diffrn_reflns_theta_max 27.57 _reflns_number_total 4337 _reflns_number_gt 3188 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _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^)+(0.0746P)^2^+0.2026P] 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 4337 _refine_ls_number_parameters 273 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0649 _refine_ls_R_factor_gt 0.0494 _refine_ls_wR_factor_ref 0.1496 _refine_ls_wR_factor_gt 0.1390 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_restrained_S_all 1.046 _refine_ls_shift/su_max 0.179 _refine_ls_shift/su_mean 0.003 _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 0.3635(3) 0.2810(3) 0.09124(13) 0.0478(5) Uani 1 1 d . . . B2 B 1.2217(3) 0.6186(3) 0.40451(14) 0.0491(5) Uani 1 1 d . . . C1 C 0.3282(3) 0.2350(3) -0.06692(12) 0.0572(5) Uani 1 1 d . . . H1 H 0.3760 0.3457 -0.0695 0.069 Uiso 1 1 calc R . . C2 C 0.2558(3) 0.1068(3) -0.13428(13) 0.0667(6) Uani 1 1 d . . . H2 H 0.2465 0.1166 -0.1889 0.080 Uiso 1 1 calc R . . C3 C 0.2011(3) -0.0357(3) -0.10530(12) 0.0603(5) Uani 1 1 d . . . H3 H 0.1473 -0.1410 -0.1366 0.072 Uiso 1 1 calc R . . C4 C 0.2407(2) 0.0053(2) -0.01922(11) 0.0451(4) Uani 1 1 d . . . C5 C 0.2194(2) -0.0955(2) 0.03921(12) 0.0470(4) Uani 1 1 d . . . C6 C 0.2784(2) -0.0255(2) 0.12109(12) 0.0477(4) Uani 1 1 d . . . C7 C 0.2829(3) -0.1001(3) 0.19090(14) 0.0622(5) Uani 1 1 d . . . H7 H 0.2422 -0.2140 0.1923 0.075 Uiso 1 1 calc R . . C8 C 0.3581(3) 0.0256(3) 0.25612(14) 0.0703(6) Uani 1 1 d . . . H8 H 0.3781 0.0128 0.3100 0.084 Uiso 1 1 calc R . . C9 C 0.3992(3) 0.1761(3) 0.22707(12) 0.0611(5) Uani 1 1 d . . . H9 H 0.4509 0.2817 0.2591 0.073 Uiso 1 1 calc R . . C10 C 0.1362(3) -0.2786(3) 0.01450(15) 0.0641(5) Uani 1 1 d . . . H10A H 0.0664 -0.2914 -0.0363 0.096 Uiso 1 1 calc R . . H10B H 0.0640 -0.2989 0.0567 0.096 Uiso 1 1 calc R . . H10C H 0.2245 -0.3634 0.0073 0.096 Uiso 1 1 calc R . . C11 C 1.2853(3) 0.7041(3) 0.56305(12) 0.0554(5) Uani 1 1 d . . . H11 H 1.3968 0.6632 0.5643 0.066 Uiso 1 1 calc R . . C12 C 1.2044(3) 0.7922(3) 0.63182(13) 0.0615(5) Uani 1 1 d . . . H12 H 1.2517 0.8203 0.6861 0.074 Uiso 1 1 calc R . . C13 C 1.0428(3) 0.8297(3) 0.60456(12) 0.0554(5) Uani 1 1 d . . . H13 H 0.9598 0.8882 0.6370 0.066 Uiso 1 1 calc R . . C14 C 1.0246(2) 0.7638(2) 0.51851(11) 0.0449(4) Uani 1 1 d . . . C15 C 0.8838(2) 0.7582(2) 0.46181(11) 0.0449(4) Uani 1 1 d . . . C16 C 0.8949(2) 0.6724(2) 0.37972(11) 0.0464(4) Uani 1 1 d . . . C17 C 0.7695(3) 0.6376(3) 0.31205(13) 0.0587(5) Uani 1 1 d . . . H17 H 0.6558 0.6728 0.3124 0.070 Uiso 1 1 calc R . . C18 C 0.8469(3) 0.5421(3) 0.24587(13) 0.0682(6) Uani 1 1 d . . . H18 H 0.7951 0.5002 0.1929 0.082 Uiso 1 1 calc R . . C19 C 1.0174(3) 0.5194(3) 0.27245(12) 0.0626(5) Uani 1 1 d . . . H19 H 1.0986 0.4594 0.2394 0.075 Uiso 1 1 calc R . . C20 C 0.7189(3) 0.8402(3) 0.48906(14) 0.0605(5) Uani 1 1 d . . . H20A H 0.6709 0.8969 0.4478 0.091 Uiso 1 1 calc R . . H20B H 0.7429 0.9267 0.5400 0.091 Uiso 1 1 calc R . . H20C H 0.6371 0.7497 0.4969 0.091 Uiso 1 1 calc R . . F1 F 0.52665(17) 0.36513(18) 0.09926(8) 0.0747(4) Uani 1 1 d . . . F2 F 0.24164(19) 0.40715(16) 0.11320(7) 0.0710(4) Uani 1 1 d . . . F3 F 1.30292(17) 0.46055(17) 0.39535(8) 0.0708(4) Uani 1 1 d . . . F4 F 1.32992(15) 0.74272(18) 0.38092(8) 0.0688(4) Uani 1 1 d . . . N1 N 0.31882(19) 0.17527(19) 0.00233(9) 0.0459(4) Uani 1 1 d . . . N2 N 0.35324(19) 0.1466(2) 0.14613(9) 0.0476(4) Uani 1 1 d . . . N3 N 1.17864(18) 0.68719(19) 0.49491(9) 0.0444(3) Uani 1 1 d . . . N4 N 1.0467(2) 0.5965(2) 0.35250(9) 0.0474(4) Uani 1 1 d . . . _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 0.0525(11) 0.0403(10) 0.0509(12) 0.0119(8) 