# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email zxie@cuhk.edu.hk _publ_contact_author_name 'Zuowei Xie' loop_ _publ_author_name 'Jian Zhang' 'Hoi-Shan Chan' 'Zuowei Xie' data_[2][PSH] _database_code_depnum_ccdc_archive 'CCDC 812778' #TrackingRef '- CIF_rev.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H43 B11 N2 O2' _chemical_formula_weight 474.48 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' O O 0.0106 0.0060 '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' _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 8.4249(4) _cell_length_b 10.9067(6) _cell_length_c 15.1728(8) _cell_angle_alpha 85.3560(10) _cell_angle_beta 86.9400(10) _cell_angle_gamma 83.3410(10) _cell_volume 1378.88(12) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 90 _cell_measurement_theta_min 15 _cell_measurement_theta_max 15 _exptl_crystal_description block _exptl_crystal_colour colourless _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 1.143 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 508 _exptl_absorpt_coefficient_mu 0.065 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6719 _exptl_absorpt_correction_T_max 0.7456 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'BRUKER KAPPA APEXII DUO DIFFRACTOMETER' _diffrn_measurement_method 'PHI & OMEGA SCAN' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 15387 _diffrn_reflns_av_R_equivalents 0.0350 _diffrn_reflns_av_sigmaI/netI 0.0337 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.35 _diffrn_reflns_theta_max 25.25 _reflns_number_total 4967 _reflns_number_gt 4130 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER KAPPA APEXII DUO DIFFRACTOMETER' _computing_cell_refinement 'BRUKER KAPPA APEXII DUO DIFFRACTOMETER' _computing_data_reduction 'BRUKER KAPPA APEXII DUO DIFFRACTOMETER' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SIEMENS SHELXTL' _computing_publication_material 'SIEMENS 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^)+(0.0868P)^2^+0.6110P] 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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4967 _refine_ls_number_parameters 337 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0626 _refine_ls_R_factor_gt 0.0523 _refine_ls_wR_factor_ref 0.1627 _refine_ls_wR_factor_gt 0.1520 _refine_ls_goodness_of_fit_ref 1.092 _refine_ls_restrained_S_all 1.092 _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 0.10888(15) 0.55696(12) 0.09030(9) 0.0293(3) Uani 1 1 d . . . O2 O 0.34879(16) 0.58696(13) 0.14757(10) 0.0360(4) Uani 1 1 d . . . N1 N 0.31164(18) 0.16168(14) 0.30953(10) 0.0261(4) Uani 1 1 d . . . N2 N 0.49714(17) 0.30934(13) 0.36974(10) 0.0225(3) Uani 1 1 d . . . B1 B -0.1712(2) 0.64374(19) 0.38622(14) 0.0259(4) Uani 1 1 d . . . H1 H -0.2363 0.5634 0.4120 0.031 Uiso 1 1 calc R . . B2 B -0.2729(2) 0.78466(19) 0.34378(14) 0.0272(5) Uani 1 1 d . . . H2 H -0.4064 0.7985 0.3409 0.033 Uiso 1 1 calc R . . B3 B -0.1534(2) 0.69118(19) 0.27254(14) 0.0243(4) Uani 1 1 d . . . H3 H -0.2063 0.6413 0.2215 0.029 Uiso 1 1 calc R . . B4 B 0.0185(2) 0.62320(18) 0.32624(13) 0.0237(4) Uani 1 1 d . . . H4 H 0.0774 0.5302 0.3091 0.028 Uiso 1 1 calc R . . B5 B 0.0029(3) 0.67557(19) 0.43560(14) 0.0265(4) Uani 1 1 d . . . H5 H 0.0507 0.6147 0.4934 0.032 Uiso 1 1 calc R . . B6 B -0.1776(3) 0.7791(2) 0.44543(14) 0.0279(5) Uani 1 1 d . . . H6 H -0.2509 0.7913 0.5085 0.033 Uiso 1 1 calc R . . B8 B 0.0293(2) 0.76062(18) 0.25115(13) 0.0231(4) Uani 1 1 d . . . B9 B 0.1405(2) 0.73399(19) 0.35734(14) 0.0258(4) Uani 1 1 d . . . H9 H 0.2706 0.7473 0.3514 0.031 Uiso 1 1 calc R . . B10 B 0.0134(3) 0.8356(2) 0.43557(14) 0.0280(5) Uani 1 1 d . . . H10 H 0.0772 0.9011 0.4702 0.034 Uiso 1 1 calc R . . B11 B -0.1544(3) 0.90549(19) 0.36480(15) 0.0293(5) Uani 1 1 d . . . H11 H -0.1620 1.0090 0.3587 0.035 Uiso 1 1 calc R . . B12 B 0.1956(2) 0.6336(2) 0.13100(13) 0.0253(4) Uani 1 1 d . . . C7 C -0.1463(2) 0.84554(16) 0.26733(12) 0.0245(4) Uani 1 1 d . . . C11 C -0.2205(2) 0.92288(18) 0.18803(13) 0.0321(4) Uani 1 1 d . . . H11A H -0.3088 0.8811 0.1678 0.039 Uiso 1 1 calc R . . H11B H -0.2670 1.0046 0.2072 0.039 Uiso 1 1 calc R . . C12 C -0.1015(3) 0.94250(18) 0.11090(14) 0.0355(5) Uani 1 1 d . . . H12A H -0.0243 0.9976 0.1275 0.043 Uiso 1 1 calc R . . H12B H -0.1593 0.9842 0.0597 0.043 Uiso 1 1 calc R . . C13 C -0.0106(2) 0.82155(18) 0.08392(12) 0.0307(4) Uani 1 1 d . . . H13A H 0.0461 0.8366 0.0259 0.037 Uiso 1 1 calc R . . H13B H -0.0878 0.7615 0.0769 0.037 Uiso 1 1 calc R . . C14 C 0.1123(2) 0.76476(17) 0.15237(12) 0.0268(4) Uani 1 1 d . . . H14A H 0.1979 0.8213 0.1511 0.032 Uiso 1 1 calc R . . C15 C 0.1831(3) 0.43950(19) 0.06521(15) 0.0379(5) Uani 1 1 d . . . H15A H 0.1051 0.3969 0.0372 0.057 Uiso 1 1 calc R . . H15B H 0.2216 0.3892 0.1179 0.057 Uiso 1 1 calc R . . H15C H 0.2735 0.4519 0.0233 0.057 Uiso 1 1 calc R . . C16 C 0.4643(2) 0.6573(2) 0.17918(16) 0.0422(5) Uani 1 1 d . . . H16A H 0.5660 0.6046 0.1862 0.063 Uiso 1 1 calc R . . H16B H 0.4258 0.6877 0.2364 0.063 Uiso 1 1 calc R . . H16C H 0.4802 0.7277 0.1366 0.063 Uiso 1 1 calc R . . C17 C 0.5292(2) 0.24590(15) 0.21504(11) 0.0225(4) Uani 1 1 d . . . C18 C 0.3951(2) 0.17641(16) 0.22334(12) 0.0259(4) Uani 1 1 d . . . C19 C 0.3479(2) 0.12320(19) 0.15170(14) 0.0362(5) Uani 1 1 d . . . H19A H 0.2580 0.0775 0.1580 0.043 Uiso 1 1 calc R . . C20 C 0.4304(3) 0.1353(2) 0.06894(14) 0.0408(5) Uani 1 1 d . . . H20A H 0.3952 0.0987 0.0198 0.049 Uiso 1 1 calc R . . C21 C 0.5594(3) 0.19857(19) 0.05917(13) 0.0362(5) Uani 1 1 d . . . H21A H 0.6148 0.2051 0.0031 0.043 Uiso 1 1 calc R . . C22 C 0.6137(2) 0.25537(17) 0.13068(12) 0.0280(4) Uani 1 1 d . . . C23 C 0.7488(2) 0.32173(18) 0.11996(13) 0.0331(5) Uani 1 1 d . . . H23A H 0.8036 0.3280 0.0637 0.040 Uiso 1 1 calc R . . C24 C 0.8021(2) 0.37689(19) 0.18835(14) 0.0351(5) Uani 1 1 d . . . H24A H 0.8942 0.4199 0.1800 0.042 Uiso 1 1 calc R . . C25 C 0.7199(2) 0.36979(18) 0.27125(13) 0.0306(4) Uani 1 1 d . . . H25A H 0.7564 0.4086 0.3190 0.037 Uiso 1 1 calc R . . C26 C 0.5881(2) 0.30763(16) 0.28387(11) 0.0225(4) Uani 1 1 d . . . C27 C 0.1387(2) 0.2012(2) 0.30668(16) 0.0456(6) Uani 1 1 d . . . H27A H 0.1214 0.2859 0.2793 0.068 Uiso 1 1 calc R . . H27B H 0.0909 0.1985 0.3670 0.068 Uiso 1 1 calc R . . H27C H 0.0888 0.1455 0.2718 0.068 Uiso 1 1 calc R . . C28 C 0.3446(3) 0.03392(18) 0.35028(15) 0.0424(5) Uani 1 1 d . . . H28A H 0.4604 0.0106 0.3509 0.064 Uiso 1 1 calc R . . H28B H 0.2962 -0.0231 0.3159 0.064 Uiso 1 1 calc R . . H28C H 0.2989 0.0297 0.4111 0.064 Uiso 1 1 calc R . . C29 C 0.5958(2) 0.26260(19) 0.44674(13) 0.0330(4) Uani 1 1 d . . . H29A H 0.6498 0.1801 0.4367 0.049 Uiso 1 1 calc R . . H29B H 0.5266 0.2579 0.5006 0.049 Uiso 1 1 calc R . . H29C H 0.6759 0.3191 0.4535 0.049 Uiso 1 1 calc R . . C30 C 0.4117(2) 0.43505(17) 0.38211(13) 0.0307(4) Uani 1 1 d . . . H30A H 0.3478 0.4628 0.3306 0.046 Uiso 1 1 calc R . . H30B H 0.4900 0.4933 0.3882 0.046 Uiso 1 1 calc R . . H30C H 0.3413 0.4315 0.4356 0.046 Uiso 1 1 calc R . . H2A H 0.414(3) 0.254(2) 0.3636(15) 0.041(6) Uiso 1 1 d . . . H8 H 0.122(3) 0.821(2) 0.3011(14) 0.038(6) Uiso 1 1 d . . . H10B H -0.001(3) 0.919(2) 0.3772(15) 0.044(6) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0266(7) 0.0304(7) 0.0314(7) -0.0065(5) -0.0018(5) -0.0021(5) O2 0.0232(7) 0.0407(8) 0.0442(9) -0.0074(6) -0.0039(6) 0.0006(6) N1 0.0224(8) 0.0250(8) 0.0312(8) -0.0020(6) 0.0003(6) -0.0050(6) N2 0.0215(7) 0.0239(8) 0.0228(8) -0.0047(6) -0.0002(6) -0.0036(6) B1 0.0274(11) 0.0247(10) 0.0266(11) -0.0011(8) -0.0008(8) -0.0074(8) B2 0.0219(10) 0.0271(10) 0.0326(11) -0.0048(9) 0.0019(8) -0.0022(8) B3 0.0216(10) 0.0245(10) 0.0272(11) -0.0027(8) -0.0007(8) -0.0036(8) B4 0.0241(10) 0.0219(10) 0.0249(10) -0.0010(8) -0.0030(8) -0.0011(8) B5 0.0304(11) 0.0259(10) 0.0238(10) -0.0002(8) -0.0013(8) -0.0063(8) B6 0.0282(11) 0.0289(11) 0.0273(11) -0.0049(8) 0.0049(8) -0.0067(9) B8 0.0233(10) 0.0215(9) 0.0239(10) -0.0011(8) -0.0022(8) -0.0003(8) B9 0.0243(10) 0.0273(10) 0.0262(11) -0.0009(8) -0.0019(8) -0.0044(8) B10 0.0286(11) 0.0265(11) 0.0304(11) -0.0051(9) 0.0003(9) -0.0077(8) B11 0.0301(11) 0.0235(10) 0.0345(12) -0.0051(9) 0.0011(9) -0.0035(9) B12 0.0219(10) 0.0333(11) 0.0203(10) 0.0011(8) 0.0013(8) -0.0041(8) C7 0.0231(9) 0.0211(9) 0.0283(10) -0.0012(7) -0.0001(7) 0.0000(7) C11 0.0305(10) 0.0272(10) 0.0358(11) 0.0020(8) -0.0031(8) 0.0059(8) C12 0.0399(11) 0.0301(10) 0.0340(11) 0.0070(8) -0.0045(9) 0.0014(9) C13 0.0348(10) 0.0326(10) 0.0233(10) 0.0026(8) -0.0022(8) -0.0008(8) C14 0.0254(9) 0.0288(10) 0.0262(10) 0.0002(7) 0.0001(7) -0.0052(7) C15 0.0397(12) 0.0315(11) 0.0428(12) -0.0084(9) -0.0020(9) -0.0008(9) C16 0.0237(10) 0.0578(14) 0.0469(13) -0.0048(11) -0.0089(9) -0.0074(9) C17 0.0235(9) 0.0193(8) 0.0234(9) -0.0007(7) -0.0013(7) 0.0020(7) C18 0.0255(9) 0.0245(9) 0.0272(10) -0.0037(7) -0.0016(7) 0.0005(7) C19 0.0331(11) 0.0377(11) 0.0405(12) -0.0135(9) -0.0053(9) -0.0058(9) C20 0.0435(12) 0.0489(13) 0.0318(11) -0.0180(9) -0.0071(9) -0.0003(10) C21 0.0411(12) 0.0414(12) 0.0245(10) -0.0075(8) -0.0008(8) 0.0060(9) C22 0.0315(10) 0.0264(9) 0.0237(9) -0.0005(7) 