Supplementary Material (ESI) for Dalton Transactions This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Westcott, Steve' _publ_contact_author_email swestcott@mta.ca _publ_section_title ; Addition of Boranes to Schiff Bases: Intramolecular Hydrogenation of Imines ; loop_ _publ_author_name S.Barnes C.Vogels A.Decken S.Westcott data_sw081154 _database_code_depnum_ccdc_archive 'CCDC 807112' _publ_section_references ; Bruker (2006). SAINT. Version 7.23A. Bruker AXS Inc., Madison, Wisconsin, USA. Bruker (1999). SMART. Version 5.054. Bruker AXS Inc., Madison, Wisconsin, USA. Sheldrick, G.M. (2008). Acta Cryst. A64, 112-122. Sheldrick, G.M. (2004). SADABS 2004. Bruker AXS Inc., Madison, Wisconsin, USA. ; _publ_section_exptl_refinement ; The crystal was twinned and the orientation matrixes for two components were determined. The data were reduced, corrected for absorption, and refined using all data. ; _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety 'C24 H44 B2 O' _chemical_formula_sum 'C24 H44 B2 O' _exptl_crystal_recrystallization_method toluene _chemical_melting_point ? _exptl_crystal_description Parallelpiped _exptl_crystal_colour Colourless _diffrn_ambient_temperature 173(1) _chemical_formula_weight 370.21 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' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_int_tables_number 2 _chemical_absolute_configuration ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.170(4) _cell_length_b 12.049(4) _cell_length_c 19.696(7) _cell_angle_alpha 88.903(9) _cell_angle_beta 78.163(7) _cell_angle_gamma 86.724(6) _cell_volume 2358.1(14) _cell_formula_units_Z 4 _cell_measurement_temperature 173(1) _cell_measurement_reflns_used 5340 _cell_measurement_theta_min 2.59 _cell_measurement_theta_max 25.56 _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.23 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.043 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 824 _exptl_absorpt_coefficient_mu 0.059 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9653 _exptl_absorpt_correction_T_max 0.9868 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2004)' _exptl_special_details ; Crystal decay was monitored by repeating the initial 50 frames at the end of the data collection and analyzing duplicate reflections. ; _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_source_type K760 _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker AXS SMART1000/P4' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 11326 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0602 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 1.06 _diffrn_reflns_theta_max 27.50 _reflns_number_total 10108 _reflns_number_gt 6364 _reflns_threshold_expression 'I > 2\s(I)' _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL (Sheldrick, 2008)' _computing_publication_material 'Bruker SHELXTL (Sheldrick, 2008)' _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^)+(0.0769P)^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 10108 _refine_ls_number_parameters 488 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1040 _refine_ls_R_factor_gt 0.0548 _refine_ls_wR_factor_ref 0.1560 _refine_ls_wR_factor_gt 0.1341 _refine_ls_goodness_of_fit_ref 0.976 _refine_ls_restrained_S_all 0.976 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group B1 B 0.7472(2) 0.16944(19) 0.48089(11) 0.0290(5) Uani 1 1 d . . . B2 B 0.6528(2) 0.3345(2) 0.40715(10) 0.0301(5) Uani 1 1 d . . . B3 B 0.8681(2) 0.8381(2) 0.09435(10) 0.0312(6) Uani 1 1 d . . . B4 B 0.7950(2) 0.6732(2) 0.02305(12) 0.0331(6) Uani 1 1 d . . . C1 C 0.69908(19) 0.16112(16) 0.56251(9) 0.0312(5) Uani 1 1 d . . . H1 H 0.7548 0.0998 0.5795 0.037 Uiso 1 1 calc R . . C2 C 0.7172(2) 0.26781(18) 0.60004(10) 0.0387(5) Uani 1 1 d . . . H2A H 0.6672 0.3307 0.5819 0.046 Uiso 1 1 calc R . . H2B H 0.8137 0.2839 0.5902 0.046 Uiso 1 1 calc R . . C3 C 0.6669(2) 0.2583(2) 0.67880(10) 0.0483(6) Uani 1 1 d . . . H3A H 0.7228 0.2005 0.6978 0.058 Uiso 1 1 calc R . . H3B H 0.6761 0.3299 0.7007 0.058 Uiso 1 1 calc R . . C4 C 0.5207(2) 0.2284(2) 0.69611(11) 0.0549(7) Uani 1 1 d . . . H4A H 0.4637 0.2900 0.6815 0.066 Uiso 1 1 calc R . . H4B H 0.4921 0.2185 0.7469 0.066 Uiso 1 1 calc R . . C5 C 0.5008(2) 0.1220(2) 0.65991(11) 0.0588(7) Uani 1 1 d . . . H5A H 0.4040 0.1071 0.6698 0.071 Uiso 1 1 calc R . . H5B H 0.5498 0.0590 0.6784 0.071 Uiso 1 1 calc R . . C6 C 0.5515(2) 0.1307(2) 0.58166(10) 0.0470(6) Uani 1 1 d . . . H6A H 0.4951 0.1879 0.5625 0.056 Uiso 1 1 calc R . . H6B H 0.5421 0.0587 0.5602 0.056 Uiso 1 1 calc R . . C7 C 0.85023(19) 0.08319(16) 0.43713(9) 0.0304(5) Uani 1 1 d . . . H7 H 0.9363 0.0868 0.4539 0.037 Uiso 1 1 calc R . . C8 C 0.8057(2) -0.03573(17) 0.45067(10) 0.0442(6) Uani 1 1 d . . . H8A H 0.7913 -0.0518 0.5011 0.053 Uiso 1 1 calc R . . H8B H 0.7189 -0.0423 0.4361 0.053 Uiso 1 1 calc R . . C9 C 0.9087(3) -0.1212(2) 0.41195(10) 0.0566(7) Uani 1 1 d . . . H9A H 0.9920 -0.1211 0.4306 0.068 Uiso 1 1 calc R . . H9B H 0.8729 -0.1961 0.4199 0.068 Uiso 1 1 calc R . . C10 C 0.9422(2) -0.09730(19) 0.33440(10) 0.0463(6) Uani 1 1 d . . . H10A H 1.0147 -0.1508 0.3117 0.056 Uiso 1 1 calc R . . H10B H 0.8619 -0.1071 0.3144 0.056 Uiso 1 1 calc R . . C11 C 0.9871(2) 0.01966(19) 0.32024(10) 0.0470(6) Uani 1 1 d . . . H11A H 1.0013 0.0351 0.2698 0.056 Uiso 1 1 calc R . . H11B H 1.0739 0.0263 0.3347 0.056 Uiso 1 1 calc R . . C12 C 0.8839(2) 0.10508(18) 0.35877(9) 0.0430(6) Uani 1 1 d . . . H12A H 0.8005 0.1042 0.3403 0.052 Uiso 1 1 calc R . . H12B H 0.9193 0.1800 0.3501 0.052 Uiso 1 1 calc R . . C13 C 0.52421(19) 0.31767(17) 0.37604(10) 0.0339(5) Uani 1 1 d . . . H13 H 0.5530 0.3242 0.3245 0.041 Uiso 1 1 calc R . . C14 C 0.4618(2) 0.20471(18) 0.39098(11) 0.0436(6) Uani 1 1 d . . . H14A H 0.5299 0.1451 0.3722 0.052 Uiso 1 1 calc R . . H14B H 0.4362 0.1935 0.4418 0.052 Uiso 1 1 calc R . . C15 C 0.3381(2) 0.1950(2) 0.35943(12) 0.0489(6) Uani 1 1 d . . . H15A H 0.3651 0.1974 0.3082 0.059 Uiso 1 1 calc R . . H15B H 0.2987 0.1225 0.3729 0.059 Uiso 1 1 calc R . . C16 C 0.2338(2) 0.2875(2) 0.38338(13) 0.0639(8) Uani 1 1 d . . . H16A H 0.1989 0.2797 0.4339 0.077 Uiso 1 1 calc R . . H16B H 0.1576 0.2817 0.3596 0.077 Uiso 1 1 calc R . . C17 C 0.2923(3) 0.4009(2) 0.36810(16) 0.0708(8) Uani 1 1 d . . . H17A H 0.3164 0.4124 0.3173 0.085 Uiso 1 1 calc R . . H17B H 0.2234 0.4595 0.3876 0.085 Uiso 1 1 calc R . . C18 C 0.4163(2) 0.4112(2) 0.39880(13) 0.0547(7) Uani 1 1 d . . . H18A H 0.3894 0.4104 0.4500 