# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_coden_Cambridge 1350 _journal_volume ? _journal_page_first ? _journal_year ? loop_ _publ_author_name 'Paton, Andrew' 'Morse, Graham' 'Lough, Alan' 'Bender, Timothy' _publ_contact_author_name 'Bender, Timothy' _publ_contact_author_email tim.bender@utoronto.ca _publ_section_title ; Variation in crystal packing of phenoxyboronsubphthalocyanines directed by para-substituents on the phenoxy group. ; # Attachment '- compound 2a k0970.cif' data_k0970 _database_code_depnum_ccdc_archive 'CCDC 783165' #TrackingRef '- compound 2a k0970.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C30 H17 B N6 O' _chemical_formula_sum 'C30 H17 B N6 O' _chemical_formula_weight 488.31 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' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.0492(5) _cell_length_b 10.7503(4) _cell_length_c 11.8342(5) _cell_angle_alpha 85.893(2) _cell_angle_beta 77.4510(19) _cell_angle_gamma 66.043(2) _cell_volume 1140.22(9) _cell_formula_units_Z 2 _cell_measurement_temperature 150(1) _cell_measurement_reflns_used 12024 _cell_measurement_theta_min 2.6 _cell_measurement_theta_max 27.5 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.422 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 504 _exptl_absorpt_coefficient_mu 0.090 # Absorption correction _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.848 _exptl_absorpt_correction_T_max 0.982 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method '\f scans and \w scans with \k offsets' _diffrn_detector_area_resol_mean 9 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12024 _diffrn_reflns_av_R_equivalents 0.0396 _diffrn_reflns_av_sigmaI/netI 0.0508 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.57 _diffrn_reflns_theta_max 27.46 _reflns_number_total 5140 _reflns_number_gt 3704 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Collect (Nonius B.V., 1997-2002)' _computing_cell_refinement 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction Denzo-SMN _computing_structure_solution 'SIR-92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXTL V6.1 (Sheldrick, 2008)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material 'SHELXTL V6.1' _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. Blessing, R. H. (1995). Acta Cryst. A51, 33-38. Nonius B.V (1997-2002). Collect. Data collection software, Delft, The Netherlands. Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A edited by C. W. Carter & R. M. Sweet pp. 307-326. London: Academic press. Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122. Spek, A.L. (2003). J. Appl. Cryst. 36, 7-13. ; _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^)+(0.0786P)^2^+0.1413P] 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 5140 _refine_ls_number_parameters 343 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0790 _refine_ls_R_factor_gt 0.0519 _refine_ls_wR_factor_ref 0.1448 _refine_ls_wR_factor_gt 0.1262 _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_restrained_S_all 1.055 _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 O1 O 0.60760(13) 0.58378(11) 0.39790(9) 0.0292(3) Uani 1 1 d . . . N1 N 0.82783(16) 0.20367(13) 0.37264(11) 0.0283(3) Uani 1 1 d . . . N2 N 0.86239(16) 0.41103(13) 0.36357(11) 0.0267(3) Uani 1 1 d . . . N3 N 0.99314(16) 0.54962(13) 0.28167(12) 0.0291(3) Uani 1 1 d . . . N4 N 0.78662(15) 0.55809(13) 0.21079(11) 0.0265(3) Uani 1 1 d . . . N5 N 0.66814(16) 0.50176(13) 0.08143(12) 0.0274(3) Uani 1 1 d . . . N6 N 0.69748(15) 0.38663(13) 0.26013(11) 0.0260(3) Uani 1 1 d . . . C1 C 0.89807(19) 0.27838(16) 0.39799(13) 0.0272(4) Uani 1 1 d . . . C2 C 1.0393(2) 0.23590(16) 0.43364(14) 0.0287(4) Uani 1 1 d . . . C3 C 1.1299(2) 0.11469(17) 0.47758(14) 0.0318(4) Uani 1 1 d . . . H3A H 1.0971 0.0433 0.4986 0.038 Uiso 1 1 calc R . . C4 C 1.2688(2) 0.10120(18) 0.48976(15) 0.0361(4) Uani 1 1 d . . . H4A H 1.3313 0.0193 0.5200 0.043 Uiso 1 1 calc R . . C5 C 1.3202(2) 0.20455(18) 0.45889(16) 0.0381(4) Uani 1 1 d . . . H5A H 1.4164 0.1917 0.4683 0.046 Uiso 1 1 calc R . . C6 C 1.2315(2) 0.32551(18) 0.41461(15) 0.0347(4) Uani 1 1 d . . . H6A H 1.2663 0.3955 0.3927 0.042 Uiso 1 1 calc R . . C7 C 1.0911(2) 0.34202(16) 0.40301(14) 0.0293(4) Uani 1 1 d . . . C8 C 0.9790(2) 0.44920(16) 0.35189(14) 0.0277(4) Uani 1 1 d . . . C9 C 0.90023(19) 0.59762(16) 0.20799(14) 0.0280(4) Uani 1 1 d . . . C10 C 0.91203(19) 0.66874(15) 0.09916(14) 0.0284(4) Uani 1 1 d . . . C11 C 0.9993(2) 0.74002(17) 0.05122(15) 0.0329(4) Uani 1 1 d . . . H11A H 1.0681 0.7482 0.0909 0.039 Uiso 1 1 calc R . . C12 C 0.9831(2) 0.79829(18) -0.05548(16) 0.0373(4) Uani 1 1 d . . . H12A H 1.0380 0.8510 -0.0876 0.045 Uiso 1 1 calc R . . C13 C 0.8876(2) 0.78133(17) -0.11711(15) 0.0353(4) Uani 1 1 d . . . H13A H 0.8798 0.8221 -0.1906 0.042 Uiso 1 1 calc R . . C14 C 0.8042(2) 0.70663(16) -0.07369(15) 0.0310(4) Uani 1 1 d . . . H14A H 0.7424 0.6925 -0.1173 0.037 Uiso 1 1 calc R . . C15 C 0.81406(19) 0.65268(15) 0.03666(14) 0.0282(4) Uani 1 1 d . . . C16 C 0.74116(19) 0.57243(15) 0.10831(14) 0.0267(4) Uani 1 1 d . . . C17 C 0.65608(19) 0.40376(16) 0.15572(14) 0.0271(4) Uani 1 1 d . . . C18 C 0.63645(18) 0.28128(16) 0.13484(14) 0.0273(4) Uani 1 1 d . . . C19 C 0.5949(2) 0.24237(17) 0.04295(15) 0.0312(4) Uani 1 1 d . . . H19A H 0.5643 0.3033 -0.0176 0.037 Uiso 1 1 calc R . . C20 C 0.5998(2) 0.11183(17) 0.04282(16) 0.0339(4) Uani 1 1 d . . . H20A H 0.5690 0.0838 -0.0177 0.041 Uiso 1 1 calc R . . C21 C 0.6488(2) 0.02070(17) 0.12963(15) 0.0330(4) Uani 1 1 d . . . H21A H 0.6503 -0.0680 0.1270 0.040 Uiso 1 1 calc R . . C22 C 0.6951(2) 0.05615(16) 0.21929(15) 0.0311(4) Uani 1 1 d . . . H22A H 0.7318 -0.0078 0.2765 0.037 Uiso 1 1 calc R . . C23 C 0.68659(19) 0.18877(16) 0.22361(14) 0.0271(4) Uani 1 1 d . . . C24 C 0.73479(19) 0.25617(16) 0.29936(14) 0.0270(4) Uani 1 1 d . . . C25 C 0.4836(2) 0.66691(16) 0.35569(14) 0.0286(4) Uani 1 1 d . . . C26 C 0.3709(2) 0.62402(19) 0.35664(16) 0.0362(4) Uani 1 1 d . . . H26A H 0.3784 0.5378 0.3871 0.043 Uiso 1 1 calc R . . C27 C 0.2468(2) 0.7070(2) 0.31311(17) 0.0439(5) Uani 1 1 d . . . H27A H 0.1702 0.6769 0.3127 0.053 Uiso 1 1 calc R . . C28 C 0.2346(2) 0.8339(2) 0.27019(17) 0.0463(5) Uani 1 1 d . . . H28A H 0.1493 0.8910 0.2409 0.056 Uiso 1 1 calc R . . C29 C 0.3467(2) 0.87704(19) 0.27021(16) 0.0417(5) Uani 1 1 d . . . H29A H 0.3384 0.9639 0.2408 0.050 Uiso 1 1 calc R . . C30 C 0.4711(2) 0.79424(17) 0.31289(15) 0.0331(4) Uani 1 1 d . . . H30A H 0.5478 0.8244 0.3130 0.040 Uiso 1 1 calc R . . B1 B 0.7286(2) 0.49110(18) 0.31435(16) 0.0271(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 O1 0.0328(7) 0.0288(6) 0.0258(6) 0.0006(4) -0.0072(5) -0.0115(5) N1 0.0338(8) 0.0303(7) 0.0243(7) 0.0027(5) -0.0076(6) -0.0158(6) N2 0.0314(8) 0.0247(7) 0.0261(7) 0.0025(5) -0.0074(6) -0.0128(6) N3 0.0327(8) 0.0263(7) 0.0315(8) 0.0019(6) -0.0099(6) -0.0136(6) N4 0.0292(8) 0.0253(7) 0.0271(7) 0.0019(5) -0.0080(6) -0.0120(6) N5 0.0291(8) 0.0241(7) 0.0292(7) 0.0032(5) -0.0085(6) -0.0099(6) N6 0.0280(8) 0.0253(7) 0.0259(7) 0.0028(5) -0.0069(6) -0.0116(6) C1 0.0328(9) 0.0266(8) 0.0218(8) 0.0029(6) -0.0053(7) -0.0119(7) C2 0.0338(10) 0.0296(8) 0.0224(8) -0.0007(6) -0.0081(7) -0.0109(7) C3 0.0408(11) 0.0295(8) 0.0248(9) 0.0019(7) -0.0107(8) -0.0122(8) C4 0.0407(11) 0.0340(9) 0.0314(9) 0.0022(7) -0.0156(8) -0.0092(8) C5 0.0354(11) 0.0414(10) 0.0379(10) -0.0013(8) -0.0157(8) -0.0115(9) C6 0.0386(11) 0.0357(9) 0.0344(10) -0.0003(7) -0.0138(8) -0.0163(8) C7 0.0359(10) 0.0296(8) 0.0251(8) -0.0004(6) -0.0097(7) -0.0140(7) C8 0.0319(9) 0.0285(8) 0.0265(8) -0.0019(6) -0.0081(7) -0.0145(7) C9 0.0294(9) 0.0239(8) 0.0324(9) -0.0005(6) -0.0065(7) -0.0121(7) C10 0.0278(9) 0.0233(8) 0.0306(9) 0.0014(6) -0.0036(7) -0.0083(7) C11 0.0291(9) 0.0301(8) 0.0377(10) 0.0013(7) -0.0029(8) -0.0123(7) C12 0.0337(10) 0.0333(9) 0.0397(10) 0.0056(8) 0.0012(8) -0.0132(8) C13 0.0371(11) 0.0320(9) 0.0295(9) 0.0049(7) -0.0011(8) -0.0101(8) C14 0.0309(10) 0.0283(8) 0.0284(9) -0.0003(6) -0.0042(7) -0.0073(7) C15 0.0285(9) 0.0221(7) 0.0298(9) 0.0006(6) -0.0039(7) -0.0070(7) C16 0.0268(9) 0.0234(8) 0.0273(9) 0.0006(6) -0.0061(7) -0.0071(7) C17 0.0248(9) 0.0280(8) 0.0280(9) 0.0012(6) -0.0072(7) -0.0094(7) C18 0.0262(9) 0.0271(8) 0.0299(9) 0.0009(6) -0.0053(7) -0.0125(7) C19 0.0311(10) 0.0322(9) 0.0322(9) 0.0033(7) -0.0110(7) -0.0128(8) C20 0.0361(10) 0.0352(9) 0.0360(10) -0.0012(7) -0.0130(8) -0.0168(8) C21 0.0368(10) 0.0290(8) 0.0362(10) 0.0002(7) -0.0081(8) -0.0160(8) C22 0.0344(10) 0.0284(8) 0.0313(9) 0.0030(7) -0.0063(7) -0.0140(8) C23 0.0266(9) 0.0291(8) 0.0262(8) 0.0012(6) -0.0036(7) -0.0126(7) C24 