0.0010(8) 0.0056(8) C23 0.0357(11) 0.0316(10) 0.0296(10) 0.0000(8) 0.0106(8) -0.0006(8) C24 0.0295(10) 0.0342(11) 0.0416(12) -0.0044(9) 0.0108(9) -0.0089(8) C25 0.0278(10) 0.0308(10) 0.0344(11) -0.0083(8) 0.0036(8) -0.0068(8) C26 0.0221(9) 0.0213(8) 0.0234(9) -0.0027(7) 0.0008(7) 0.0002(7) C27 0.0237(10) 0.0711(16) 0.0419(13) -0.0085(11) -0.0006(9) -0.0024(10) C28 0.0545(14) 0.0254(10) 0.0475(13) 0.0010(9) 0.0031(11) -0.0110(9) C29 0.0311(10) 0.0420(11) 0.0260(10) 0.0002(8) -0.0061(8) -0.0044(8) C30 0.0294(10) 0.0270(10) 0.0350(11) -0.0073(8) 0.0070(8) 0.0000(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 B12 1.374(2) . ? O1 C15 1.430(2) . ? O2 B12 1.360(2) . ? O2 C16 1.431(2) . ? N1 C18 1.458(2) . ? N1 C27 1.472(2) . ? N1 C28 1.480(2) . ? N2 C26 1.476(2) . ? N2 C29 1.492(2) . ? N2 C30 1.494(2) . ? B1 B2 1.762(3) . ? B1 B5 1.764(3) . ? B1 B3 1.764(3) . ? B1 B6 1.784(3) . ? B1 B4 1.797(3) . ? B2 C7 1.683(3) . ? B2 B3 1.745(3) . ? B2 B6 1.770(3) . ? B2 B11 1.801(3) . ? B3 C7 1.687(3) . ? B3 B4 1.758(3) . ? B3 B8 1.796(3) . ? B4 B9 1.781(3) . ? B4 B5 1.791(3) . ? B4 B8 1.816(3) . ? B5 B9 1.750(3) . ? B5 B10 1.758(3) . ? B5 B6 1.793(3) . ? B6 B10 1.783(3) . ? B6 B11 1.788(3) . ? B8 C14 1.619(3) . ? B8 C7 1.669(3) . ? B8 B9 1.892(3) . ? B9 B10 1.894(3) . ? B10 B11 1.874(3) . ? B11 C7 1.660(3) . ? B12 C14 1.569(3) . ? C7 C11 1.531(3) . ? C11 C12 1.518(3) . ? C12 C13 1.521(3) . ? C13 C14 1.548(3) . ? C17 C18 1.426(3) . ? C17 C26 1.427(2) . ? C17 C22 1.433(2) . ? C18 C19 1.371(3) . ? C19 C20 1.407(3) . ? C20 C21 1.349(3) . ? C21 C22 1.414(3) . ? C22 C23 1.413(3) . ? C23 C24 1.362(3) . ? C24 C25 1.404(3) . ? C25 C26 1.364(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 B12 O1 C15 119.97(15) . . ? B12 O2 C16 123.89(17) . . ? C18 N1 C27 112.95(15) . . ? C18 N1 C28 111.38(15) . . ? C27 N1 C28 111.68(17) . . ? C26 N2 C29 113.58(14) . . ? C26 N2 C30 110.86(14) . . ? C29 N2 C30 111.54(15) . . ? B2 B1 B5 108.53(14) . . ? B2 B1 B3 59.33(11) . . ? B5 B1 B3 107.67(14) . . ? B2 B1 B6 59.90(12) . . ? B5 B1 B6 60.70(12) . . ? B3 B1 B6 107.14(14) . . ? B2 B1 B4 107.17(14) . . ? B5 B1 B4 60.41(11) . . ? B3 B1 B4 59.16(11) . . ? B6 B1 B4 108.26(14) . . ? C7 B2 B3 58.93(11) . . ? C7 B2 B1 105.98(14) . . ? B3 B2 B1 60.40(12) . . ? C7 B2 B6 105.41(14) . . ? B3 B2 B6 108.60(15) . . ? B1 B2 B6 60.67(12) . . ? C7 B2 B11 56.79(11) . . ? B3 B2 B11 105.32(14) . . ? B1 B2 B11 107.13(15) . . ? B6 B2 B11 60.10(12) . . ? C7 B3 B2 58.69(11) . . ? C7 B3 B4 106.36(14) . . ? B2 B3 B4 109.68(15) . . ? C7 B3 B1 105.69(14) . . ? B2 B3 B1 60.27(12) . . ? B4 B3 B1 61.35(12) . . ? C7 B3 B8 57.17(10) . . ? B2 B3 B8 106.46(14) . . ? B4 B3 B8 61.43(11) . . ? B1 B3 B8 108.87(14) . . ? B3 B4 B9 113.04(14) . . ? B3 B4 B5 106.72(14) . . ? B9 B4 B5 58.66(11) . . ? B3 B4 B1 59.49(11) . . ? B9 B4 B1 108.84(14) . . ? B5 B4 B1 58.89(11) . . ? B3 B4 B8 60.32(11) . . ? B9 B4 B8 63.48(11) . . ? B5 B4 B8 106.03(14) . . ? B1 B4 B8 106.57(14) . . ? B9 B5 B10 65.35(12) . . ? B9 B5 B1 111.81(15) . . ? B10 B5 B1 111.68(15) . . ? B9 B5 B4 60.38(12) . . ? B10 B5 B4 112.52(15) . . ? B1 B5 B4 60.70(12) . . ? B9 B5 B6 112.02(15) . . ? B10 B5 B6 60.27(12) . . ? B1 B5 B6 60.20(12) . . ? B4 B5 B6 108.10(15) . . ? B2 B6 B10 113.81(15) . . ? B2 B6 B1 59.43(12) . . ? B10 B6 B1 109.58(15) . . ? B2 B6 B11 60.80(12) . . ? B10 B6 B11 63.30(12) . . ? B1 B6 B11 106.72(15) . . ? B2 B6 B5 106.88(15) . . ? B10 B6 B5 58.90(11) . . ? B1 B6 B5 59.10(12) . . ? B11 B6 B5 105.67(14) . . ? C14 B8 C7 118.19(15) . . ? C14 B8 B3 119.63(15) . . ? C7 B8 B3 58.13(11) . . ? C14 B8 B4 125.93(15) . . ? C7 B8 B4 104.57(14) . . ? B3 B8 B4 58.25(11) . . ? C14 B8 B9 125.17(15) . . ? C7 B8 B9 110.56(14) . . ? B3 B8 B9 106.29(14) . . ? B4 B8 B9 57.37(10) . . ? B5 B9 B4 60.96(12) . . ? B5 B9 B8 104.50(14) . . ? B4 B9 B8 59.15(11) . . ? B5 B9 B10 57.52(11) . . ? B4 B9 B10 106.82(14) . . ? B8 B9 B10 103.34(13) . . ? B5 B10 B6 60.83(12) . . ? B5 B10 B11 103.53(14) . . ? B6 B10 B11 58.49(12) . . ? B5 B10 B9 57.13(11) . . ? B6 B10 B9 106.02(14) . . ? B11 B10 B9 102.31(14) . . ? C7 B11 B6 105.58(14) . . ? C7 B11 B2 58.02(11) . . ? B6 B11 B2 59.10(12) . . ? C7 B11 B10 112.29(15) . . ? B6 B11 B10 58.21(12) . . ? B2 B11 B10 108.18(14) . . ? O2 B12 O1 115.29(17) . . ? O2 B12 C14 126.49(17) . . ? O1 B12 C14 118.21(16) . . ? C11 C7 B11 119.38(15) . . ? C11 C7 B8 118.33(15) . . ? B11 C7 B8 110.20(14) . . ? C11 C7 B2 117.03(15) . . ? B11 C7 B2 65.20(12) . . ? B8 C7 B2 115.63(14) . . ? C11 C7 B3 117.45(15) . . ? B11 C7 B3 114.78(15) . . ? B8 C7 B3 64.71(12) . . ? B2 C7 B3 62.38(11) . . ? C12 C11 C7 113.25(16) . . ? C11 C12 C13 112.36(16) . . ? C12 C13 C14 112.50(16) . . ? C13 C14 B12 113.57(16) . . ? C13 C14 B8 110.34(15) . . ? B12 C14 B8 110.85(14) . . ? C18 C17 C26 125.70(16) . . ? C18 C17 C22 117.96(16) . . ? C26 C17 C22 116.34(16) . . ? C19 C18 C17 120.33(18) . . ? C19 C18 N1 120.96(17) . . ? C17 C18 N1 118.70(15) . . ? C18 C19 C20 120.99(19) . . ? C21 C20 C19 120.21(19) . . ? C20 C21 C22 121.34(19) . . ? C23 C22 C21 121.05(18) . . ? C23 C22 C17 119.78(17) . . ? C21 C22 C17 119.16(18) . . ? C24 C23 C22 121.56(18) . . ? C23 C24 C25 119.51(18) . . ? C26 C25 C24 120.60(18) . . ? C25 C26 C17 122.19(17) . . ? C25 C26 N2 119.43(16) . . ? C17 C26 N2 118.30(15) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.25 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.528 _refine_diff_density_min -0.484 _refine_diff_density_rms 0.048 #===END data_[2i][PSH] _database_code_depnum_ccdc_archive 'CCDC 812779' #TrackingRef '- CIF_rev.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H39 B11 N2 O' _chemical_formula_weight 442.44 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 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 15.5726(6) _cell_length_b 9.8303(4) _cell_length_c 18.0313(7) _cell_angle_alpha 90.00 _cell_angle_beta 104.0970(10) _cell_angle_gamma 90.00 _cell_volume 2677.16(18) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 126 _cell_measurement_theta_min 15 _cell_measurement_theta_max 15 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.098 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 944 _exptl_absorpt_coefficient_mu 0.060 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6588 _exptl_absorpt_correction_T_max 0.7456 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'BRUKER KAPPA APEXII DUO DIFFRACTOMETER' _diffrn_measurement_method 'PHI & OMEGa SCAN' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 35060 _diffrn_reflns_av_R_equivalents 0.0294 _diffrn_reflns_av_sigmaI/netI 0.0171 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.33 _diffrn_reflns_theta_max 25.10 _reflns_number_total 4716 _reflns_number_gt 3796 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER KAPPA APEXII DUO DIFFRACTOMETER' _computing_cell_refinement 'BRUKER KAPPA APEXII DUO DIFFRACTOMETER' _computing_data_reduction 'BRUKER KAPPA APEXII DUO DIFFRACTOMETER' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SIEMENS SHELXTL' _computing_publication_material 'SIEMENS 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^)+(0.1745P)^2^+4.8493P] 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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4716 _refine_ls_number_parameters 307 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1151 _refine_ls_R_factor_gt 0.0992 _refine_ls_wR_factor_ref 0.3083 _refine_ls_wR_factor_gt 0.2791 _refine_ls_goodness_of_fit_ref 1.040 _refine_ls_restrained_S_all 1.040 _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 0.1481(2) 0.2736(3) 0.13808(15) 0.0557(8) Uani 1 1 d . . . N1 N 0.37159(17) 0.6671(3) 0.04785(14) 0.0298(6) Uani 1 1 d . . . N2 N 0.35304(17) 0.8675(3) 0.13614(14) 0.0307(6) Uani 1 1 d . . . H2A H 0.3783 0.7999 0.1122 0.037 Uiso 1 1 calc R . . C21 C 0.2761(2) 0.6695(3) 0.01440(17) 0.0316(7) Uani 1 1 d . . . C22 C 0.2379(2) 0.5840(4) -0.04402(19) 0.0418(8) Uani 1 1 d . . . H22A H 0.2740 0.5234 -0.0641 0.050 Uiso 1 1 calc R . . C23 C 0.1457(3) 0.5848(4) -0.0748(2) 0.0492(10) Uani 1 1 d . . . H23A H 0.1201 0.5250 -0.1156 0.059 Uiso 1 1 calc R . . C24 C 0.0931(2) 0.6702(4) -0.0466(2) 0.0468(9) Uani 1 1 d . . . H24A H 0.0309 0.6690 -0.0674 0.056 Uiso 1 1 calc R . . C25 C 0.1299(2) 0.7613(4) 0.0137(2) 0.0396(8) Uani 1 1 d . . . C26 C 0.0751(2) 0.8529(4) 0.0423(2) 0.0495(9) Uani 1 1 d . . . H26A H 0.0129 0.8513 0.0215 0.059 Uiso 1 1 calc R . . C27 C 0.1100(3) 0.9426(4) 0.0985(3) 0.0527(10) Uani 1 1 d . . . H27A H 0.0723 1.0035 0.1167 0.063 Uiso 1 1 calc R . . C28 C 0.2018(2) 0.9457(4) 0.1302(2) 0.0430(8) Uani 1 1 d . . . H28A H 0.2260 1.0086 0.1698 0.052 Uiso 1 1 calc R . . C29 C 0.2566(2) 0.8589(3) 0.10429(18) 0.0332(7) Uani 1 1 d . . . C30 C 0.2236(2) 0.7630(3) 0.04518(17) 0.0317(7) Uani 1 1 d . . . C31 C 0.4242(2) 0.6925(4) -0.0090(2) 0.0422(8) Uani 1 1 d . . . H31A H 0.4050 0.7780 -0.0359 0.063 Uiso 1 1 calc R . . H31B H 0.4154 0.6175 -0.0459 0.063 Uiso 1 1 calc R . . H31C H 0.4871 0.6989 0.0172 0.063 Uiso 1 1 calc R . . C32 C 0.3989(2) 0.5377(3) 0.08941(18) 0.0360(8) Uani 1 1 d . . . H32A H 0.3638 0.5232 0.1270 0.054 Uiso 1 1 calc