0.066 Uiso 1 1 calc R . . H18B H 0.4553 0.4836 0.3845 0.066 Uiso 1 1 calc R . . C19 C 0.7342(2) 0.44314(17) 0.39548(9) 0.0330(5) Uani 1 1 d . . . H19 H 0.6714 0.5048 0.4180 0.040 Uiso 1 1 calc R . . C20 C 0.7750(2) 0.4751(2) 0.31830(10) 0.0489(6) Uani 1 1 d . . . H20A H 0.8322 0.4134 0.2932 0.059 Uiso 1 1 calc R . . H20B H 0.6930 0.4849 0.2986 0.059 Uiso 1 1 calc R . . C21 C 0.8512(2) 0.5814(2) 0.30644(12) 0.0591(7) Uani 1 1 d . . . H21A H 0.8811 0.5943 0.2560 0.071 Uiso 1 1 calc R . . H21B H 0.7900 0.6451 0.3257 0.071 Uiso 1 1 calc R . . C22 C 0.9723(2) 0.5751(2) 0.34021(11) 0.0485(6) Uani 1 1 d . . . H22A H 1.0160 0.6469 0.3340 0.058 Uiso 1 1 calc R . . H22B H 1.0383 0.5167 0.3175 0.058 Uiso 1 1 calc R . . C23 C 0.9310(2) 0.5487(2) 0.41686(10) 0.0469(6) Uani 1 1 d . . . H23A H 0.8718 0.6107 0.4403 0.056 Uiso 1 1 calc R . . H23B H 1.0120 0.5415 0.4375 0.056 Uiso 1 1 calc R . . C24 C 0.8573(2) 0.44165(19) 0.42895(11) 0.0428(6) Uani 1 1 d . . . H24A H 0.8282 0.4291 0.4795 0.051 Uiso 1 1 calc R . . H24B H 0.9201 0.3788 0.4099 0.051 Uiso 1 1 calc R . . C25 C 0.77833(19) 0.95005(17) 0.10236(9) 0.0319(5) Uani 1 1 d . . . H25 H 0.8358 1.0094 0.0782 0.038 Uiso 1 1 calc R . . C26 C 0.6537(2) 0.94928(19) 0.06924(11) 0.0417(5) Uani 1 1 d . . . H26A H 0.6835 0.9362 0.0188 0.050 Uiso 1 1 calc R . . H26B H 0.5986 0.8869 0.0893 0.050 Uiso 1 1 calc R . . C27 C 0.5673(2) 1.0570(2) 0.08028(11) 0.0494(6) Uani 1 1 d . . . H27A H 0.6184 1.1182 0.0553 0.059 Uiso 1 1 calc R . . H27B H 0.4861 1.0499 0.0606 0.059 Uiso 1 1 calc R . . C28 C 0.5252(2) 1.0852(2) 0.15661(11) 0.0491(6) Uani 1 1 d . . . H28A H 0.4663 1.0279 0.1808 0.059 Uiso 1 1 calc R . . H28B H 0.4732 1.1576 0.1618 0.059 Uiso 1 1 calc R . . C29 C 0.6474(2) 1.09114(19) 0.18956(11) 0.0448(6) Uani 1 1 d . . . H29A H 0.7012 1.1537 0.1687 0.054 Uiso 1 1 calc R . . H29B H 0.6173 1.1054 0.2398 0.054 Uiso 1 1 calc R . . C30 C 0.7346(2) 0.98365(18) 0.17903(9) 0.0374(5) Uani 1 1 d . . . H30A H 0.6841 0.9232 0.2052 0.045 Uiso 1 1 calc R . . H30B H 0.8159 0.9923 0.1984 0.045 Uiso 1 1 calc R . . C31 C 0.99722(19) 0.81855(16) 0.12638(10) 0.0318(5) Uani 1 1 d . . . H31 H 0.9658 0.8226 0.1779 0.038 Uiso 1 1 calc R . . C32 C 1.0958(2) 0.91087(19) 0.10610(12) 0.0485(6) Uani 1 1 d . . . H32A H 1.1251 0.9128 0.0550 0.058 Uiso 1 1 calc R . . H32B H 1.0488 0.9833 0.1208 0.058 Uiso 1 1 calc R . . C33 C 1.2197(2) 0.8951(2) 0.13859(14) 0.0592(7) Uani 1 1 d . . . H33A H 1.2832 0.9532 0.1206 0.071 Uiso 1 1 calc R . . H33B H 1.1923 0.9038 0.1895 0.071 Uiso 1 1 calc R . . C34 C 1.2900(2) 0.7811(2) 0.12235(12) 0.0610(7) Uani 1 1 d . . . H34A H 1.3276 0.7759 0.0719 0.073 Uiso 1 1 calc R . . H34B H 1.3656 0.7713 0.1470 0.073 Uiso 1 1 calc R . . C35 C 1.1941(2) 0.6895(2) 0.14402(13) 0.0566(7) Uani 1 1 d . . . H35A H 1.1648 0.6892 0.1952 0.068 Uiso 1 1 calc R . . H35B H 1.2413 0.6168 0.1301 0.068 Uiso 1 1 calc R . . C36 C 1.0715(2) 0.70451(19) 0.11129(12) 0.0483(6) Uani 1 1 d . . . H36A H 1.0089 0.6457 0.1290 0.058 Uiso 1 1 calc R . . H36B H 1.1000 0.6953 0.0605 0.058 Uiso 1 1 calc R . . C37 C 0.6927(2) 0.58788(16) 0.06181(9) 0.0325(5) Uani 1 1 d . . . H37 H 0.6102 0.5976 0.0416 0.039 Uiso 1 1 calc R . . C38 C 0.6472(2) 0.60586(18) 0.14026(10) 0.0434(6) Uani 1 1 d . . . H38A H 0.7267 0.5986 0.1621 0.052 Uiso 1 1 calc R . . H38B H 0.6065 0.6822 0.1487 0.052 Uiso 1 1 calc R . . C39 C 0.5452(2) 0.5227(2) 0.17396(11) 0.0475(6) Uani 1 1 d . . . H39A H 0.5223 0.5348 0.2247 0.057 Uiso 1 1 calc R . . H39B H 0.4617 0.5351 0.1557 0.057 Uiso 1 1 calc R . . C40 C 0.6006(2) 0.4038(2) 0.15955(10) 0.0480(6) Uani 1 1 d . . . H40A H 0.5301 0.3520 0.1791 0.058 Uiso 1 1 calc R . . H40B H 0.6774 0.3886 0.1828 0.058 Uiso 1 1 calc R . . C41 C 0.6468(3) 0.3831(2) 0.08212(11) 0.0522(6) Uani 1 1 d . . . H41A H 0.5677 0.3879 0.0599 0.063 Uiso 1 1 calc R . . H41B H 0.6894 0.3071 0.0748 0.063 Uiso 1 1 calc R . . C42 C 0.7468(2) 0.46734(17) 0.04820(10) 0.0423(6) Uani 1 1 d . . . H42A H 0.7693 0.4547 -0.0025 0.051 Uiso 1 1 calc R . . H42B H 0.8307 0.4553 0.0661 0.051 Uiso 1 1 calc R . . C43 C 0.8572(2) 0.66561(17) -0.05763(10) 0.0341(5) Uani 1 1 d . . . H43 H 0.9153 0.5953 -0.0647 0.041 Uiso 1 1 calc R . . C44 C 0.7479(2) 0.6551(2) -0.10023(10) 0.0480(6) Uani 1 1 d . . . H44A H 0.6960 0.5893 -0.0838 0.058 Uiso 1 1 calc R . . H44B H 0.6850 0.7216 -0.0926 0.058 Uiso 1 1 calc R . . C45 C 0.8067(3) 0.6437(2) -0.17793(11) 0.0642(8) Uani 1 1 d . . . H45A H 0.8607 0.5725 -0.1865 0.077 Uiso 1 1 calc R . . H45B H 0.7325 0.6424 -0.2035 0.077 Uiso 1 1 calc R . . C46 C 0.8948(2) 0.7392(2) -0.20477(12) 0.0611(7) Uani 1 1 d . . . H46A H 0.9350 0.7278 -0.2545 0.073 Uiso 1 1 calc R . . H46B H 0.8389 0.8097 -0.2005 0.073 Uiso 1 1 calc R . . C47 C 1.0053(2) 0.7474(2) -0.16475(11) 0.0572(7) Uani 1 1 d . . . H47A H 1.0585 0.8123 -0.1817 0.069 Uiso 1 1 calc R . . H47B H 1.0664 0.6798 -0.1727 0.069 Uiso 1 1 calc R . . C48 C 0.9470(2) 0.7596(2) -0.08711(11) 0.0489(6) Uani 1 1 d . . . H48A H 1.0219 0.7612 -0.0620 0.059 Uiso 1 1 calc R . . H48B H 0.8940 0.8314 -0.0790 0.059 Uiso 1 1 calc R . . O1 O 0.69144(13) 0.25388(12) 0.44863(7) 0.0386(4) Uani 1 1 d . . . O2 O 0.83219(15) 0.75464(13) 0.05890(7) 0.0518(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 B1 0.0266(12) 0.0284(13) 0.0345(12) 0.0008(11) -0.0104(9) -0.0070(10) B2 0.0320(13) 0.0334(14) 0.0219(11) -0.0056(10) -0.0011(9) 0.0096(11) B3 0.0361(13) 0.0353(14) 0.0216(11) -0.0030(10) -0.0013(9) -0.0133(11) B4 0.0304(13) 0.0286(14) 0.0440(14) -0.0081(11) -0.0170(10) 0.0051(11) C1 0.0332(11) 0.0288(12) 0.0305(10) -0.0022(9) -0.0042(8) 0.0003(9) C2 0.0379(12) 0.0417(14) 0.0371(11) -0.0058(10) -0.0078(9) -0.0043(10) C3 0.0511(15) 0.0558(16) 0.0375(12) -0.0140(11) -0.0059(10) -0.0055(12) C4 0.0513(15) 0.0664(18) 0.0417(13) -0.0156(12) 0.0047(11) -0.0037(13) C5 0.0511(15) 0.081(2) 0.0407(13) -0.0106(13) 0.0058(11) -0.0236(14) C6 0.0429(13) 0.0597(16) 0.0370(12) -0.0095(11) -0.0003(10) -0.0162(12) C7 0.0286(11) 0.0355(12) 0.0281(10) 0.0001(9) -0.0072(8) -0.0038(9) C8 0.0575(15) 0.0384(14) 0.0309(11) 0.0006(10) 0.0035(10) -0.0007(12) C9 0.0855(19) 0.0387(14) 0.0378(12) -0.0023(11) 0.0026(12) 0.0093(13) C10 0.0515(14) 0.0494(15) 0.0346(11) -0.0086(11) -0.0020(10) 0.0038(12) C11 0.0487(14) 0.0527(16) 0.0341(11) -0.0043(11) 0.0050(10) -0.0036(12) C12 0.0522(14) 0.0406(14) 0.0318(11) 0.0025(10) 0.0018(10) -0.0051(11) C13 0.0349(12) 0.0363(13) 0.0309(11) -0.0029(9) -0.0084(9) 0.0012(10) C14 0.0409(13) 0.0446(15) 0.0461(13) -0.0001(11) -0.0106(10) -0.0035(11) C15 