0.0018(9) 0.0027(8) B2 0.0422(10) 0.0547(12) 0.0512(12) 0.0132(9) 0.0055(9) 0.0051(9) C1 0.0694(13) 0.0564(11) 0.0536(11) 0.0247(9) 0.0141(9) 0.0126(9) C2 0.0931(16) 0.0664(13) 0.0437(11) 0.0156(9) 0.0072(10) 0.0208(12) C3 0.0774(14) 0.0513(11) 0.0493(11) 0.0049(9) 0.0003(10) 0.0130(10) C4 0.0483(10) 0.0395(9) 0.0470(10) 0.0081(7) 0.0029(7) 0.0079(7) C5 0.0421(9) 0.0426(9) 0.0583(11) 0.0146(8) 0.0051(8) 0.0063(7) C6 0.0461(9) 0.0464(10) 0.0552(11) 0.0198(8) 0.0073(8) 0.0057(7) C7 0.0613(12) 0.0707(13) 0.0657(13) 0.0360(11) 0.0126(10) 0.0076(10) C8 0.0759(15) 0.0917(17) 0.0520(12) 0.0320(12) 0.0083(11) 0.0146(13) C9 0.0652(13) 0.0708(13) 0.0466(11) 0.0130(9) -0.0033(9) 0.0109(10) C10 0.0663(13) 0.0446(11) 0.0815(15) 0.0161(10) 0.0040(11) -0.0020(9) C11 0.0475(10) 0.0650(12) 0.0573(12) 0.0246(9) -0.0044(8) -0.0023(9) C12 0.0618(12) 0.0770(14) 0.0433(10) 0.0132(9) -0.0052(9) -0.0073(10) C13 0.0555(11) 0.0620(12) 0.0467(10) 0.0087(9) 0.0069(8) -0.0032(9) C14 0.0425(9) 0.0467(9) 0.0463(10) 0.0123(7) 0.0051(7) -0.0015(7) C15 0.0401(9) 0.0428(9) 0.0529(10) 0.0138(7) 0.0035(7) -0.0022(7) C16 0.0446(9) 0.0448(9) 0.0501(10) 0.0140(7) -0.0028(8) -0.0027(7) C17 0.0564(11) 0.0601(12) 0.0594(12) 0.0188(10) -0.0135(9) -0.0027(9) C18 0.0833(16) 0.0685(13) 0.0489(12) 0.0115(10) -0.0162(11) -0.0001(12) C19 0.0765(14) 0.0644(13) 0.0440(11) 0.0069(9) 0.0024(10) 0.0036(11) C20 0.0440(10) 0.0662(13) 0.0722(14) 0.0159(10) 0.0081(9) 0.0052(9) F1 0.0733(8) 0.0709(8) 0.0790(9) 0.0243(7) -0.0086(7) -0.0255(6) F2 0.1011(10) 0.0554(7) 0.0578(7) 0.0105(5) 0.0073(6) 0.0315(7) F3 0.0692(8) 0.0714(8) 0.0708(8) 0.0097(6) 0.0053(6) 0.0270(6) F4 0.0558(7) 0.0889(9) 0.0649(8) 0.0262(7) 0.0090(6) -0.0144(6) N1 0.0496(8) 0.0430(8) 0.0482(8) 0.0152(6) 0.0076(7) 0.0075(6) N2 0.0492(8) 0.0494(8) 0.0454(8) 0.0135(6) 0.0009(6) 0.0066(7) N3 0.0391(7) 0.0483(8) 0.0464(8) 0.0136(6) -0.0002(6) -0.0007(6) N4 0.0497(8) 0.0497(8) 0.0428(8) 0.0109(6) 0.0019(6) 0.0016(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. ; _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 F1 1.379(3) . ? B1 F2 1.389(2) . ? B1 N2 1.535(3) . ? B1 N1 1.536(3) . ? B2 F3 1.380(2) . ? B2 F4 1.386(2) . ? B2 N4 1.541(3) . ? B2 N3 1.545(3) . ? C1 N1 1.342(2) . ? C1 C2 1.392(3) . ? C1 H1 0.9300 . ? C2 C3 1.362(3) . ? C2 H2 0.9300 . ? C3 C4 1.411(3) . ? C3 H3 0.9300 . ? C4 N1 1.386(2) . ? C4 C5 1.392(2) . ? C5 C6 1.393(3) . ? C5 C10 1.491(3) . ? C6 N2 1.393(2) . ? C6 C7 1.411(3) . ? C7 C8 1.367(3) . ? C7 H7 0.9300 . ? C8 C9 1.391(3) . ? C8 H8 0.9300 . ? C9 N2 1.341(2) . ? C9 H9 0.9300 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 N3 1.340(2) . ? C11 C12 1.395(3) . ? C11 H11 0.9300 . ? C12 C13 1.366(3) . ? C12 H12 0.9300 . ? C13 C14 1.408(3) . ? C13 H13 0.9300 . ? C14 C15 1.389(3) . ? C14 N3 1.390(2) . ? C15 C16 1.392(3) . ? C15 C20 1.496(3) . ? C16 N4 1.389(2) . ? C16 C17 1.411(3) . ? C17 C18 1.369(3) . ? C17 H17 0.9300 . ? C18 C19 1.393(3) . ? C18 H18 0.9300 . ? C19 N4 1.337(2) . ? C19 H19 0.9300 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? _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 F1 B1 F2 109.18(16) . . ? F1 B1 N2 111.41(16) . . ? F2 B1 N2 109.19(16) . . ? F1 B1 N1 110.89(16) . . ? F2 B1 N1 109.79(16) . . ? N2 B1 N1 106.34(14) . . ? F3 B2 F4 109.10(16) . . ? F3 B2 N4 111.81(17) . . ? F4 B2 N4 109.39(16) . . ? F3 B2 N3 110.54(16) . . ? F4 B2 N3 109.98(16) . . ? N4 B2 N3 105.98(14) . . ? N1 C1 C2 109.96(19) . . ? N1 C1 H1 125.0 . . ? C2 C1 H1 125.0 . . ? C3 C2 C1 107.23(18) . . ? C3 C2 H2 126.4 . . ? C1 C2 H2 126.4 . . ? C2 C3 C4 107.71(18) . . ? C2 C3 H3 126.1 . . ? C4 C3 H3 126.1 . . ? N1 C4 C5 121.39(17) . . ? N1 C4 C3 107.38(16) . . ? C5 C4 