R . . H32B H 0.4618 0.5424 0.1157 0.054 Uiso 1 1 calc R . . H32C H 0.3892 0.4620 0.0529 0.054 Uiso 1 1 calc R . . C33 C 0.3804(3) 0.8387(4) 0.21953(19) 0.0462(9) Uani 1 1 d . . . H33A H 0.3560 0.7508 0.2300 0.069 Uiso 1 1 calc R . . H33B H 0.3580 0.9105 0.2475 0.069 Uiso 1 1 calc R . . H33C H 0.4451 0.8358 0.2361 0.069 Uiso 1 1 calc R . . C34 C 0.3899(2) 0.9990(3) 0.1172(2) 0.0373(8) Uani 1 1 d . . . H34A H 0.3712 1.0146 0.0619 0.056 Uiso 1 1 calc R . . H34B H 0.4547 0.9960 0.1331 0.056 Uiso 1 1 calc R . . H34C H 0.3681 1.0732 0.1441 0.056 Uiso 1 1 calc R . . B1 B 0.3711(3) 0.4361(4) 0.3908(2) 0.0385(9) Uani 1 1 d . . . H1 H 0.4288 0.4750 0.4357 0.046 Uiso 1 1 calc R . . B2 B 0.2939(3) 0.5521(5) 0.3398(2) 0.0547(12) Uani 1 1 d . . . H2 H 0.3020 0.6645 0.3489 0.066 Uiso 1 1 calc R . . B3 B 0.2634(3) 0.4353(5) 0.4057(2) 0.0497(11) Uani 1 1 d . . . H3 H 0.2479 0.4710 0.4600 0.060 Uiso 1 1 calc R . . B4 B 0.3203(3) 0.2765(5) 0.4011(2) 0.0429(9) Uani 1 1 d . . . H4 H 0.3437 0.2096 0.4523 0.052 Uiso 1 1 calc R . . B5 B 0.3830(3) 0.2963(4) 0.3332(2) 0.0378(9) Uani 1 1 d . . . H5 H 0.4492 0.2467 0.3398 0.045 Uiso 1 1 calc R . . B6 B 0.3594(3) 0.4588(4) 0.2904(2) 0.0369(9) Uani 1 1 d . . . H6 H 0.4087 0.5132 0.2652 0.044 Uiso 1 1 calc R . . B8 B 0.2017(3) 0.2908(6) 0.3578(3) 0.0588(14) Uani 1 1 d . . . H8 H 0.1486 0.2417 0.3807 0.071 Uiso 1 1 calc R . . B9 B 0.2835(3) 0.2002(5) 0.3116(2) 0.0452(10) Uani 1 1 d . . . H9 H 0.2608 0.0975 0.2878 0.054 Uiso 1 1 calc R . . B10 B 0.3054(3) 0.3151(4) 0.2417(2) 0.0389(9) Uani 1 1 d . . . H10 H 0.3235 0.2765 0.1891 0.047 Uiso 1 1 calc R . . B11 B 0.2447(3) 0.4733(5) 0.2502(2) 0.0472(10) Uani 1 1 d . . . H11 H 0.2103 0.5437 0.2035 0.057 Uiso 1 1 calc R . . B12 B 0.1888(3) 0.2901(5) 0.2143(3) 0.0504(11) Uani 1 1 d . . . C7 C 0.1994(3) 0.4672(5) 0.3228(2) 0.0607(12) Uani 1 1 d . . . C11 C 0.1101(3) 0.5349(7) 0.3157(3) 0.0821(18) Uani 1 1 d . . . H11A H 0.0917 0.5255 0.3643 0.099 Uiso 1 1 calc R . . H11B H 0.1141 0.6330 0.3047 0.099 Uiso 1 1 calc R . . C12 C 0.0430(3) 0.4671(7) 0.2516(3) 0.0805(18) Uani 1 1 d . . . H12A H 0.0575 0.4871 0.2022 0.097 Uiso 1 1 calc R . . H12B H -0.0167 0.5039 0.2495 0.097 Uiso 1 1 calc R . . C13 C 0.0433(3) 0.3115(7) 0.2643(3) 0.0751(15) Uani 1 1 d . . . H13A H 0.0012 0.2687 0.2204 0.090 Uiso 1 1 calc R . . H13B H 0.0223 0.2922 0.3108 0.090 Uiso 1 1 calc R . . C14 C 0.1357(3) 0.2463(5) 0.2731(2) 0.0602(11) Uani 1 1 d . . . H14A H 0.1291 0.1450 0.2714 0.072 Uiso 1 1 calc R . . C15 C 0.1846(3) 0.3119(5) 0.0751(2) 0.0533(10) Uani 1 1 d . . . H15A H 0.1424 0.2893 0.0268 0.080 Uiso 1 1 calc R . . H15B H 0.2401 0.2624 0.0785 0.080 Uiso 1 1 calc R . . H15C H 0.1962 0.4099 0.0771 0.080 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 0.0641(18) 0.0612(18) 0.0394(14) -0.0073(12) 0.0079(12) -0.0135(14) N1 0.0334(14) 0.0281(13) 0.0267(13) 0.0004(10) 0.0048(10) 0.0032(10) N2 0.0362(14) 0.0266(13) 0.0275(13) -0.0034(10) 0.0044(10) 0.0021(11) C21 0.0345(16) 0.0312(16) 0.0262(15) 0.0033(12) 0.0019(12) 0.0024(13) C22 0.047(2) 0.0412(19) 0.0324(17) -0.0063(14) -0.0001(14) 0.0043(15) C23 0.048(2) 0.053(2) 0.0387(19) -0.0091(17) -0.0060(16) -0.0039(17) C24 0.0381(19) 0.048(2) 0.047(2) 0.0010(16) -0.0043(15) -0.0040(16) C25 0.0338(17) 0.0393(18) 0.0439(19) 0.0047(15) 0.0058(14) -0.0012(14) C26 0.0332(18) 0.047(2) 0.068(3) -0.0047(19) 0.0119(17) -0.0003(15) C27 0.039(2) 0.053(2) 0.072(3) -0.009(2) 0.0244(18) 0.0040(17) C28 0.0428(19) 0.0395(19) 0.050(2) -0.0087(16) 0.0176(16) -0.0005(15) C29 0.0347(17) 0.0306(16) 0.0349(16) 0.0011(13) 0.0097(13) -0.0017(13) C30 0.0361(17) 0.0283(16) 0.0304(15) 0.0037(12) 0.0075(13) 0.0000(13) C31 0.0424(19) 0.051(2) 0.0346(17) 0.0050(15) 0.0124(14) 0.0024(16) C32 0.0414(18) 0.0294(16) 0.0319(16) 0.0009(13) -0.0014(13) 0.0020(13) C33 0.061(2) 0.046(2) 0.0290(17) 0.0006(15) 0.0060(15) 0.0116(17) C34 0.0321(16) 0.0322(17) 0.0439(18) -0.0015(14) 0.0022(13) -0.0013(13) B1 0.044(2) 0.040(2) 0.0275(18) -0.0011(15) 0.0014(15) -0.0008(16) B2 0.069(3) 0.050(3) 0.038(2) -0.0062(19) 0.000(2) 0.020(2) B3 0.044(2) 0.072(3) 0.0301(19) -0.0175(19) 0.0025(16) 0.012(2) B4 0.047(2) 0.047(2) 0.035(2) 0.0004(17) 0.0098(17) -0.0051(18) B5 0.041(2) 0.036(2) 0.0369(19) 0.0021(16) 0.0106(16) 0.0071(16) B6 0.043(2) 0.038(2) 0.0253(17) 0.0020(15) 0.0002(15) 0.0062(16) B8 0.043(2) 0.095(4) 0.042(2) -0.025(2) 0.0165(19) -0.024(2) B9 0.058(3) 0.044(2) 0.035(2) -0.0036(17) 0.0125(18) -0.0059(19) B10 0.046(2) 0.040(2) 0.0324(19) -0.0074(16) 0.0121(16) 0.0006(17) B11 0.045(2) 0.050(2) 0.040(2) -0.0058(18) -0.0008(17) 0.0003(19) B12 0.058(3) 0.046(2) 0.043(2) -0.0071(19) 0.005(2) -0.008(2) C7 0.053(2) 0.085(3) 0.038(2) -0.017(2) 0.0000(17) 0.019(2) C11 0.053(3) 0.121(5) 0.064(3) -0.033(3) -0.003(2) 0.024(3) C12 0.036(2) 0.122(5) 0.075(3) -0.034(3) -0.003(2) 0.017(3) C13 0.051(3) 0.114(5) 0.057(3) -0.021(3) 0.008(2) -0.021(3) C14 0.058(3) 0.074(3) 0.046(2) -0.008(2) 0.0064(19) -0.013(2) C15 0.059(2) 0.068(3) 0.0301(18) -0.0025(17) 0.0059(16) -0.013(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 O1 B12 1.377(5) . ? O1 C15 1.438(5) . ? N1 C21 1.462(4) . ? N1 C31 1.482(4) . ? N1 C32 1.486(4) . ? N2 C29 1.474(4) . ? N2 C33 1.487(4) . ? N2 C34 1.488(4) . ? C21 C22 1.365(5) . ? C21 C30 1.429(5) . ? C22 C23 1.408(5) . ? C23 C24 1.356(6) . ? C24 C25 1.417(5) . ? C25 C26 1.422(5) . ? C25 C30 1.431(5) . ? C26 C27 1.353(6) . ? C27 C28 1.405(5) . ? C28 C29 1.366(5) . ? C29 C30 1.422(5) . ? B1 B2 1.748(6) . ? B1 B5 1.760(5) . ? B1 B3 1.762(6) . ? B1 B4 1.787(6) . ? B1 B6 1.789(5) . ? B2 C7 1.654(8) . ? B2 B6 1.766(6) . ? B2 B11 1.787(6) . ? B2 B3 1.797(8) . ? B3 C7 1.613(5) . ? B3 B4 1.808(6) . ? B3 B8 1.812(7) . ? B4 B9 1.746(6) . ? B4 B5 1.754(6) . ? B4 B8 1.827(6) . ? B5 B6 1.773(5) . ? B5 B9 1.775(6) . ? B5 B10 1.802(6) . ? B6 B11 1.762(6) . ? B6 B10 1.765(5) . ? B8 C14 1.678(6) . ? B8 C7 1.843(8) . ? B8 B9 1.905(7) . ? B9 B10 1.786(6) . ? B10 B12 1.778(6) . ? B10 B11 1.845(6) . ? B11 C7 1.632(6) . ? B11 B12 2.036(7) . ? B12 C14 1.556(6) . ? C7 C11 1.519(6) . ? C11 C12 1.511(7) . ? C12 C13 1.547(9) . ? C13 C14 1.548(7) . ? 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 B12 O1 C15 125.7(3) . . ? C21 N1 C31 113.0(2) . . ? C21 N1 C32 111.1(2) . . ? C31 N1 C32 110.8(3) . . ? C29 N2 C33 113.4(3) . . ? C29 N2 C34 111.9(2) . . ? C33 N2 C34 111.5(3) . . ? C22 C21 C30 120.8(3) . . ? C22 C21 N1 121.1(3) . . ? C30 C21 N1 118.1(3) . . ? C21 C22 C23 120.7(3) . . ? C24 C23 C22 120.5(3) . . ? C23 C24 C25 120.7(3) . . ? C24 C25 C26 120.8(3) . . ? C24 C25 C30 119.6(3) . . ? C26 C25 C30 119.6(3) . . ? C27 C26 C25 121.2(3) . . ? C26 C27 C28 120.1(3) . . ? C29 C28 C27 120.4(3) . . ? C28 C29 C30 121.9(3) . . ? C28 C29 N2 119.5(3) . . ? C30 C29 N2 118.5(3) . . ? C29 C30 C21 125.5(3) . . ? C29 C30 C25 116.9(3) . . ? C21 C30 C25 117.6(3) . . ? B2 B1 B5 110.9(3) . . ? B2 B1 B3 61.6(3) . . ? B5 B1 B3 109.2(3) . . ? B2 B1 B4 111.3(3) . . ? B5 B1 B4 59.3(2) . . ? B3 B1 B4 61.2(3) . . ? B2 B1 B6 59.9(2) . . ? B5 B1 B6 59.9(2) . . ? B3 B1 B6 106.8(3) . . ? B4 B1 B6 106.0(3) . . ? C7 B2 B1 103.6(4) . . ? C7 B2 B6 104.0(3) . . ? B1 B2 B6 61.2(2) . . ? C7 B2 B11 56.5(3) . . ? B1 B2 B11 106.3(3) . . ? B6 B2 B11 59.5(2) . . ? C7 B2 B3 55.5(3) . . ? B1 B2 B3 59.6(2) . . ? B6 B2 B3 106.3(3) . . ? B11 B2 B3 101.4(3) . . ? C7 B3 B1 104.7(3) . . ? C7 B3 B2 57.7(3) . . ? B1 B3 B2 58.8(2) . . ? C7 B3 B4 108.9(3) . . ? B1 B3 B4 60.1(2) . . ? B2 B3 B4 108.1(3) . . ? C7 B3 B8 64.8(3) . . ? B1 B3 B8 110.1(3) . . ? B2 B3 B8 112.3(3) . . ? B4 B3 B8 60.6(3) . . ? B9 B4 B5 61.0(2) . . ? B9 B4 B1 109.6(3) . . ? B5 B4 B1 59.6(2) . . ? B9 B4 B3 111.0(3) . . ? B5 B4 B3 107.4(3) . . ? B1 B4 B3 58.7(2) . . ? B9 B4 B8 64.4(3) . . ? B5 B4 B8 111.7(3) . . ? B1 B4 B8 108.3(3) . . ? B3 B4 B8 59.8(3) . . ? B4 B5 B1 61.1(2) . . ? B4 B5 B6 108.2(3) . . ? B1 B5 B6 60.8(2) . . ? B4 B5 B9 59.3(2) . . ? B1 B5 B9 109.4(3) . . ? B6 B5 B9 107.8(3) . . ? B4 B5 B10 106.7(3) . . ? B1 B5 B10 108.5(3) . . ? B6 B5 B10 59.2(2) . . ? B9 B5 B10 59.9(2) . . ? B11 B6 B10 63.1(2) . . ? B11 B6 B2 60.9(2) . . ? B10 B6 B2 113.8(3) . . ? B11 B6 B5 109.5(3) . . ? B10 B6 B5 61.2(2) . . ? B2 B6 B5 109.5(3) . . ? B11 B6 B1 105.7(3) . . ? B10 B6 B1 108.8(3) . . ? B2 B6 B1 58.9(2) . . ? B5 B6 B1 59.2(2) . . ? C14 B8 B3 140.7(4) . . ? C14 B8 B4 134.4(4) . . ? B3 B8 B4 59.6(2) . . ? C14 B8 C7 88.7(3) . . ? B3 B8 C7 52.4(2) . . ? B4 B8 C7 98.8(3) . . ? C14 B8 B9 78.8(3) . . ? B3 B8 B9 104.0(3) . . ? B4 B8 B9 55.7(2) . . ? C7 B8 B9 104.4(3) . . ? B4 B9 B5 59.7(2) . . ? B4 B9 B10 107.8(3) . . ? B5 B9 B10 60.8(2) . . ? B4 B9 B8 59.9(2) . . ? B5 B9 B8 107.2(3) . . ? B10 B9 B8 106.0(3) . . ? B6 B10 B12 125.4(3) . . ? B6 B10 B9 107.7(3) . . ? B12 B10 B9 75.6(3) . . ? B6 B10 B5 59.6(2) . . ? B12 B10 B5 130.7(3) . . ? B9 B10 B5 59.3(2) . . ? B6 B10 B11 58.4(2) . . ? B12 B10 B11 68.4(3) . . ? B9 B10 B11 106.6(3) . . ? B5 B10 B11 104.7(3) . . ? C7 B11 B6 105.1(3) . . ? C7 B11 B2 57.6(3) . . ? B6 B11 B2 59.7(2) . . ? C7 B11 B10 111.4(3) . . ? B6 B11 B10 58.5(2) . . ? B2 B11 B10 109.0(3) . . ? C7 B11 B12 89.2(3) . . ? B6 B11 B12 111.8(3) . . ? B2 B11 B12 136.6(3) . . ? B10 B11 B12 54.3(2) . . ? O1 B12 C14 117.1(4) . . ? O1 B12 B10 119.0(4) . . ? C14 B12 B10 121.7(3) . . ? O1 B12 B11 118.6(3) . . ? C14 B12 B11 106.6(3) . . ? B10 B12 B11 57.4(2) . . ? C11 C7 B3 120.6(4) . . ? C11 C7 B11 118.9(4) . . ? B3 C7 B11 117.4(3) . . ? C11 C7 B2 123.3(5) . . ? B3 C7 B2 66.7(3) . . ? B11 C7 B2 65.9(3) . . ? C11 C7 B8 112.4(4) . . ? B3 C7 B8 62.8(3) . . ? B11 C7 B8 109.5(3) . . ? B2 C7 B8 118.0(3) . . ? C12 C11 C7 108.6(4) . . ? C11 C12 C13 110.3(5) . . ? C12 C13 C14 113.2(4) . . ? C13 C14 B12 116.8(4) . . ? C13 C14 B8 109.5(4) . . ? B12 C14 B8 103.8(3) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.10 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.891 _refine_diff_density_min -0.494 _refine_diff_density_rms 0.084 #===END data_3 _database_code_depnum_ccdc_archive 'CCDC 812780' #TrackingRef '- CIF_rev.