0.0439(14) 0.0584(17) 0.0471(13) -0.0035(12) -0.0126(11) -0.0120(12) C16 0.0372(14) 0.093(2) 0.0647(17) -0.0243(15) -0.0169(12) 0.0001(15) C17 0.0482(16) 0.069(2) 0.104(2) -0.0243(17) -0.0404(15) 0.0182(15) C18 0.0421(14) 0.0509(16) 0.0766(17) -0.0184(13) -0.0275(12) 0.0127(12) C19 0.0364(12) 0.0334(12) 0.0294(10) -0.0020(9) -0.0091(9) 0.0050(10) C20 0.0523(15) 0.0627(17) 0.0371(12) 0.0106(12) -0.0193(10) -0.0161(13) C21 0.0596(17) 0.0725(19) 0.0514(14) 0.0237(13) -0.0225(12) -0.0226(14) C22 0.0448(14) 0.0554(16) 0.0461(13) 0.0053(12) -0.0098(11) -0.0108(12) C23 0.0466(14) 0.0553(16) 0.0435(13) 0.0033(12) -0.0179(10) -0.0133(12) C24 0.0480(14) 0.0466(14) 0.0372(12) 0.0037(11) -0.0160(10) -0.0071(11) C25 0.0328(11) 0.0360(12) 0.0293(10) 0.0015(9) -0.0095(8) -0.0107(10) C26 0.0409(13) 0.0518(15) 0.0364(11) -0.0052(11) -0.0159(10) -0.0061(11) C27 0.0423(14) 0.0572(17) 0.0550(14) 0.0006(12) -0.0250(11) -0.0026(12) C28 0.0385(13) 0.0530(16) 0.0580(15) -0.0056(12) -0.0163(11) 0.0045(12) C29 0.0411(13) 0.0510(15) 0.0439(12) -0.0104(11) -0.0139(10) 0.0058(12) C30 0.0372(12) 0.0459(14) 0.0304(11) -0.0047(10) -0.0105(9) 0.0009(11) C31 0.0371(12) 0.0295(12) 0.0280(10) -0.0040(9) -0.0039(8) -0.0031(10) C32 0.0414(14) 0.0441(15) 0.0625(15) 0.0060(12) -0.0151(11) -0.0103(12) C33 0.0433(15) 0.0603(18) 0.0788(18) 0.0085(15) -0.0210(13) -0.0152(13) C34 0.0403(15) 0.087(2) 0.0543(15) 0.0005(14) -0.0089(11) 0.0093(15) C35 0.0578(17) 0.0503(16) 0.0615(16) -0.0072(13) -0.0160(13) 0.0151(14) C36 0.0507(15) 0.0399(15) 0.0555(15) -0.0076(11) -0.0146(11) 0.0035(12) C37 0.0336(12) 0.0356(13) 0.0300(10) -0.0103(9) -0.0106(8) 0.0027(10) C38 0.0548(15) 0.0400(14) 0.0329(11) -0.0101(10) -0.0047(10) 0.0063(12) C39 0.0429(14) 0.0607(17) 0.0352(12) -0.0019(11) -0.0021(10) 0.0073(12) C40 0.0485(15) 0.0512(16) 0.0415(13) 0.0014(11) -0.0024(10) -0.0036(12) C41 0.0665(17) 0.0411(15) 0.0453(13) -0.0053(11) -0.0005(11) -0.0105(13) C42 0.0521(14) 0.0327(13) 0.0370(11) -0.0073(10) 0.0033(10) -0.0009(11) C43 0.0333(12) 0.0291(12) 0.0408(12) 0.0001(10) -0.0096(9) -0.0026(9) C44 0.0438(14) 0.0617(17) 0.0413(12) 0.0022(12) -0.0108(10) -0.0189(12) C45 0.0644(17) 0.097(2) 0.0350(12) 0.0058(13) -0.0112(11) -0.0345(16) C46 0.0562(16) 0.080(2) 0.0464(14) 0.0182(14) -0.0072(12) -0.0197(15) C47 0.0447(15) 0.0694(18) 0.0571(15) 0.0168(14) -0.0070(12) -0.0185(13) C48 0.0428(14) 0.0494(15) 0.0580(14) 0.0047(12) -0.0147(11) -0.0174(12) O1 0.0400(9) 0.0367(9) 0.0400(8) 0.0018(7) -0.0118(6) 0.0035(7) O2 0.0577(10) 0.0461(10) 0.0565(10) -0.0173(8) -0.0198(8) -0.0101(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag B1 O1 1.348(3) . ? B1 C7 1.568(3) . ? B1 C1 1.584(3) . ? B2 O1 1.350(3) . ? B2 C19 1.577(3) . ? B2 C13 1.578(3) . ? B3 O2 1.343(3) . ? B3 C31 1.574(3) . ? B3 C25 1.577(3) . ? B4 O2 1.336(3) . ? B4 C37 1.577(3) . ? B4 C43 1.588(3) . ? C1 C2 1.534(3) . ? C1 C6 1.535(3) . ? C1 H1 1.0000 . ? C2 C3 1.535(3) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.517(3) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.522(3) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.525(3) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.529(3) . ? C7 C12 1.532(2) . ? C7 H7 1.0000 . ? C8 C9 1.522(3) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.521(3) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C11 1.509(3) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.522(3) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.533(3) . ? C13 C18 1.533(3) . ? C13 H13 1.0000 . ? C14 C15 1.524(3) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 C16 1.506(3) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 C17 1.521(4) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 C18 1.519(3) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 C24 1.528(3) . ? C19 C20 1.539(2) . ? C19 H19 1.0000 . ? C20 C21 1.524(3) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C21 C22 1.513(3) . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C22 C23 1.514(3) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C23 C24 1.519(3) . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? C25 C30 1.539(2) . ? C25 C26 1.540(3) . ? C25 H25 1.0000 . ? C26 C27 1.519(3) . ? C26 H26A 0.9900 . ? C26 H26B 0.9900 . ? C27 C28 1.516(3) . ? C27 H27A 0.9900 . ? C27 H27B 0.9900 . ? C28 C29 1.521(3) . ? C28 H28A 0.9900 . ? C28 H28B 0.9900 . ? C29 C30 1.520(3) . ? C29 H29A 0.9900 . ? C29 H29B 0.9900 . ? C30 H30A 0.9900 . ? C30 H30B 0.9900 . ? C31 C32 1.532(3) . ? C31 C36 1.534(3) . ? C31 H31 1.0000 . ? C32 C33 1.527(3) . ? C32 H32A 0.9900 . ? C32 H32B 0.9900 . ? C33 C34 1.521(3) . ? C33 H33A 0.9900 . ? C33 H33B 0.9900 . ? C34 C35 1.512(3) . ? C34 H34A 0.9900 . ? C34 H34B 0.9900 . ? C35 C36 1.517(3) . ? C35 H35A 0.9900 . ? C35 H35B 0.9900 . ? C36 H36A 0.9900 . ? C36 H36B 0.9900 . ? C37 C42 1.532(3) . ? C37 C38 1.535(3) . ? C37 H37 1.0000 . ? C38 C39 1.527(3) . ? C38 H38A 0.9900 . ? C38 H38B 0.9900 . ? C39 C40 1.519(3) . ? C39 H39A 0.9900 . ? C39 H39B 0.9900 . ? C40 C41 1.522(3) . ? C40 H40A 0.9900 . ? C40 H40B 0.9900 . ? C41 C42 1.525(3) . ? C41 H41A 0.9900 . ? C41 H41B 0.9900 . ? C42 H42A 0.9900 . ? C42 H42B 0.9900 . ? C43 C48 1.526(3) . ? C43 C44 1.536(3) . ? C43 H43 1.0000 . ? C44 C45 1.530(3) . ? C44 H44A 0.9900 . ? C44 H44B 0.9900 . ? C45 C46 1.520(3) . ? C45 H45A 0.9900 . ? C45 H45B 0.9900 . ? C46 C47 1.507(3) . ? C46 H46A 0.9900 . ? C46 H46B 0.9900 . ? C47 C48 1.529(3) . ? C47 H47A 0.9900 . ? C47 H47B 0.9900 . ? C48 H48A 0.9900 . ? C48 H48B 0.9900 . ? 