C3 131.18(18) . . ? C4 C5 C6 119.67(17) . . ? C4 C5 C10 120.45(18) . . ? C6 C5 C10 119.87(18) . . ? C5 C6 N2 121.01(16) . . ? C5 C6 C7 131.59(19) . . ? N2 C6 C7 107.38(18) . . ? C8 C7 C6 107.6(2) . . ? C8 C7 H7 126.2 . . ? C6 C7 H7 126.2 . . ? C7 C8 C9 107.34(19) . . ? C7 C8 H8 126.3 . . ? C9 C8 H8 126.3 . . ? N2 C9 C8 110.1(2) . . ? N2 C9 H9 125.0 . . ? C8 C9 H9 125.0 . . ? C5 C10 H10A 109.5 . . ? C5 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C5 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? N3 C11 C12 109.99(18) . . ? N3 C11 H11 125.0 . . ? C12 C11 H11 125.0 . . ? C13 C12 C11 107.19(18) . . ? C13 C12 H12 126.4 . . ? C11 C12 H12 126.4 . . ? C12 C13 C14 107.62(18) . . ? C12 C13 H13 126.2 . . ? C14 C13 H13 126.2 . . ? C15 C14 N3 121.37(16) . . ? C15 C14 C13 131.02(17) . . ? N3 C14 C13 107.51(16) . . ? C14 C15 C16 119.83(16) . . ? C14 C15 C20 120.24(17) . . ? C16 C15 C20 119.92(17) . . ? N4 C16 C15 121.19(16) . . ? N4 C16 C17 107.65(17) . . ? C15 C16 C17 131.11(18) . . ? C18 C17 C16 107.10(19) . . ? C18 C17 H17 126.4 . . ? C16 C17 H17 126.4 . . ? C17 C18 C19 107.50(19) . . ? C17 C18 H18 126.3 . . ? C19 C18 H18 126.3 . . ? N4 C19 C18 109.89(19) . . ? N4 C19 H19 125.1 . . ? C18 C19 H19 125.1 . . ? C15 C20 H20A 109.5 . . ? C15 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C15 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C1 N1 C4 107.72(16) . . ? C1 N1 B1 127.11(16) . . ? C4 N1 B1 124.74(15) . . ? C9 N2 C6 107.64(17) . . ? C9 N2 B1 127.13(17) . . ? C6 N2 B1 125.00(16) . . ? C11 N3 C14 107.69(15) . . ? C11 N3 B2 127.58(16) . . ? C14 N3 B2 124.29(15) . . ? C19 N4 C16 107.86(16) . . ? C19 N4 B2 127.08(17) . . ? C16 N4 B2 124.71(15) . . ? _diffrn_measured_fraction_theta_max 0.972 _diffrn_reflns_theta_full 27.57 _diffrn_measured_fraction_theta_full 0.972 _refine_diff_density_max 0.283 _refine_diff_density_min -0.240 _refine_diff_density_rms 0.047 data_100927b_0m _database_code_depnum_ccdc_archive 'CCDC 881437' #TrackingRef 'Name-2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H12 B F2 N3' _chemical_formula_weight 271.08 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 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 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 10.1547(12) _cell_length_b 9.1479(11) _cell_length_c 14.0759(17) _cell_angle_alpha 90.00 _cell_angle_beta 97.5220(10) _cell_angle_gamma 90.00 _cell_volume 1296.3(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2988 _cell_measurement_theta_min 2.02 _cell_measurement_theta_max 27.62 _exptl_crystal_description block _exptl_crystal_colour purple _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.389 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 560 _exptl_absorpt_coefficient_mu 0.104 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9550 _exptl_absorpt_correction_T_max 0.9816 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10895 _diffrn_reflns_av_R_equivalents 0.0270 _diffrn_reflns_av_sigmaI/netI 0.0213 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.02 _diffrn_reflns_theta_max 27.62 _reflns_number_total 2988 _reflns_number_gt 2143 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SMART' _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^)+(0.0668P)^2^+0.1382P] 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 0.025(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2988 _refine_ls_number_parameters 183 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0568 _refine_ls_R_factor_gt 0.0416 _refine_ls_wR_factor_ref 0.1370 _refine_ls_wR_factor_gt 0.1216 _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_restrained_S_all 1.048 _refine_ls_shift/su_max 0.023 _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 B1 B 0.18087(18) 0.17619(18) 0.40934(12) 0.0662(4) Uani 1 1 d . . . C1 C -0.0013(2) 0.3075(2) 0.48718(14) 0.0906(5) Uani 1 1 d . . . H1 H -0.0275 0.3711 0.4367 0.109 Uiso 1 1 calc R . . F1 F 0.09890(9) 0.16090(12) 0.32261(6) 0.0834(3) Uani 1 1 d . . . N1 N 0.09513(14) 0.20461(14) 0.48820(9) 0.0726(4) Uani 1 1 d . . . C2 C -0.0546(3) 0.3035(2) 0.57231(16) 0.1056(7) Uani 1 1 d . . . H2 H -0.1221 0.3630 0.5893 0.127 Uiso 1 1 calc R . . F2 F 0.26783(11) 0.29069(10) 0.40117(8) 0.1003(4) Uani 1 1 d . . . N2 N 0.26024(12) 0.03540(13) 0.43476(8) 0.0657(3) Uani 1 1 d . . . C3 C 0.0106(2) 0.1953(2) 0.62730(14) 0.0963(6) Uani 1 1 d . . . H3 H -0.0047 0.1682 0.6886 0.116 Uiso 1 1 calc R . . N3 N 0.29231(13) 0.07162(14) 0.21987(9) 0.0717(4) Uani 1 1 d . . . H3A H 0.2243 0.1225 0.2299 0.086 Uiso 1 1 calc R . . C4 C 0.10358(18) 0.13359(19) 0.57512(11) 0.0778(5) Uani 1 1 d . . . C5 C 0.19457(18) 0.0191(2) 0.59507(11) 0.0852(5) Uani 1 1 d . . . C6 C 0.2067(2) -0.0543(3) 0.69206(14) 0.1194(8) Uani 1 1 d . . . H6A H 0.2807 -0.1205 0.6983 0.179 Uiso 1 1 calc R . . H6B H 0.1267 -0.1075 0.6980 0.179 Uiso 1 1 calc R . . H6C H 0.2204 0.0186 0.7415 0.179 Uiso 1 1 calc R . . C7 C 0.27033(17) -0.0273(2) 0.52678(12) 0.0803(5) Uani 1 1 d . . . C8 C 0.3634(2) -0.1410(2) 0.52938(16) 0.1074(7) Uani 1 1 d . . . H8 H 0.3908 -0.2003 0.5819 0.129 Uiso 1 1 calc R . . C9 C 0.4065(2) -0.1499(2) 0.44326(17) 0.1011(6) Uani 1 1 d . . . H9 H 0.4678 -0.2170 0.4258 0.121 Uiso 1 1 calc R . . C10 C 0.34200(15) -0.03914(18) 0.38367(12) 0.0724(4) Uani 1 1 d . . . C11 C 0.36450(15) -0.01557(16) 0.28658(11) 0.0693(4) Uani 1 1 d . . . C12 C 0.46414(17) -0.0762(2) 0.24106(14) 0.0852(5) Uani 1 1 d . . . H12 H 0.5286 -0.1414 0.2682 0.102 Uiso 1 1 calc R . . C13 C 0.45154(18) -0.0234(2) 0.14823(14) 0.0861(5) Uani 1 1 d . . . H13 H 0.5068 -0.0449 0.1024 0.103 Uiso 1 1 calc R . . C14 C 0.34339(18) 0.06611(18) 0.13628(12) 0.0794(4) Uani 1 1 d . . . H14 H 0.3105 0.1149 0.0802 0.095 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 B1 0.0737(10) 0.0640(9) 0.0604(9) 0.0034(7) 0.0065(7) -0.0085(8) C1 0.1147(14) 0.0712(10) 0.0908(12) -0.0158(8) 0.0320(11) -0.0037(10) F1 0.0780(6) 0.1132(7) 0.0577(5) 0.0092(4) 0.0045(4) 0.0256(5) N1 0.0878(9) 0.0672(7) 0.0638(7) -0.0072(6) 0.0132(6) -0.0177(6) C2 0.1328(18) 0.0910(13) 0.1020(15) -0.0312(12) 0.0488(13) -0.0233(12) F2 0.1160(8) 0.0727(6) 0.1196(9) 0.0060(5) 0.0433(7) -0.0248(5) N2 0.0632(7) 0.0713(7) 0.0591(7) 0.0097(5) -0.0043(5) -0.0076(6) C3 0.1161(14) 0.1073(14) 0.0699(10) -0.0289(10) 0.0290(10) -0.0510(12) N3 0.0734(8) 0.0733(8) 0.0684(8) 0.0031(6) 0.0090(6) 0.0115(6) C4 0.0872(10) 0.0884(11) 0.0568(8) -0.0083(7) 0.0061(7) -0.0370(9) C5 0.0825(11) 0.1096(13) 0.0592(9) 0.0132(8) -0.0067(8) -0.0380(10) C6 0.1035(14) 0.179(2) 0.0714(12) 0.0426(13) -0.0048(10) -0.0382(15) C7 0.0754(9) 0.0932(11) 0.0672(9) 0.0225(8) -0.0099(8) -0.0142(9) C8 0.0970(13) 0.1177(16) 0.1022(15) 0.0502(13) -0.0071(11) 0.0081(12) C9 0.0879(12) 0.1006(14) 0.1124(16) 0.0357(11) 0.0040(11) 0.0236(10) C10 0.0643(8) 0.0721(9) 0.0780(10) 0.0110(7) -0.0017(7) 0.0010(7) C11 0.0633(8) 0.0659(8) 0.0772(10) 0.0017(7) 0.0034(7) 0.0019(7) C12 0.0731(10) 0.0791(10) 0.1036(13) 0.0006(9) 0.0123(9) 0.0126(8) C13 0.0845(11) 0.0827(11) 0.0950(13) -0.0121(9) 0.0263(10) 0.0019(9) C14 0.0892(11) 0.0806(10) 0.0698(10) -0.0016(8) 0.0156(8) 0.0025(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 B1 F2 1.3844(19) . ? B1 F1 1.3917(19) . ? B1 N1 1.520(2) . ? B1 N2 1.537(2) . ? C1 N1 1.357(2) . ? C1 C2 1.378(3) . ? N1 C4 1.378(2) . ? C2 C3 1.372(3) . ? N2 C10 1.352(2) . ? N2 C7 1.4079(19) . ? C3 C4 