0.0298(9) 0.0265(8) 0.0258(8) 0.0033(6) -0.0040(7) -0.0136(7) C25 0.0304(9) 0.0314(8) 0.0221(8) -0.0035(6) -0.0030(7) -0.0113(7) C26 0.0363(11) 0.0413(10) 0.0327(10) -0.0006(7) -0.0038(8) -0.0187(9) C27 0.0345(11) 0.0625(13) 0.0372(11) -0.0056(9) -0.0056(9) -0.0219(10) C28 0.0368(11) 0.0538(12) 0.0379(11) -0.0070(9) -0.0117(9) -0.0046(10) C29 0.0490(13) 0.0340(9) 0.0349(10) -0.0009(8) -0.0113(9) -0.0078(9) C30 0.0382(11) 0.0303(9) 0.0306(9) -0.0009(7) -0.0060(8) -0.0138(8) B1 0.0312(10) 0.0277(9) 0.0261(9) 0.0014(7) -0.0071(8) -0.0151(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 O1 C25 1.379(2) . ? O1 B1 1.443(2) . ? N1 C24 1.341(2) . ? N1 C1 1.349(2) . ? N2 C8 1.368(2) . ? N2 C1 1.376(2) . ? N2 B1 1.489(2) . ? N3 C9 1.340(2) . ? N3 C8 1.349(2) . ? N4 C16 1.364(2) . ? N4 C9 1.364(2) . ? N4 B1 1.505(2) . ? N5 C16 1.344(2) . ? N5 C17 1.350(2) . ? N6 C17 1.365(2) . ? N6 C24 1.371(2) . ? N6 B1 1.499(2) . ? C1 C2 1.452(2) . ? C2 C3 1.394(2) . ? C2 C7 1.430(2) . ? C3 C4 1.382(3) . ? C4 C5 1.400(3) . ? C5 C6 1.387(3) . ? C6 C7 1.385(3) . ? C7 C8 1.451(2) . ? C9 C10 1.457(2) . ? C10 C11 1.395(2) . ? C10 C15 1.421(2) . ? C11 C12 1.381(3) . ? C12 C13 1.397(3) . ? C13 C14 1.383(2) . ? C14 C15 1.397(2) . ? C15 C16 1.462(2) . ? C17 C18 1.453(2) . ? C18 C19 1.391(2) . ? C18 C23 1.421(2) . ? C19 C20 1.384(2) . ? C20 C21 1.393(3) . ? C21 C22 1.380(2) . ? C22 C23 1.397(2) . ? C23 C24 1.459(2) . ? C25 C26 1.383(3) . ? C25 C30 1.391(2) . ? C26 C27 1.387(3) . ? C27 C28 1.388(3) . ? C28 C29 1.381(3) . ? C29 C30 1.384(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C25 O1 B1 115.52(13) . . ? C24 N1 C1 117.72(13) . . ? C8 N2 C1 112.52(14) . . ? C8 N2 B1 122.35(13) . . ? C1 N2 B1 123.22(14) . . ? C9 N3 C8 116.71(14) . . ? C16 N4 C9 114.05(13) . . ? C16 N4 B1 123.25(14) . . ? C9 N4 B1 122.40(14) . . ? C16 N5 C17 116.36(14) . . ? C17 N6 C24 113.15(13) . . ? C17 N6 B1 123.04(13) . . ? C24 N6 B1 122.73(14) . . ? N1 C1 N2 121.98(15) . . ? N1 C1 C2 130.25(15) . . ? N2 C1 C2 105.85(14) . . ? C3 C2 C7 119.85(17) . . ? C3 C2 C1 132.77(16) . . ? C7 C2 C1 107.03(14) . . ? C4 C3 C2 118.18(16) . . ? C3 C4 C5 122.05(17) . . ? C6 C5 C4 120.42(18) . . ? C7 C6 C5 118.55(17) . . ? C6 C7 C2 120.94(16) . . ? C6 C7 C8 131.66(16) . . ? C2 C7 C8 107.11(15) . . ? N3 C8 N2 123.19(16) . . ? N3 C8 C7 128.86(16) . . ? N2 C8 C7 106.16(14) . . ? N3 C9 N4 122.30(14) . . ? N3 C9 C10 131.15(16) . . ? N4 C9 C10 105.06(15) . . ? C11 C10 C15 120.21(16) . . ? C11 C10 C9 132.29(17) . . ? C15 C10 C9 107.47(14) . . ? C12 C11 C10 118.20(18) . . ? C11 C12 C13 121.38(16) . . ? C14 C13 C12 121.60(17) . . ? C13 C14 C15 117.60(17) . . ? C14 C15 C10 120.89(15) . . ? C14 C15 C16 131.99(16) . . ? C10 C15 C16 107.10(14) . . ? N5 C16 N4 122.56(14) . . ? N5 C16 C15 131.24(15) . . ? N4 C16 C15 105.09(14) . . ? N5 C17 N6 122.99(14) . . ? N5 C17 C18 129.48(15) . . ? N6 C17 C18 105.84(13) . . ? C19 C18 C23 121.12(15) . . ? C19 C18 C17 131.41(15) . . ? C23 C18 C17 107.09(14) . . ? C20 C19 C18 117.72(16) . . ? C19 C20 C21 121.39(16) . . ? C22 C21 C20 121.62(15) . . ? C21 C22 C23 118.13(16) . . ? C22 C23 C18 119.95(16) . . ? C22 C23 C24 132.42(16) . . ? C18 C23 C24 107.31(13) . . ? N1 C24 N6 122.42(14) . . ? N1 C24 C23 130.36(14) . . ? N6 C24 C23 105.31(14) . . ? O1 C25 C26 119.96(15) . . ? O1 C25 C30 120.17(15) . . ? C26 C25 C30 119.86(17) . . ? C25 C26 C27 119.99(18) . . ? C26 C27 C28 120.10(19) . . ? C29 C28 C27 119.8(2) . . ? C28 C29 C30 120.28(18) . . ? C29 C30 C25 119.94(18) . . ? O1 B1 N2 112.77(14) . . ? O1 B1 N6 116.61(14) . . ? N2 B1 N6 104.68(13) . . ? O1 B1 N4 114.77(14) . . ? N2 B1 N4 103.90(14) . . ? N6 B1 N4 102.68(13) . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 27.46 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.277 _refine_diff_density_min -0.257 _refine_diff_density_rms 0.052 # Attachment '- compound 2b k0971.cif' data_k0971 _database_code_depnum_ccdc_archive 'CCDC 783166' #TrackingRef '- compound 2b k0971.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C31 H19 B N6 O' _chemical_formula_sum 'C31 H19 B N6 O' _chemical_formula_weight 502.33 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' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.1555(3) _cell_length_b 10.9258(4) _cell_length_c 11.7215(4) _cell_angle_alpha 86.3530(17) _cell_angle_beta 78.496(2) _cell_angle_gamma 66.9870(18) _cell_volume 1172.88(7) _cell_formula_units_Z 2 _cell_measurement_temperature 150(1) _cell_measurement_reflns_used 14448 _cell_measurement_theta_min 2.6 _cell_measurement_theta_max 27.5 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.422 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 520 _exptl_absorpt_coefficient_mu 0.090 # Absorption correction _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.804 _exptl_absorpt_correction_T_max 0.983 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(1) _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 'Nonius KappaCCD' _diffrn_measurement_method '\f scans and \w scans with \k offsets' _diffrn_detector_area_resol_mean 9 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14448 _diffrn_reflns_av_R_equivalents 0.0441 _diffrn_reflns_av_sigmaI/netI 0.0458 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.56 _diffrn_reflns_theta_max 27.53 _reflns_number_total 5309 _reflns_number_gt 4092 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Collect (Nonius B.V., 1997-2002)' _computing_cell_refinement 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction Denzo-SMN _computing_structure_solution 'SIR-92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXTL V6.1 (Sheldrick, 2008)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material 'SHELXTL V6.1' _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. Blessing, R. H. (1995). Acta Cryst. A51, 33-38. Nonius B.V (1997-2002). Collect. Data collection software, Delft, The Netherlands. Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A edited by C. W. Carter & R. M. Sweet pp. 307-326. London: Academic press. Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122. Spek, A.L. (2003). J. Appl. Cryst. 36, 7-13. ; _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^)+(0.0646P)^2^+0.2749P] 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 5309 _refine_ls_number_parameters 353 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0651 _refine_ls_R_factor_gt 0.0465 _refine_ls_wR_factor_ref 0.1264 _refine_ls_wR_factor_gt 0.1138 _refine_ls_goodness_of_fit_ref 1.058 _refine_ls_restrained_S_all 1.058 _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 O1 O 0.88558(11) 0.42376(10) 0.09910(8) 0.0254(2) Uani 1 1 d . . . N1 N 0.50827(13) 0.45686(12) 0.21915(11) 0.0265(3) Uani 1 1 d . . . N2 N 0.63788(13) 0.59180(12) 0.13403(10) 0.0233(3) Uani 1 1 d . . . N3 N 0.67407(13) 0.79540(12) 0.12362(10) 0.0245(3) Uani 1 1 d . . . N4 N 0.80490(13) 0.61680(12) 0.23661(10) 0.0233(3) Uani 1 1 d . . . N5 N 0.83787(13) 0.50397(12) 0.41640(11) 0.0250(3) Uani 1 1 d . . . N6 N 0.71601(13) 0.44839(12) 0.28779(10) 0.0236(3) Uani 1 1 d . . . C1 C 0.52240(16) 0.55397(14) 0.14680(12) 0.0247(3) Uani 1 1 d . . . C2 C 0.41186(16) 0.65814(15) 0.09559(13) 0.0260(3) Uani 1 1 d . . . C3 C 0.27185(17) 0.67411(16) 0.08627(14) 0.0312(3) Uani 1 1 d . . . H3A H 0.2375 0.6050 0.1078 0.037 Uiso 1 1 calc R . . C4 C 0.18358(18) 0.79334(17) 0.04479(14) 0.0336(4) Uani 1 1 d . . . H4A H 0.0879 0.8058 0.0370 0.040 Uiso 1 1 calc R . . C5 C 0.23359(17) 0.89589(16) 0.01421(13) 0.0307(3) Uani 1 1 d . . . H5A H 0.1709 0.9767 -0.0141 0.037 Uiso 1 1 calc R . . C6 C 0.37194(17) 0.88244(15) 0.02417(12) 0.0279(3) Uani 1 1 d . . . H6A H 0.4043 0.9530 0.0038 0.033 Uiso 1 1 calc R . . C7 C 0.46280(16) 0.76266(15) 0.06495(12) 0.0247(3) Uani 1 1 d . . . C8 C 0.60416(15) 0.72085(14) 0.09913(12) 0.0235(3) Uani 1 1 d . . . C9 C 0.76747(15) 0.74471(14) 0.19772(12) 0.0237(3) Uani 1 1 d . . . C10 C 0.81405(15) 0.81278(15) 0.27464(13) 0.0244(3) Uani 1 1 d . . . C11 C 0.80312(16) 0.94419(15) 0.27987(13) 0.0276(3) Uani 1 1 d . . . H11A H 0.7673 1.0059 0.2216 0.033 Uiso 1 1 calc R . . C12 C 0.84595(17) 0.98157(16) 0.37217(14) 0.0306(3) Uani 1 1 d . . . H12A H 0.8418 1.0696 0.3760 0.037 Uiso 1 1 calc R . . C13 C 0.89526(17) 0.89265(16) 0.46011(14) 0.0314(3) Uani 1 1 d . . . H13A H 0.9239 0.9217 0.5223 0.038 Uiso 1 1 calc R . . C14 C 0.90334(16) 0.76320(15) 0.45872(13) 0.0280(3) Uani 1 1 d . . . H14A H 0.9345 0.7040 0.5198 0.034 Uiso 1 1 calc R . . C15 C 0.86415(15) 0.72285(14) 0.36454(13) 0.0247(3) Uani 1 1 d . . . C16 C 0.84718(15) 0.60087(15) 0.34238(12) 0.0240(3) Uani 1 1 d . . . C17 C 0.76490(15) 0.43351(14) 0.39024(12) 