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 O1 B1 C7 119.77(17) . . ? O1 B1 C1 116.76(18) . . ? C7 B1 C1 123.44(18) . . ? O1 B2 C19 118.19(19) . . ? O1 B2 C13 118.29(19) . . ? C19 B2 C13 123.44(18) . . ? O2 B3 C31 118.2(2) . . ? O2 B3 C25 118.5(2) . . ? C31 B3 C25 123.31(18) . . ? O2 B4 C37 119.43(19) . . ? O2 B4 C43 118.2(2) . . ? C37 B4 C43 122.40(18) . . ? C2 C1 C6 109.67(16) . . ? C2 C1 B1 113.19(16) . . ? C6 C1 B1 110.51(16) . . ? C2 C1 H1 107.8 . . ? C6 C1 H1 107.8 . . ? B1 C1 H1 107.8 . . ? C1 C2 C3 112.06(17) . . ? C1 C2 H2A 109.2 . . ? C3 C2 H2A 109.2 . . ? C1 C2 H2B 109.2 . . ? C3 C2 H2B 109.2 . . ? H2A C2 H2B 107.9 . . ? C4 C3 C2 110.90(18) . . ? C4 C3 H3A 109.5 . . ? C2 C3 H3A 109.5 . . ? C4 C3 H3B 109.5 . . ? C2 C3 H3B 109.5 . . ? H3A C3 H3B 108.0 . . ? C3 C4 C5 111.11(19) . . ? C3 C4 H4A 109.4 . . ? C5 C4 H4A 109.4 . . ? C3 C4 H4B 109.4 . . ? C5 C4 H4B 109.4 . . ? H4A C4 H4B 108.0 . . ? C4 C5 C6 111.4(2) . . ? C4 C5 H5A 109.3 . . ? C6 C5 H5A 109.3 . . ? C4 C5 H5B 109.3 . . ? C6 C5 H5B 109.3 . . ? H5A C5 H5B 108.0 . . ? C5 C6 C1 112.25(18) . . ? C5 C6 H6A 109.2 . . ? C1 C6 H6A 109.2 . . ? C5 C6 H6B 109.2 . . ? C1 C6 H6B 109.2 . . ? H6A C6 H6B 107.9 . . ? C8 C7 C12 109.28(17) . . ? C8 C7 B1 111.57(15) . . ? C12 C7 B1 115.77(17) . . ? C8 C7 H7 106.6 . . ? C12 C7 H7 106.6 . . ? B1 C7 H7 106.6 . . ? C9 C8 C7 112.27(17) . . ? C9 C8 H8A 109.1 . . ? C7 C8 H8A 109.1 . . ? C9 C8 H8B 109.1 . . ? C7 C8 H8B 109.1 . . ? H8A C8 H8B 107.9 . . ? C10 C9 C8 111.99(19) . . ? C10 C9 H9A 109.2 . . ? C8 C9 H9A 109.2 . . ? C10 C9 H9B 109.2 . . ? C8 C9 H9B 109.2 . . ? H9A C9 H9B 107.9 . . ? C11 C10 C9 110.85(19) . . ? C11 C10 H10A 109.5 . . ? C9 C10 H10A 109.5 . . ? C11 C10 H10B 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 108.1 . . ? C10 C11 C12 111.70(17) . . ? C10 C11 H11A 109.3 . . ? C12 C11 H11A 109.3 . . ? C10 C11 H11B 109.3 . . ? C12 C11 H11B 109.3 . . ? H11A C11 H11B 107.9 . . ? C11 C12 C7 112.60(18) . . ? C11 C12 H12A 109.1 . . ? C7 C12 H12A 109.1 . . ? C11 C12 H12B 109.1 . . ? C7 C12 H12B 109.1 . . ? H12A C12 H12B 107.8 . . ? C14 C13 C18 109.68(18) . . ? C14 C13 B2 115.74(17) . . ? C18 C13 B2 110.89(18) . . ? C14 C13 H13 106.7 . . ? C18 C13 H13 106.7 . . ? B2 C13 H13 106.7 . . ? C15 C14 C13 112.62(18) . . ? C15 C14 H14A 109.1 . . ? C13 C14 H14A 109.1 . . ? C15 C14 H14B 109.1 . . ? C13 C14 H14B 109.1 . . ? H14A C14 H14B 107.8 . . ? C16 C15 C14 111.3(2) . . ? C16 C15 H15A 109.4 . . ? C14 C15 H15A 109.4 . . ? C16 C15 H15B 109.4 . . ? C14 C15 H15B 109.4 . . ? H15A C15 H15B 108.0 . . ? C15 C16 C17 111.3(2) . . ? C15 C16 H16A 109.4 . . ? C17 C16 H16A 109.4 . . ? C15 C16 H16B 109.4 . . ? C17 C16 H16B 109.4 . . ? H16A C16 H16B 108.0 . . ? C18 C17 C16 111.7(2) . . ? C18 C17 H17A 109.3 . . ? C16 C17 H17A 109.3 . . ? C18 C17 H17B 109.3 . . ? C16 C17 H17B 109.3 . . ? H17A C17 H17B 107.9 . . ? C17 C18 C13 112.8(2) . . ? C17 C18 H18A 109.0 . . ? C13 C18 H18A 109.0 . . ? C17 C18 H18B 109.0 . . ? C13 C18 H18B 109.0 . . ? H18A C18 H18B 107.8 . . ? C24 C19 C20 109.67(16) . . ? C24 C19 B2 115.13(17) . . ? C20 C19 B2 112.48(17) . . ? C24 C19 H19 106.3 . . ? C20 C19 H19 106.3 . . ? B2 C19 H19 106.3 . . ? C21 C20 C19 112.99(19) . . ? C21 C20 H20A 109.0 . . ? C19 C20 H20A 109.0 . . ? C21 C20 H20B 109.0 . . ? C19 C20 H20B 109.0 . . ? H20A C20 H20B 107.8 . . ? C22 C21 C20 111.7(2) . . ? C22 C21 H21A 109.3 . . ? C20 C21 H21A 109.3 . . ? C22 C21 H21B 109.3 . . ? C20 C21 H21B 109.3 . . ? H21A C21 H21B 107.9 . . ? C21 C22 C23 110.64(18) . . ? C21 C22 H22A 109.5 . . ? C23 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? C23 C22 H22B 109.5 . . ? H22A C22 H22B 108.1 . . ? C22 C23 C24 111.36(19) . . ? C22 C23 H23A 109.4 . . ? C24 C23 H23A 109.4 . . ? C22 C23 H23B 109.4 . . ? C24 C23 H23B 109.4 . . ? H23A C23 H23B 108.0 . . ? C23 C24 C19 112.96(18) . . ? C23 C24 H24A 109.0 . . ? C19 C24 H24A 109.0 . . ? C23 C24 H24B 109.0 . . ? C19 C24 H24B 109.0 . . ? H24A C24 H24B 107.8 . . ? C30 C25 C26 109.54(16) . . ? C30 C25 B3 111.20(15) . . ? C26 C25 B3 114.52(18) . . ? C30 C25 H25 107.1 . . ? C26 C25 H25 107.1 . . ? B3 C25 H25 107.1 . . ? C27 C26 C25 112.93(19) . . ? C27 C26 H26A 109.0 . . ? C25 C26 H26A 109.0 . . ? C27 C26 H26B 109.0 . . ? C25 C26 H26B 109.0 . . ? H26A C26 H26B 107.8 . . ? C28 C27 C26 111.53(18) . . ? C28 C27 H27A 109.3 . . ? C26 C27 H27A 109.3 . . ? C28 C27 H27B 109.3 . . ? C26 C27 H27B 109.3 . . ? H27A C27 H27B 108.0 . . ? C27 C28 C29 110.89(18) . . ? C27 C28 H28A 109.5 . . ? C29 C28 H28A 109.5 . . ? C27 C28 H28B 109.5 . . ? C29 C28 H28B 109.5 . . ? H28A C28 H28B 108.0 . . ? C30 C29 C28 111.19(19) . . ? C30 C29 H29A 109.4 . . ? C28 C29 H29A 109.4 . . ? C30 C29 H29B 109.4 . . ? C28 C29 H29B 109.4 . . ? H29A C29 H29B 108.0 . . ? C29 C30 C25 113.26(16) . . ? C29 C30 H30A 108.9 . . ? C25 C30 H30A 108.9 . . ? C29 C30 H30B 108.9 . . ? C25 C30 H30B 108.9 . . ? H30A C30 H30B 107.7 . . ? C32 C31 C36 109.95(17) . . ? C32 C31 B3 112.19(17) . . ? C36 C31 B3 114.92(18) . . ? C32 C31 H31 106.4 . . ? C36 C31 H31 106.4 . . ? B3 C31 H31 106.4 . . ? C33 C32 C31 112.88(19) . . ? C33 C32 H32A 109.0 . . ? C31 C32 H32A 109.0 . . ? C33 C32 H32B 109.0 . . ? C31 C32 H32B 109.0 . . ? H32A C32 H32B 107.8 . . ? C34 C33 C32 111.3(2) . . ? C34 C33 H33A 109.4 . . ? C32 C33 H33A 109.4 . . ? C34 C33 H33B 109.4 . . ? C32 C33 H33B 109.4 . . ? H33A C33 H33B 108.0 . . ? C35 C34 C33 111.34(19) . . ? C35 C34 H34A 109.4 . . ? C33 C34 H34A 109.4 . . ? C35 C34 H34B 109.4 . . ? C33 C34 H34B 109.4 . . ? H34A C34 H34B 108.0 . . ? C34 C35 C36 111.6(2) . . ? C34 C35 H35A 109.3 . . ? C36 C35 H35A 109.3 . . ? C34 C35 H35B 109.3 . . ? C36 C35 H35B 109.3 . . ? H35A C35 H35B 108.0 . . ? C35 C36 C31 112.8(2) . . ? C35 C36 H36A 109.0 . . ? C31 C36 H36A 109.0 . . ? C35 C36 H36B 109.0 . . ? C31 C36 H36B 109.0 . . ? H36A C36 H36B 107.8 . . ? C42 C37 C38 109.43(16) . . ? C42 C37 B4 111.77(16) . . ? C38 C37 B4 114.99(17) . . ? C42 C37 H37 106.7 . . ? C38 C37 H37 106.7 . . ? B4 C37 H37 106.7 . . ? C39 C38 C37 112.12(18) . . ? C39 C38 H38A 109.2 . . ? C37 C38 H38A 109.2 . . ? C39 C38 H38B 109.2 . . ? C37 C38 H38B 109.2 . . ? H38A C38 H38B 107.9 . . ? C40 C39 C38 111.24(17) . . ? C40 C39 H39A 109.4 . . ? C38 C39 H39A 109.4 . . ? C40 C39 H39B 109.4 . . ? C38 C39 H39B 109.4 . . ? H39A C39 H39B 108.0 . . ? C39 C40 C41 111.51(18) . . ? C39 C40 H40A 109.3 . . ? C41 C40 H40A 109.3 . . ? C39 C40 H40B 109.3 . . ? C41 C40 H40B 109.3 . . ? H40A C40 H40B 108.0 . . ? C40 C41 C42 111.42(19) . . ? C40 C41 H41A 109.3 . . ? C42 C41 H41A 109.3 . . ? C40 C41 H41B 109.3 . . ? C42 C41 H41B 109.3 . . ? H41A C41 H41B 108.0 . . ? C41 C42 C37 112.80(17) . . ? C41 C42 H42A 109.0 . . ? C37 C42 H42A 109.0 . . ? C41 C42 H42B 109.0 . . ? C37 C42 H42B 109.0 . . ? H42A C42 H42B 107.8 . . ? C48 C43 C44 109.73(17) . . ? C48 C43 B4 115.09(18) . . ? C44 C43 B4 111.68(16) . . ? C48 C43 H43 106.6 . . ? C44 C43 H43 106.6 . . ? B4 C43 H43 106.6 . . ? C45 C44 C43 112.32(18) . . ? C45 C44 H44A 109.1 . . ? C43 C44 H44A 109.1 . . ? C45 C44 H44B 109.1 . . ? C43 C44 H44B 109.1 . . ? H44A C44 H44B 107.9 . . ? C46 C45 C44 111.2(2) . . ? C46 C45 H45A 109.4 . . ? C44 C45 H45A 109.4 . . ? C46 C45 H45B 109.4 . . ? C44 C45 H45B 109.4 . . ? H45A C45 H45B 108.0 . . ? C47 C46 C45 111.0(2) . . ? C47 C46 H46A 109.4 . . ? C45 C46 H46A 109.4 . . ? C47 C46 H46B 109.4 . . ? C45 C46 H46B 109.4 . . ? H46A C46 H46B 108.0 . . ? C46 C47 C48 110.87(19) . . ? C46 C47 H47A 109.5 . . ? C48 C47 H47A 109.5 . . ? C46 C47 H47B 