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H27 B11 N2' _chemical_formula_weight 354.30 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' 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' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 9.2420(15) _cell_length_b 12.376(2) _cell_length_c 18.093(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2069.5(6) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 183 _cell_measurement_theta_min 15 _cell_measurement_theta_max 15 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.137 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 744 _exptl_absorpt_coefficient_mu 0.058 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4765 _exptl_absorpt_correction_T_max 0.7456 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'BRUKER KAPPA APEXII DUO DIFFRACTOMETER' _diffrn_measurement_method 'PHI & OMEGA SCAN' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 16530 _diffrn_reflns_av_R_equivalents 0.1046 _diffrn_reflns_av_sigmaI/netI 0.1194 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.99 _diffrn_reflns_theta_max 25.25 _reflns_number_total 3724 _reflns_number_gt 1742 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER KAPPA APEXII DUO DIFFRACTOMETER' _computing_cell_refinement 'BRUKER KAPPA APEXII DUO DIFFRACTOMETER' _computing_data_reduction 'BRUKER KAPPA APEXII DUO DIFFRACTOMETER' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SIEMENS SHELXTL' _computing_publication_material 'SIEMENS 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^)+(0.0714P)^2^+0.0000P] 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 riding _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0082(17) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3724 _refine_ls_number_parameters 262 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1639 _refine_ls_R_factor_gt 0.0581 _refine_ls_wR_factor_ref 0.1558 _refine_ls_wR_factor_gt 0.1161 _refine_ls_goodness_of_fit_ref 0.971 _refine_ls_restrained_S_all 0.971 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.5983(4) 0.6194(3) 0.47151(18) 0.0518(9) Uani 1 1 d . . . N2 N 0.6159(4) 0.6004(3) 0.61070(16) 0.0522(9) Uani 1 1 d . . . C2 C 0.1784(4) 0.3970(3) 0.47991(18) 0.0474(10) Uani 1 1 d . . . C11 C 0.1219(5) 0.3747(3) 0.5578(2) 0.0619(12) Uani 1 1 d . . . H11A H 0.0604 0.4341 0.5731 0.074 Uiso 1 1 calc R . . H11B H 0.0634 0.3096 0.5570 0.074 Uiso 1 1 calc R . . C12 C 0.2410(6) 0.3612(4) 0.6126(2) 0.0864(16) Uani 1 1 d . . . H12A H 0.1990 0.3577 0.6616 0.104 Uiso 1 1 calc R . . H12B H 0.2887 0.2927 0.6033 0.104 Uiso 1 1 calc R . . C13 C 0.3520(5) 0.4482(4) 0.6117(2) 0.0750(15) Uani 1 1 d . . . H13A H 0.4232 0.4317 0.6495 0.090 Uiso 1 1 calc R . . H13B H 0.3051 0.5152 0.6260 0.090 Uiso 1 1 calc R . . C14 C 0.4340(4) 0.4687(3) 0.53799(18) 0.0518(11) Uani 1 1 d . . . H14A H 0.5138 0.4166 0.5356 0.062 Uiso 1 1 calc R . . C15 C 0.6993(5) 0.5564(4) 0.4418(2) 0.0658(13) Uani 1 1 d . . . H15A H 0.7198 0.4906 0.4643 0.079 Uiso 1 1 calc R . . C16 C 0.7735(5) 0.5839(5) 0.3801(3) 0.0913(18) Uani 1 1 d . . . H16A H 0.8436 0.5378 0.3611 0.110 Uiso 1 1 calc R . . C17 C 0.7448(7) 0.6788(6) 0.3464(3) 0.102(2) Uani 1 1 d . . . H17A H 0.7938 0.6980 0.3035 0.122 Uiso 1 1 calc R . . C18 C 0.6447(8) 0.7454(5) 0.3755(3) 0.098(2) Uani 1 1 d . . . H18A H 0.6248 0.8113 0.3530 0.118 Uiso 1 1 calc R . . C19 C 0.5715(5) 0.7154(4) 0.4390(3) 0.0743(14) Uani 1 1 d . . . H19A H 0.5032 0.7618 0.4595 0.089 Uiso 1 1 calc R . . C20 C 0.6237(5) 0.6962(4) 0.6432(2) 0.0597(12) Uani 1 1 d . . . H20A H 0.5632 0.7511 0.6264 0.072 Uiso 1 1 calc R . . C21 C 0.7162(5) 0.7182(4) 0.7000(2) 0.0654(13) Uani 1 1 d . . . H21A H 0.7187 0.7866 0.7212 0.078 Uiso 1 1 calc R . . C22 C 0.8058(5) 0.6375(4) 0.7255(2) 0.0687(13) Uani 1 1 d . . . H22A H 0.8696 0.6501 0.7643 0.082 Uiso 1 1 calc R . . C23 C 0.7987(6) 0.5384(4) 0.6925(2) 0.0757(15) Uani 1 1 d . . . H23A H 0.8583 0.4826 0.7086 0.091 Uiso 1 1 calc R . . C24 C 0.7031(5) 0.5213(4) 0.6354(2) 0.0694(14) Uani 1 1 d . . . H24A H 0.6988 0.4535 0.6134 0.083 Uiso 1 1 calc R . . B1 B 0.2506(5) 0.3027(4) 0.4283(3) 0.0511(13) Uani 1 1 d . . . B3 B 0.3267(6) 0.2866(4) 0.3414(2) 0.0565(13) Uani 1 1 d . . . H3 H 0.3717 0.2103 0.3204 0.068 Uiso 1 1 calc R . . B4 B 0.3317(5) 0.4469(3) 0.4682(2) 0.0428(12) Uani 1 1 d . . . B5 B 0.0751(6) 0.3916(4) 0.4111(2) 0.0560(14) Uani 1 1 d . . . H5 H -0.0411 0.3756 0.4185 0.067 Uiso 1 1 calc R . . B6 B 0.1599(6) 0.3316(4) 0.3287(3) 0.0637(15) Uani 1 1 d . . . H6 H 0.0899 0.2850 0.2912 0.076 Uiso 1 1 calc R . . B7 B 0.4178(5) 0.3844(4) 0.3832(2) 0.0486(12) Uani 1 1 d . . . H7 H 0.5362 0.3757 0.3851 0.058 Uiso 1 1 calc R . . B8 B 0.1692(5) 0.5120(3) 0.4351(2) 0.0503(12) Uani 1 1 d . . . H8 H 0.1225 0.5881 0.4556 0.060 Uiso 1 1 calc R . . B9 B 0.3088(5) 0.4153(4) 0.3049(2) 0.0531(13) Uani 1 1 d . . . H9 H 0.3457 0.4362 0.2489 0.064 Uiso 1 1 calc R . . B10 B 0.3270(5) 0.5096(4) 0.3787(2) 0.0465(12) Uani 1 1 d . . . H10 H 0.3874 0.5850 0.3695 0.056 Uiso 1 1 calc R . . B11 B 0.1494(5) 0.4745(4) 0.3403(2) 0.0531(13) Uani 1 1 d . . . H11 H 0.0816 0.5246 0.3040 0.064 Uiso 1 1 calc R . . B12 B 0.5033(6) 0.5852(4) 0.5419(2) 0.0539(13) Uani 1 1 d . . . H12 H 0.399(4) 0.650(2) 0.5478(17) 0.048(9) Uiso 1 1 d . . . H1 H 0.256(3) 0.224(3) 0.4526(18) 0.052(10) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.057(3) 0.057(2) 0.0406(19) 0.0094(19) -0.0093(17) -0.0108(19) N2 0.066(3) 0.058(2) 0.0319(17) 0.0016(18) -0.0093(16) -0.002(2) C2 0.056(3) 0.053(2) 0.034(2) 0.001(2) 0.0083(19) -0.003(2) C11 0.069(3) 0.073(3) 0.043(2) 0.011(2) 0.013(2) -0.012(2) C12 0.095(4) 0.120(4) 0.044(3) 0.012(3) 0.010(3) -0.023(4) C13 0.097(4) 0.099(3) 0.028(2) 0.004(2) 0.003(2) -0.024(3) C14 0.065(3) 0.063(3) 0.028(2) 0.006(2) 0.0004(19) -0.005(2) C15 0.060(4) 0.087(4) 0.051(3) 0.016(3) -0.007(2) -0.002(3) C16 0.062(4) 0.161(6) 0.052(3) 0.017(4) -0.002(3) -0.006(4) C17 0.089(5) 0.156(7) 0.061(4) 0.034(4) -0.013(3) -0.048(4) C18 0.139(6) 0.085(4) 0.071(4) 0.041(4) -0.044(4) -0.053(4) C19 0.094(4) 0.063(3) 0.066(3) 0.005(3) -0.031(3) -0.016(3) C20 0.073(3) 0.060(3) 0.046(3) -0.003(2) -0.009(2) 0.000(2) C21 0.084(4) 0.063(3) 0.049(3) -0.017(2) -0.011(2) -0.004(3) C22 0.077(4) 0.080(3) 0.050(3) -0.004(3) -0.018(2) -0.001(3) C23 0.083(4) 0.074(3) 0.069(3) -0.003(3) -0.034(3) 0.007(3) C24 0.096(4) 0.060(3) 0.052(3) -0.010(2) -0.018(3) 0.010(3) B1 0.056(3) 0.047(3) 0.051(3) -0.010(3) -0.004(2) -0.002(2) B3 0.064(4) 0.062(3) 0.043(3) -0.011(2) -0.001(2) 0.006(3) B4 0.053(3) 0.047(3) 0.028(2) 0.003(2) 0.001(2) -0.005(2) B5 0.048(4) 0.068(3) 0.052(3) 0.007(3) -0.009(2) -0.006(3) B6 0.074(4) 0.068(3) 0.049(3) -0.016(3) -0.009(3) -0.011(3) B7 0.044(3) 0.065(3) 0.037(2) -0.002(2) 0.004(2) 0.002(2) B8 0.062(4) 0.048(3) 0.041(2) 0.002(2) 0.002(2) 0.003(2) B9 0.057(4) 0.072(3) 0.030(2) -0.006(2) -0.006(2) -0.001(3) B10 0.054(3) 0.055(3) 0.031(2) 0.000(2) 0.000(2) -0.004(2) B11 0.053(4) 0.066(3) 0.041(3) -0.004(3) -0.007(2) 0.003(3) B12 0.058(4) 0.069(3) 0.035(3) 0.001(3) -0.006(2) -0.004(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 N1 C15 1.330(5) . ? N1 C19 1.348(5) . ? N1 B12 1.604(6) . ? N2 C20 1.325(5) . ? N2 C24 1.345(5) . ? N2 B12 1.634(5) . ? C2 C11 1.527(5) . ? C2 B4 1.561(6) . ? C2 B5 1.570(6) . ? C2 B1 1.637(6) . ? C2 B8 1.640(5) . ? C11 C12 1.491(6) . ? C12 C13 1.487(6) . ? C13 C14 1.555(5) . ? C14 B12 1.579(6) . ? C14 B4 1.601(6) . ? C15 C16 1.353(6) . ? C16 C17 1.349(7) . ? C17 C18 1.346(7) . ? C18 C19 1.385(7) . ? C20 C21 1.365(5) . ? C21 C22 1.377(6) . ? C22 C23 1.365(5) . ? C23 C24 1.375(6) . ? B1 B3 1.734(7) . ? B1 B5 1.984(7) . ? B1 B7 2.019(7) . ? B1 B6 2.019(7) . ? B1 B4 2.066(6) . ? B3 B6 1.655(7) . ? B3 B7 1.658(7) . ? B3 B9 1.731(7) . ? B4 B10 1.796(6) . ? B4 B8 1.807(6) . ? B4 B7 1.895(6) . ? B5 B11 1.779(6) . ? B5 B8 1.779(7) . ? B5 B6 1.841(7) . ? B6 B9 1.775(7) . ? B6 B11 1.783(6) . ? B7 B10 1.764(6) . ? B7 B9 1.781(6) . ? B8 B10 1.781(6) . ? B8 B11 1.787(6) . ? B9 B11 1.766(7) . ? B9 B10 1.783(6) . ? B10 B11 1.835(7) . ? 