0.0239(3) Uani 1 1 d . . . C18 C 0.69382(16) 0.35592(14) 0.46376(13) 0.0247(3) Uani 1 1 d . . . C19 C 0.70700(17) 0.30300(15) 0.57431(13) 0.0281(3) Uani 1 1 d . . . H19A H 0.7731 0.3140 0.6158 0.034 Uiso 1 1 calc R . . C20 C 0.62051(17) 0.23387(16) 0.62164(14) 0.0314(4) Uani 1 1 d . . . H20A H 0.6316 0.1926 0.6949 0.038 Uiso 1 1 calc R . . C21 C 0.51716(17) 0.22366(16) 0.56385(14) 0.0317(4) Uani 1 1 d . . . H21A H 0.4586 0.1766 0.5991 0.038 Uiso 1 1 calc R . . C22 C 0.49844(17) 0.28077(15) 0.45622(14) 0.0289(3) Uani 1 1 d . . . H22A H 0.4249 0.2772 0.4192 0.035 Uiso 1 1 calc R . . C23 C 0.59033(16) 0.34352(14) 0.40395(13) 0.0254(3) Uani 1 1 d . . . C24 C 0.60151(16) 0.41093(14) 0.29347(13) 0.0246(3) Uani 1 1 d . . . C25 C 1.00991(15) 0.34356(14) 0.14036(12) 0.0239(3) Uani 1 1 d . . . C26 C 1.02532(17) 0.21733(15) 0.18135(13) 0.0270(3) Uani 1 1 d . . . H26A H 0.9503 0.1859 0.1818 0.032 Uiso 1 1 calc R . . C27 C 1.15076(17) 0.13761(15) 0.22157(13) 0.0291(3) Uani 1 1 d . . . H27A H 1.1607 0.0515 0.2494 0.035 Uiso 1 1 calc R . . C28 C 1.26252(17) 0.18132(15) 0.22194(13) 0.0283(3) Uani 1 1 d . . . C29 C 1.24445(17) 0.30823(16) 0.18134(13) 0.0291(3) Uani 1 1 d . . . H29A H 1.3188 0.3404 0.1817 0.035 Uiso 1 1 calc R . . C30 C 1.11954(16) 0.38882(15) 0.14028(13) 0.0270(3) Uani 1 1 d . . . H30A H 1.1095 0.4749 0.1122 0.032 Uiso 1 1 calc R . . C31 C 1.39955(18) 0.09249(17) 0.26411(15) 0.0366(4) Uani 1 1 d . . . H31A H 1.4417 0.0071 0.2219 0.055 Uiso 1 1 calc R . . H31B H 1.3759 0.0775 0.3477 0.055 Uiso 1 1 calc R . . H31C H 1.4700 0.1352 0.2501 0.055 Uiso 1 1 calc R . . B1 B 0.77115(18) 0.51407(16) 0.18300(14) 0.0235(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0268(5) 0.0251(5) 0.0232(5) 0.0021(4) -0.0074(4) -0.0080(4) N1 0.0303(7) 0.0237(7) 0.0283(6) 0.0021(5) -0.0092(5) -0.0121(5) N2 0.0266(6) 0.0224(6) 0.0228(6) 0.0031(5) -0.0076(5) -0.0106(5) N3 0.0276(6) 0.0261(7) 0.0222(6) 0.0030(5) -0.0070(5) -0.0120(5) N4 0.0243(6) 0.0224(6) 0.0239(6) 0.0043(5) -0.0072(5) -0.0091(5) N5 0.0259(6) 0.0235(6) 0.0269(6) 0.0038(5) -0.0082(5) -0.0098(5) N6 0.0258(6) 0.0227(6) 0.0243(6) 0.0030(5) -0.0074(5) -0.0107(5) C1 0.0284(7) 0.0251(8) 0.0239(7) -0.0003(6) -0.0077(6) -0.0123(6) C2 0.0305(8) 0.0276(8) 0.0225(7) 0.0010(6) -0.0095(6) -0.0122(6) C3 0.0327(8) 0.0329(9) 0.0327(8) 0.0015(7) -0.0127(7) -0.0146(7) C4 0.0308(8) 0.0385(9) 0.0338(9) 0.0014(7) -0.0147(7) -0.0116(7) C5 0.0335(8) 0.0309(9) 0.0269(8) 0.0031(6) -0.0137(7) -0.0082(7) C6 0.0335(8) 0.0285(8) 0.0224(7) 0.0017(6) -0.0088(6) -0.0112(7) C7 0.0296(7) 0.0275(8) 0.0189(7) 0.0009(6) -0.0074(6) -0.0118(6) C8 0.0265(7) 0.0238(7) 0.0197(7) 0.0025(6) -0.0050(6) -0.0094(6) C9 0.0252(7) 0.0239(7) 0.0226(7) 0.0034(6) -0.0044(6) -0.0105(6) C10 0.0225(7) 0.0270(8) 0.0251(7) 0.0021(6) -0.0051(6) -0.0112(6) C11 0.0294(8) 0.0252(8) 0.0298(8) 0.0054(6) -0.0076(6) -0.0119(6) C12 0.0335(8) 0.0254(8) 0.0358(8) 0.0002(6) -0.0083(7) -0.0138(7) C13 0.0350(8) 0.0325(9) 0.0319(8) -0.0002(7) -0.0117(7) -0.0158(7) C14 0.0282(8) 0.0310(8) 0.0283(8) 0.0046(6) -0.0107(6) -0.0133(7) C15 0.0228(7) 0.0267(8) 0.0262(7) 0.0033(6) -0.0057(6) -0.0111(6) C16 0.0236(7) 0.0253(7) 0.0232(7) 0.0020(6) -0.0069(6) -0.0087(6) C17 0.0247(7) 0.0213(7) 0.0241(7) 0.0018(6) -0.0062(6) -0.0066(6) C18 0.0263(7) 0.0204(7) 0.0257(7) 0.0003(6) -0.0037(6) -0.0076(6) C19 0.0302(8) 0.0264(8) 0.0252(7) 0.0013(6) -0.0050(6) -0.0087(6) C20 0.0370(9) 0.0286(8) 0.0252(8) 0.0037(6) -0.0025(7) -0.0112(7) C21 0.0319(8) 0.0286(8) 0.0326(8) 0.0028(7) 0.0011(7) -0.0132(7) C22 0.0285(8) 0.0268(8) 0.0321(8) 0.0007(6) -0.0039(6) -0.0125(6) C23 0.0270(7) 0.0209(7) 0.0268(7) 0.0014(6) -0.0043(6) -0.0082(6) C24 0.0261(7) 0.0214(7) 0.0271(7) 0.0000(6) -0.0060(6) -0.0096(6) C25 0.0259(7) 0.0248(7) 0.0188(7) 0.0006(6) -0.0046(6) -0.0073(6) C26 0.0323(8) 0.0250(8) 0.0262(7) 0.0013(6) -0.0072(6) -0.0133(6) C27 0.0357(8) 0.0237(8) 0.0270(8) 0.0016(6) -0.0080(7) -0.0098(7) C28 0.0300(8) 0.0281(8) 0.0235(7) -0.0015(6) -0.0058(6) -0.0072(6) C29 0.0279(8) 0.0329(9) 0.0272(8) 0.0004(6) -0.0044(6) -0.0128(7) C30 0.0296(8) 0.0253(8) 0.0268(7) 0.0034(6) -0.0039(6) -0.0125(6) C31 0.0352(9) 0.0360(9) 0.0343(9) -0.0003(7) -0.0125(7) -0.0063(7) B1 0.0265(8) 0.0227(8) 0.0234(8) 0.0031(6) -0.0075(7) -0.0108(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 O1 C25 1.3858(17) . ? O1 B1 1.436(2) . ? N1 C24 1.3450(19) . ? N1 C1 1.3497(18) . ? N2 C1 1.3674(18) . ? N2 C8 1.3703(18) . ? N2 B1 1.4938(19) . ? N3 C8 1.3465(18) . ? N3 C9 1.3482(18) . ? N4 C9 1.3704(18) . ? N4 C16 1.3705(18) . ? N4 B1 1.500(2) . ? N5 C17 1.3425(18) . ? N5 C16 1.3459(18) . ? N6 C24 1.3644(18) . ? N6 C17 1.3657(18) . ? N6 B1 1.505(2) . ? C1 C2 1.449(2) . ? C2 C3 1.389(2) . ? C2 C7 1.427(2) . ? C3 C4 1.385(2) . ? C4 C5 1.401(2) . ? C5 C6 1.382(2) . ? C6 C7 1.395(2) . ? C7 C8 1.457(2) . ? C9 C10 1.456(2) . ? C10 C11 1.400(2) . ? C10 C15 1.423(2) . ? C11 C12 1.382(2) . ? C12 C13 1.398(2) . ? C13 C14 1.385(2) . ? C14 C15 1.395(2) . ? C15 C16 1.454(2) . ? C17 C18 1.456(2) . ? C18 C19 1.395(2) . ? C18 C23 1.425(2) . ? C19 C20 1.386(2) . ? C20 C21 1.399(2) . ? C21 C22 1.386(2) . ? C22 C23 1.391(2) . ? C23 C24 1.455(2) . ? C25 C30 1.384(2) . ? C25 C26 1.391(2) . ? C26 C27 1.387(2) . ? C27 C28 1.394(2) . ? C28 C29 1.391(2) . ? C28 C31 1.510(2) . ? C29 C30 1.390(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 C25 O1 B1 115.61(11) . . ? C24 N1 C1 116.86(12) . . ? C1 N2 C8 112.73(12) . . ? C1 N2 B1 122.47(12) . . ? C8 N2 B1 122.91(12) . . ? C8 N3 C9 117.28(12) . . ? C9 N4 C16 112.83(12) . . ? C9 N4 B1 122.92(12) . . ? C16 N4 B1 122.90(12) . . ? C17 N5 C16 116.63(12) . . ? C24 N6 C17 113.41(12) . . ? C24 N6 B1 122.89(12) . . ? C17 N6 B1 123.35(12) . . ? N1 C1 N2 123.12(13) . . ? N1 C1 C2 128.78(13) . . ? N2 C1 C2 106.10(12) . . ? C3 C2 C7 120.90(14) . . ? C3 C2 C1 131.41(14) . . ? C7 C2 C1 107.23(12) . . ? C4 C3 C2 118.33(15) . . ? C3 C4 C5 120.86(14) . . ? C6 C5 C4 121.65(14) . . ? C5 C6 C7 118.30(14) . . ? C6 C7 C2 119.96(13) . . ? C6 C7 C8 132.69(14) . . ? C2 C7 C8 106.88(12) . . ? N3 C8 N2 122.72(12) . . ? N3 C8 C7 129.34(13) . . ? N2 C8 C7 105.80(12) . . ? N3 C9 N4 122.35(12) . . ? N3 C9 C10 129.74(13) . . ? N4 C9 C10 105.81(12) . . ? C11 C10 C15 120.08(13) . . ? C11 C10 C9 132.39(13) . . ? C15 C10 C9 107.13(12) . . ? C12 C11 C10 118.14(14) . . ? C11 C12 C13 121.46(14) . . ? C14 C13 C12 121.56(14) . . ? C13 C14 C15 117.69(14) . . ? C14 C15 C10 121.03(13) . . ? C14 C15 C16 131.32(13) . . ? C10 C15 C16 107.24(12) . . ? N5 C16 N4 123.04(13) . . ? N5 C16 C15 129.37(13) . . ? N4 C16 C15 105.82(12) . . ? N5 C17 N6 122.20(13) . . ? N5 C17 C18 130.79(13) . . ? N6 C17 C18 105.59(12) . . ? C19 C18 C23 120.74(13) . . ? C19 C18 C17 132.21(14) . . ? C23 C18 C17 106.99(12) . . ? C20 C19 C18 117.83(14) . . ? C19 C20 C21 121.37(14) . . ? C22 C21 C20 121.35(14) . . ? C21 C22 C23 118.15(14) . . ? C22 C23 C18 120.37(14) . . ? C22 C23 C24 132.34(14) . . ? C18 C23 C24 107.22(12) . . ? N1 C24 N6 122.10(13) . . ? N1 C24 C23 130.93(13) . . ? N6 C24 C23 105.60(12) . . ? C30 C25 O1 119.94(13) . . ? C30 C25 C26 119.80(13) . . ? O1 C25 C26 120.25(13) . . ? C27 C26 C25 119.71(14) . . ? C26 C27 C28 121.33(14) . . ? C29 C28 C27 118.03(14) . . ? C29 C28 C31 121.25(14) . . ? C27 C28 C31 120.72(14) . . ? C30 C29 C28 121.18(14) . . ? C25 C30 C29 119.95(14) . . ? O1 B1 N2 112.57(12) . . ? O1 B1 N4 117.09(12) . . ? N2 B1 N4 104.67(12) . . ? O1 B1 N6 114.56(12) . . ? N2 B1 N6 103.83(12) . . ? N4 B1 N6 102.66(12) . . ? _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 27.53 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.201 _refine_diff_density_min -0.282 _refine_diff_density_rms 0.049 # Attachment '- compound 2c k09107.cif' data_k09107 _database_code_depnum_ccdc_archive 'CCDC 783167' #TrackingRef '- compound 2c k09107.