109.5 . . ? C48 C47 H47B 109.5 . . ? H47A C47 H47B 108.1 . . ? C43 C48 C47 112.81(19) . . ? C43 C48 H48A 109.0 . . ? C47 C48 H48A 109.0 . . ? C43 C48 H48B 109.0 . . ? C47 C48 H48B 109.0 . . ? H48A C48 H48B 107.8 . . ? B1 O1 B2 170.31(17) . . ? B4 O2 B3 178.8(2) . . ? _diffrn_measured_fraction_theta_max 0.933 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.264 _refine_diff_density_min -0.179 _refine_diff_density_rms 0.044 data_sw100894 _database_code_depnum_ccdc_archive 'CCDC 807113' _publ_section_references ; Bruker (2006). SAINT. Version 7.23A. Bruker AXS inc., Madison, Wisconsin, USA. Bruker (1999). SMART. Version 5.054. Bruker AXS Inc., Madison, Wisconsin, USA. Sheldrick, G.M. (2008). Acta Cryst. A64, 112-122. Sheldrick, G.M. (2008). SADABS 2008. Bruker AXS Inc., Madison, Wisconsin, USA. ; _publ_section_exptl_refinement ; Hydrogen atoms were included in calculated positions and refined using a riding model. The structure contains voids that were found to contain only negligible electron densities. ; _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety 'C32 H36 B N O2' _chemical_formula_sum 'C32 H36 B N O2' _exptl_crystal_recrystallization_method hexane _chemical_melting_point ? _exptl_crystal_description Rod _exptl_crystal_colour Colourless _diffrn_ambient_temperature 213(1) _chemical_formula_weight 477.43 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 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' _symmetry_int_tables_number 15 _chemical_absolute_configuration ? 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' '-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 22.194(4) _cell_length_b 7.8827(13) _cell_length_c 32.456(6) _cell_angle_alpha 90.00 _cell_angle_beta 100.937(5) _cell_angle_gamma 90.00 _cell_volume 5575.0(17) _cell_formula_units_Z 8 _cell_measurement_temperature 213(1) _cell_measurement_reflns_used 5986 _cell_measurement_theta_min 2.56 _cell_measurement_theta_max 27.82 _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.138 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2048 _exptl_absorpt_coefficient_mu 0.069 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9663 _exptl_absorpt_correction_T_max 0.9931 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2008)' _exptl_special_details ; Crystal decay was monitored by repeating the initial 50 frames at the end of the data collection and analyzing duplicate reflections ; _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_source_type K760 _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker AXS SMART1000/P4' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 18597 _diffrn_reflns_av_R_equivalents 0.0493 _diffrn_reflns_av_sigmaI/netI 0.0639 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_h_max 28 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -40 _diffrn_reflns_limit_l_max 42 _diffrn_reflns_theta_min 1.28 _diffrn_reflns_theta_max 27.50 _reflns_number_total 6208 _reflns_number_gt 3342 _reflns_threshold_expression 'I > 2\s(I)' _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL (Sheldrick, 2008)' _computing_publication_material 'Bruker SHELXTL (Sheldrick, 2008)' _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^)+(0.0729P)^2^+4.3722P] 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 6208 _refine_ls_number_parameters 332 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1245 _refine_ls_R_factor_gt 0.0625 _refine_ls_wR_factor_ref 0.1886 _refine_ls_wR_factor_gt 0.1511 _refine_ls_goodness_of_fit_ref 1.072 _refine_ls_restrained_S_all 1.072 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group B1 B 0.11799(13) 0.8373(4) 0.08926(9) 0.0369(7) Uani 1 1 d . . . O1 O 0.16440(7) 0.7368(2) 0.11063(5) 0.0392(4) Uani 1 1 d . . . N1 N 0.31038(12) 0.6941(3) 0.21425(8) 0.0635(7) Uani 1 1 d . . . H1 H 0.3333 0.7756 0.2267 0.076 Uiso 1 1 calc R . . O2 O 0.36569(14) 0.0291(3) 0.26449(7) 0.0942(9) Uani 1 1 d . . . C1 C 0.22320(11) 0.7171(3) 0.10274(8) 0.0365(6) Uani 1 1 d . . . C2 C 0.27085(12) 0.7085(3) 0.13744(8) 0.0410(6) Uani 1 1 d . . . C3 C 0.32914(12) 0.6760(4) 0.12946(10) 0.0514(7) Uani 1 1 d . . . H3 H 0.3625 0.6703 0.1521 0.062 Uiso 1 1 calc R . . C4 C 0.33952(13) 0.6520(4) 0.08931(10) 0.0531(8) Uani 1 1 d . . . H4 H 0.3794 0.6293 0.0849 0.064 Uiso 1 1 calc R . . C5 C 0.29142(12) 0.6615(4) 0.05579(9) 0.0489(7) Uani 1 1 d . . . H5 H 0.2983 0.6460 0.0283 0.059 Uiso 1 1 calc R . . C6 C 0.23293(12) 0.6939(3) 0.06258(8) 0.0406(6) Uani 1 1 d . . . H6 H 0.1999 0.7000 0.0398 0.049 Uiso 1 1 calc R . . C7 C 0.25893(14) 0.7360(4) 0.18136(9) 0.0566(8) Uani 1 1 d . . . H7A H 0.2481 0.8553 0.1843 0.068 Uiso 1 1 calc R . . H7B H 0.2236 0.6670 0.1850 0.068 Uiso 1 1 calc R . . C8 C 0.32430(13) 0.5281(4) 0.22659(8) 0.0489(7) Uani 1 1 d . . . C9 C 0.37717(18) 0.4938(4) 0.25492(11) 0.0810(12) Uani 1 1 d . . . H9 H 0.4035 0.5837 0.2654 0.097 Uiso 1 1 calc R . . C10 C 0.3926(2) 0.3305(5) 0.26847(12) 0.0930(14) Uani 1 1 d . . . H10 H 0.4290 0.3104 0.2880 0.112 Uiso 1 1 calc R . . C11 C 0.35443(17) 0.1968(4) 0.25336(9) 0.0624(9) Uani 1 1 d . . . C12 C 0.30338(14) 0.2288(4) 0.22457(9) 0.0571(8) Uani 1 1 d . . . H12 H 0.2777 0.1384 0.2135 0.069 Uiso 1 1 calc R . . C13 C 0.28815(13) 0.3917(4) 0.21109(9) 0.0555(8) Uani 1 1 d . . . H13 H 0.2524 0.4102 0.1909 0.067 Uiso 1 1 calc R . . C14 C 0.4133(3) -0.0021(6) 0.29942(16) 0.168(3) Uani 1 1 d . . . H14A H 0.4527 0.0176 0.2915 0.252 Uiso 1 1 calc R . . H14B H 0.4111 -0.1188 0.3085 0.252 Uiso 1 1 calc R . . H14C H 0.4088 0.0736 0.3222 0.252 Uiso 1 1 calc R . . C15 C 0.05390(11) 0.7884(3) 0.10052(8) 0.0384(6) Uani 1 1 d . . . C16 C 0.03058(11) 0.6227(3) 0.09317(9) 0.0431(7) Uani 1 1 d . . . C17 C -0.02267(12) 0.5760(4) 0.10657(9) 0.0513(7) Uani 1 1 d . . . H17 H -0.0380 0.4656 0.1008 0.062 Uiso 1 1 calc R . . C18 C -0.05427(12) 0.6862(4) 0.12826(10) 0.0541(8) Uani 1 1 d . . . C19 C -0.03172(12) 0.8494(4) 0.13476(9) 0.0511(7) Uani 1 1 d . . . H19 H -0.0527 0.9267 0.1490 0.061 Uiso 1 1 calc R . . C20 C 0.02084(11) 0.9039(3) 0.12102(8) 0.0410(6) Uani 1 1 d . . . C21 C 0.06277(14) 0.4926(4) 0.07085(10) 0.0571(8) Uani 1 1 d . . . H21A H 0.0945 0.4370 0.0910 0.086 Uiso 1 1 calc R . . H21B H 0.0811 0.5484 0.0496 0.086 Uiso 1 1 calc R . . H21C H 0.0333 0.4089 0.0576 0.086 Uiso 1 1 calc R . . C22 C -0.11063(15) 0.6311(6) 0.14436(12) 0.0841(12) Uani 1 1 d . . . H22A H -0.0986 0.5860 0.1725 0.126 Uiso 1 1 calc R . . H22B H -0.1320 0.5442 0.1261 0.126 Uiso 1 1 calc R . . H22C H -0.1375 0.7278 0.1448 0.126 