1.390(3) . ? N3 C14 1.347(2) . ? N3 C11 1.3694(19) . ? C4 C5 1.401(3) . ? C5 C7 1.374(3) . ? C5 C6 1.512(2) . ? C7 C8 1.403(3) . ? C8 C9 1.344(3) . ? C9 C10 1.420(2) . ? C10 C11 1.431(2) . ? C11 C12 1.383(2) . ? C12 C13 1.383(3) . ? C13 C14 1.362(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 F2 B1 F1 108.54(13) . . ? F2 B1 N1 111.34(13) . . ? F1 B1 N1 108.89(13) . . ? F2 B1 N2 109.43(13) . . ? F1 B1 N2 110.81(13) . . ? N1 B1 N2 107.84(12) . . ? N1 C1 C2 109.72(19) . . ? C1 N1 C4 107.30(15) . . ? C1 N1 B1 126.33(14) . . ? C4 N1 B1 126.34(15) . . ? C3 C2 C1 107.1(2) . . ? C10 N2 C7 107.95(14) . . ? C10 N2 B1 129.70(13) . . ? C7 N2 B1 121.89(14) . . ? C2 C3 C4 107.82(18) . . ? C14 N3 C11 110.13(13) . . ? N1 C4 C3 108.06(18) . . ? N1 C4 C5 119.56(15) . . ? C3 C4 C5 132.37(18) . . ? C7 C5 C4 120.36(15) . . ? C7 C5 C6 120.5(2) . . ? C4 C5 C6 119.12(19) . . ? C5 C7 C8 130.35(17) . . ? C5 C7 N2 122.53(17) . . ? C8 C7 N2 107.07(17) . . ? C9 C8 C7 108.61(16) . . ? C8 C9 C10 108.08(18) . . ? N2 C10 C9 108.27(16) . . ? N2 C10 C11 128.17(14) . . ? C9 C10 C11 123.56(17) . . ? N3 C11 C12 105.93(15) . . ? N3 C11 C10 127.19(14) . . ? C12 C11 C10 126.88(15) . . ? C11 C12 C13 108.34(16) . . ? C14 C13 C12 107.46(16) . . ? N3 C14 C13 108.12(16) . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 27.62 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.142 _refine_diff_density_min -0.150 _refine_diff_density_rms 0.027 data_101224a_0m _database_code_depnum_ccdc_archive 'CCDC 881438' #TrackingRef 'Name-3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C38 H28 B2 F4 N6' _chemical_formula_weight 666.28 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.9192(12) _cell_length_b 11.0064(12) _cell_length_c 13.8604(16) _cell_angle_alpha 89.033(2) _cell_angle_beta 78.752(2) _cell_angle_gamma 79.179(2) _cell_volume 1604.4(3) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 7280 _cell_measurement_theta_min 1.5 _cell_measurement_theta_max 27.59 _exptl_crystal_description block _exptl_crystal_colour purple _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.379 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 688 _exptl_absorpt_coefficient_mu 0.099 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9731 _exptl_absorpt_correction_T_max 0.9770 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14193 _diffrn_reflns_av_R_equivalents 0.0699 _diffrn_reflns_av_sigmaI/netI 0.1474 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.50 _diffrn_reflns_theta_max 27.59 _reflns_number_total 7280 _reflns_number_gt 2410 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SMART' _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^)+(0.0000P)^2^+0.0050P] 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 7280 _refine_ls_number_parameters 451 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2121 _refine_ls_R_factor_gt 0.0553 _refine_ls_wR_factor_ref 0.0898 _refine_ls_wR_factor_gt 0.0670 _refine_ls_goodness_of_fit_ref 0.998 _refine_ls_restrained_S_all 0.998 _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 0.6565(4) 0.7253(4) 0.2932(3) 0.0595(12) Uani 1 1 d . . . C1 C 0.8678(3) 0.7407(3) 0.3424(2) 0.0621(10) Uani 1 1 d . . . H1 H 0.8676 0.8225 0.3246 0.075 Uiso 1 1 calc R . . F1 F 0.59449(18) 0.83383(16) 0.34226(16) 0.0989(7) Uani 1 1 d . . . N1 N 0.7768(2) 0.6766(2) 0.33274(17) 0.0522(7) Uani 1 1 d . . . B2 B 0.2397(4) 0.3063(4) 0.2138(3) 0.0551(11) Uani 1 1 d . . . C2 C 0.9611(3) 0.6670(3) 0.3825(2) 0.0674(10) Uani 1 1 d . . . H2 H 1.0334 0.6899 0.3969 0.081 Uiso 1 1 calc R . . F2 F 0.68527(19) 0.7472(2) 0.19418(15) 0.1104(8) Uani 1 1 d . . . N2 N 0.5719(2) 0.6269(2) 0.31078(16) 0.0432(7) Uani 1 1 d . . . C3 C 0.9264(3) 0.5520(3) 0.3971(2) 0.0571(9) Uani 1 1 d . . . H3 H 0.9717 0.4833 0.4231 0.068 Uiso 1 1 calc R . . F3 F 0.16817(14) 0.41674(15) 0.25928(12) 0.0639(5) Uani 1 1 d . . . N3 N 0.3942(2) 0.8512(2) 0.24112(18) 0.0630(8) Uani 1 1 d . . . H3A H 0.4604 0.8773 0.2507 0.076 Uiso 1 1 calc R . . C4 C 0.8116(3) 0.5576(3) 0.3660(2) 0.0456(8) Uani 1 1 d . . . F4 F 0.15673(15) 0.23828(16) 0.18661(12) 0.0739(6) Uani 1 1 d . . . N4 N 0.3150(2) 0.2375(2) 0.28581(19) 0.0493(7) Uani 1 1 d . . . C5 C 0.7304(3) 0.4713(3) 0.3687(2) 0.0468(8) Uani 1 1 d . . . N5 N 0.3362(2) 0.3310(2) 0.12155(19) 0.0470(7) Uani 1 1 d . . . C6 C 0.6143(3) 0.5063(3) 0.3416(2) 0.0455(8) Uani 1 1 d . . . N6 N 0.1034(3) 0.5333(2) 0.0998(2) 0.0679(8) Uani 1 1 d . . . H6 H 0.0860 0.5017 0.1569 0.082 Uiso 1 1 calc R . . C7 C 0.5174(3) 0.4381(3) 0.3382(2) 0.0591(10) Uani 1 1 d . . . H7 H 0.5198 0.3555 0.3546 0.071 Uiso 1 1 calc R . . C8 C 0.4208(3) 0.5136(3) 0.3073(2) 0.0590(10) Uani 1 1 d . . . H8 H 0.3450 0.4923 0.2988 0.071 Uiso 1 1 calc R . . C9 C 0.4553(3) 0.6316(3) 0.2900(2) 0.0484(8) Uani 1 1 d . . . C10 C 0.3748(3) 0.7323(3) 0.2548(2) 0.0504(9) Uani 1 1 d . . . C11 C 0.2569(3) 0.7308(3) 0.2312(2) 0.0646(10) Uani 1 1 d . . . H11 H 0.2178 0.6625 0.2335 0.078 Uiso 1 1 calc R . . C12 C 0.2078(3) 0.8492(4) 0.2036(2) 0.0766(11) Uani 1 1 d . . . H12 H 0.1303 0.8740 0.1841 0.092 Uiso 1 1 calc R . . C13 C 0.2936(4) 0.9220(3) 0.2102(2) 0.0761(12) Uani 1 1 d . . . H13 H 0.2850 1.0057 0.1961 0.091 Uiso 1 1 calc R . . C14 C 0.7727(3) 0.3431(3) 0.4001(2) 0.0501(9) Uani 1 1 d . . . C15 C 0.8913(3) 0.2765(3) 0.3575(2) 0.0581(9) Uani 1 1 d . . . H15 H 0.9450 0.3126 0.3098 0.070 Uiso 1 1 calc R . . C16 C 0.9296(3) 0.1564(3) 0.3858(3) 0.0719(11) Uani 1 1 d . . . H16 H 1.0096 0.1125 0.3574 0.086 Uiso 1 1 calc R . . C17 C 0.8510(4) 0.1014(3) 0.4553(3) 0.0785(12) Uani 1 1 d . . . H17 H 0.8770 0.0204 0.4737 0.094 Uiso 1 1 calc R . . C18 C 0.7337(4) 0.1673(3) 0.4973(2) 0.0770(12) Uani 1 1 d . . . H18 H 0.6801 0.1306 0.5445 0.092 Uiso 1 1 calc R . . C19 C 0.6939(3) 0.2876(3) 0.4704(2) 0.0636(10) Uani 1 1 d . . . H19 H 0.6142 0.3312 0.4996 0.076 Uiso 1 1 calc R . . C20 C 0.2723(3) 0.2202(3) 0.3821(3) 0.0634(10) Uani 1 1 d . . . H20 H 0.1919 0.2549 0.4171 0.076 Uiso 1 1 calc R . . C21 C 0.3654(3) 0.1430(3) 0.4216(2) 0.0670(10) Uani 1 1 d . . . H21 H 0.3592 0.1173 0.4863 0.080 Uiso 1 1 calc R . . C22 C 0.4692(3) 0.1119(3) 0.3452(3) 0.0556(9) Uani 1 1 d . . . H22 H 0.5459 0.0605 0.3494 0.067 Uiso 1 1 calc R . . C23 C 0.4387(3) 0.1709(3) 0.2612(2) 0.0447(8) Uani 1 1 d . . . C24 C 0.5080(3) 0.1785(3) 0.1656(2) 0.0465(8) Uani 1 1 d . . . C25 C 0.4594(3) 0.2580(3) 0.0991(2) 0.0489(9) Uani 1 1 d . . . C26 C 0.5174(3) 0.2906(3) 0.0045(2) 0.0560(9) Uani 1 1 d . . . H26 H 0.5984 0.2557 -0.0292 0.067 Uiso 1 1 calc R . . C27 C 0.4346(3) 0.3817(3) -0.0288(2) 0.0611(10) Uani 1 1 d . . . H27 H 0.4493 0.4214 -0.0885 0.073 Uiso 1 1 calc R . . C28 C 0.3211(3) 0.4056(3) 0.0443(3) 0.0515(9) Uani 1 1 d . . . C29 C 0.2141(3) 0.4986(3) 0.0328(3) 0.0574(9) Uani 1 1 d . . . C30 C 0.2033(4) 0.5723(3) -0.0490(3) 0.0788(12) Uani 1 1 d . . . H30 H 0.2642 0.5699 -0.1065 0.095 Uiso 1 1 calc R . . C31 C 0.0841(4) 0.6505(3) -0.0291(3) 0.0884(13) Uani 1 1 d . . . H31 H 0.0510 0.7092 -0.0709 0.106 Uiso 1 1 calc R . . C32 C 0.0256(4) 0.6247(3) 0.0630(3) 0.0827(13) Uani 1 1 d . . . H32 H -0.0547 0.6636 0.0952 0.099 Uiso 1 1 calc R . . C33 C 0.6386(3) 0.1027(3) 0.1370(2) 0.0456(8) Uani 1 1 d . . . C34 C 0.7340(3) 0.1156(3) 0.1865(2) 0.0647(10) Uani 1 1 d . . . H34 H 0.7173 0.1731 0.2380 0.078 Uiso 1 1 calc R . . C35 C 0.8540(3) 0.0435(3) 0.1599(3) 0.0744(11) Uani 1 1 d . . . H35 H 0.9179 