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C34 H25 B N6 O' _chemical_formula_sum 'C34 H25 B N6 O' _chemical_formula_weight 544.41 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.5535(2) _cell_length_b 12.7466(4) _cell_length_c 13.2395(4) _cell_angle_alpha 79.9663(14) _cell_angle_beta 78.2792(16) _cell_angle_gamma 70.9358(17) _cell_volume 1326.76(7) _cell_formula_units_Z 2 _cell_measurement_temperature 150(1) _cell_measurement_reflns_used 15623 _cell_measurement_theta_min 2.6 _cell_measurement_theta_max 27.5 _exptl_crystal_description plate _exptl_crystal_colour purple _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.363 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 568 _exptl_absorpt_coefficient_mu 0.085 # Absorption correction _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.788 _exptl_absorpt_correction_T_max 0.992 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method '\f scans and \w scans with \k offsets' _diffrn_detector_area_resol_mean 9 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15623 _diffrn_reflns_av_R_equivalents 0.0566 _diffrn_reflns_av_sigmaI/netI 0.0760 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.55 _diffrn_reflns_theta_max 27.48 _reflns_number_total 6009 _reflns_number_gt 3552 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Collect (Nonius B.V., 1997-2002)' _computing_cell_refinement 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction Denzo-SMN _computing_structure_solution 'SIR-92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXTL V6.1 (Sheldrick, 2008)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material 'SHELXTL V6.1' _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. Blessing, R. H. (1995). Acta Cryst. A51, 33-38. Nonius B.V (1997-2002). Collect. Data collection software, Delft, The Netherlands. Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A edited by C. W. Carter & R. M. Sweet pp. 307-326. London: Academic press. Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122. Spek, A.L. (2003). J. Appl. Cryst. 36, 7-13. ; _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^)+(0.0965P)^2^] 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 6009 _refine_ls_number_parameters 382 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1178 _refine_ls_R_factor_gt 0.0601 _refine_ls_wR_factor_ref 0.1787 _refine_ls_wR_factor_gt 0.1434 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.045 _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 O1 O 0.52505(17) 0.87599(12) 0.71320(11) 0.0311(4) Uani 1 1 d . . . N1 N 0.4300(2) 0.78943(16) 0.99441(14) 0.0325(5) Uani 1 1 d . . . N2 N 0.65827(19) 0.81368(14) 0.86523(13) 0.0274(4) Uani 1 1 d . . . N3 N 0.9465(2) 0.76425(15) 0.79113(14) 0.0307(4) Uani 1 1 d . . . N4 N 0.7563(2) 0.69691(15) 0.73114(13) 0.0288(4) Uani 1 1 d . . . N5 N 0.6254(2) 0.55780(16) 0.73318(14) 0.0325(5) Uani 1 1 d . . . N6 N 0.4949(2) 0.70798(15) 0.83584(13) 0.0286(4) Uani 1 1 d . . . C1 C 0.5633(2) 0.82794(18) 0.96144(17) 0.0297(5) Uani 1 1 d . . . C2 C 0.6608(3) 0.86169(18) 1.02083(17) 0.0313(5) Uani 1 1 d . . . C3 C 0.6291(3) 0.8913(2) 1.12053(18) 0.0382(6) Uani 1 1 d . . . H3B H 0.5226 0.8980 1.1622 0.046 Uiso 1 1 calc R . . C4 C 0.7540(3) 0.9106(2) 1.1581(2) 0.0420(6) Uani 1 1 d . . . H4A H 0.7333 0.9313 1.2262 0.050 Uiso 1 1 calc R . . C5 C 0.9115(3) 0.9004(2) 1.09758(19) 0.0417(6) Uani 1 1 d . . . H5B H 0.9957 0.9143 1.1255 0.050 Uiso 1 1 calc R . . C6 C 0.9472(3) 0.87055(19) 0.99870(18) 0.0343(5) Uani 1 1 d . . . H6A H 1.0551 0.8624 0.9587 0.041 Uiso 1 1 calc R . . C7 C 0.8204(3) 0.85249(18) 0.95865(17) 0.0301(5) Uani 1 1 d . . . C8 C 0.8183(2) 0.81432(18) 0.86204(17) 0.0283(5) Uani 1 1 d . . . C9 C 0.9149(2) 0.70096(19) 0.73086(17) 0.0291(5) Uani 1 1 d . . . C10 C 1.0278(3) 0.60696(19) 0.67750(16) 0.0296(5) Uani 1 1 d . . . C11 C 1.2021(3) 0.5705(2) 0.64981(18) 0.0365(6) Uani 1 1 d . . . H11A H 1.2695 0.6126 0.6605 0.044 Uiso 1 1 calc R . . C12 C 1.2731(3) 0.4711(2) 0.60642(19) 0.0426(6) Uani 1 1 d . . . H12A H 1.3909 0.4461 0.5850 0.051 Uiso 1 1 calc R . . C13 C 1.1765(3) 0.4068(2) 0.59323(19) 0.0440(6) Uani 1 1 d . . . H13A H 1.2292 0.3383 0.5643 0.053 Uiso 1 1 calc R . . C14 C 1.0047(3) 0.4418(2) 0.62181(19) 0.0408(6) Uani 1 1 d . . . H14A H 0.9390 0.3971 0.6141 0.049 Uiso 1 1 calc R . . C15 C 0.9298(3) 0.54280(19) 0.66180(17) 0.0312(5) Uani 1 1 d . . . C16 C 0.7560(3) 0.59882(19) 0.70288(17) 0.0301(5) Uani 1 1 d . . . C17 C 0.5021(3) 0.60891(19) 0.80540(17) 0.0298(5) Uani 1 1 d . . . C18 C 0.3840(2) 0.56503(19) 0.88165(18) 0.0317(5) Uani 1 1 d . . . C19 C 0.3375(3) 0.4690(2) 0.88899(19) 0.0354(6) Uani 1 1 d . . . H19A H 0.3798 0.4204 0.8363 0.043 Uiso 1 1 calc R . . C20 C 0.2266(3) 0.4465(2) 0.97626(19) 0.0378(6) Uani 1 1 d . . . H20A H 0.1900 0.3826 0.9823 0.045 Uiso 1 1 calc R . . C21 C 0.1684(3) 0.5157(2) 1.05472(19) 0.0396(6) Uani 1 1 d . . . H21A H 0.0924 0.4980 1.1132 0.048 Uiso 1 1 calc R . . C22 C 0.2179(2) 0.6097(2) 1.05024(18) 0.0366(6) Uani 1 1 d . . . H22A H 0.1808 0.6548 1.1056 0.044 Uiso 1 1 calc R . . C23 C 0.3243(2) 0.63588(19) 0.96142(17) 0.0317(5) Uani 1 1 d . . . C24 C 0.4060(2) 0.72315(19) 0.93402(17) 0.0298(5) Uani 1 1 d . . . C25 C 0.4502(2) 0.86208(17) 0.63495(16) 0.0275(5) Uani 1 1 d . . . C26 C 0.2905(2) 0.85433(19) 0.65463(17) 0.0319(5) Uani 1 1 d . . . H26A H 0.2316 0.8544 0.7237 0.038 Uiso 1 1 calc R . . C27 C 0.2139(3) 0.84632(19) 0.57419(17) 0.0327(5) Uani 1 1 d . . . H27A H 0.1037 0.8399 0.5896 0.039 Uiso 1 1 calc R . . C28 C 0.2948(2) 0.84752(18) 0.47172(17) 0.0293(5) Uani 1 1 d . . . C29 C 0.4566(3) 0.8556(2) 0.45426(18) 0.0354(6) Uani 1 1 d . . . H29A H 0.5154 0.8566 0.3852 0.042 Uiso 1 1 calc R . . C30 C 0.5356(3) 0.86219(19) 0.53359(18) 0.0332(5) Uani 1 1 d . . . H30A H 0.6468 0.8668 0.5189 0.040 Uiso 1 1 calc R . . C31 C 0.2105(3) 0.84356(19) 0.38124(17) 0.0328(5) Uani 1 1 d . . . C32 C 0.0330(3) 0.8350(2) 0.4171(2) 0.0409(6) Uani 1 1 d . . . H32A H -0.0382 0.9026 0.4482 0.061 Uiso 1 1 calc R . . H32B H 0.0360 0.7695 0.4688 0.061 Uiso 1 1 calc R . . H32C H -0.0125 0.8275 0.3575 0.061 Uiso 1 1 calc R . . C33 C 0.3154(3) 0.7435(2) 0.3227(2) 0.0436(6) Uani 1 1 d . . . H33A H 0.4288 0.7490 0.2982 0.065 Uiso 1 1 calc R . . H33B H 0.2636 0.7434 0.2632 0.065 Uiso 1 1 calc R . . H33C H 0.3210 0.6741 0.3694 0.065 Uiso 1 1 calc R . . C34 C 0.1985(3) 0.9522(2) 0.30713(19) 0.0412(6) Uani 1 1 d . . . H34A H 0.3093 0.9633 0.2880 0.062 Uiso 1 1 calc R . . H34B H 0.1202 1.0154 0.3417 0.062 Uiso 1 1 calc R . . H34C H 0.1583 0.9470 0.2445 0.062 Uiso 1 1 calc R . . B1 B 0.6018(3) 0.7794(2) 0.78031(19) 0.0279(6) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0360(8) 0.0310(9) 0.0290(9) -0.0010(7) -0.0111(6) -0.0112(7) N1 0.0286(9) 0.0339(11) 0.0342(11) -0.0050(9) -0.0035(8) -0.0085(8) N2 0.0276(9) 0.0265(10) 0.0276(10) -0.0027(8) -0.0033(7) -0.0086(7) N3 0.0320(9) 0.0294(11) 0.0302(11) -0.0016(9) -0.0049(8) -0.0097(8) N4 0.0316(9) 0.0275(10) 0.0279(10) -0.0030(8) -0.0052(8) -0.0096(8) N5 0.0357(10) 0.0339(11) 0.0311(11) -0.0045(9) -0.0079(8) -0.0127(8) N6 0.0290(9) 0.0292(11) 0.0283(10) -0.0029(8) -0.0072(8) -0.0084(8) C1 0.0287(11) 0.0275(12) 0.0309(13) -0.0028(10) -0.0055(9) -0.0056(9) C2 0.0322(11) 0.0274(12) 0.0340(13) -0.0042(10) -0.0055(9) -0.0082(9) C3 0.0395(13) 0.0388(14) 0.0339(14) -0.0093(11) -0.0018(10) -0.0083(11) C4 0.0532(15) 0.0388(15) 0.0364(14) -0.0099(12) -0.0111(11) -0.0118(12) C5 0.0470(14) 0.0407(15) 0.0442(16) -0.0076(12) -0.0141(11) -0.0168(12) C6 0.0341(12) 0.0321(13) 0.0385(14) -0.0041(11) -0.0094(10) -0.0104(10) C7 0.0353(11) 0.0247(12) 0.0303(12) -0.0013(10) -0.0072(9) -0.0091(9) C8 0.0298(11) 0.0251(12) 0.0299(12) 0.0005(10) -0.0041(9) -0.0106(9) C9 0.0308(11) 0.0290(12) 0.0281(12) -0.0009(10) -0.0042(9) -0.0113(9) C10 0.0333(11) 0.0302(13) 0.0234(11) -0.0003(10) -0.0052(9) -0.0081(10) C11 0.0350(12) 0.0393(14) 0.0332(13) 0.0016(11) -0.0081(10) -0.0097(11) C12 0.0342(12) 0.0456(16) 0.0386(15) -0.0061(13) -0.0051(10) 0.0009(11) C13 0.0506(15) 0.0357(15) 0.0398(15) -0.0125(12) -0.0079(11) -0.0007(12) C14 0.0473(14) 0.0335(14) 0.0411(15) -0.0072(12) -0.0078(11) -0.0095(11) C15 0.0366(12) 0.0308(13) 0.0247(12) -0.0044(10) -0.0042(9) -0.0081(10) C16 0.0364(12) 0.0295(13) 0.0254(12) -0.0024(10) -0.0072(9) -0.0100(10) C17 0.0322(11) 0.0289(12) 0.0300(12) -0.0005(10) -0.0111(9) -0.0093(9) C18 0.0261(11) 0.0333(13) 0.0363(13) 0.0027(11) -0.0118(9) -0.0090(9) C19 0.0346(12) 0.0324(13) 0.0403(14) 0.0021(11) -0.0154(10) -0.0091(10) C20 0.0339(12) 0.0323(13) 0.0505(16) 0.0073(12) -0.0172(11) -0.0141(10) C21 0.0316(12) 0.0461(16) 0.0414(15) 0.0125(13) -0.0128(10) -0.0167(11) C22 0.0289(11) 0.0449(15) 0.0345(13) 0.0037(11) -0.0088(9) -0.0111(10) C23 0.0271(11) 0.0341(13) 0.0349(13) 0.0022(11) -0.0117(9) -0.0096(10) C24 0.0267(10) 0.0308(13) 0.0310(12) -0.0022(10) -0.0057(9) -0.0072(9) C25 0.0312(11) 0.0237(12) 0.0285(12) -0.0011(10) -0.0081(9) -0.0084(9) C26 0.0293(11) 0.0370(14) 0.0289(12) -0.0037(11) -0.0012(9) -0.0114(10) C27 0.0289(11) 0.0317(13) 0.0364(14) -0.0024(11) -0.0042(10) -0.0091(10) C28 0.0319(11) 0.0244(12) 0.0302(12) -0.0005(10) -0.0057(9) -0.0074(9) C29 0.0323(11) 0.0428(15) 0.0292(13) -0.0038(11) -0.0005(9) -0.0114(10) C30 0.0280(11) 0.0376(14) 0.0346(13) -0.0049(11) -0.0038(9) -0.0111(10) C31 0.0367(12) 0.0323(13) 0.0329(13) -0.0040(11) -0.0101(10) -0.0124(10) C32 0.0408(13) 0.0435(15) 0.0436(15) -0.0014(12) -0.0141(11) -0.0170(11) C33 0.0476(14) 0.0421(15) 