Uiso 1 1 calc R . . C23 C 0.04232(14) 1.0834(4) 0.12968(10) 0.0583(8) Uani 1 1 d . . . H23A H 0.0101 1.1492 0.1385 0.087 Uiso 1 1 calc R . . H23B H 0.0523 1.1326 0.1044 0.087 Uiso 1 1 calc R . . H23C H 0.0785 1.0841 0.1518 0.087 Uiso 1 1 calc R . . C24 C 0.13035(10) 0.9825(3) 0.05854(8) 0.0352(6) Uani 1 1 d . . . C25 C 0.09922(10) 0.9879(3) 0.01645(8) 0.0362(6) Uani 1 1 d . . . C26 C 0.11056(11) 1.1180(3) -0.00981(8) 0.0409(6) Uani 1 1 d . . . H26 H 0.0889 1.1199 -0.0377 0.049 Uiso 1 1 calc R . . C27 C 0.15299(11) 1.2460(3) 0.00376(9) 0.0411(6) Uani 1 1 d . . . C28 C 0.18286(11) 1.2410(3) 0.04540(9) 0.0426(7) Uani 1 1 d . . . H28 H 0.2113 1.3269 0.0554 0.051 Uiso 1 1 calc R . . C29 C 0.17249(11) 1.1145(3) 0.07280(8) 0.0387(6) Uani 1 1 d . . . C30 C 0.05598(12) 0.8480(3) -0.00235(9) 0.0458(7) Uani 1 1 d . . . H30A H 0.0317 0.8863 -0.0288 0.069 Uiso 1 1 calc R . . H30B H 0.0290 0.8192 0.0169 0.069 Uiso 1 1 calc R . . H30C H 0.0795 0.7488 -0.0072 0.069 Uiso 1 1 calc R . . C31 C 0.16466(15) 1.3856(4) -0.02552(10) 0.0590(8) Uani 1 1 d . . . H31A H 0.1317 1.4682 -0.0284 0.088 Uiso 1 1 calc R . . H31B H 0.1664 1.3379 -0.0528 0.088 Uiso 1 1 calc R . . H31C H 0.2034 1.4406 -0.0142 0.088 Uiso 1 1 calc R . . C32 C 0.20661(14) 1.1245(4) 0.11769(9) 0.0558(8) Uani 1 1 d . . . H32A H 0.2464 1.0708 0.1200 0.084 Uiso 1 1 calc R . . H32B H 0.1832 1.0666 0.1359 0.084 Uiso 1 1 calc R . . H32C H 0.2121 1.2425 0.1261 0.084 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 B1 0.0382(15) 0.0302(16) 0.0397(16) -0.0054(13) 0.0009(12) 0.0026(13) O1 0.0346(9) 0.0349(10) 0.0469(10) 0.0039(8) 0.0051(8) 0.0042(8) N1 0.0781(17) 0.0473(16) 0.0518(15) -0.0059(12) -0.0210(13) 0.0124(13) O2 0.154(2) 0.0451(14) 0.0638(15) 0.0012(11) -0.0303(16) 0.0081(15) C1 0.0360(13) 0.0250(13) 0.0479(16) 0.0031(11) 0.0064(11) 0.0028(10) C2 0.0417(14) 0.0309(14) 0.0469(16) 0.0022(12) -0.0006(12) 0.0057(12) C3 0.0413(15) 0.0470(18) 0.0603(19) 0.0008(14) -0.0047(13) 0.0063(13) C4 0.0380(15) 0.0531(19) 0.068(2) 0.0088(15) 0.0109(14) 0.0097(13) C5 0.0507(16) 0.0453(17) 0.0518(17) 0.0103(14) 0.0127(14) 0.0062(13) C6 0.0421(14) 0.0336(15) 0.0436(16) 0.0046(12) 0.0021(12) 0.0038(12) C7 0.0664(19) 0.0530(19) 0.0445(17) 0.0000(14) -0.0044(14) 0.0226(15) C8 0.0588(17) 0.0465(18) 0.0359(15) -0.0038(13) -0.0048(13) 0.0088(14) C9 0.100(3) 0.048(2) 0.072(2) -0.0044(17) -0.040(2) 0.0013(19) C10 0.116(3) 0.053(2) 0.082(3) -0.0007(19) -0.054(2) 0.011(2) C11 0.096(2) 0.0420(18) 0.0411(17) -0.0012(14) -0.0090(16) 0.0079(17) C12 0.0625(19) 0.054(2) 0.0519(18) -0.0085(15) 0.0029(15) -0.0060(16) C13 0.0518(17) 0.055(2) 0.0530(18) -0.0073(15) -0.0072(14) 0.0052(15) C14 0.271(7) 0.055(3) 0.120(4) 0.007(3) -0.109(5) 0.037(3) C15 0.0361(13) 0.0328(14) 0.0434(15) 0.0028(12) -0.0002(11) 0.0047(11) C16 0.0401(14) 0.0347(15) 0.0529(17) 0.0041(13) 0.0048(12) 0.0018(12) C17 0.0444(15) 0.0482(18) 0.0593(18) 0.0037(15) 0.0049(14) -0.0092(14) C18 0.0385(15) 0.066(2) 0.0570(18) 0.0057(16) 0.0078(13) -0.0014(15) C19 0.0407(15) 0.062(2) 0.0498(17) -0.0009(15) 0.0066(13) 0.0115(14) C20 0.0389(14) 0.0410(16) 0.0402(15) 0.0034(12) 0.0000(11) 0.0080(12) C21 0.0601(18) 0.0337(16) 0.079(2) -0.0084(15) 0.0179(16) -0.0039(14) C22 0.060(2) 0.111(3) 0.087(3) 0.003(2) 0.0284(19) -0.011(2) C23 0.0657(19) 0.0444(18) 0.065(2) -0.0040(15) 0.0120(16) 0.0101(15) C24 0.0295(12) 0.0286(13) 0.0455(14) -0.0028(11) 0.0019(10) 0.0031(10) C25 0.0315(12) 0.0310(14) 0.0448(15) -0.0024(12) 0.0042(11) 0.0030(11) C26 0.0386(13) 0.0387(15) 0.0441(15) -0.0020(13) 0.0042(11) 0.0051(12) C27 0.0376(13) 0.0337(15) 0.0529(17) 0.0037(12) 0.0109(12) 0.0038(11) C28 0.0342(13) 0.0298(14) 0.0617(18) -0.0014(13) 0.0040(12) -0.0020(11) C29 0.0326(13) 0.0308(14) 0.0491(15) 0.0002(12) -0.0013(11) 0.0027(11) C30 0.0454(15) 0.0419(16) 0.0458(16) -0.0041(13) -0.0026(12) -0.0025(12) C31 0.0656(19) 0.0471(18) 0.065(2) 0.0108(15) 0.0146(16) -0.0050(15) C32 0.0559(17) 0.0383(16) 0.0631(19) -0.0014(14) -0.0142(14) -0.0060(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag B1 O1 1.378(3) . ? B1 C24 1.576(4) . ? B1 C15 1.582(4) . ? O1 C1 1.385(3) . ? N1 C8 1.386(4) . ? N1 C7 1.446(3) . ? N1 H1 0.8700 . ? O2 C11 1.381(4) . ? O2 C14 1.417(5) . ? C1 C6 1.373(4) . ? C1 C2 1.393(3) . ? C2 C3 1.391(4) . ? C2 C7 1.514(4) . ? C3 C4 1.379(4) . ? C3 H3 0.9400 . ? C4 C5 1.374(4) . ? C4 H4 0.9400 . ? C5 C6 1.381(4) . ? C5 H5 0.9400 . ? C6 H6 0.9400 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C8 C9 1.374(4) . ? C8 C13 1.378(4) . ? C9 C10 1.382(5) . ? C9 H9 0.9400 . ? C10 C11 1.382(5) . ? C10 H10 0.9400 . ? C11 C12 1.349(4) . ? C12 C13 1.378(4) . ? C12 H12 0.9400 . ? C13 H13 0.9400 . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C14 H14C 0.9700 . ? C15 C16 1.408(4) . ? C15 C20 1.413(4) . ? C16 C17 1.385(4) . ? C16 C21 1.511(4) . ? C17 C18 1.389(4) . ? C17 H17 0.9400 . ? C18 C19 1.382(4) . ? C18 C22 1.508(4) . ? C19 C20 1.393(4) . ? C19 H19 0.9400 . ? C20 C23 1.502(4) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C21 H21C 0.9700 . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C22 H22C 0.9700 . ? C23 H23A 0.9700 . ? C23 H23B 0.9700 . ? C23 H23C 0.9700 . ? C24 C25 1.410(3) . ? C24 C29 1.417(3) . ? C25 C26 1.387(4) . ? C25 C30 1.513(3) . ? C26 C27 1.393(4) . ? C26 H26 0.9400 . ? C27 C28 1.388(4) . ? C27 C31 1.508(4) . ? C28 C29 1.384(4) . ? C28 H28 0.9400 . ? C29 C32 1.511(4) . ? C30 H30A 0.9700 . ? C30 H30B 0.9700 . ? C30 H30C 0.9700 . ? C31 H31A 0.9700 . ? C31 H31B 0.9700 . ? C31 H31C 0.9700 . ? C32 H32A 0.9700 . ? C32 H32B 0.9700 . ? C32 H32C 0.9700 . ? 