0.0535 0.1929 0.089 Uiso 1 1 calc R . . C36 C 0.8789(3) -0.0422(3) 0.0852(3) 0.0684(11) Uani 1 1 d . . . H36 H 0.9598 -0.0902 0.0675 0.082 Uiso 1 1 calc R . . C37 C 0.7858(3) -0.0576(3) 0.0366(2) 0.0686(10) Uani 1 1 d . . . H37 H 0.8029 -0.1168 -0.0137 0.082 Uiso 1 1 calc R . . C38 C 0.6658(3) 0.0146(3) 0.0619(2) 0.0622(10) Uani 1 1 d . . . H38 H 0.6027 0.0040 0.0281 0.075 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 B1 0.067(3) 0.054(3) 0.068(3) 0.014(3) -0.028(3) -0.024(3) C1 0.056(2) 0.065(3) 0.069(3) 0.001(2) -0.009(2) -0.023(2) F1 0.0994(16) 0.0419(12) 0.175(2) -0.0145(13) -0.0823(15) -0.0026(12) N1 0.0498(19) 0.0520(19) 0.0572(19) 0.0008(15) -0.0090(15) -0.0172(16) B2 0.047(3) 0.052(3) 0.065(3) -0.013(2) -0.008(2) -0.010(2) C2 0.052(3) 0.077(3) 0.077(3) -0.009(2) -0.011(2) -0.022(2) F2 0.1192(18) 0.158(2) 0.0874(17) 0.0684(15) -0.0488(14) -0.0861(16) N2 0.0441(18) 0.0389(17) 0.0466(17) 0.0014(13) -0.0105(14) -0.0064(14) C3 0.051(2) 0.061(2) 0.058(2) -0.0044(19) -0.0144(19) -0.004(2) F3 0.0511(12) 0.0615(13) 0.0681(13) -0.0092(10) -0.0018(9) 0.0075(10) N3 0.066(2) 0.053(2) 0.078(2) 0.0074(16) -0.0316(17) -0.0144(17) C4 0.048(2) 0.046(2) 0.041(2) 0.0001(16) -0.0111(17) -0.0020(19) F4 0.0566(13) 0.0859(14) 0.0835(14) -0.0056(11) -0.0120(10) -0.0253(11) N4 0.0462(19) 0.0490(17) 0.0491(19) -0.0012(15) -0.0028(15) -0.0063(15) C5 0.055(2) 0.043(2) 0.039(2) -0.0017(16) -0.0024(17) -0.0083(19) N5 0.0390(18) 0.0469(17) 0.0506(19) -0.0026(14) -0.0038(15) -0.0018(14) C6 0.046(2) 0.041(2) 0.051(2) 0.0032(17) -0.0102(18) -0.0112(19) N6 0.055(2) 0.061(2) 0.085(2) 0.0023(18) -0.0170(19) -0.0004(17) C7 0.065(3) 0.038(2) 0.075(3) 0.0033(18) -0.014(2) -0.010(2) C8 0.057(2) 0.049(2) 0.076(3) 0.0000(19) -0.017(2) -0.017(2) C9 0.055(2) 0.042(2) 0.047(2) -0.0028(17) -0.0101(18) -0.0073(19) C10 0.057(2) 0.045(2) 0.052(2) -0.0059(18) -0.0124(18) -0.012(2) C11 0.049(2) 0.070(3) 0.077(3) -0.002(2) -0.015(2) -0.015(2) C12 0.066(3) 0.075(3) 0.093(3) 0.000(2) -0.033(2) -0.005(2) C13 0.087(3) 0.056(3) 0.091(3) 0.010(2) -0.044(3) 0.000(2) C14 0.055(2) 0.047(2) 0.046(2) -0.0036(17) -0.0062(18) -0.007(2) C15 0.056(3) 0.054(2) 0.063(3) 0.0001(19) -0.010(2) -0.009(2) C16 0.064(3) 0.062(3) 0.089(3) -0.003(2) -0.026(2) 0.003(2) C17 0.097(4) 0.052(3) 0.090(3) 0.010(2) -0.036(3) -0.005(3) C18 0.097(3) 0.063(3) 0.065(3) 0.017(2) -0.007(2) -0.011(2) C19 0.069(3) 0.057(2) 0.057(2) 0.0046(19) 0.000(2) -0.004(2) C20 0.063(3) 0.060(2) 0.057(3) 0.001(2) 0.009(2) -0.007(2) C21 0.083(3) 0.058(2) 0.054(3) 0.010(2) -0.005(2) -0.008(2) C22 0.063(3) 0.044(2) 0.058(2) 0.0018(19) -0.011(2) -0.0074(18) C23 0.041(2) 0.039(2) 0.050(2) -0.0074(17) -0.0023(19) -0.0040(17) C24 0.042(2) 0.044(2) 0.053(2) -0.0063(17) -0.0075(19) -0.0050(17) C25 0.040(2) 0.052(2) 0.049(2) -0.0050(18) -0.0026(18) 0.0007(18) C26 0.050(2) 0.060(2) 0.051(2) -0.0033(18) -0.0028(19) 0.0007(19) C27 0.062(3) 0.071(3) 0.045(2) 0.0041(19) -0.005(2) -0.002(2) C28 0.043(2) 0.051(2) 0.059(3) -0.0043(19) -0.0114(19) -0.0029(18) C29 0.051(3) 0.057(2) 0.063(3) -0.002(2) -0.015(2) -0.002(2) C30 0.078(3) 0.073(3) 0.078(3) 0.005(2) -0.017(2) 0.006(2) C31 0.092(4) 0.069(3) 0.105(4) 0.016(3) -0.042(3) 0.005(3) C32 0.069(3) 0.064(3) 0.114(4) 0.002(3) -0.036(3) 0.008(2) C33 0.041(2) 0.044(2) 0.047(2) -0.0005(17) -0.0069(17) 0.0013(17) C34 0.053(2) 0.063(2) 0.075(3) -0.0211(19) -0.021(2) 0.008(2) C35 0.049(2) 0.082(3) 0.091(3) -0.013(2) -0.024(2) 0.003(2) C36 0.051(3) 0.062(3) 0.080(3) 0.002(2) -0.003(2) 0.012(2) C37 0.059(3) 0.065(3) 0.071(3) -0.016(2) -0.009(2) 0.012(2) C38 0.055(2) 0.063(2) 0.065(3) -0.015(2) -0.0172(19) 0.004(2) _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 F2 