0.0448(16) -0.0128(13) -0.0140(12) -0.0106(12) C34 0.0448(13) 0.0412(15) 0.0366(14) 0.0050(12) -0.0142(11) -0.0116(11) B1 0.0289(12) 0.0284(14) 0.0270(14) -0.0036(11) -0.0039(10) -0.0097(10) _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 O1 C25 1.387(2) . ? O1 B1 1.437(3) . ? N1 C24 1.346(3) . ? N1 C1 1.349(3) . ? N2 C8 1.363(3) . ? N2 C1 1.371(3) . ? N2 B1 1.490(3) . ? N3 C9 1.348(3) . ? N3 C8 1.351(3) . ? N4 C16 1.367(3) . ? N4 C9 1.373(3) . ? N4 B1 1.502(3) . ? N5 C16 1.345(3) . ? N5 C17 1.345(3) . ? N6 C17 1.370(3) . ? N6 C24 1.377(3) . ? N6 B1 1.497(3) . ? C1 C2 1.455(3) . ? C2 C3 1.385(3) . ? C2 C7 1.424(3) . ? C3 C4 1.371(3) . ? C4 C5 1.399(3) . ? C5 C6 1.374(3) . ? C6 C7 1.396(3) . ? C7 C8 1.451(3) . ? C9 C10 1.459(3) . ? C10 C11 1.399(3) . ? C10 C15 1.412(3) . ? C11 C12 1.383(3) . ? C12 C13 1.391(4) . ? C13 C14 1.381(3) . ? C14 C15 1.382(3) . ? C15 C16 1.459(3) . ? C17 C18 1.453(3) . ? C18 C19 1.388(3) . ? C18 C23 1.415(3) . ? C19 C20 1.390(3) . ? C20 C21 1.388(3) . ? C21 C22 1.383(3) . ? C22 C23 1.396(3) . ? C23 C24 1.457(3) . ? C25 C26 1.370(3) . ? C25 C30 1.391(3) . ? C26 C27 1.393(3) . ? C27 C28 1.392(3) . ? C28 C29 1.390(3) . ? C28 C31 1.534(3) . ? C29 C30 1.387(3) . ? C31 C32 1.529(3) . ? C31 C33 1.532(3) . ? C31 C34 1.538(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C25 O1 B1 118.86(17) . . ? C24 N1 C1 116.79(18) . . ? C8 N2 C1 112.77(18) . . ? C8 N2 B1 123.50(17) . . ? C1 N2 B1 122.73(17) . . ? C9 N3 C8 117.07(18) . . ? C16 N4 C9 112.76(17) . . ? C16 N4 B1 123.23(17) . . ? C9 N4 B1 122.62(19) . . ? C16 N5 C17 116.92(19) . . ? C17 N6 C24 112.39(18) . . ? C17 N6 B1 123.80(18) . . ? C24 N6 B1 122.48(19) . . ? N1 C1 N2 122.5(2) . . ? N1 C1 C2 129.7(2) . . ? N2 C1 C2 105.84(17) . . ? C3 C2 C7 120.2(2) . . ? C3 C2 C1 132.8(2) . . ? C7 C2 C1 106.88(19) . . ? C4 C3 C2 118.9(2) . . ? C3 C4 C5 121.0(2) . . ? C6 C5 C4 121.5(2) . . ? C5 C6 C7 118.2(2) . . ? C6 C7 C2 120.2(2) . . ? C6 C7 C8 132.3(2) . . ? C2 C7 C8 107.24(18) . . ? N3 C8 N2 122.4(2) . . ? N3 C8 C7 130.02(19) . . ? N2 C8 C7 106.03(17) . . ? N3 C9 N4 122.50(19) . . ? N3 C9 C10 130.15(19) . . ? N4 C9 C10 105.52(18) . . ? C11 C10 C15 120.3(2) . . ? C11 C10 C9 132.3(2) . . ? C15 C10 C9 107.21(17) . . ? C12 C11 C10 117.9(2) . . ? C11 C12 C13 121.7(2) . . ? C14 C13 C12 120.6(2) . . ? C13 C14 C15 118.9(2) . . ? C14 C15 C10 120.6(2) . . ? C14 C15 C16 131.8(2) . . ? C10 C15 C16 107.45(19) . . ? N5 C16 N4 122.76(19) . . ? N5 C16 C15 129.7(2) . . ? N4 C16 C15 105.66(18) . . ? N5 C17 N6 122.22(19) . . ? N5 C17 C18 129.9(2) . . ? N6 C17 C18 106.19(18) . . ? C19 C18 C23 121.2(2) . . ? C19 C18 C17 131.4(2) . . ? C23 C18 C17 107.16(19) . . ? C18 C19 C20 117.5(2) . . ? C21 C20 C19 121.3(2) . . ? C22 C21 C20 121.9(2) . . ? C21 C22 C23 117.7(2) . . ? C22 C23 C18 120.4(2) . . ? C22 C23 C24 131.9(2) . . ? C18 C23 C24 107.51(18) . . ? N1 C24 N6 122.62(19) . . ? N1 C24 C23 130.0(2) . . ? N6 C24 C23 105.61(19) . . ? C26 C25 O1 121.24(19) . . ? C26 C25 C30 119.5(2) . . ? O1 C25 C30 119.20(18) . . ? C25 C26 C27 120.5(2) . . ? C28 C27 C26 121.59(19) . . ? C29 C28 C27 116.5(2) . . ? C29 C28 C31 120.89(19) . . ? C27 C28 C31 122.56(18) . . ? C30 C29 C28 122.7(2) . . ? C29 C30 C25 119.25(19) . . ? C32 C31 C33 108.85(19) . . ? C32 C31 C28 112.55(18) . . ? C33 C31 C28 109.88(18) . . ? C32 C31 C34 107.78(18) . . ? C33 C31 C34 109.4(2) . . ? C28 C31 C34 108.38(18) . . ? O1 B1 N2 110.24(19) . . ? O1 B1 N6 117.11(18) . . ? N2 B1 N6 104.18(18) . . ? O1 B1 N4 116.27(18) . . ? N2 B1 N4 104.17(17) . . ? N6 B1 N4 103.45(18) . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.280 _refine_diff_density_min -0.296 _refine_diff_density_rms 0.061 # Attachment '- compound 2d k09104.cif' data_k09104 _database_code_depnum_ccdc_archive 'CCDC 783168' #TrackingRef '- compound 2d k09104.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C38 H33 B N6 O, 0.5(C6 H6)' _chemical_formula_sum 'C41 H36 B N6 O' _chemical_formula_weight 639.57 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' O O 0.0106 0.0060 '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 21/c' _symmetry_space_group_name_Hall '-P 2ybc' 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 16.4530(4) _cell_length_b 11.9941(2) _cell_length_c 17.5406(4) _cell_angle_alpha 90.00 _cell_angle_beta 108.1900(11) _cell_angle_gamma 90.00 _cell_volume 3288.46(12) _cell_formula_units_Z 4 _cell_measurement_temperature 150(1) _cell_measurement_reflns_used 21335 _cell_measurement_theta_min 2.6 _cell_measurement_theta_max 27.5 _exptl_crystal_description block _exptl_crystal_colour purple _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.292 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1348 _exptl_absorpt_coefficient_mu 0.079 # Absorption correction _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.937 _exptl_absorpt_correction_T_max 0.994 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method '\f scans and \w scans with \k offsets' _diffrn_detector_area_resol_mean 9 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 21335 _diffrn_reflns_av_R_equivalents 0.0473 _diffrn_reflns_av_sigmaI/netI 0.0653 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.61 _diffrn_reflns_theta_max 27.50 _reflns_number_total 7488 _reflns_number_gt 4574 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Collect (Nonius B.V., 1997-2002)' _computing_cell_refinement 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction Denzo-SMN _computing_structure_solution 'SIR-92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXTL V6.1 (Sheldrick, 2008)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material 'SHELXTL V6.1' _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. Blessing, R. H. (1995). Acta Cryst. A51, 33-38. Nonius B.V (1997-2002). Collect. Data collection software, Delft, The Netherlands. Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A edited by C. W. Carter & R. M. Sweet pp. 307-326. London: Academic press. Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122. Spek, A.L. (2003). J. Appl. Cryst. 36, 7-13. ; _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^)+(0.0672P)^2^+1.1772P] 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 7488 _refine_ls_number_parameters 470 _refine_ls_number_restraints 26 _refine_ls_R_factor_all 0.1108 _refine_ls_R_factor_gt 0.0562 _refine_ls_wR_factor_ref 0.1595 _refine_ls_wR_factor_gt 0.1309 _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_restrained_S_all 1.065 _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 O1 O 0.76671(8) 0.17645(12) 0.34260(8) 0.0290(3) Uani 1 1 d . . . N1 N 0.96610(10) 0.33413(14) 0.41908(10) 0.0286(4) Uani 1 1 d . . . N2 N 0.84734(10) 0.33012(13) 0.29888(10) 0.0266(4) Uani 1 1 d . . . N3 N 0.78410(11) 0.33845(13) 0.15715(10) 0.0278(4) Uani 1 1 d . . . N4 N 0.81940(10) 0.16412(13) 0.22356(9) 0.0253(4) Uani 1 1 d . . . N5 N 0.91278(10) 0.00906(14) 0.26963(10) 0.0282(4) Uani 1 1 d . . . N6 N 0.91393(10) 0.16306(13) 0.35498(9) 0.0256(4) Uani 1 1 d . . . C1 C 0.90809(13) 0.38642(17) 0.35775(12) 0.0283(5) Uani 1 1 d . . . C2 C 0.90717(13) 0.50005(17) 0.32825(12) 0.0293(5) Uani 1 1 d . . . C3 C 0.95155(14) 0.59530(18) 0.36306(14) 0.0360(5) Uani 1 1 d . . . H3A H 0.9891 0.5947 0.4166 0.043 Uiso 1 1 calc R . . C4 C 0.93890(16) 0.69110(19) 0.31664(15) 0.0433(6) Uani 1 1 d . . . H4A H 0.9672 0.7578 0.3396 0.052 Uiso 1 1 calc R . . C5 C 0.88574(16) 0.69225(19) 0.23719(15) 0.0414(6) Uani 1 1 d . . . H5A H 0.8793 0.7592 0.2069 0.050 Uiso 1 1 calc R . . C6 C 0.84236(14) 0.59761(17) 0.20180(14) 0.0343(5) Uani 1 1 d . . . H6A H 0.8067 0.5983 0.1475 0.041 Uiso 1 1 calc R . . C7 C 0.85227(13) 0.50134(16) 0.24784(12) 0.0288(5) Uani 1 1 d . . . C8 C 0.81920(12) 0.38858(17) 0.22857(12) 0.0265(4) Uani 1 1 d . . . C9 C 0.78923(12) 0.22644(17) 0.15524(12) 0.0268(4) Uani 1 1 d . . . C10 C 0.78740(13) 0.15203(17) 0.08922(12) 0.0282(5) Uani 1 1 d . . . C11 C 0.75574(14) 0.16460(18) 0.00638(12) 0.0322(5) Uani 1 1 d . . . H11A H 0.7272 0.2310 -0.0169 0.039 Uiso 1 1 calc R . . C12 C 0.76701(15) 0.07786(18) -0.04097(13) 0.0364(5) Uani 1 1 d . . . H12A H 0.7442 0.0837 -0.0977 0.044 Uiso 1 1 calc R . . C13 C 0.81130(14) -0.01827(19) -0.00712(13) 0.0373(5) Uani 1 1 d . . . H13A H 0.8190 -0.0758 -0.0414 0.045 Uiso 1 1 calc R . . C14 C 0.84426(13) -0.03206(18) 0.07494(13) 0.0326(5) Uani 1 1 d . . . H14A H 0.8757 -0.0970 0.0974 0.039 Uiso 1 1 calc R . . C15 C 0.82989(13) 0.05227(17) 0.12372(12) 0.0282(5) Uani 1 1 d . . . C16 C 0.85460(13) 0.06511(16) 0.21062(12) 0.0276(5) Uani 1 1 d . . . C17 C 0.94439(13) 0.06229(16) 0.34018(12) 0.0264(4) Uani 1 1 d . . . C18 C 1.02329(13) 0.04496(16) 