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 C15 N1 C19 118.0(4) . . ? C15 N1 B12 123.4(3) . . ? C19 N1 B12 118.6(4) . . ? C20 N2 C24 118.1(3) . . ? C20 N2 B12 118.4(3) . . ? C24 N2 B12 123.5(3) . . ? C11 C2 B4 120.5(3) . . ? C11 C2 B5 121.1(4) . . ? B4 C2 B5 117.5(3) . . ? C11 C2 B1 122.5(3) . . ? B4 C2 B1 80.4(3) . . ? B5 C2 B1 76.4(3) . . ? C11 C2 B8 126.5(3) . . ? B4 C2 B8 68.7(3) . . ? B5 C2 B8 67.3(3) . . ? B1 C2 B8 111.0(3) . . ? C12 C11 C2 112.4(3) . . ? C13 C12 C11 114.9(4) . . ? C12 C13 C14 117.6(3) . . ? C13 C14 B12 108.0(3) . . ? C13 C14 B4 111.2(3) . . ? B12 C14 B4 115.4(3) . . ? N1 C15 C16 122.8(5) . . ? C17 C16 C15 119.5(6) . . ? C18 C17 C16 119.4(6) . . ? C17 C18 C19 119.7(5) . . ? N1 C19 C18 120.6(5) . . ? N2 C20 C21 123.1(4) . . ? C20 C21 C22 119.0(4) . . ? C23 C22 C21 118.4(4) . . ? C22 C23 C24 119.8(5) . . ? N2 C24 C23 121.5(4) . . ? C2 B1 B3 139.9(4) . . ? C2 B1 B5 50.3(2) . . ? B3 B1 B5 104.7(3) . . ? C2 B1 B7 100.7(3) . . ? B3 B1 B7 51.7(2) . . ? B5 B1 B7 106.6(3) . . ? C2 B1 B6 102.4(3) . . ? B3 B1 B6 51.7(3) . . ? B5 B1 B6 54.8(2) . . ? B7 B1 B6 82.5(3) . . ? C2 B1 B4 48.2(2) . . ? B3 B1 B4 105.6(3) . . ? B5 B1 B4 82.7(3) . . ? B7 B1 B4 55.3(2) . . ? B6 B1 B4 108.0(3) . . ? B6 B3 B7 106.9(4) . . ? B6 B3 B9 63.2(3) . . ? B7 B3 B9 63.3(3) . . ? B6 B3 B1 73.1(3) . . ? B7 B3 B1 73.0(3) . . ? B9 B3 B1 101.6(3) . . ? C2 B4 C14 119.7(3) . . ? C2 B4 B10 105.8(3) . . ? C14 B4 B10 130.7(3) . . ? C2 B4 B8 57.7(3) . . ? C14 B4 B8 132.6(3) . . ? B10 B4 B8 59.2(2) . . ? C2 B4 B7 109.3(3) . . ? C14 B4 B7 117.5(3) . . ? B10 B4 B7 57.0(2) . . ? B8 B4 B7 105.2(3) . . ? C2 B4 B1 51.4(2) . . ? C14 B4 B1 129.5(3) . . ? B10 B4 B1 92.9(3) . . ? B8 B4 B1 88.1(3) . . ? B7 B4 B1 61.1(2) . . ? C2 B5 B11 108.2(3) . . ? C2 B5 B8 58.2(3) . . ? B11 B5 B8 60.3(2) . . ? C2 B5 B6 113.6(4) . . ? B11 B5 B6 59.0(2) . . ? B8 B5 B6 109.1(3) . . ? C2 B5 B1 53.3(2) . . ? B11 B5 B1 96.7(3) . . ? B8 B5 B1 91.5(3) . . ? B6 B5 B1 63.6(3) . . ? B3 B6 B9 60.5(3) . . ? B3 B6 B11 111.6(4) . . ? B9 B6 B11 59.5(3) . . ? B3 B6 B5 114.8(4) . . ? B9 B6 B5 106.9(3) . . ? B11 B6 B5 58.8(3) . . ? B3 B6 B1 55.2(3) . . ? B9 B6 B1 89.9(3) . . ? B11 B6 B1 95.3(3) . . ? B5 B6 B1 61.6(3) . . ? B3 B7 B10 112.3(4) . . ? B3 B7 B9 60.4(3) . . ? B10 B7 B9 60.4(2) . . ? B3 B7 B4 117.1(3) . . ? B10 B7 B4 58.6(2) . . ? B9 B7 B4 108.7(3) . . ? B3 B7 B1 55.2(2) . . ? B10 B7 B1 95.4(3) . . ? B9 B7 B1 89.7(3) . . ? B4 B7 B1 63.6(2) . . ? C2 B8 B5 54.5(2) . . ? C2 B8 B10 103.1(3) . . ? B5 B8 B10 104.3(3) . . ? C2 B8 B11 104.7(3) . . ? B5 B8 B11 59.8(2) . . ? B10 B8 B11 61.9(2) . . ? C2 B8 B4 53.6(2) . . ? B5 B8 B4 96.5(3) . . ? B10 B8 B4 60.1(2) . . ? B11 B8 B4 106.7(3) . . ? B3 B9 B11 108.8(4) . . ? B3 B9 B6 56.3(3) . . ? B11 B9 B6 60.5(3) . . ? B3 B9 B7 56.3(3) . . ? B11 B9 B7 105.8(3) . . ? B6 B9 B7 96.9(3) . . ? B3 B9 B10 107.9(3) . . ? B11 B9 B10 62.3(3) . . ? B6 B9 B10 105.9(3) . . ? B7 B9 B10 59.4(2) . . ? B7 B10 B8 112.2(3) . . ? B7 B10 B9 60.3(2) . . ? B8 B10 B9 111.3(3) . . ? B7 B10 B4 64.3(2) . . ? B8 B10 B4 60.7(2) . . ? B9 B10 B4 113.2(3) . . ? B7 B10 B11 103.6(3) . . ? B8 B10 B11 59.2(2) . . ? B9 B10 B11 58.4(2) . . ? B4 B10 B11 105.1(3) . . ? B9 B11 B5 110.1(3) . . ? B9 B11 B6 60.0(3) . . ? B5 B11 B6 62.2(3) . . ? B9 B11 B8 111.8(3) . . ? B5 B11 B8 59.9(2) . . ? B6 B11 B8 111.5(3) . . ? B9 B11 B10 59.3(3) . . ? B5 B11 B10 102.1(3) . . ? B6 B11 B10 103.4(3) . . ? B8 B11 B10 58.9(2) . . ? C14 B12 N1 115.4(3) . . ? C14 B12 N2 113.4(3) . . ? N1 B12 N2 103.0(3) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.25 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.253 _refine_diff_density_min -0.190 _refine_diff_density_rms 0.040 #===END data_4 _database_code_depnum_ccdc_archive 'CCDC 812781' #TrackingRef '- CIF_rev.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H23 B11 N2' _chemical_formula_weight 350.26 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pna2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y+1/2, z' '-x+1/2, y+1/2, z+1/2' _cell_length_a 24.3055(18) _cell_length_b 16.5785(11) _cell_length_c 14.2903(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 5758.3(7) _cell_formula_units_Z 12 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 73 _cell_measurement_theta_min 15 _cell_measurement_theta_max 15 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.212 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2184 _exptl_absorpt_coefficient_mu 0.062 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6775 _exptl_absorpt_correction_T_max 0.7456 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'BRUKER KAPPA APEXII DUO DIFFRACTOMETER' _diffrn_measurement_method 'PHI & OMEGA SCAN' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 47700 _diffrn_reflns_av_R_equivalents 0.0672 _diffrn_reflns_av_sigmaI/netI 0.0598 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 28 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.49 _diffrn_reflns_theta_max 25.25 _reflns_number_total 10305 _reflns_number_gt 6102 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER KAPPA APEXII DUO DIFFRACTOMETER' _computing_cell_refinement 'BRUKER KAPPA APEXII DUO DIFFRACTOMETER' _computing_data_reduction 'BRUKER KAPPA APEXII DUO DIFFRACTOMETER' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SIEMENS SHELXTL' _computing_publication_material 'SIEMENS 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^)+(0.1205P)^2^+9.7991P] 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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 10305 _refine_ls_number_parameters 757 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1480 _refine_ls_R_factor_gt 0.0816 _refine_ls_wR_factor_ref 0.2716 _refine_ls_wR_factor_gt 0.2045 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.038 _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 N1' N 0.13793(19) 0.1077(3) 0.4694(4) 0.0302(12) Uani 1 1 d . . . N2' N 0.14115(19) 0.1268(3) 0.3134(4) 0.0273(12) Uani 1 1 d . . . C1' C 0.0029(3) 0.0013(4) 0.3818(5) 0.0297(13) Uani 1 1 d . . . C2' C -0.0225(2) -0.0867(4) 0.4108(5) 0.0337(15) Uani 1 1 d . . . C11' C -0.0298(2) 0.0627(4) 0.4356(5) 0.0363(15) Uani 1 1 d . . . H11A H -0.0069 0.0870 0.4854 0.044 Uiso 1 1 calc R . . H11B H -0.0425 0.1062 0.3933 0.044 Uiso 1 1 calc R . . C12' C -0.0781(3) 0.0197(4) 0.4775(7) 0.061(2) Uani 1 1 d . . . H12A H -0.1116 0.0319 0.4408 0.073 Uiso 1 1 calc R . . H12B H -0.0840 0.0388 0.5423 0.073 Uiso 1 1 calc R . . C13' C -0.0682(3) -0.0719(4) 0.4780(5) 0.0435(16) Uani 1 1 d . . . H13A H -0.0578 -0.0905 0.5414 0.052 Uiso 1 1 calc R . . H13B H -0.1018 -0.1011 0.4582 0.052 Uiso 1 1 calc R . . C14' C 0.1289(3) 0.0858(4) 0.5622(5) 0.0409(17) Uani 1 1 d . . . H14A H 0.1029 0.0446 0.5760 0.049 Uiso 1 1 calc R . . C15' C 0.1567(3) 0.1227(5) 0.6347(5) 0.058(2) Uani 1 1 d . . . H15A H 0.1500 0.1063 0.6973 0.070 Uiso 1 1 calc R . . C16' C 0.1963(3) 0.1863(5) 0.6157(5) 0.063(2) Uani 1 1 d . . . H16A H 0.2169 0.2099 0.6652 0.076 Uiso 1 1 calc R . . C17' C 0.2032(3) 0.2117(4) 0.5259(5) 0.0457(18) Uani 1 1 d . . . H17A H 0.2267 0.2561 0.5130 0.055 Uiso 1 1 calc R . . C18' C 0.1753(2) 0.1718(4) 0.4508(5) 0.0331(15) Uani 1 1 d . . . C19' C 0.1770(3) 0.1830(4) 0.3557(5) 0.0329(15) Uani 1 1 d . . . C20' C 0.2088(3) 0.2363(4) 0.2997(5) 0.0434(17) Uani 1 1 d . . . H20A H 0.2327 0.2741 0.3289 0.052 Uiso 1 1 calc R . . C21' C 0.2055(3) 0.2339(4) 0.2064(6) 0.053(2) Uani 1 1 d . . . H21A H 0.2277 0.2680 0.1687 0.064 Uiso 1 1 calc R . . C22' C 0.1673(3) 0.1783(4) 0.1646(5) 0.0407(16) Uani 1 1 d . . . H22A H 0.1632 0.1778 0.0985 0.049 Uiso 1 1 calc R . . C23' C 0.1377(3) 0.1278(4) 0.2158(5) 0.0384(16) Uani 1 1 d . . . H23A H 0.1135 0.0913 0.1853 0.046 Uiso 1 1 calc R . . B3' B 0.0421(3) -0.0608(4) 0.4517(5) 0.0278(15) Uani 1 1 d . . . H3' H 0.0521 -0.0489 0.5269 0.033 Uiso 1 1 calc R . . B4' B 0.0729(3) -0.0014(4) 0.3637(5) 0.0249(15) Uani 1 1 d . . . B5' B 0.0242(3) 0.0033(4) 0.2704(5) 0.0334(16) Uani 1 1 d . . . H5' H 0.0227 0.0579 0.2244 0.040 Uiso 1 1 calc R . . B6' B -0.0361(3) -0.0487(4) 0.3004(6) 0.0368(17) Uani 1 1 d . . . H6' H -0.0774 -0.0286 0.2745 0.044 Uiso 1 1 calc R . . B7' B 0.0276(3) -0.1592(4) 0.4119(6) 0.0360(17) Uani 1 1 d . . . H7' H 0.0279 -0.2126 0.4598 0.043 Uiso 1 1 calc R . . B8' B 0.0895(3) -0.1079(4) 0.3791(6) 0.0331(16) Uani 1 1 d . . . H8' H 0.1310 -0.1279 0.4040 0.040 Uiso 1 1 calc R . . B9' B 0.0778(3) -0.0680(4) 0.2650(5) 0.0359(17) Uani 1 1 d . . . H9' H 0.1124 -0.0614 0.2138 0.043 Uiso 1 1 calc R . . B10' B 0.0112(3) -0.0965(4) 0.2274(6) 0.0400(18) Uani 1 1 d . . . H10' H 0.0019 -0.1092 0.1521 0.048 Uiso 1 1 calc R . . B11' B -0.0213(3) -0.1518(4) 0.3190(6) 0.0405(18) Uani 1 1 d . . . H11' H -0.0529 -0.1998 0.3064 0.049 Uiso 1 1 calc R . . B12' B 0.0508(3) -0.1645(4) 0.2946(6) 0.0415(19) Uani 1 1 d . . . H12' H 0.0674 -0.2217 0.2638 0.050 Uiso 1 1 calc R . . B13' B 0.1154(3) 0.0775(4) 0.3838(5) 0.0267(15) Uani 1 1 d . . . N1 N 0.3064(2) 0.3929(3) 0.2953(4) 0.0300(12) Uani 1 1 d . . . N2 N 0.3055(2) 0.3702(3) 0.4497(4) 0.0297(12) Uani 1 1 d . . . C1 C 0.1696(3) 0.4955(4) 0.3762(6) 0.0416(19) Uani 1 1 d . . . C2 C 0.1443(3) 0.5849(5) 0.3546(6) 0.057(2) Uani 1 1 d . . . C11 C 0.1374(3) 0.4358(4) 0.3155(6) 0.057(2) Uani 1 1 d . . . H11C H 0.1621 0.4108 0.2686 0.068 Uiso 1 