1.375(4) . ? B1 F1 1.375(4) . ? B1 N1 1.523(4) . ? B1 N2 1.537(4) . ? C1 N1 1.348(3) . ? C1 C2 1.379(4) . ? N1 C4 1.391(3) . ? B2 F4 1.385(4) . ? B2 F3 1.401(4) . ? B2 N4 1.519(4) . ? B2 N5 1.546(4) . ? C2 C3 1.389(4) . ? N2 C9 1.351(3) . ? N2 C6 1.408(3) . ? C3 C4 1.394(4) . ? N3 C13 1.359(3) . ? N3 C10 1.369(3) . ? C4 C5 1.411(4) . ? N4 C20 1.348(3) . ? N4 C23 1.390(3) . ? C5 C6 1.376(3) . ? C5 C14 1.485(4) . ? N5 C28 1.356(3) . ? N5 C25 1.411(3) . ? C6 C7 1.416(3) . ? N6 C32 1.351(3) . ? N6 C29 1.367(3) . ? C7 C8 1.350(3) . ? C8 C9 1.423(3) . ? C9 C10 1.421(4) . ? C10 C11 1.392(4) . ? C11 C12 1.390(4) . ? C12 C13 1.359(4) . ? C14 C19 1.384(3) . ? C14 C15 1.386(4) . ? C15 C16 1.384(4) . ? C16 C17 1.373(4) . ? C17 C18 1.372(4) . ? C18 C19 1.382(4) . ? C20 C21 1.390(4) . ? C21 C22 1.386(4) . ? C22 C23 1.390(3) . ? C23 C24 1.402(4) . ? C24 C25 1.374(3) . ? C24 C33 1.494(4) . ? C25 C26 1.412(4) . ? C26 C27 1.357(3) . ? C27 C28 1.424(4) . ? C28 C29 1.434(4) . ? C29 C30 1.394(4) . ? C30 C31 1.399(4) . ? C31 C32 1.362(4) . ? C33 C34 1.383(4) . ? C33 C38 1.384(4) . ? C34 C35 1.383(4) . ? C35 C36 1.364(4) . ? C36 C37 1.361(4) . ? C37 C38 1.382(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 F2 B1 F1 109.1(3) . . ? F2 B1 N1 110.8(3) . . ? F1 B1 N1 109.2(3) . . ? F2 B1 N2 109.4(3) . . ? F1 B1 N2 110.4(3) . . ? N1 B1 N2 108.0(3) . . ? N1 C1 C2 110.1(3) . . ? C1 N1 C4 107.9(3) . . ? C1 N1 B1 126.5(3) . . ? C4 N1 B1 125.6(3) . . ? F4 B2 F3 108.2(3) . . ? F4 B2 N4 111.9(3) . . ? F3 B2 N4 108.4(3) . . ? F4 B2 N5 109.3(3) . . ? F3 B2 N5 111.6(3) . . ? N4 B2 N5 107.4(3) . . ? C1 C2 C3 106.8(3) . . ? C9 N2 C6 107.9(3) . . ? C9 N2 B1 128.6(3) . . ? C6 N2 B1 123.1(3) . . ? C2 C3 C4 107.9(3) . . ? C13 N3 C10 110.2(3) . . ? N1 C4 C3 107.3(3) . . ? N1 C4 C5 120.3(3) . . ? C3 C4 C5 132.2(3) . . ? C20 N4 C23 107.5(3) . . ? C20 N4 B2 127.0(3) . . ? C23 N4 B2 125.3(3) . . ? C6 C5 C4 119.9(3) . . ? C6 C5 C14 121.1(3) . . ? C4 C5 C14 119.1(3) . . ? C28 N5 C25 107.6(3) . . ? C28 N5 B2 130.8(3) . . ? C25 N5 B2 121.0(3) . . ? C5 C6 N2 122.4(3) . . ? C5 C6 C7 130.5(3) . . ? N2 C6 C7 107.2(3) . . ? C32 N6 C29 109.8(3) . . ? C8 C7 C6 108.2(3) . . ? C7 C8 C9 107.9(3) . . ? N2 C9 C10 129.0(3) . . ? N2 C9 C8 108.8(3) . . ? C10 C9 C8 122.2(3) . . ? N3 C10 C11 105.8(3) . . ? N3 C10 C9 127.4(3) . . ? C11 C10 C9 126.7(3) . . ? C12 C11 C10 108.2(3) . . ? C13 C12 C11 107.7(3) . . ? C12 C13 N3 108.1(3) . . ? C19 C14 C15 119.1(3) . . ? C19 C14 C5 120.8(3) . . ? C15 C14 C5 120.2(3) . . ? C16 C15 C14 120.0(3) . . ? C17 C16 C15 120.8(3) . . ? C18 C17 C16 119.1(4) . . ? C17 C18 C19 121.0(3) . . ? C18 C19 C14 120.1(3) . . ? N4 C20 C21 110.3(3) . . ? C22 C21 C20 106.3(3) . . ? C21 C22 C23 108.0(3) . . ? C22 C23 N4 107.9(3) . . ? C22 C23 C24 133.0(3) . . ? N4 C23 C24 119.0(3) . . ? C25 C24 C23 120.9(3) . . ? C25 C24 C33 119.5(3) . . ? C23 C24 C33 119.5(3) . . ? C24 C25 N5 122.1(3) . . ? C24 C25 C26 130.2(3) . . ? N5 C25 C26 107.5(3) . . ? C27 C26 C25 108.2(3) . . ? C26 C27 C28 107.7(3) . . ? N5 C28 C27 109.0(3) . . ? N5 C28 C29 128.9(3) . . ? C27 C28 C29 122.1(3) . . ? N6 C29 C30 106.5(3) . . ? N6 C29 C28 127.0(3) . . ? C30 C29 C28 126.5(4) . . ? C29 C30 C31 107.6(3) . . ? C32 C31 C30 107.2(4) . . ? N6 C32 C31 108.8(4) . . ? C34 C33 C38 118.4(3) . . ? C34 C33 C24 121.1(3) . . ? C38 C33 C24 120.4(3) . . ? C33 C34 C35 120.4(3) . . ? C36 C35 C34 120.2(3) . . ? C37 C36 C35 120.3(3) . . ? C36 C37 C38 120.1(3) . . ? C37 C38 C33 120.6(3) . . ? _diffrn_measured_fraction_theta_max 0.978 _diffrn_reflns_theta_full 27.59 _diffrn_measured_fraction_theta_full 0.978 _refine_diff_density_max 0.165 _refine_diff_density_min -0.207 _refine_diff_density_rms 0.043