0.40628(12) 0.0266(4) Uani 1 1 d . . . C19 C 1.08036(13) -0.04322(17) 0.42666(12) 0.0305(5) Uani 1 1 d . . . H19A H 1.0708 -0.1092 0.3951 0.037 Uiso 1 1 calc R . . C20 C 1.15116(14) -0.03340(19) 0.49360(13) 0.0348(5) Uani 1 1 d . . . H20A H 1.1897 -0.0943 0.5093 0.042 Uiso 1 1 calc R . . C21 C 1.16716(14) 0.06416(19) 0.53865(13) 0.0368(5) Uani 1 1 d . . . H21A H 1.2164 0.0684 0.5847 0.044 Uiso 1 1 calc R . . C22 C 1.11325(13) 0.15510(18) 0.51814(12) 0.0322(5) Uani 1 1 d . . . H22A H 1.1259 0.2223 0.5482 0.039 Uiso 1 1 calc R . . C23 C 1.03985(13) 0.14560(17) 0.45224(12) 0.0279(5) Uani 1 1 d . . . C24 C 0.97093(12) 0.22242(17) 0.41431(11) 0.0263(4) Uani 1 1 d . . . C25 C 0.67987(12) 0.19014(16) 0.31531(12) 0.0257(4) Uani 1 1 d . A . C26 C 0.63288(13) 0.12548(17) 0.35180(13) 0.0313(5) Uani 1 1 d . . . H26A H 0.6616 0.0747 0.3930 0.038 Uiso 1 1 calc R . . C27 C 0.54479(13) 0.13380(17) 0.32913(13) 0.0332(5) Uani 1 1 d . A . H27A H 0.5141 0.0878 0.3547 0.040 Uiso 1 1 calc R . . C28 C 0.49979(13) 0.20780(19) 0.26982(13) 0.0343(5) Uani 1 1 d . . . C29 C 0.54803(14) 0.2724(2) 0.23462(14) 0.0408(6) Uani 1 1 d . A . H29A H 0.5195 0.3238 0.1939 0.049 Uiso 1 1 calc R . . C30 C 0.63710(14) 0.26483(19) 0.25671(13) 0.0349(5) Uani 1 1 d . . . H30A H 0.6681 0.3109 0.2315 0.042 Uiso 1 1 calc R A . C31 C 0.40238(15) 0.2161(2) 0.24753(15) 0.0491(7) Uani 1 1 d D A 1 C32 C 0.3652(2) 0.0968(3) 0.2298(2) 0.0602(12) Uani 0.769(4) 1 d PD A 1 H32A H 0.3784 0.0665 0.1832 0.090 Uiso 0.769(4) 1 calc PR A 1 H32B H 0.3030 0.0994 0.2186 0.090 Uiso 0.769(4) 1 calc PR A 1 H32C H 0.3906 0.0491 0.2765 0.090 Uiso 0.769(4) 1 calc PR A 1 C33 C 0.3618(2) 0.2838(5) 0.1730(3) 0.0723(15) Uani 0.769(4) 1 d PD A 1 H33A H 0.3822 0.2570 0.1294 0.108 Uiso 0.769(4) 1 calc PR A 1 H33B H 0.3773 0.3625 0.1837 0.108 Uiso 0.769(4) 1 calc PR A 1 H33C H 0.2994 0.2760 0.1573 0.108 Uiso 0.769(4) 1 calc PR A 1 C34 C 0.3755(2) 0.2509(3) 0.3231(2) 0.0512(10) Uani 0.769(4) 1 d PD A 1 H34A H 0.3125 0.2441 0.3074 0.061 Uiso 0.769(4) 1 calc PR A 1 H34B H 0.3993 0.1937 0.3648 0.061 Uiso 0.769(4) 1 calc PR A 1 C35 C 0.3988(3) 0.3657(3) 0.3645(2) 0.0655(10) Uani 0.769(4) 1 d PD A 1 C36 C 0.3658(3) 0.3638(4) 0.4369(3) 0.0767(14) Uani 0.769(4) 1 d PD A 1 H36A H 0.3038 0.3514 0.4187 0.115 Uiso 0.769(4) 1 calc PR A 1 H36B H 0.3785 0.4352 0.4652 0.115 Uiso 0.769(4) 1 calc PR A 1 H36C H 0.3940 0.3035 0.4733 0.115 Uiso 0.769(4) 1 calc PR A 1 C37 C 0.3521(5) 0.4624(5) 0.3123(4) 0.165(4) Uani 0.769(4) 1 d PD A 1 H37A H 0.2907 0.4463 0.2924 0.248 Uiso 0.769(4) 1 calc PR A 1 H37B H 0.3740 0.4720 0.2668 0.248 Uiso 0.769(4) 1 calc PR A 1 H37C H 0.3617 0.5310 0.3443 0.248 Uiso 0.769(4) 1 calc PR A 1 C38 C 0.4954(4) 0.3890(7) 0.3942(6) 0.151(4) Uani 0.769(4) 1 d PD A 1 H38A H 0.5174 0.3908 0.3483 0.226 Uiso 0.769(4) 1 calc PR A 1 H38B H 0.5245 0.3300 0.4314 0.226 Uiso 0.769(4) 1 calc PR A 1 H38C H 0.5060 0.4611 0.4219 0.226 Uiso 0.769(4) 1 calc PR A 1 C31A C 0.40238(15) 0.2161(2) 0.24753(15) 0.0491(7) Uani 0.00 1 d PD A 2 C32A C 0.3551(8) 0.1290(9) 0.2795(8) 0.061(4) Uiso 0.231(4) 1 d PD A 2 H32D H 0.3707 0.0546 0.2657 0.092 Uiso 0.231(4) 1 calc PR A 2 H32E H 0.2933 0.1400 0.2556 0.092 Uiso 0.231(4) 1 calc PR A 2 H32F H 0.3706 0.1359 0.3380 0.092 Uiso 0.231(4) 1 calc PR A 2 C33A C 0.3708(10) 0.2220(13) 0.1557(3) 0.065(5) Uiso 0.231(4) 1 d PD A 2 H33D H 0.3794 0.1496 0.1335 0.097 Uiso 0.231(4) 1 calc PR A 2 H33E H 0.4031 0.2793 0.1376 0.097 Uiso 0.231(4) 1 calc PR A 2 H33F H 0.3098 0.2409 0.1373 0.097 Uiso 0.231(4) 1 calc PR A 2 C34A C 0.3828(7) 0.3411(5) 0.2684(6) 0.042(3) Uiso 0.231(4) 1 d PD A 2 H34C H 0.4136 0.3902 0.2413 0.050 Uiso 0.231(4) 1 calc PR A 2 H34D H 0.3210 0.3533 0.2410 0.050 Uiso 0.231(4) 1 calc PR A 2 C35A C 0.4013(7) 0.3880(8) 0.3547(6) 0.0655(10) Uani 0.231(4) 1 d PD A 2 C36A C 0.3394(8) 0.3324(11) 0.3930(10) 0.071(5) Uiso 0.231(4) 1 d PD A 2 H36D H 0.2803 0.3465 0.3597 0.106 Uiso 0.231(4) 1 calc PR A 2 H36E H 0.3485 0.3633 0.4468 0.106 Uiso 0.231(4) 1 calc PR A 2 H36F H 0.3499 0.2518 0.3971 0.106 Uiso 0.231(4) 1 calc PR A 2 C37A C 0.3873(7) 0.5144(8) 0.3576(8) 0.056(4) Uiso 0.231(4) 1 d PD A 2 H37D H 0.3297 0.5333 0.3229 0.083 Uiso 0.231(4) 1 calc PR A 2 H37E H 0.4297 0.5536 0.3388 0.083 Uiso 0.231(4) 1 calc PR A 2 H37F H 0.3936 0.5369 0.4128 0.083 Uiso 0.231(4) 1 calc PR A 2 C38A C 0.4923(6) 0.3643(11) 0.4105(8) 0.028(3) Uiso 0.231(4) 1 d PD A 2 H38D H 0.5036 0.2840 0.4115 0.042 Uiso 0.231(4) 1 calc PR A 2 H38E H 0.4976 0.3901 0.4648 0.042 Uiso 0.231(4) 1 calc PR A 2 H38F H 0.5338 0.4038 0.3906 0.042 Uiso 0.231(4) 1 calc PR A 2 B1 B 0.82961(15) 0.20850(19) 0.30551(13) 0.0262(5) Uani 1 1 d . . . C1S C 0.5707(3) -0.0567(4) 0.4999(3) 0.0909(12) Uani 1 1 d . . . H1S H 0.6203 -0.0971 0.4994 0.109 Uiso 1 1 calc R . . C2S C 0.5792(3) 0.0440(5) 0.5341(2) 0.0899(13) Uani 1 1 d . . . H2S H 0.6344 0.0750 0.5582 0.108 Uiso 1 1 calc R . . C3S C 0.5075(4) 0.1018(3) 0.5341(2) 0.0929(14) Uani 1 1 d . . . H3S H 0.5128 0.1737 0.5579 0.111 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 O1 0.0197(7) 0.0388(8) 0.0280(8) 0.0038(6) 0.0069(6) 0.0003(6) N1 0.0240(9) 0.0320(9) 0.0292(9) -0.0014(7) 0.0077(7) 0.0020(8) N2 0.0228(9) 0.0301(9) 0.0269(9) -0.0002(7) 0.0079(7) 0.0008(7) N3 0.0256(9) 0.0305(9) 0.0278(9) 0.0009(7) 0.0090(7) -0.0002(8) N4 0.0222(8) 0.0271(9) 0.0255(9) 0.0014(7) 0.0057(7) -0.0002(7) N5 0.0249(9) 0.0308(9) 0.0282(9) 0.0018(7) 0.0073(8) -0.0002(7) N6 0.0222(9) 0.0277(9) 0.0261(9) -0.0003(7) 0.0063(7) 0.0000(7) C1 0.0242(11) 0.0318(11) 0.0290(11) -0.0053(9) 0.0085(9) -0.0016(9) C2 0.0275(11) 0.0294(11) 0.0329(11) -0.0030(9) 0.0122(9) 0.0006(9) C3 0.0310(12) 0.0358(12) 0.0401(13) -0.0067(10) 0.0094(10) 0.0003(10) C4 0.0476(15) 0.0286(11) 0.0556(16) -0.0090(11) 0.0189(13) -0.0058(11) C5 0.0478(14) 0.0309(12) 0.0491(15) 0.0046(11) 0.0204(12) -0.0005(11) C6 0.0361(12) 0.0328(12) 0.0375(12) 0.0015(10) 0.0164(10) 0.0026(10) C7 0.0261(11) 0.0292(11) 0.0343(12) -0.0009(9) 0.0139(9) 0.0021(9) C8 0.0220(10) 0.0313(11) 0.0274(11) 0.0023(9) 0.0094(8) 0.0018(9) C9 0.0213(10) 0.0315(11) 0.0268(11) 0.0033(9) 0.0067(8) -0.0015(9) C10 0.0241(10) 0.0309(11) 0.0291(11) 0.0002(9) 0.0078(9) -0.0043(9) C11 0.0335(12) 0.0350(11) 0.0270(11) 0.0040(9) 0.0077(9) -0.0029(10) C12 0.0426(13) 0.0418(13) 0.0256(11) 0.0000(10) 0.0120(10) -0.0067(11) C13 0.0426(13) 0.0396(12) 0.0340(12) -0.0048(10) 0.0182(10) -0.0022(11) C14 0.0303(12) 0.0347(11) 0.0336(12) -0.0008(9) 0.0114(9) -0.0019(10) C15 0.0254(11) 0.0321(11) 0.0265(11) -0.0008(9) 0.0070(9) -0.0028(9) C16 0.0239(10) 0.0281(10) 0.0301(11) 0.0004(9) 0.0075(9) -0.0004(9) C17 0.0239(10) 0.0283(10) 0.0277(11) 0.0012(8) 0.0089(9) -0.0010(9) C18 0.0227(10) 0.0321(11) 0.0259(10) 0.0026(9) 0.0091(8) -0.0008(9) C19 0.0262(11) 0.0330(11) 0.0325(11) 0.0025(9) 0.0096(9) 0.0026(9) C20 0.0286(11) 0.0384(12) 0.0359(12) 0.0046(10) 0.0077(10) 0.0064(10) C21 0.0270(11) 0.0450(13) 0.0322(12) 0.0013(10) 0.0002(9) 0.0044(10) C22 0.0261(11) 0.0368(12) 0.0309(11) -0.0028(9) 0.0049(9) 0.0002(10) C23 0.0233(10) 0.0345(11) 0.0271(11) 0.0023(9) 0.0095(9) 0.0010(9) C24 0.0215(10) 0.0327(11) 0.0242(10) -0.0020(9) 0.0064(8) -0.0013(9) C25 0.0215(10) 0.0292(10) 0.0255(10) -0.0021(8) 0.0061(8) 0.0000(9) C26 0.0279(11) 0.0317(11) 0.0332(11) 0.0048(9) 0.0078(9) 0.0017(9) C27 0.0257(11) 0.0351(12) 0.0401(12) 0.0054(10) 0.0120(10) -0.0019(10) C28 0.0246(11) 0.0430(13) 0.0340(12) 0.0033(10) 0.0074(9) 0.0023(10) C29 0.0287(12) 0.0552(15) 0.0381(13) 0.0186(11) 0.0100(10) 0.0098(11) C30 0.0268(11) 0.0449(13) 0.0359(12) 0.0120(10) 0.0142(10) 0.0028(10) C31 0.0246(12) 0.0733(18) 0.0474(15) 0.0115(13) 0.0085(11) 0.0048(12) C32 0.0248(17) 0.091(3) 0.059(2) 0.009(2) 0.0052(16) -0.0187(18) C33 0.0215(18) 0.104(4) 0.083(3) 0.052(3) 0.0035(18) 0.012(2) C34 0.0288(17) 0.061(2) 0.069(2) 0.0260(19) 0.0236(16) 0.0124(16) C35 0.068(2) 0.051(2) 0.098(3) 0.0147(19) 0.056(2) 0.0158(18) C36 0.089(3) 0.068(3) 0.093(4) 0.016(3) 0.057(3) 0.023(3) C37 0.305(10) 0.090(4) 0.172(7) 0.083(5) 0.177(8) 0.112(6) C38 0.140(6) 0.116(6) 0.252(10) -0.104(6) 0.143(7) -0.057(5) C31A 0.0246(12) 0.0733(18) 0.0474(15) 0.0115(13) 0.0085(11) 0.0048(12) C35A 0.068(2) 0.051(2) 0.098(3) 0.0147(19) 0.056(2) 0.0158(18) B1 0.0241(12) 0.0300(12) 0.0235(11) 0.0008(9) 0.0061(10) -0.0010(10) C1S 0.108(4) 0.104(3) 0.073(3) 0.037(2) 0.047(3) 0.015(3) C2S 0.095(3) 0.116(4) 0.0456(19) 0.021(2) 0.0031(19) -0.045(3) C3S 0.169(5) 0.067(2) 0.047(2) -0.0004(17) 0.042(3) -0.022(3) _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 O1 C25 1.368(2) . ? O1 B1 1.436(3) . ? N1 C24 1.346(3) . ? N1 C1 1.349(3) . ? N2 C8 1.368(2) . ? N2 C1 1.370(2) . ? N2 B1 1.499(3) . ? N3 C8 1.346(3) . ? N3 C9 1.347(3) . ? N4 C9 1.367(2) . ? N4 C16 1.371(3) . ? N4 B1 1.492(3) . ? N5 C17 1.344(3) . ? N5 C16 1.350(2) . ? N6 C24 1.364(2) . ? N6 C17 1.364(2) . ? N6 B1 1.491(3) . ? C1 C2 1.456(3) . ? C2 C3 1.390(3) . ? C2 C7 1.418(3) . ? C3 C4 1.386(3) . ? C4 C5 1.395(3) . ? C5 C6 1.381(3) . ? C6 C7 1.389(3) . ? C7 C8 1.458(3) . ? C9 C10 1.455(3) . ? C10 C11 1.390(3) . ? C10 C15 1.422(3) . ? C11 C12 1.380(3) . ? C12 C13 1.394(3) . ? C13 C14 1.381(3) . ? C14 C15 1.392(3) . ? C15 C16 1.458(3) . ? C17 C18 1.460(3) . ? C18 C19 1.385(3) . ? C18 C23 1.430(3) . ? C19 C20 1.377(3) . ? C20 C21 1.390(3) . ? C21 C22 1.381(3) . ? C22 C23 1.391(3) . ? C23 C24 1.451(3) . ? C25 C30 1.379(3) . ? C25 C26 1.385(3) . ? C26 C27 1.382(3) . ? C27 C28 1.392(3) . ? C28 C29 1.385(3) . ? C28 C31 1.530(3) . ? C29 C30 1.397(3) . ? C31 C33 1.507(3) . ? C31 C32 1.550(3) . ? C31 C34 1.578(4) . ? C34 C35 1.547(5) . ? C35 C37 1.528(4) . ? C35 C36 1.530(4) . ? C35 C38 1.536(4) . ? C34A C35A 1.554(6) . ? C35A C36A 1.537(5) . ? C35A C37A 1.537(5) . ? C35A C38A 1.538(5) . ? C1S C2S 1.337(6) . ? C1S C3S 1.352(6) 3_656 ? C2S C3S 1.369(6) . ? C3S C1S 1.352(6) 3_656 ? 