1 calc R . . H11D H 0.1216 0.3925 0.3549 0.068 Uiso 1 1 calc R . . C12 C 0.0919(3) 0.4822(5) 0.2670(7) 0.083(3) Uani 1 1 d . . . H12C H 0.0560 0.4669 0.2944 0.099 Uiso 1 1 calc R . . H12D H 0.0913 0.4678 0.1997 0.099 Uiso 1 1 calc R . . C13 C 0.1001(3) 0.5735(5) 0.2770(6) 0.062(2) Uani 1 1 d . . . H13C H 0.0652 0.5999 0.2952 0.075 Uiso 1 1 calc R . . H13D H 0.1129 0.5971 0.2172 0.075 Uiso 1 1 calc R . . C14 C 0.2996(3) 0.4183(4) 0.2004(5) 0.0437(17) Uani 1 1 d . . . H14B H 0.2755 0.4616 0.1857 0.052 Uiso 1 1 calc R . . C15 C 0.3277(3) 0.3805(4) 0.1319(5) 0.0462(17) Uani 1 1 d . . . H15B H 0.3211 0.3961 0.0689 0.055 Uiso 1 1 calc R . . C16 C 0.3658(3) 0.3201(5) 0.1488(6) 0.063(2) Uani 1 1 d . . . H16B H 0.3871 0.2988 0.0989 0.075 Uiso 1 1 calc R . . C17 C 0.3727(3) 0.2907(4) 0.2401(6) 0.051(2) Uani 1 1 d . . . H17B H 0.3970 0.2471 0.2525 0.061 Uiso 1 1 calc R . . C18 C 0.3424(2) 0.3279(4) 0.3141(5) 0.0335(15) Uani 1 1 d . . . C19 C 0.3422(2) 0.3148(4) 0.4094(5) 0.0359(16) Uani 1 1 d . . . C20 C 0.3727(3) 0.2587(4) 0.4639(6) 0.0493(19) Uani 1 1 d . . . H20B H 0.3970 0.2213 0.4350 0.059 Uiso 1 1 calc R . . C21 C 0.3664(3) 0.2598(4) 0.5566(6) 0.054(2) Uani 1 1 d . . . H21B H 0.3871 0.2239 0.5945 0.065 Uiso 1 1 calc R . . C22 C 0.3282(3) 0.3154(4) 0.5998(5) 0.053(2) Uani 1 1 d . . . H22B H 0.3229 0.3138 0.6657 0.063 Uiso 1 1 calc R . . C23 C 0.2999(3) 0.3698(4) 0.5476(5) 0.0344(15) Uani 1 1 d . . . H23B H 0.2763 0.4077 0.5773 0.041 Uiso 1 1 calc R . . B3 B 0.2087(3) 0.5605(5) 0.3133(5) 0.047(2) Uani 1 1 d . . . H3 H 0.2194 0.5516 0.2378 0.057 Uiso 1 1 calc R . . B4 B 0.2385(3) 0.5000(4) 0.4019(6) 0.0373(19) Uani 1 1 d . . . B5 B 0.1861(3) 0.4889(4) 0.4894(6) 0.0464(19) Uani 1 1 d . . . H5 H 0.1832 0.4322 0.5317 0.056 Uiso 1 1 calc R . . B6 B 0.1269(4) 0.5432(5) 0.4546(7) 0.054(2) Uani 1 1 d . . . H6 H 0.0843 0.5227 0.4728 0.065 Uiso 1 1 calc R . . B7 B 0.1946(3) 0.6584(5) 0.3594(6) 0.0455(19) Uani 1 1 d . . . H7 H 0.1974 0.7135 0.3142 0.055 Uiso 1 1 calc R . . B8 B 0.2546(3) 0.6050(4) 0.3966(6) 0.0362(18) Uani 1 1 d . . . H8 H 0.2971 0.6261 0.3784 0.043 Uiso 1 1 calc R . . B9 B 0.2396(3) 0.5601(4) 0.5055(5) 0.0404(17) Uani 1 1 d . . . H9 H 0.2723 0.5516 0.5598 0.048 Uiso 1 1 calc R . . B10 B 0.1698(4) 0.5856(4) 0.5357(6) 0.053(2) Uani 1 1 d . . . H10 H 0.1560 0.5930 0.6100 0.064 Uiso 1 1 calc R . . B11 B 0.1444(3) 0.6480(4) 0.4456(6) 0.049(2) Uani 1 1 d . . . H11 H 0.1142 0.6979 0.4577 0.059 Uiso 1 1 calc R . . B12 B 0.2119(3) 0.6578(4) 0.4782(6) 0.0451(19) Uani 1 1 d . . . H12 H 0.2265 0.7136 0.5147 0.054 Uiso 1 1 calc R . . B13 B 0.2817(3) 0.4213(4) 0.3800(6) 0.0300(15) Uani 1 1 d . . . N1" N 0.4689(2) 0.1192(3) 0.3065(4) 0.0300(12) Uani 1 1 d . . . N2" N 0.4808(2) 0.1123(3) 0.4626(4) 0.0404(14) Uani 1 1 d . . . C1" C 0.3394(3) 0.0021(4) 0.3800(5) 0.0419(19) Uani 1 1 d . . . C2" C 0.3130(3) -0.0841(5) 0.3475(7) 0.061(2) Uani 1 1 d . . . C11" C 0.3100(3) 0.0692(4) 0.3305(5) 0.0512(18) Uani 1 1 d . . . H11E H 0.3337 0.0932 0.2816 0.061 Uiso 1 1 calc R . . H11F H 0.2991 0.1119 0.3752 0.061 Uiso 1 1 calc R . . C12" C 0.2582(3) 0.0291(6) 0.2859(8) 0.083(3) Uani 1 1 d . . . H12E H 0.2509 0.0529 0.2236 0.099 Uiso 1 1 calc R . . H12F H 0.2256 0.0384 0.3260 0.099 Uiso 1 1 calc R . . C13" C 0.2692(3) -0.0634(5) 0.2761(7) 0.072(2) Uani 1 1 d . . . H13E H 0.2352 -0.0944 0.2886 0.087 Uiso 1 1 calc R . . H13F H 0.2822 -0.0763 0.2122 0.087 Uiso 1 1 calc R . . C14" C 0.4566(3) 0.1091(4) 0.2106(5) 0.0447(17) Uani 1 1 d . . . H14C H 0.4330 0.0670 0.1904 0.054 Uiso 1 1 calc R . . C15" C 0.4790(3) 0.1601(5) 0.1487(6) 0.062(2) Uani 1 1 d . . . H15C H 0.4692 0.1541 0.0847 0.074 Uiso 1 1 calc R . . C16" C 0.5158(3) 0.2214(5) 0.1723(7) 0.074(3) Uani 1 1 d . . . H16C H 0.5311 0.2552 0.1253 0.089 Uiso 1 1 calc R . . C17" C 0.5293(3) 0.2319(4) 0.2649(7) 0.067(3) Uani 1 1 d . . . H17C H 0.5543 0.2732 0.2825 0.081 Uiso 1 1 calc R . . C18" C 0.5056(3) 0.1805(4) 0.3353(6) 0.0425(18) Uani 1 1 d . . . C19" C 0.5127(3) 0.1759(4) 0.4295(6) 0.0458(19) Uani 1 1 d . . . C20" C 0.5456(3) 0.2245(5) 0.4905(8) 0.077(3) Uani 1 1 d . . . H20C H 0.5658 0.2693 0.4673 0.092 Uiso 1 1 calc R . . C23" C 0.4817(3) 0.0942(5) 0.5588(5) 0.059(2) Uani 1 1 d . . . H23C H 0.4610 0.0505 0.5834 0.070 Uiso 1 1 calc R . . B3" B 0.3795(3) -0.0576(5) 0.3013(7) 0.057(2) Uani 1 1 d . . . H3" H 0.3904 -0.0419 0.2273 0.068 Uiso 1 1 calc R . . B4" B 0.4087(3) -0.0069(4) 0.3969(6) 0.042(2) Uani 1 1 d . . . B5" B 0.3593(3) -0.0031(5) 0.4923(7) 0.053(2) Uani 1 1 d . . . H5" H 0.3588 0.0486 0.5428 0.063 Uiso 1 1 calc R . . B6" B 0.2982(4) -0.0540(6) 0.4515(8) 0.069(3) Uani 1 1 d . . . H6" H 0.2558 -0.0356 0.4735 0.082 Uiso 1 1 calc R . . B7" B 0.3619(4) -0.1583(5) 0.3366(10) 0.079(4) Uani 1 1 d . . . H7" H 0.3614 -0.2081 0.2836 0.094 Uiso 1 1 calc R . . B8" B 0.4233(3) -0.1118(5) 0.3754(6) 0.0394(19) Uani 1 1 d . . . H8" H 0.4648 -0.1324 0.3511 0.047 Uiso 1 1 calc R . . B9" B 0.4112(3) -0.0783(5) 0.4925(6) 0.051(2) Uani 1 1 d . . . H9" H 0.4452 -0.0769 0.5453 0.061 Uiso 1 1 calc R . . B10" B 0.3424(4) -0.1032(5) 0.5266(9) 0.076(3) Uani 1 1 d . . . H10" H 0.3306 -0.1168 0.6007 0.092 Uiso 1 1 calc R . . B11" B 0.3140(4) -0.1546(6) 0.4302(10) 0.084(4) Uani 1 1 d . . . H11" H 0.2832 -0.2042 0.4396 0.101 Uiso 1 1 calc R . . B12" B 0.3829(4) -0.1714(5) 0.4527(7) 0.064(3) Uani 1 1 d . . . H12" H 0.3979 -0.2312 0.4785 0.077 Uiso 1 1 calc R . . B13" B 0.4514(3) 0.0727(4) 0.3872(5) 0.0279(15) Uani 1 1 d . . . C21" C 0.5468(4) 0.2049(7) 0.5803(8) 0.103(4) Uani 1 1 d . . . H21C H 0.5707 0.2339 0.6209 0.124 Uiso 1 1 calc R . . C22" C 0.5144(4) 0.1431(7) 0.6175(7) 0.095(3) Uani 1 1 d . . . H22C H 0.5144 0.1339 0.6831 0.114 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1' 0.027(3) 0.024(2) 0.039(3) -0.004(2) 0.002(2) -0.004(2) N2' 0.021(2) 0.031(3) 0.030(3) 0.007(2) 0.000(2) -0.0041(19) C1' 0.022(3) 0.030(3) 0.037(3) -0.001(3) -0.003(3) -0.001(2) C2' 0.031(3) 0.032(3) 0.038(4) -0.001(3) 0.000(3) -0.007(3) C11' 0.027(3) 0.037(3) 0.045(4) -0.003(3) -0.002(3) 0.006(3) C12' 0.040(4) 0.050(4) 0.092(7) -0.011(4) 0.020(4) 0.006(3) C13' 0.041(4) 0.045(4) 0.044(4) 0.002(3) 0.007(3) 0.000(3) C14' 0.041(4) 0.048(4) 0.034(4) -0.002(3) 0.000(3) -0.019(3) C15' 0.068(5) 0.071(5) 0.036(4) -0.008(4) 0.012(4) -0.038(4) C16' 0.059(5) 0.084(6) 0.047(4) -0.020(4) 0.006(4) -0.047(4) C17' 0.046(4) 0.045(4) 0.046(4) -0.013(3) 0.008(3) -0.025(3) C18' 0.028(3) 0.031(3) 0.040(4) 0.000(3) 0.005(3) -0.011(3) C19' 0.031(3) 0.029(3) 0.039(4) -0.003(3) -0.002(3) -0.003(3) C20' 0.046(4) 0.030(3) 0.054(4) 0.007(3) -0.003(3) -0.015(3) C21' 0.062(5) 0.038(4) 0.060(5) 0.015(4) 0.005(4) -0.016(3) C22' 0.043(4) 0.044(4) 0.035(4) 0.005(3) -0.001(3) 0.000(3) C23' 0.034(3) 0.051(4) 0.030(4) 0.005(3) -0.005(3) -0.001(3) B3' 0.029(3) 0.023(3) 0.031(4) -0.004(3) -0.006(3) 0.005(3) B4' 0.028(4) 0.021(3) 0.025(4) -0.005(3) 0.003(3) -0.006(3) B5' 0.032(4) 0.036(4) 0.033(4) -0.002(3) -0.001(3) -0.008(3) B6' 0.035(4) 0.040(4) 0.035(4) 0.002(3) -0.006(3) -0.007(3) B7' 0.045(4) 0.024(3) 0.039(4) -0.003(3) 0.002(4) -0.004(3) B8' 0.034(4) 0.025(3) 0.040(4) -0.004(3) 0.003(3) -0.003(3) B9' 0.039(4) 0.038(4) 0.031(4) -0.010(3) 0.011(3) -0.003(3) B10' 0.049(4) 0.036(4) 0.035(4) -0.013(3) 0.010(4) -0.004(3) B11' 0.044(4) 0.035(4) 0.043(4) -0.008(4) 0.003(4) -0.012(3) B12' 0.051(5) 0.030(4) 0.044(4) -0.012(3) 0.012(4) -0.002(3) B13' 0.021(3) 0.026(3) 0.034(4) -0.008(3) -0.001(3) 0.001(3) N1 0.031(3) 0.030(3) 0.029(3) -0.001(2) 0.003(2) 0.002(2) N2 0.026(3) 0.028(3) 0.035(3) -0.005(2) -0.003(2) 0.002(2) C1 0.031(4) 0.037(4) 0.057(5) -0.023(4) -0.011(3) 0.006(3) C2 0.044(4) 0.055(5) 0.072(6) -0.032(4) -0.012(4) 0.017(3) C11 0.052(4) 0.038(4) 0.081(5) -0.016(4) -0.019(4) -0.001(3) C12 0.074(6) 0.061(5) 0.113(8) -0.014(5) -0.054(5) -0.001(4) C13 0.057(4) 0.071(5) 0.060(5) -0.007(4) -0.019(4) 0.021(4) C14 0.059(4) 0.036(3) 0.037(4) 0.003(3) 0.005(3) 0.003(3) C15 0.057(4) 0.047(4) 0.035(4) -0.004(3) 0.011(3) 0.006(3) C16 0.074(6) 0.069(5) 0.045(5) -0.006(4) 0.023(4) 0.006(4) C17 0.049(4) 0.032(4) 0.072(6) -0.008(4) 0.021(4) 0.006(3) C18 0.029(3) 0.024(3) 0.048(4) -0.006(3) 0.001(3) 0.002(2) C19 0.027(3) 0.031(4) 0.050(4) -0.008(3) -0.006(3) 0.003(3) C20 0.051(4) 0.038(4) 0.059(5) 0.000(3) -0.020(4) 0.005(3) C21 0.060(5) 0.035(4) 0.068(6) 0.005(4) -0.018(4) 0.000(3) C22 0.064(5) 0.052(4) 0.042(4) 0.003(3) -0.021(4) -0.034(4) C23 0.039(3) 0.029(3) 0.035(4) -0.004(3) -0.007(3) -0.012(3) B3 0.058(5) 0.050(4) 0.034(4) -0.012(4) -0.010(4) 0.027(4) B4 0.025(4) 0.037(4) 0.049(5) -0.006(3) -0.009(3) 0.004(3) B5 0.041(4) 0.038(4) 0.061(5) 0.001(4) 0.013(4) -0.003(3) B6 0.042(4) 0.045(4) 0.075(6) -0.009(4) 0.000(4) 0.014(4) B7 0.051(5) 0.039(4) 0.047(5) -0.008(3) 0.007(4) 0.013(4) B8 0.030(4) 0.031(4) 0.047(5) 0.000(3) -0.001(4) 0.001(3) B9 0.042(4) 0.040(4) 0.039(4) -0.008(3) -0.003(3) -0.001(3) B10 0.064(5) 0.042(4) 0.054(5) 0.000(4) 0.033(4) 0.009(4) B11 0.055(5) 0.032(4) 0.061(5) -0.012(4) 0.012(4) 0.013(3) B12 0.051(4) 0.032(4) 0.052(5) -0.016(4) 0.004(4) 0.003(3) B13 0.025(3) 0.028(4) 0.036(4) -0.007(3) 0.000(3) 0.001(3) N1" 0.026(2) 