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 O1 B1 C24 122.2(2) . . ? O1 B1 C15 111.2(2) . . ? C24 B1 C15 126.6(2) . . ? B1 O1 C1 127.7(2) . . ? C8 N1 C7 122.1(3) . . ? C8 N1 H1 119.0 . . ? C7 N1 H1 119.0 . . ? C11 O2 C14 116.5(3) . . ? C6 C1 O1 120.9(2) . . ? C6 C1 C2 121.9(2) . . ? O1 C1 C2 116.9(2) . . ? C3 C2 C1 116.7(3) . . ? C3 C2 C7 122.5(2) . . ? C1 C2 C7 120.9(2) . . ? C4 C3 C2 122.0(3) . . ? C4 C3 H3 119.0 . . ? C2 C3 H3 119.0 . . ? C5 C4 C3 119.8(3) . . ? C5 C4 H4 120.1 . . ? C3 C4 H4 120.1 . . ? C4 C5 C6 119.8(3) . . ? C4 C5 H5 120.1 . . ? C6 C5 H5 120.1 . . ? C1 C6 C5 119.9(2) . . ? C1 C6 H6 120.1 . . ? C5 C6 H6 120.1 . . ? N1 C7 C2 114.1(2) . . ? N1 C7 H7A 108.7 . . ? C2 C7 H7A 108.7 . . ? N1 C7 H7B 108.7 . . ? C2 C7 H7B 108.7 . . ? H7A C7 H7B 107.6 . . ? C9 C8 C13 117.1(3) . . ? C9 C8 N1 119.6(3) . . ? C13 C8 N1 123.3(3) . . ? C8 C9 C10 121.6(3) . . ? C8 C9 H9 119.2 . . ? C10 C9 H9 119.2 . . ? C11 C10 C9 120.0(3) . . ? C11 C10 H10 120.0 . . ? C9 C10 H10 120.0 . . ? C12 C11 O2 116.5(3) . . ? C12 C11 C10 118.7(3) . . ? O2 C11 C10 124.7(3) . . ? C11 C12 C13 121.1(3) . . ? C11 C12 H12 119.4 . . ? C13 C12 H12 119.4 . . ? C8 C13 C12 121.4(3) . . ? C8 C13 H13 119.3 . . ? C12 C13 H13 119.3 . . ? O2 C14 H14A 109.5 . . ? O2 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? O2 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C16 C15 C20 118.1(2) . . ? C16 C15 B1 120.3(2) . . ? C20 C15 B1 121.4(2) . . ? C17 C16 C15 120.1(3) . . ? C17 C16 C21 118.6(3) . . ? C15 C16 C21 121.2(2) . . ? C16 C17 C18 122.4(3) . . ? C16 C17 H17 118.8 . . ? C18 C17 H17 118.8 . . ? C19 C18 C17 117.2(3) . . ? C19 C18 C22 121.0(3) . . ? C17 C18 C22 121.8(3) . . ? C18 C19 C20 122.6(3) . . ? C18 C19 H19 118.7 . . ? C20 C19 H19 118.7 . . ? C19 C20 C15 119.5(3) . . ? C19 C20 C23 119.1(3) . . ? C15 C20 C23 121.4(2) . . ? C16 C21 H21A 109.5 . . ? C16 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C16 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C18 C22 H22A 109.5 . . ? C18 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C18 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C20 C23 H23A 109.5 . . ? C20 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C20 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C25 C24 C29 117.8(2) . . ? C25 C24 B1 121.5(2) . . ? C29 C24 B1 120.7(2) . . ? C26 C25 C24 120.4(2) . . ? C26 C25 C30 117.8(2) . . ? C24 C25 C30 121.7(2) . . ? C25 C26 C27 122.1(2) . . ? C25 C26 H26 118.9 . . ? C27 C26 H26 118.9 . . ? C28 C27 C26 117.2(2) . . ? C28 C27 C31 121.8(2) . . ? C26 C27 C31 121.1(3) . . ? C29 C28 C27 122.6(2) . . ? C29 C28 H28 118.7 . . ? C27 C28 H28 118.7 . . ? C28 C29 C24 119.9(2) . . ? C28 C29 C32 117.9(2) . . ? C24 C29 C32 122.2(2) . . ? C25 C30 H30A 109.5 . . ? C25 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? C25 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? C27 C31 H31A 109.5 . . ? C27 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? C27 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? C29 C32 H32A 109.5 . . ? C29 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C29 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.968 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.331 _refine_diff_density_min -0.175 _refine_diff_density_rms 0.048 data_sw080135 _database_code_depnum_ccdc_archive 'CCDC 807114' _publ_section_references ; Bruker (2006). SAINT. Version 7.23A. Bruker AXS Inc., Madison, Wisconsin, USA. Bruker (1999). SMART. Version 5.054. Bruker AXS Inc., Madison, Wisconsin, USA. Sheldrick, G.M. (2008). SHELXTL. Acta Cryst. A64, 112-122. Sheldrick, G.M. (2004). SADABS 2004. Bruker AXS Inc., Madison, Wisconsin, USA. ; _publ_section_exptl_refinement ; The structure was refined using merged Fridel pairs because the structure contains only light atoms. ; _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C27 H36 B N O' _chemical_formula_sum 'C27 H36 B N O' _chemical_formula_weight 401.38 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_space_group_name_Hall 'P 2ac 2ab ' _symmetry_int_tables_number 19 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 8.9551(13) _cell_length_b 15.564(2) _cell_length_c 16.659(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2321.8(6) _cell_formula_units_Z 4 _cell_measurement_temperature 173(1) _cell_measurement_reflns_used 5778 _cell_measurement_theta_min 2.2745 _cell_measurement_theta_max 28.0755 _exptl_crystal_description Parallelpiped _exptl_crystal_colour Orange _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.33 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.148 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 872 _exptl_absorpt_coefficient_mu 0.067 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9638 _exptl_absorpt_correction_T_max 0.9784 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2004)' _exptl_special_details ; Crystal decay was monitored by repeating the initial 50 frames at the end of the data collection and analyzing duplicate reflections. ; _diffrn_ambient_temperature 173(1) _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_source_type K760 _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker AXS SMART1000/P4' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 16167 _diffrn_reflns_av_R_equivalents 0.0253 _diffrn_reflns_av_sigmaI/netI 0.0172 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.79 _diffrn_reflns_theta_max 27.49 _reflns_number_total 2990 _reflns_number_gt 2739 _reflns_threshold_expression 'I > 2\s(I)' _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0468P)^2^+0.3957P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2990 _refine_ls_number_parameters 415 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0382 _refine_ls_R_factor_gt 0.0322 _refine_ls_wR_factor_ref 0.0872 _refine_ls_wR_factor_gt 0.0796 _refine_ls_goodness_of_fit_ref 1.076 _refine_ls_restrained_S_all 1.076 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group B1 B 0.7479(2) 0.61088(11) 0.28229(10) 0.0229(3) Uani 1 1 d . . . N1 N 0.59302(15) 0.64358(8) 0.23801(7) 0.0222(3) Uani 1 1 d . . . O1 O 0.68860(13) 0.55429(7) 0.34863(7) 0.0266(3) Uani 1 1 d . . . C1 C 0.5874(2) 0.58840(10) 0.39774(10) 0.0264(3) Uani 1 1 d . . . C2 C 0.5780(2) 0.56152(13) 0.47800(11) 0.0349(4) Uani 1 1 d . . . C3 C 0.4710(3) 0.59696(14) 0.52743(11) 0.0404(5) Uani 1 1 d . . . C4 C 0.3680(2) 0.65697(13) 0.49927(11) 0.0394(4) Uani 1 1 d . . . C5 C 0.3722(2) 0.68204(12) 0.41984(11) 0.0319(4) Uani 1 1 d . . . C6 C 0.48296(19) 0.64866(11) 0.36866(9) 0.0252(3) Uani 1 1 d . . . C7 C 0.48131(19) 0.66402(10) 0.28367(10) 0.0245(3) Uani 1 1 d . . . C8 C 0.57274(18) 0.64341(10) 0.15108(9) 0.0229(3) Uani 1 1 d . . . C9 C 0.5756(2) 0.72024(11) 0.10742(10) 0.0278(3) Uani 1 1 d . . . C10 C 0.5735(2) 0.71347(12) 0.02358(10) 0.0360(4) Uani 1 1 d . . . C11 C 0.5651(3) 0.63459(13) -0.01389(10) 0.0380(4) Uani 1 1 d . . . C12 C 0.5510(2) 0.56006(12) 0.03108(10) 0.0324(4) Uani 1 1 d . . . C13 C 0.55255(18) 0.56281(10) 0.11464(10) 0.0254(3) Uani 1 1 d . . . C14 C 0.5668(2) 0.80904(11) 0.14555(11) 0.0313(4) Uani 1 1 d . . . C15 C 0.6718(3) 0.87473(14) 0.10742(14) 0.0466(5) Uani 1 1 d . . . C16 C 0.4049(3) 0.84083(14) 0.14061(15) 0.0436(5) Uani 1 1 d . . . C17 C 0.5144(2) 0.48295(11) 0.16356(11) 0.0281(3) Uani 1 1 d . . . C18 C 0.3442(2) 0.47824(15) 0.17294(15) 0.0422(5) Uani 1 1 d . . . C19 C 0.5737(3) 0.39926(12) 0.12828(13) 0.0403(5) Uani 