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 C25 O1 B1 129.14(16) . . ? C24 N1 C1 116.99(17) . . ? C8 N2 C1 112.88(16) . . ? C8 N2 B1 123.33(16) . . ? C1 N2 B1 122.34(16) . . ? C8 N3 C9 117.16(17) . . ? C9 N4 C16 112.64(16) . . ? C9 N4 B1 123.37(16) . . ? C16 N4 B1 122.83(16) . . ? C17 N5 C16 116.57(17) . . ? C24 N6 C17 113.69(16) . . ? C24 N6 B1 123.13(16) . . ? C17 N6 B1 122.92(16) . . ? N1 C1 N2 122.68(18) . . ? N1 C1 C2 130.14(18) . . ? N2 C1 C2 105.62(17) . . ? C3 C2 C7 120.8(2) . . ? C3 C2 C1 131.9(2) . . ? C7 C2 C1 107.24(17) . . ? C4 C3 C2 117.5(2) . . ? C3 C4 C5 121.8(2) . . ? C6 C5 C4 121.0(2) . . ? C5 C6 C7 118.1(2) . . ? C6 C7 C2 120.66(19) . . ? C6 C7 C8 132.0(2) . . ? C2 C7 C8 107.24(17) . . ? N3 C8 N2 122.42(18) . . ? N3 C8 C7 130.60(18) . . ? N2 C8 C7 105.65(17) . . ? N3 C9 N4 122.12(18) . . ? N3 C9 C10 130.21(18) . . ? N4 C9 C10 105.90(17) . . ? C11 C10 C15 120.66(19) . . ? C11 C10 C9 132.32(19) . . ? C15 C10 C9 106.99(17) . . ? C12 C11 C10 118.1(2) . . ? C11 C12 C13 121.2(2) . . ? C14 C13 C12 121.7(2) . . ? C13 C14 C15 117.8(2) . . ? C14 C15 C10 120.35(19) . . ? C14 C15 C16 132.38(19) . . ? C10 C15 C16 107.18(17) . . ? N5 C16 N4 122.67(18) . . ? N5 C16 C15 130.45(18) . . ? N4 C16 C15 105.68(16) . . ? N5 C17 N6 122.44(17) . . ? N5 C17 C18 130.97(18) . . ? N6 C17 C18 105.27(16) . . ? C19 C18 C23 120.31(18) . . ? C19 C18 C17 132.58(19) . . ? C23 C18 C17 107.05(17) . . ? C20 C19 C18 118.7(2) . . ? C19 C20 C21 121.1(2) . . ? C22 C21 C20 121.6(2) . . ? C21 C22 C23 118.2(2) . . ? C22 C23 C18 120.05(19) . . ? C22 C23 C24 132.85(19) . . ? C18 C23 C24 107.06(17) . . ? N1 C24 N6 121.80(17) . . ? N1 C24 C23 131.01(18) . . ? N6 C24 C23 105.73(17) . . ? O1 C25 C30 124.95(18) . . ? O1 C25 C26 116.36(17) . . ? C30 C25 C26 118.66(19) . . ? C27 C26 C25 120.88(19) . . ? C26 C27 C28 121.8(2) . . ? C29 C28 C27 116.4(2) . . ? C29 C28 C31 123.37(19) . . ? C27 C28 C31 120.21(19) . . ? C28 C29 C30 122.5(2) . . ? C25 C30 C29 119.7(2) . . ? C33 C31 C28 113.7(2) . . ? C33 C31 C32 106.4(3) . . ? C28 C31 C32 107.9(2) . . ? C33 C31 C34 115.0(3) . . ? C28 C31 C34 110.4(2) . . ? C32 C31 C34 102.5(2) . . ? C35 C34 C31 122.4(3) . . ? C37 C35 C36 105.4(3) . . ? C37 C35 C38 109.8(5) . . ? C36 C35 C38 108.6(5) . . ? C37 C35 C34 113.0(4) . . ? C36 C35 C34 106.0(3) . . ? C38 C35 C34 113.5(4) . . ? C36A C35A C37A 106.7(6) . . ? C36A C35A C38A 106.8(6) . . ? C37A C35A C38A 106.7(6) . . ? C36A C35A C34A 108.3(11) . . ? C37A C35A C34A 113.8(9) . . ? C38A C35A C34A 114.1(10) . . ? O1 B1 N6 108.04(16) . . ? O1 B1 N4 117.43(17) . . ? N6 B1 N4 103.58(16) . . ? O1 B1 N2 118.73(18) . . ? N6 B1 N2 103.45(16) . . ? N4 B1 N2 103.80(16) . . ? C2S C1S C3S 120.7(4) . 3_656 ? C1S C2S C3S 119.3(4) . . ? C1S C3S C2S 120.0(4) 3_656 . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.438 _refine_diff_density_min -0.423 _refine_diff_density_rms 0.053 _vrf_PLAT220_k09104 ; PROBLEM: Large Non-Solvent C Ueq(max)/Ueq(min) ... 6.42 Ratio RESPONSE: The atoms of the tetramethylbutyl group are disordered over two sites. The disorder has been modelled carefully. One of the atoms of the major disorder component has a larger than normal anisotropic displacement parameter [ADP]. ; _vrf_PLAT222_k09104 ; PROBLEM: Large Non-Solvent H Ueq(max)/Ueq(min) ... 6.70 Ratio RESPONSE: H atom bonded to C atom above. ; _vrf_PLAT242_k09104 ; PROBLEM: Check Low Ueq as Compared to Neighbors for C35 RESPONSE: The C atom with a large ADP is bonded to this atom. ; _vrf_PLAT331_k09104 ; PROBLEM: Small Average Phenyl C-C Dist. C1S -C3S_a 1.35 Ang. RESPONSE: A benzene solvent molecule lies on an inversion center. No constraints were applied to the bond lengths. ; # Attachment '- compound 2e k08356.cif' data_k08356 _database_code_depnum_ccdc_archive 'CCDC 783169' #TrackingRef '- compound 2e k08356.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C30 H16 B F N6 O' _chemical_formula_sum 'C30 H16 B F N6 O' _chemical_formula_weight 506.30 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' O O 0.0106 0.0060 '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_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.0420(3) _cell_length_b 10.7558(4) _cell_length_c 11.7366(4) _cell_angle_alpha 85.8210(18) _cell_angle_beta 77.1560(19) _cell_angle_gamma 66.5820(19) _cell_volume 1133.97(7) _cell_formula_units_Z 2 _cell_measurement_temperature 150(1) _cell_measurement_reflns_used 10460 _cell_measurement_theta_min 2.6 _cell_measurement_theta_max 27.5 _exptl_crystal_description plate _exptl_crystal_colour red _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.483 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 520 _exptl_absorpt_coefficient_mu 0.099 # Absorption correction _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.753 _exptl_absorpt_correction_T_max 0.990 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(1) _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 'Nonius KappaCCD' _diffrn_measurement_method '\f scans and \w scans \k offsets' _diffrn_detector_area_resol_mean 9 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10460 _diffrn_reflns_av_R_equivalents 0.0511 _diffrn_reflns_av_sigmaI/netI 0.0705 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.57 _diffrn_reflns_theta_max 27.54 _reflns_number_total 5099 _reflns_number_gt 3251 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Collect (Nonius B.V., 1997-2002)' _computing_cell_refinement 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction Denzo-SMN _computing_structure_solution 'SIR-92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXTL V6.1 (Sheldrick, 2008)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material 'SHELXTL V6.1' _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. Blessing, R. H. (1995). Acta Cryst. A51, 33-38. Nonius B.V (1997-2002). Collect. Data collection software, Delft, The Netherlands. Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A edited by C. W. Carter & R. M. Sweet pp. 307-326. London: Academic press. Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122. Spek, A.L. (2003). J. Appl. Cryst. 36, 7-13. ; _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^)+(0.0750P)^2^+0.2255P] 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 5099 _refine_ls_number_parameters 352 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1005 _refine_ls_R_factor_gt 0.0553 _refine_ls_wR_factor_ref 0.1536 _refine_ls_wR_factor_gt 0.1262 _refine_ls_goodness_of_fit_ref 1.021 _refine_ls_restrained_S_all 1.021 _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 F1 F 0.12235(15) 0.40554(16) 0.22936(13) 0.0513(4) Uani 1 1 d . . . O1 O 0.61071(15) 0.08084(15) 0.40049(12) 0.0259(3) Uani 1 1 d . . . N1 N 0.66992(18) 0.00021(18) 0.08182(15) 0.0263(4) Uani 1 1 d . . . N2 N 0.69924(18) -0.11502(17) 0.26152(14) 0.0238(4) Uani 1 1 d . . . N3 N 0.82785(19) -0.29705(18) 0.37522(14) 0.0258(4) Uani 1 1 d . . . N4 N 0.86429(18) -0.09010(18) 0.36506(14) 0.0236(4) Uani 1 1 d . . . N5 N 0.99545(19) 0.04855(18) 0.28163(15) 0.0268(4) Uani 1 1 d . . . N6 N 0.78912(18) 0.05621(18) 0.21114(14) 0.0240(4) Uani 1 1 d . . . C1 C 0.6577(2) -0.0973(2) 0.15622(17) 0.0244(5) Uani 1 1 d . . . C2 C 0.6365(2) -0.2193(2) 0.13588(17) 0.0244(5) Uani 1 1 d . . . C3 C 0.5934(2) -0.2579(2) 0.04353(19) 0.0290(5) Uani 1 1 d . . . H3A H 0.5619 -0.1968 -0.0170 0.035 Uiso 1 1 calc R . . C4 C 0.5982(2) -0.3877(2) 0.04335(19) 0.0317(5) Uani 1 1 d . . . H4A H 0.5658 -0.4151 -0.0170 0.038 Uiso 