0.030(3) 0.034(3) 0.006(2) 0.001(2) 0.001(2) N2" 0.034(3) 0.039(3) 0.048(4) -0.009(3) -0.004(2) -0.004(2) C1" 0.028(4) 0.037(4) 0.061(5) 0.018(4) -0.010(3) -0.008(3) C2" 0.040(4) 0.052(4) 0.093(7) 0.010(4) -0.015(4) -0.010(3) C11" 0.050(4) 0.045(4) 0.058(5) -0.003(3) -0.013(3) 0.014(3) C12" 0.055(5) 0.088(6) 0.106(8) 0.005(6) -0.031(5) 0.009(5) C13" 0.045(4) 0.088(6) 0.084(6) -0.013(5) -0.010(4) -0.004(4) C14" 0.035(3) 0.067(5) 0.032(4) 0.011(3) -0.007(3) 0.007(3) C15" 0.048(4) 0.086(6) 0.051(5) 0.025(4) 0.012(3) 0.012(4) C16" 0.057(5) 0.084(7) 0.080(6) 0.041(5) 0.016(5) 0.002(4) C17" 0.047(4) 0.044(4) 0.111(8) 0.029(5) 0.000(5) -0.014(3) C18" 0.030(3) 0.026(3) 0.071(5) 0.011(3) 0.002(3) -0.001(3) C19" 0.030(3) 0.034(4) 0.074(5) -0.015(3) -0.008(3) -0.004(3) C20" 0.054(5) 0.054(5) 0.123(9) -0.044(5) -0.031(5) -0.002(4) C23" 0.054(4) 0.083(6) 0.039(4) -0.012(4) -0.002(3) 0.002(4) B3" 0.054(5) 0.030(4) 0.086(7) -0.002(4) -0.043(5) 0.000(3) B4" 0.027(4) 0.031(4) 0.066(6) -0.005(4) 0.008(4) -0.003(3) B5" 0.045(4) 0.045(4) 0.068(6) 0.012(4) 0.017(4) 0.008(3) B6" 0.046(5) 0.076(6) 0.084(7) 0.038(6) -0.007(5) -0.024(5) B7" 0.053(6) 0.029(4) 0.154(11) -0.001(6) -0.033(7) -0.008(4) B8" 0.041(4) 0.031(4) 0.046(5) -0.001(3) -0.007(4) 0.001(3) B9" 0.050(5) 0.045(4) 0.058(5) 0.017(4) 0.000(4) 0.013(3) B10" 0.077(7) 0.051(5) 0.101(8) 0.026(5) 0.032(6) -0.007(5) B11" 0.074(7) 0.051(6) 0.127(10) 0.017(6) 0.031(7) -0.015(5) B12" 0.070(6) 0.036(4) 0.087(7) 0.021(4) 0.009(5) 0.001(4) B13" 0.029(4) 0.025(3) 0.030(4) -0.003(3) 0.002(3) 0.000(3) C21" 0.079(7) 0.144(10) 0.086(8) -0.066(7) 0.006(6) -0.043(7) C22" 0.072(6) 0.160(11) 0.053(5) -0.030(6) -0.005(5) 0.006(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1' C14' 1.392(8) . ? N1' C18' 1.423(7) . ? N1' B13' 1.431(8) . ? N2' C23' 1.398(8) . ? N2' C19' 1.412(8) . ? N2' B13' 1.439(9) . ? C1' C11' 1.502(9) . ? C1' C2' 1.639(8) . ? C1' B5' 1.675(10) . ? C1' B6' 1.715(10) . ? C1' B4' 1.721(9) . ? C1' B3' 1.722(9) . ? C2' C13' 1.487(9) . ? C2' B11' 1.699(10) . ? C2' B7' 1.711(9) . ? C2' B3' 1.731(8) . ? C2' B6' 1.731(10) . ? C11' C12' 1.500(9) . ? C12' C13' 1.538(9) . ? C14' C15' 1.380(10) . ? C15' C16' 1.453(9) . ? C16' C17' 1.361(10) . ? C17' C18' 1.432(9) . ? C18' C19' 1.373(10) . ? C19' C20' 1.421(9) . ? C20' C21' 1.336(10) . ? C21' C22' 1.438(10) . ? C22' C23' 1.324(9) . ? B3' B8' 1.735(10) . ? B3' B7' 1.763(9) . ? B3' B4' 1.764(10) . ? B4' B13' 1.691(9) . ? B4' B5' 1.785(10) . ? B4' B9' 1.795(10) . ? B4' B8' 1.825(10) . ? B5' B6' 1.752(9) . ? B5' B9' 1.761(10) . ? B5' B10' 1.793(10) . ? B6' B10' 1.743(10) . ? B6' B11' 1.767(11) . ? B7' B12' 1.772(11) . ? B7' B11' 1.786(11) . ? B7' B8' 1.791(10) . ? B8' B9' 1.783(11) . ? B8' B12' 1.796(11) . ? B9' B10' 1.770(10) . ? B9' B12' 1.780(10) . ? B10' B12' 1.765(11) . ? B10' B11' 1.782(11) . ? B11' B12' 1.799(11) . ? N1 C18 1.412(7) . ? N1 B13 1.430(9) . ? N1 C14 1.431(8) . ? N2 C19 1.405(8) . ? N2 C23 1.405(8) . ? N2 B13 1.430(9) . ? C1 C11 1.530(9) . ? C1 C2 1.634(10) . ? C1 B5 1.671(11) . ? C1 B3 1.694(12) . ? C1 B4 1.718(9) . ? C1 B6 1.720(11) . ? C2 C13 1.555(10) . ? C2 B6 1.643(13) . ? C2 B11 1.669(10) . ? C2 B3 1.722(10) . ? C2 B7 1.729(12) . ? C11 C12 1.516(10) . ? C12 C13 1.532(10) . ? C14 C15 1.348(9) . ? C15 C16 1.385(10) . ? C16 C17 1.404(11) . ? C17 C18 1.430(10) . ? C18 C19 1.379(11) . ? C19 C20 1.422(9) . ? C20 C21 1.334(11) . ? C21 C22 1.446(10) . ? C22 C23 1.359(10) . ? B3 B4 1.770(11) . ? B3 B7 1.786(10) . ? B3 B8 1.791(11) . ? B4 B13 1.704(10) . ? B4 B9 1.784(11) . ? B4 B8 1.786(10) . ? B4 B5 1.795(11) . ? B5 B6 1.770(11) . ? B5 B9 1.772(10) . ? B5 B10 1.780(10) . ? B6 B10 1.710(13) . ? B6 B11 1.793(11) . ? B7 B11 1.743(12) . ? B7 B12 1.749(11) . ? B7 B8 1.787(11) . ? B8 B9 1.763(11) . ? B8 B12 1.789(11) . ? B9 B12 1.796(11) . ? B9 B10 1.801(11) . ? B10 B11 1.762(12) . ? B10 B12 1.777(11) . ? B11 B12 1.713(11) . ? N1" C14" 1.412(8) . ? N1" C18" 1.415(8) . ? N1" B13" 1.451(9) . ? N2" C19" 1.391(9) . ? N2" C23" 1.407(9) . ? N2" B13" 1.450(9) . ? C1" C11" 1.499(9) . ? C1" C2" 1.634(10) . ? C1" B5" 1.679(12) . ? C1" B6" 1.706(11) . ? C1" B4" 1.710(10) . ? C1" B3" 1.788(13) . ? C2" C13" 1.513(11) . ? C2" B6" 1.608(14) . ? C2" B11" 1.662(14) . ? C2" B7" 1.718(12) . ? C2" B3" 1.801(12) . ? C11" C12" 1.560(10) . ? C12" C13" 1.563(12) . ? C14" C15" 1.338(10) . ? C15" C16" 1.395(12) . ? C16" C17" 1.376(13) . ? C17" C18" 1.437(10) . ? C18" C19" 1.360(10) . ? C19" C20" 1.431(10) . ? C20" C21" 1.324(14) . ? C23" C22" 1.412(12) . ? B3" B8" 1.750(11) . ? B3" B4" 1.754(12) . ? B3" B7" 1.795(12) . ? B4" B13" 1.685(10) . ? B4" B8" 1.801(11) . ? B4" B9" 1.807(11) . ? B4" B5" 1.819(11) . ? B5" B9" 1.773(10) . ? B5" B10" 1.778(11) . ? B5" B6" 1.804(12) . ? B6" B10" 1.724(14) . ? B6" B11" 1.739(15) . ? B7" B12" 1.750(17) . ? B7" B8" 1.768(12) . ? B7" B11" 1.773(17) . ? B8" B12" 1.778(12) . ? B8" B9" 1.788(12) . ? B9" B12" 1.784(12) . ? B9" B10" 1.790(12) . ? B10" B11" 1.761(18) . ? B10" B12" 1.833(14) . ? B11" B12" 1.726(14) . ? C21" C22" 1.398(14) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C14' N1' C18' 118.2(5) . . ? C14' N1' B13' 131.5(5) . . ? C18' N1' B13' 110.2(5) . . ? C23' N2' C19' 117.1(5) . . ? C23' N2' B13' 132.7(6) . . ? C19' N2' B13' 110.2(5) . . ? C11' C1' C2' 105.9(5) . . ? C11' C1' B5' 129.5(6) . . ? C2' C1' B5' 112.0(5) . . ? C11' C1' B6' 112.5(6) . . ? C2' C1' B6' 62.1(4) . . ? B5' C1' B6' 62.2(4) . . ? C11' C1' B4' 128.1(5) . . ? C2' C1' B4' 112.8(5) . . ? B5' C1' B4' 63.4(4) . . ? B6' C1' B4' 115.5(5) . . ? C11' C1' B3' 113.7(5) . . ? C2' C1' B3' 61.9(4) . . ? B5' C1' B3' 113.1(5) . . ? B6' C1' B3' 114.2(5) . . ? B4' C1' B3' 61.6(4) . . ? C13' C2' C1' 107.3(5) . . ? C13' C2' B11' 128.1(5) . . ? C1' C2' B11' 111.3(5) . . ? C13' C2' B7' 129.9(6) . . ? C1' C2' B7' 111.1(5) . . ? B11' C2' B7' 63.2(4) . . ? C13' C2' B3' 114.8(5) . . ? C1' C2' B3' 61.4(4) . . ? B11' C2' B3' 113.7(5) . . ? B7' C2' B3' 61.6(4) . . ? C13' C2' B6' 112.7(5) . . ? C1' C2' B6' 61.1(4) . . ? B11' C2' B6' 62.0(4) . . ? B7' C2' B6' 113.5(5) . . ? B3' C2' B6' 113.0(5) . . ? C12' C11' C1' 107.2(5) . . ? C11' C12' C13' 110.4(5) . . ? C2' C13' C12' 106.1(6) . . ? C15' C14' N1' 121.5(6) . . ? C14' C15' C16' 120.4(7) . . ? C17' C16' C15' 118.8(6) . . ? C16' C17' C18' 120.3(6) . . ? C19' C18' N1' 107.8(6) . . ? C19' C18' C17' 131.7(6) . . ? N1' C18' C17' 120.5(6) . . ? C18' C19' N2' 108.4(5) . . ? C18' C19' C20' 131.2(6) . . ? N2' C19' C20' 120.4(6) . . ? C21' C20' C19' 120.7(7) . . ? C20' C21' C22' 118.3(7) . . ? C23' C22' C21' 121.7(7) . . ? C22' C23' N2' 121.8(6) . . ? C1' B3' C2' 56.7(4) . . ? C1' B3' B8' 106.9(5) . . ? C2' B3' B8' 106.8(5) . . ? C1' B3' B7' 104.8(5) . . ? C2' B3' B7' 58.6(4) . . ? B8' B3' B7' 61.6(4) . . ? C1' B3' B4' 59.2(4) . . ? C2' B3' B4' 106.4(5) . . ? B8' B3' B4' 62.9(4) . . ? B7' B3' B4' 111.8(5) . . ? B13' B4' C1' 123.9(5) . . ? B13' B4' B3' 124.7(5) . . ? C1' B4' B3' 59.2(4) . . ? B13' B4' B5' 119.9(5) . . ? C1' B4' B5' 57.0(4) . . ? B3' B4' B5' 106.0(5) . . ? B13' B4' B9' 124.7(5) . . ? C1' B4' B9' 101.5(5) . . ? B3' B4' B9' 104.2(5) . . ? B5' B4' B9' 58.9(4) . . ? B13' B4' B8' 126.3(5) . . ? C1' B4' B8' 103.0(4) . . ? B3' B4' B8' 57.8(4) . . ? B5' B4' B8' 106.2(5) . . ? B9' B4' B8' 59.0(4) . . ? C1' B5' B6' 60.0(4) . . ? C1' B5' B9' 104.9(5) . . ? B6' B5' B9' 107.4(5) . . ? C1' B5' B4' 59.6(4) . . ? B6' B5' B4' 110.5(5) . . ? B9' B5' B4' 60.8(4) . . ? C1' B5' B10' 104.7(5) . . ? B6' B5' B10' 58.9(4) . . ? B9' B5' B10' 59.7(4) . . ? B4' B5' B10' 109.4(5) . . ? C1' B6' C2' 56.8(4) . . ? C1' B6' B10' 105.2(5) . . ? C2' B6' B10' 104.7(5) . . ? C1' B6' B5' 57.8(4) . . ? C2' B6' B5' 104.1(5) . . ? B10' B6' B5' 61.7(4) . . ? C1' B6' B11' 104.7(5) . . ? C2' B6' B11' 58.1(4) . . ? B10' B6' B11' 61.0(4) . . ? B5' B6' B11' 110.0(5) . . ? C2' B7' B3' 59.8(4) . . ? C2' B7' B12' 104.7(5) . . ? B3' B7' B12' 106.7(5) . . ? C2' B7' B11' 58.1(4) . . ? B3' B7' B11' 108.1(5) . . ? B12' B7' B11' 60.7(5) . . ? C2' B7' B8' 105.2(5) . . ? B3' B7' B8' 58.4(4) . . ? B12' B7' B8' 60.5(4) . . ? B11' B7' B8' 109.4(6) . . ? B3' B8' B9' 105.9(5) . . ? B3' B8' B7' 60.0(4) . . ? B9' B8' B7' 106.4(5) . . ? B3' B8' B12' 106.8(5) . . ? B9' B8' B12' 59.6(4) . . ? B7' B8' B12' 59.2(4) . . ? B3' B8' B4' 59.4(4) . . ? B9' B8' B4' 59.7(4) . . ? B7' B8' B4' 107.8(5) . . ? B12' B8' B4' 108.0(5) . . ? B5' B9' B10' 61.0(4) . . ? B5' B9' B12' 108.6(5) . . ? B10' B9' B12' 59.6(4) . . ? B5' B9' B8' 109.1(5) . . ? B10' B9' B8' 108.9(5) . . ? B12' B9' B8' 60.5(4) . . ? B5' B9' B4' 60.3(4) . . ? B10' B9' B4' 110.0(5) . . ? B12' B9' B4' 110.0(5) . . ? B8' B9' B4' 61.3(4) . . ? B6' B10' B12' 108.9(6) . . ? B6' B10' B9' 107.5(5) . . ? B12' B10' B9' 60.5(4) . . ? B6' B10' B11' 60.1(4) . . ? B12' B10' B11' 60.9(4) . . ? B9' B10' B11' 108.7(6) . . ? B6' B10' B5' 59.4(4) . . ? B12' B10' B5' 107.9(5) . . ? B9' B10' B5' 59.2(4) . . ? B11' B10' B5' 107.5(5) . . ? C2' B11' B6' 59.9(4) . . ? C2' B11' B10' 104.4(5) . . ? B6' B11' B10' 58.8(4) . . ? C2' B11' B7' 58.7(4) . . ? B6' B11' B7' 108.3(5) . . ? B10' B11' B7' 106.7(5) . . ? C2' B11' B12' 104.0(5) . . ? B6' B11' B12' 106.4(5) . . ? B10' B11' B12' 59.1(4) . . ? B7' B11' B12' 59.2(4) . . ? B10' B12' B7' 108.0(5) . . ? B10' B12' B9' 59.9(4) . . ? B7' B12' B9' 107.3(5) . . ? B10' B12' B8' 108.6(5) . . ? B7' B12' B8' 60.3(4) . . ? B9' B12' B8' 59.8(4) . . ? B10' B12' B11' 60.0(4) . . ? B7' B12' B11' 60.0(4) . . ? B9' B12' B11' 107.5(5) . . ? B8' B12' B11' 108.6(5) . . ? N1' B13' N2' 103.4(5) . . ? N1' B13' B4' 130.5(6) . . ? N2' B13' B4' 125.9(6) . . ? C18 N1 B13 110.5(5) . . ? C18 N1 C14 118.5(5) . . ? B13 N1 C14 131.0(5) . . ? C19 N2 C23 117.8(6) . . ? C19 N2 B13 111.0(6) . . ? C23 N2 B13 131.1(6) . . ? C11 C1 C2 106.7(6) . . ? C11 C1 B5 129.0(7) . . ? C2 C1 B5 109.4(5) . . ? C11 C1 B3 113.4(7) . . ? C2 C1 B3 62.3(5) . . ? B5 C1 B3 114.8(5) . . ? C11 C1 B4 130.4(6) . . ? C2 C1 B4 111.6(5) . . ? B5 C1 B4 64.0(5) . . ? B3 C1 B4 62.5(4) . . ? C11 C1 B6 111.0(6) . . ? C2 C1 B6 58.6(5) . . ? B5 C1 B6 62.9(5) . . ? B3 C1 B6 113.1(5) . . ? B4 C1 B6 115.4(6) . . ? C13 C2 C1 106.5(6) . . ? C13 C2 B6 113.0(7) . . ? C1 C2 B6 63.3(5) . . ? C13 C2 B11 129.3(6) . . ? C1 C2 B11 114.9(6) . . ? B6 C2 B11 65.5(5) . . ? C13 C2 B3 110.8(6) . . ? C1 C2 B3 60.6(4) . . ? B6 C2 B3 115.7(6) . . ? B11 C2 B3 114.4(6) . . ? C13 C2 B7 127.1(7) . . ? C1 C2 B7 111.4(5) . . ? B6 C2 B7 116.4(6) . . ? B11 C2 B7 61.7(5) . . ? B3 C2 B7 62.3(4) . . ? C12 C11 C1 107.7(6) . . ? C11 C12 C13 111.3(6) . . ? C12 C13 C2 106.1(6) . . ? C15 C14 N1 119.5(6) . . ? C14 C15 C16 123.3(7) . . ? C15 C16 C17 119.6(7) . . ? C16 C17 C18 118.4(6) . . ? C19 C18 N1 107.8(6) . . ? C19 C18 C17 131.6(6) . . ? N1 C18 C17 120.5(7) . . ? C18 C19 N2 107.7(6) . . ? C18 C19 C20 130.0(6) . . ? N2 C19 C20 122.3(7) . . ? C21 C20 C19 118.4(7) . . ? C20 C21 C22 120.5(7) . . ? C23 C22 C21 120.9(7) . . ? C22 C23 N2 120.0(7) . . ? C1 B3 C2 57.1(4) . . ? C1 B3 B4 59.4(4) . . ? C2 B3 B4 105.1(6) . . ? C1 B3 B7 106.0(5) . . ? C2 B3 B7 59.0(4) . . ? B4 B3 B7 109.3(5) . . ? C1 B3 B8 105.1(5) . . ? C2 B3 B8 104.0(5) . . ? B4 B3 B8 60.2(4) . . ? B7 B3 B8 59.9(4) . . ? B13 B4 C1 121.9(5) . . ? B13 B4 B3 123.7(6) . . ? C1 B4 B3 58.1(4) . . ? B13 B4 B9 124.9(6) . . ? C1 B4 B9 102.5(5) . . ? B3 B4 B9 106.4(5) . . ? B13 B4 B8 127.1(6) . . ? C1 B4 B8 104.3(5) . . ? B3 B4 B8 60.5(4) . . ? B9 B4 B8 59.2(4) . . ? B13 B4 B5 119.1(6) . . ? C1 B4 B5 56.7(4) . . ? B3 B4 B5 105.4(5) . . ? B9 B4 B5 59.3(4) . . ? B8 B4 B5 106.6(5) . . ? C1 B5 B6 59.9(5) . . ? C1 B5 B9 105.0(5) . . ? B6 B5 B9 107.1(5) . . ? C1 B5 B10 104.3(6) . . ? B6 B5 B10 57.6(5) . . ? B9 B5 B10 61.0(4) . . ? C1 B5 B4 59.3(4) . . ? B6 B5 B4 109.2(6) . . ? B9 B5 B4 60.0(4) . . ? B10 B5 B4 108.9(5) . . ? C2 B6 B10 105.1(6) . . ? C2 B6 C1 58.1(5) . . ? B10 B6 C1 105.2(6) . . ? C2 B6 B5 104.4(6) . . ? B10 B6 B5 61.5(5) . . ? C1 B6 B5 57.2(4) . . ? C2 B6 B11 57.9(5) . . ? B10 B6 B11 60.4(5) . . ? C1 B6 B11 104.8(6) . . ? B5 B6 B11 108.7(6) . . ? C2 B7 B11 57.5(4) . . ? C2 B7 B12 101.8(6) . . ? B11 B7 B12 58.8(5) . . ? C2 B7 B3 58.6(4) . . ? B11 B7 B3 107.7(6) . . ? B12 B7 B3 107.8(6) . . ? C2 B7 B8 103.9(5) . . ? B11 B7 B8 108.2(6) . . ? B12 B7 B8 60.8(5) . . ? B3 B7 B8 60.2(4) . . ? B9 B8 B4 60.4(4) . . ? B9 B8 B7 107.6(6) . . ? B4 B8 B7 108.5(5) . . ? B9 B8 B12 60.7(4) . . ? B4 B8 B12 108.8(6) . . ? B7 B8 B12 58.6(4) . . ? B9 B8 B3 106.4(5) . . ? B4 B8 B3 59.3(4) . . ? B7 B8 B3 59.9(4) . . ? B12 B8 B3 105.8(5) . . ? B8 B9 B5 108.6(6) . . ? B8 B9 B4 60.5(4) . . ? B5 B9 B4 60.6(4) . . ? B8 B9 B12 60.4(4) . . ? B5 B9 B12 107.4(5) . . ? B4 B9 B12 108.6(5) . . ? B8 B9 B10 107.9(5) . . ? B5 B9 B10 59.7(4) . . ? B4 B9 B10 108.5(5) . . ? B12 B9 B10 59.2(4) . . ? B6 B10 B11 62.1(5) . . ? B6 B10 B12 108.3(6) . . ? B11 B10 B12 57.9(4) . . ? B6 B10 B5 60.9(5) . . ? B11 B10 B5 109.6(6) . . ? B12 B10 B5 107.8(5) . . ? B6 B10 B9 108.4(6) . . ? B11 B10 B9 107.0(5) . . ? B12 B10 B9 60.2(4) . . ? B5 B10 B9 59.3(4) . . ? C2 B11 B12 105.8(5) . . ? C2 B11 B7 60.8(5) . . ? B12 B11 B7 60.8(5) . . ? C2 B11 B10 101.7(5) . . ? B12 B11 B10 61.5(5) . . ? B7 B11 B10 109.3(6) . . ? C2 B11 B6 56.5(5) . . ? B12 B11 B6 107.5(6) . . ? B7 B11 B6 108.3(6) . . ? B10 B11 B6 57.5(5) . . ? B11 B12 B7 60.5(5) . . ? B11 B12 B10 60.6(5) . . ? B7 B12 B10 108.3(6) . . ? B11 B12 B8 109.4(5) . . ? B7 B12 B8 60.7(4) . . ? B10 B12 B8 107.9(5) . . ? B11 B12 B9 109.4(5) . . ? B7 B12 B9 107.8(5) . . ? B10 B12 B9 60.6(4) . . ? B8 B12 B9 58.9(4) . . ? N2 B13 N1 103.0(5) . . ? N2 B13 B4 125.0(6) . . ? N1 B13 B4 131.8(6) . . ? C14" N1" C18" 120.0(6) . . ? C14" N1" B13" 130.3(6) . . ? C18" N1" B13" 109.6(5) . . ? C19" N2" C23" 119.0(6) . . ? C19" N2" B13" 111.4(6) . . ? C23" N2" B13" 129.6(6) . . ? C11" C1" C2" 109.1(6) . . ? C11" C1" B5" 128.8(7) . . ? C2" C1" B5" 109.9(6) . . ? C11" C1" B6" 114.0(6) . . ? C2" C1" B6" 57.5(5) . . ? B5" C1" B6" 64.4(5) . . ? C11" C1" B4" 127.0(6) . . ? C2" C1" B4" 110.5(5) . . ? B5" C1" B4" 64.9(5) . . ? B6" C1" B4" 116.5(6) . . ? C11" C1" B3" 112.0(6) . . ? C2" C1" B3" 63.4(5) . . ? B5" C1" B3" 114.6(5) . . ? B6" C1" B3" 113.3(6) . . ? B4" C1" B3" 60.2(4) . . ? C13" C2" B6" 113.3(7) . . ? C13" C2" C1" 105.6(6) . . ? B6" C2" C1" 63.5(5) . . ? C13" C2" B11" 130.5(7) . . ? B6" C2" B11" 64.2(7) . . ? C1" C2" B11" 114.0(7) . . ? C13" C2" B7" 126.0(8) . . ? B6" C2" B7" 117.4(8) . . ? C1" C2" B7" 112.3(6) . . ? B11" C2" B7" 63.3(6) . . ? C13" C2" B3" 109.2(7) . . ? B6" C2" B3" 117.6(6) . . ? C1" C2" B3" 62.5(5) . . ? B11" C2" B3" 114.7(6) . . ? B7" C2" B3" 61.3(5) . . ? C1" C11" C12" 105.2(6) . . ? C11" C12" C13" 108.4(6) . . ? C2" C13" C12" 106.5(7) . . ? C15" C14" N1" 118.8(7) . . ? C14" C15" C16" 124.1(8) . . ? C17" C16" C15" 118.5(8) . . ? C16" C17" C18" 120.2(7) . . ? C19" C18" N1" 109.1(6) . . ? C19" C18" C17" 132.5(7) . . ? N1" C18" C17" 118.4(7) . . ? C18" C19" N2" 108.0(6) . . ? C18" C19" C20" 129.9(8) . . ? N2" C19" C20" 122.1(9) . . ? C21" C20" C19" 117.7(9) . . ? N2" C23" C22" 117.8(8) . . ? B8" B3" B4" 61.9(5) . . ? B8" B3" C1" 103.6(7) . . ? B4" B3" C1" 57.7(4) . . ? B8" B3" B7" 59.8(5) . . ? B4" B3" B7" 108.8(7) . . ? C1" B3" B7" 102.0(7) . . ? B8" B3" C2" 101.5(6) . . ? B4" B3" C2" 101.2(7) . . ? C1" B3" C2" 54.2(5) . . ? B7" B3" C2" 57.1(5) . . ? B13" B4" C1" 121.8(5) . . ? B13" B4" B3" 124.1(7) . . ? C1" B4" B3" 62.1(5) . . ? B13" B4" B8" 128.4(6) . . ? C1" B4" B8" 104.7(5) . . ? B3" B4" B8" 58.9(4) . . ? B13" B4" B9" 123.6(6) . . ? C1" B4" B9" 101.4(5) . . ? B3" B4" B9" 106.8(6) . . ? B8" B4" B9" 59.4(5) . . ? B13" B4" B5" 116.2(6) . . ? C1" B4" B5" 56.7(4) . . ? B3" B4" B5" 109.4(6) . . ? B8" B4" B5" 106.9(6) . . ? B9" B4" B5" 58.5(4) . . ? C1" B5" B9" 104.0(6) . . ? C1" B5" B10" 104.2(7) . . ? B9" B5" B10" 60.6(5) . . ? C1" B5" B6" 58.5(5) . . ? B9" B5" B6" 105.0(6) . . ? B10" B5" B6" 57.5(5) . . ? C1" B5" B4" 58.4(5) . . ? B9" B5" B4" 60.4(4) . . ? B10" B5" B4" 109.1(6) . . ? B6" B5" B4" 106.6(7) . . ? C2" B6" C1" 59.0(5) . . ? C2" B6" B10" 106.8(8) . . ? C1" B6" B10" 105.4(6) . . ? C2" B6" B11" 59.4(6) . . ? C1" B6" B11" 106.7(8) . . ? B10" B6" B11" 61.1(7) . . ? C2" B6" B5" 105.1(7) . . ? C1" B6" B5" 57.1(4) . . ? B10" B6" B5" 60.5(5) . . ? B11" B6" B5" 108.8(7) . . ? C2" B7" B12" 101.8(8) . . ? C2" B7" B8" 104.1(6) . . ? B12" B7" B8" 60.7(5) . . ? C2" B7" B11" 56.8(6) . . ? B12" B7" B11" 58.7(7) . . ? B8" B7" B11" 107.6(9) . . ? C2" B7" B3" 61.7(5) . . ? B12" B7" B3" 108.2(7) . . ? B8" B7" B3" 58.8(4) . . ? B11" B7" B3" 109.7(7) . . ? B3" B8" B7" 61.4(5) . . ? B3" B8" B12" 109.0(6) . . ? B7" B8" B12" 59.1(6) . . ? B3" B8" B9" 107.9(6) . . ? B7" B8" B9" 106.9(7) . . ? B12" B8" B9" 60.0(5) . . ? B3" B8" B4" 59.2(5) . . ? B7" B8" B4" 108.0(6) . . ? B12" B8" B4" 108.8(6) . . ? B9" B8" B4" 60.5(5) . . ? B5" B9" B12" 109.4(6) . . ? B5" B9" B8" 109.5(6) . . ? B12" B9" B8" 59.7(5) . . ? B5" B9" B10" 59.8(4) . . ? B12" B9" B10" 61.7(5) . . ? B8" B9" B10" 109.6(7) . . ? B5" B9" B4" 61.1(4) . . ? B12" B9" B4" 108.2(6) . . ? B8" B9" B4" 60.1(4) . . ? B10" B9" B4" 109.0(6) . . ? B6" B10" B11" 59.9(7) . . ? B6" B10" B5" 62.0(5) . . ? B11" B10" B5" 109.1(8) . . ? B6" B10" B9" 107.7(6) . . ? B11" B10" B9" 105.3(7) . . ? B5" B10" B9" 59.6(4) . . ? B6" B10" B12" 105.6(8) . . ? B11" B10" B12" 57.4(6) . . ? B5" B10" B12" 107.0(6) . . ? B9" B10" B12" 59.0(5) . . ? C2" B11" B12" 105.2(6) . . ? C2" B11" B6" 56.4(6) . . ? B12" B11" B6" 109.6(7) . . ? C2" B11" B10" 102.8(7) . . ? B12" B11" B10" 63.4(6) . . ? B6" B11" B10" 59.0(6) . . ? C2" B11" B7" 59.9(6) . . ? B12" B11" B7" 60.0(6) . . ? B6" B11" B7" 108.1(7) . . ? B10" B11" B7" 110.5(7) . . ? B11" B12" B7" 61.3(7) . . ? B11" B12" B8" 109.2(7) . . ? B7" B12" B8" 60.1(5) . . ? B11" B12" B9" 107.1(6) . . ? B7" B12" B9" 107.9(6) . . ? B8" B12" B9" 60.3(5) . . ? B11" B12" B10" 59.2(6) . . ? B7" B12" B10" 108.2(7) . . ? B8" B12" B10" 108.2(6) . . ? B9" B12" B10" 59.3(5) . . ? N2" B13" N1" 101.9(5) . . ? N2" B13" B4" 126.7(6) . . ? N1" B13" B4" 131.5(6) . . ? C20" C21" C22" 122.4(9) . . ? C21" C22" C23" 120.8(9) . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 25.25 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.599 _refine_diff_density_min -0.337 _refine_diff_density_rms 0.075 #===END