1 1 calc R . . C5 C 0.6491(2) -0.4799(2) 0.12917(19) 0.0300(5) Uani 1 1 d . . . H5A H 0.6517 -0.5688 0.1256 0.036 Uiso 1 1 calc R . . C6 C 0.6960(2) -0.4445(2) 0.21960(18) 0.0273(5) Uani 1 1 d . . . H6A H 0.7335 -0.5087 0.2766 0.033 Uiso 1 1 calc R . . C7 C 0.6868(2) -0.3123(2) 0.22476(17) 0.0243(5) Uani 1 1 d . . . C8 C 0.7355(2) -0.2446(2) 0.30078(17) 0.0237(5) Uani 1 1 d . . . C9 C 0.8982(2) -0.2219(2) 0.39990(17) 0.0236(5) Uani 1 1 d . . . C10 C 1.0397(2) -0.2645(2) 0.43435(17) 0.0245(5) Uani 1 1 d . . . C11 C 1.1293(2) -0.3850(2) 0.47796(17) 0.0286(5) Uani 1 1 d . . . H11A H 1.0955 -0.4559 0.5002 0.034 Uiso 1 1 calc R . . C12 C 1.2688(2) -0.3986(2) 0.48805(18) 0.0320(5) Uani 1 1 d . . . H12A H 1.3310 -0.4802 0.5182 0.038 Uiso 1 1 calc R . . C13 C 1.3209(2) -0.2966(2) 0.4554(2) 0.0344(6) Uani 1 1 d . . . H13A H 1.4178 -0.3099 0.4633 0.041 Uiso 1 1 calc R . . C14 C 1.2338(2) -0.1761(2) 0.41168(19) 0.0316(5) Uani 1 1 d . . . H14A H 1.2699 -0.1068 0.3886 0.038 Uiso 1 1 calc R . . C15 C 1.0924(2) -0.1590(2) 0.40238(17) 0.0250(5) Uani 1 1 d . . . C16 C 0.9813(2) -0.0520(2) 0.35221(17) 0.0252(5) Uani 1 1 d . . . C17 C 0.9024(2) 0.0970(2) 0.20754(18) 0.0249(5) Uani 1 1 d . . . C18 C 0.9138(2) 0.1690(2) 0.09816(18) 0.0253(5) Uani 1 1 d . . . C19 C 0.9981(2) 0.2437(2) 0.05074(19) 0.0291(5) Uani 1 1 d . . . H19A H 1.0660 0.2533 0.0908 0.035 Uiso 1 1 calc R . . C20 C 0.9804(2) 0.3034(2) -0.05584(19) 0.0325(5) Uani 1 1 d . . . H20A H 1.0337 0.3582 -0.0877 0.039 Uiso 1 1 calc R . . C21 C 0.8855(2) 0.2850(2) -0.11832(19) 0.0316(5) Uani 1 1 d . . . H21A H 0.8768 0.3263 -0.1921 0.038 Uiso 1 1 calc R . . C22 C 0.8043(2) 0.2076(2) -0.07419(18) 0.0288(5) Uani 1 1 d . . . H22A H 0.7428 0.1926 -0.1179 0.035 Uiso 1 1 calc R . . C23 C 0.8150(2) 0.1525(2) 0.03573(18) 0.0257(5) Uani 1 1 d . . . C24 C 0.7437(2) 0.0712(2) 0.10789(17) 0.0244(5) Uani 1 1 d . . . C25 C 0.4872(2) 0.1633(2) 0.35777(17) 0.0244(5) Uani 1 1 d . . . C26 C 0.4753(2) 0.2899(2) 0.31538(18) 0.0284(5) Uani 1 1 d . . . H26A H 0.5519 0.3204 0.3159 0.034 Uiso 1 1 calc R . . C27 C 0.3518(2) 0.3723(2) 0.27204(19) 0.0329(5) Uani 1 1 d . . . H27A H 0.3422 0.4596 0.2431 0.040 Uiso 1 1 calc R . . C28 C 0.2438(2) 0.3248(2) 0.27195(19) 0.0338(6) Uani 1 1 d . . . C29 C 0.2529(2) 0.1996(3) 0.31285(19) 0.0330(5) Uani 1 1 d . . . H29A H 0.1766 0.1692 0.3109 0.040 Uiso 1 1 calc R . . C30 C 0.3760(2) 0.1184(2) 0.35723(18) 0.0286(5) Uani 1 1 d . . . H30A H 0.3840 0.0318 0.3872 0.034 Uiso 1 1 calc R . . B1 B 0.7316(3) -0.0107(3) 0.3154(2) 0.0240(5) 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 0.0421(8) 0.0476(10) 0.0576(9) 0.0072(8) -0.0270(7) -0.0030(7) O1 0.0283(7) 0.0257(9) 0.0237(7) 0.0016(6) -0.0079(6) -0.0096(6) N1 0.0283(9) 0.0223(10) 0.0287(10) 0.0006(8) -0.0080(8) -0.0092(8) N2 0.0257(9) 0.0199(10) 0.0261(9) 0.0029(7) -0.0082(7) -0.0082(7) N3 0.0306(9) 0.0233(10) 0.0248(9) 0.0014(8) -0.0086(8) -0.0106(8) N4 0.0267(9) 0.0228(10) 0.0229(9) 0.0021(7) -0.0083(7) -0.0099(8) N5 0.0311(9) 0.0216(10) 0.0293(10) 0.0012(8) -0.0102(8) -0.0100(8) N6 0.0257(9) 0.0221(10) 0.0246(9) 0.0012(7) -0.0078(7) -0.0087(7) C1 0.0242(10) 0.0229(12) 0.0253(11) 0.0012(9) -0.0077(9) -0.0072(9) C2 0.0238(10) 0.0238(12) 0.0261(11) 0.0025(9) -0.0069(9) -0.0095(9) C3 0.0308(11) 0.0258(12) 0.0325(12) 0.0029(10) -0.0116(10) -0.0112(10) C4 0.0350(12) 0.0319(13) 0.0321(12) -0.0007(10) -0.0122(10) -0.0143(10) C5 0.0318(11) 0.0262(12) 0.0335(12) -0.0002(10) -0.0070(10) -0.0128(10) C6 0.0307(11) 0.0232(12) 0.0270(11) 0.0013(9) -0.0051(9) -0.0102(9) C7 0.0244(10) 0.0244(12) 0.0245(11) 0.0004(9) -0.0038(9) -0.0107(9) C8 0.0274(11) 0.0227(12) 0.0208(10) 0.0022(9) -0.0044(9) -0.0102(9) C9 0.0296(11) 0.0201(11) 0.0201(10) 0.0012(8) -0.0061(9) -0.0083(9) C10 0.0298(11) 0.0250(12) 0.0193(10) 0.0000(9) -0.0090(9) -0.0093(9) C11 0.0374(12) 0.0267(12) 0.0219(11) 0.0021(9) -0.0104(9) -0.0107(10) C12 0.0378(12) 0.0285(13) 0.0281(12) 0.0021(10) -0.0162(10) -0.0068(10) C13 0.0308(12) 0.0369(14) 0.0365(13) -0.0007(11) -0.0162(10) -0.0092(11) C14 0.0343(12) 0.0307(13) 0.0338(12) 0.0001(10) -0.0124(10) -0.0140(10) C15 0.0304(11) 0.0232(12) 0.0215(10) -0.0015(9) -0.0095(9) -0.0081(9) C16 0.0296(11) 0.0231(12) 0.0249(11) -0.0015(9) -0.0076(9) -0.0111(9) C17 0.0282(11) 0.0194(11) 0.0283(11) -0.0001(9) -0.0084(9) -0.0093(9) C18 0.0255(10) 0.0199(11) 0.0266(11) -0.0002(9) -0.0045(9) -0.0052(9) C19 0.0282(11) 0.0233(12) 0.0344(12) 0.0013(10) -0.0047(10) -0.0099(9) C20 0.0303(12) 0.0270(13) 0.0361(13) 0.0026(10) 0.0008(10) -0.0113(10) C21 0.0323(12) 0.0262(13) 0.0272(11) 0.0039(10) -0.0016(10) -0.0051(10) C22 0.0296(11) 0.0262(12) 0.0264(11) -0.0018(9) -0.0063(9) -0.0059(9) C23 0.0270(11) 0.0193(11) 0.0274(11) 0.0007(9) -0.0067(9) -0.0050(9) C24 0.0266(10) 0.0190(11) 0.0258(11) -0.0003(9) -0.0096(9) -0.0049(9) C25 0.0263(11) 0.0239(12) 0.0193(10) -0.0019(9) -0.0045(8) -0.0057(9) C26 0.0337(12) 0.0254(12) 0.0273(11) 0.0003(9) -0.0080(10) -0.0119(10) C27 0.0408(13) 0.0245(13) 0.0297(12) 0.0003(10) -0.0087(10) -0.0083(10) C28 0.0297(12) 0.0354(14) 0.0293(12) -0.0018(10) -0.0108(10) -0.0027(10) C29 0.0308(12) 0.0384(15) 0.0309(12) -0.0002(11) -0.0078(10) -0.0138(11) C30 0.0314(11) 0.0277(13) 0.0272(11) 0.0015(9) -0.0057(9) -0.0127(10) B1 0.0270(12) 0.0234(13) 0.0230(12) 0.0022(10) -0.0071(10) -0.0106(10) _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 C28 1.363(2) . ? O1 C25 1.383(2) . ? O1 B1 1.447(3) . ? N1 C1 1.341(3) . ? N1 C24 1.345(3) . ? N2 C8 1.366(3) . ? N2 C1 1.367(2) . ? N2 B1 1.500(3) . ? N3 C8 1.347(3) . ? N3 C9 1.347(3) . ? N4 C16 1.366(3) . ? N4 C9 1.373(3) . ? N4 B1 1.488(3) . ? N5 C17 1.345(3) . ? N5 C16 1.347(3) . ? N6 C24 1.364(2) . ? N6 C17 1.364(3) . ? N6 B1 1.496(3) . ? C1 C2 1.453(3) . ? C2 C3 1.397(3) . ? C2 C7 1.423(3) . ? C3 C4 1.378(3) . ? C4 C5 1.393(3) . ? C5 C6 1.385(3) . ? C6 C7 1.393(3) . ? C7 C8 1.462(3) . ? C9 C10 1.451(3) . ? C10 C11 1.390(3) . ? C10 C15 1.426(3) . ? C11 C12 1.381(3) . ? C12 C13 1.389(3) . ? C13 C14 1.382(3) . ? C14 C15 1.386(3) . ? C15 C16 1.446(3) . ? C17 C18 1.456(3) . ? C18 C19 1.392(3) . ? C18 C23 1.426(3) . ? C19 C20 1.378(3) . ? C20 C21 1.403(3) . ? C21 C22 1.384(3) . ? C22 C23 1.388(3) . ? C23 C24 1.455(3) . ? C25 C30 1.383(3) . ? C25 C26 1.384(3) . ? C26 C27 1.388(3) . ? C27 C28 1.370(3) . ? C28 C29 1.371(3) . ? C29 C30 1.388(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C25 O1 B1 115.24(15) . . ? C1 N1 C24 116.67(17) . . ? C8 N2 C1 113.31(17) . . ? C8 N2 B1 122.95(17) . . ? C1 N2 B1 122.62(18) . . ? C8 N3 C9 117.16(18) . . ? C16 N4 C9 112.80(17) . . ? C16 N4 B1 122.11(18) . . ? C9 N4 B1 123.09(17) . . ? C17 N5 C16 117.04(17) . . ? C24 N6 C17 113.60(17) . . ? C24 N6 B1 123.70(17) . . ? C17 N6 B1 122.44(16) . . ? N1 C1 N2 123.19(18) . . ? N1 C1 C2 129.73(18) . . ? N2 C1 C2 105.50(17) . . ? C3 C2 C7 120.8(2) . . ? C3 C2 C1 131.4(2) . . ? C7 C2 C1 107.41(17) . . ? C4 C3 C2 117.6(2) . . ? C3 C4 C5 121.8(2) . . ? C6 C5 C4 121.3(2) . . ? C5 C6 C7 118.2(2) . . ? C6 C7 C2 120.14(18) . . ? C6 C7 C8 132.58(19) . . ? C2 C7 C8 106.90(18) . . ? N3 C8 N2 122.51(18) . . ? N3 C8 C7 130.17(19) . . ? N2 C8 C7 105.55(17) . . ? N3 C9 N4 122.56(18) . . ? N3 C9 C10 129.67(19) . . ? N4 C9 C10 105.72(17) . . ? C11 C10 C15 119.98(19) . . ? C11 C10 C9 132.8(2) . . ? C15 C10 C9 106.85(18) . . ? C12 C11 C10 118.1(2) . . ? C11 C12 C13 122.0(2) . . ? C14 C13 C12 120.9(2) . . ? C13 C14 C15 118.3(2) . . ? C14 C15 C10 120.8(2) . . ? C14 C15 C16 131.4(2) . . ? C10 C15 C16 107.51(17) . . ? N5 C16 N4 123.14(18) . . ? N5 C16 C15 129.20(19) . . ? N4 C16 C15 105.87(18) . . ? N5 C17 N6 121.72(19) . . ? N5 C17 C18 131.42(19) . . ? N6 C17 C18 105.33(16) . . ? C19 C18 C23 120.3(2) . . ? C19 C18 C17 132.45(19) . . ? C23 C18 C17 107.28(18) . . ? C20 C19 C18 118.3(2) . . ? C19 C20 C21 121.4(2) . . ? C22 C21 C20 121.1(2) . . ? C21 C22 C23 118.2(2) . . ? C22 C23 C18 120.7(2) . . ? C22 C23 C24 132.4(2) . . ? C18 C23 C24 106.97(17) . . ? N1 C24 N6 121.96(19) . . ? N1 C24 C23 131.48(18) . . ? N6 C24 C23 105.58(17) . . ? C30 C25 O1 119.71(19) . . ? C30 C25 C26 120.18(19) . . ? O1 C25 C26 120.11(18) . . ? C25 C26 C27 120.1(2) . . ? C28 C27 C26 118.4(2) . . ? F1 C28 C27 118.5(2) . . ? F1 C28 C29 118.7(2) . . ? C27 C28 C29 122.7(2) . . ? C28 C29 C30 118.5(2) . . ? C25 C30 C29 120.0(2) . . ? O1 B1 N4 112.56(17) . . ? O1 B1 N6 114.95(18) . . ? N4 B1 N6 104.39(17) . . ? O1 B1 N2 116.16(17) . . ? N4 B1 N2 104.65(17) . . ? N6 B1 N2 102.79(16) . . ? _diffrn_measured_fraction_theta_max 0.978 _diffrn_reflns_theta_full 27.54 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.311 _refine_diff_density_min -0.301 _refine_diff_density_rms 0.064