1 1 d . . . C20 C 0.86164(18) 0.55678(11) 0.22751(10) 0.0267(3) Uani 1 1 d . . . C21 C 0.9734(2) 0.51505(12) 0.28640(12) 0.0315(4) Uani 1 1 d . . . C22 C 1.0537(2) 0.57833(12) 0.34266(11) 0.0333(4) Uani 1 1 d . . . C23 C 0.9558(2) 0.65029(12) 0.37835(10) 0.0305(4) Uani 1 1 d . . . C24 C 0.9382(2) 0.61327(13) 0.16290(10) 0.0325(4) Uani 1 1 d . . . C25 C 1.0111(2) 0.69612(14) 0.19449(11) 0.0372(4) Uani 1 1 d . . . C26 C 0.9143(2) 0.74607(12) 0.25461(11) 0.0337(4) Uani 1 1 d . . . C27 C 0.84101(19) 0.69040(11) 0.31999(9) 0.0259(3) Uani 1 1 d . . . H2 H 0.649(3) 0.5173(15) 0.4974(14) 0.046(6) Uiso 1 1 d . . . H3 H 0.473(3) 0.5786(15) 0.5823(14) 0.046(6) Uiso 1 1 d . . . H4 H 0.296(3) 0.6806(14) 0.5323(13) 0.044(6) Uiso 1 1 d . . . H5 H 0.299(3) 0.7223(14) 0.3975(13) 0.039(6) Uiso 1 1 d . . . H7 H 0.390(2) 0.6839(13) 0.2597(11) 0.029(5) Uiso 1 1 d . . . H10 H 0.579(2) 0.7649(14) -0.0096(14) 0.037(6) Uiso 1 1 d . . . H11 H 0.568(3) 0.6299(14) -0.0714(13) 0.040(6) Uiso 1 1 d . . . H12 H 0.537(3) 0.5059(14) 0.0045(13) 0.038(6) Uiso 1 1 d . . . H14 H 0.593(2) 0.8046(12) 0.2028(12) 0.025(5) Uiso 1 1 d . . . H15A H 0.773(4) 0.852(2) 0.1074(17) 0.070(8) Uiso 1 1 d . . . H15B H 0.668(3) 0.9291(18) 0.1367(15) 0.061(8) Uiso 1 1 d . . . H15C H 0.642(3) 0.8888(15) 0.0520(15) 0.050(7) Uiso 1 1 d . . . H16A H 0.392(3) 0.8966(17) 0.1681(15) 0.056(7) Uiso 1 1 d . . . H16B H 0.379(3) 0.8453(16) 0.0845(15) 0.049(7) Uiso 1 1 d . . . H16C H 0.334(3) 0.7991(16) 0.1683(14) 0.051(7) Uiso 1 1 d . . . H17 H 0.560(2) 0.4896(12) 0.2171(13) 0.029(5) Uiso 1 1 d . . . H18A H 0.304(3) 0.5306(17) 0.2018(16) 0.063(8) Uiso 1 1 d . . . H18B H 0.296(4) 0.4749(18) 0.1200(17) 0.070(8) Uiso 1 1 d . . . H18C H 0.312(3) 0.4271(15) 0.2031(14) 0.047(6) Uiso 1 1 d . . . H19A H 0.525(3) 0.3850(16) 0.0780(16) 0.057(7) Uiso 1 1 d . . . H19B H 0.550(3) 0.3503(15) 0.1647(14) 0.048(6) Uiso 1 1 d . . . H19C H 0.682(4) 0.4010(18) 0.1164(17) 0.068(8) Uiso 1 1 d . . . H20 H 0.812(2) 0.5087(13) 0.1994(13) 0.032(5) Uiso 1 1 d . . . H21A H 0.917(3) 0.4730(13) 0.3217(13) 0.037(5) Uiso 1 1 d . . . H21B H 1.052(2) 0.4816(13) 0.2564(12) 0.036(6) Uiso 1 1 d . . . H22A H 1.097(3) 0.5451(15) 0.3871(15) 0.049(6) Uiso 1 1 d . . . H22B H 1.139(3) 0.6058(14) 0.3155(12) 0.036(5) Uiso 1 1 d . . . H23A H 0.897(3) 0.6236(14) 0.4242(13) 0.042(6) Uiso 1 1 d . . . H23B H 1.019(3) 0.6954(14) 0.4018(13) 0.034(5) Uiso 1 1 d . . . H24A H 1.015(3) 0.5792(14) 0.1343(12) 0.037(6) Uiso 1 1 d . . . H24B H 0.859(3) 0.6276(13) 0.1216(12) 0.036(6) Uiso 1 1 d . . . H25A H 1.112(3) 0.6852(15) 0.2198(13) 0.043(6) Uiso 1 1 d . . . H25B H 1.033(2) 0.7349(13) 0.1478(12) 0.037(6) Uiso 1 1 d . . . H26A H 0.974(3) 0.7927(15) 0.2798(13) 0.044(6) Uiso 1 1 d . . . H26B H 0.832(3) 0.7763(14) 0.2255(13) 0.042(6) Uiso 1 1 d . . . H27 H 0.773(2) 0.7308(13) 0.3536(12) 0.032(5) 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 B1 0.0250(8) 0.0235(8) 0.0203(8) 0.0000(7) -0.0003(7) 0.0006(7) N1 0.0271(6) 0.0205(6) 0.0190(6) -0.0014(5) -0.0012(5) 0.0003(5) O1 0.0291(5) 0.0265(5) 0.0243(5) 0.0039(5) 0.0022(5) -0.0001(5) C1 0.0300(8) 0.0262(7) 0.0229(7) -0.0012(6) 0.0013(7) -0.0066(7) C2 0.0398(9) 0.0396(9) 0.0254(8) 0.0039(7) 0.0002(8) -0.0076(9) C3 0.0485(11) 0.0495(11) 0.0232(8) -0.0004(8) 0.0064(8) -0.0131(9) C4 0.0451(10) 0.0415(10) 0.0316(9) -0.0107(8) 0.0145(9) -0.0104(9) C5 0.0332(9) 0.0297(8) 0.0328(9) -0.0079(7) 0.0081(8) -0.0046(7) C6 0.0288(8) 0.0245(7) 0.0224(7) -0.0033(6) 0.0026(6) -0.0046(6) C7 0.0265(7) 0.0220(7) 0.0251(7) -0.0025(6) 0.0000(7) -0.0005(6) C8 0.0242(7) 0.0255(7) 0.0189(7) -0.0012(6) -0.0012(6) 0.0019(7) C9 0.0318(8) 0.0269(8) 0.0246(8) 0.0008(6) -0.0022(7) 0.0026(7) C10 0.0497(11) 0.0343(9) 0.0240(8) 0.0061(7) -0.0018(8) 0.0050(9) C11 0.0521(11) 0.0434(10) 0.0185(8) -0.0009(7) -0.0023(8) 0.0055(10) C12 0.0408(10) 0.0318(8) 0.0246(8) -0.0083(7) -0.0031(8) 0.0024(8) C13 0.0264(8) 0.0261(8) 0.0237(8) -0.0031(6) -0.0016(6) 0.0028(7) C14 0.0421(10) 0.0239(8) 0.0278(8) 0.0025(6) -0.0056(8) 0.0011(8) C15 0.0606(14) 0.0342(11) 0.0450(12) 0.0109(9) -0.0049(11) -0.0085(10) C16 0.0504(12) 0.0310(9) 0.0494(13) -0.0021(9) -0.0071(10) 0.0123(9) C17 0.0317(8) 0.0257(8) 0.0269(8) -0.0038(7) -0.0005(7) -0.0013(7) C18 0.0350(10) 0.0410(10) 0.0507(13) 0.0006(10) 0.0034(9) -0.0076(9) C19 0.0554(13) 0.0237(8) 0.0419(11) -0.0040(8) 0.0078(10) 0.0006(9) C20 0.0269(7) 0.0284(8) 0.0249(8) -0.0031(7) 0.0005(7) 0.0003(7) C21 0.0288(8) 0.0300(8) 0.0358(9) 0.0024(8) 0.0017(8) 0.0041(7) C22 0.0277(8) 0.0414(10) 0.0307(9) 0.0055(8) -0.0027(8) 0.0029(8) C23 0.0312(8) 0.0358(9) 0.0245(8) -0.0008(7) -0.0054(7) -0.0018(8) C24 0.0304(9) 0.0431(10) 0.0239(8) -0.0001(7) 0.0040(7) 0.0015(8) C25 0.0353(9) 0.0461(10) 0.0302(9) 0.0116(8) 0.0031(8) -0.0080(9) C26 0.0373(9) 0.0282(8) 0.0356(9) 0.0039(7) -0.0032(8) -0.0061(8) C27 0.0280(8) 0.0258(7) 0.0239(7) -0.0018(6) -0.0018(7) -0.0016(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag B1 O1 1.510(2) . ? B1 C20 1.606(2) . ? B1 C27 1.619(2) . ? B1 N1 1.651(2) . ? N1 C7 1.296(2) . ? N1 C8 1.4596(19) . ? O1 C1 1.331(2) . ? C1 C2 1.403(2) . ? C1 C6 1.411(2) . ? C2 C3 1.378(3) . ? C2 H2 0.99(2) . ? C3 C4 1.394(3) . ? C3 H3 0.96(2) . ? C4 C5 1.380(3) . ? C4 H4 0.93(2) . ? C5 C6 1.407(2) . ? C5 H5 0.98(2) . ? C6 C7 1.436(2) . ? C7 H7 0.96(2) . ? C8 C9 1.400(2) . ? C8 C13 1.405(2) . ? C9 C10 1.401(2) . ? C9 C14 1.523(2) . ? C10 C11 1.379(3) . ? C10 H10 0.97(2) . ? C11 C12 1.387(3) . ? C11 H11 0.96(2) . ? C12 C13 1.393(2) . ? C12 H12 0.96(2) . ? C13 C17 1.525(2) . ? C14 C15 1.527(3) . ? C14 C16 1.534(3) . ? C14 H14 0.984(19) . ? C15 H15A 0.97(3) . ? C15 H15B 0.98(3) . ? C15 H15C 0.99(2) . ? C16 H16A 0.99(3) . ? C16 H16B 0.97(3) . ? C16 H16C 1.02(3) . ? C17 C19 1.525(2) . ? C17 C18 1.534(3) . ? C17 H17 0.98(2) . ? C18 H18A 1.01(3) . ? C18 H18B 0.98(3) . ? C18 H18C 0.98(2) . ? C19 H19A 0.97(3) . ? C19 H19B 1.00(2) . ? C19 H19C 0.99(3) . ? C20 C21 1.545(2) . ? C20 C24 1.550(2) . ? C20 H20 0.99(2) . ? C21 C22 1.538(3) . ? C21 H21A 1.01(2) . ? C21 H21B 1.01(2) . ? C22 C23 1.541(3) . ? C22 H22A 0.98(3) . ? C22 H22B 0.99(2) . ? C23 C27 1.547(2) . ? C23 H23A 1.02(2) . ? C23 H23B 0.98(2) . ? C24 C25 1.538(3) . ? C24 H24A 0.99(2) . ? C24 H24B 1.01(2) . ? C25 C26 1.536(3) . ? C25 H25A 1.01(2) . ? C25 H25B 1.00(2) . ? C26 C27 1.539(2) . ? C26 H26A 1.00(2) . ? C26 H26B 1.00(2) . ? C27 H27 1.04(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 O1 B1 C20 109.45(13) . . ? O1 B1 C27 110.07(13) . . ? C20 B1 C27 107.11(14) . . ? O1 B1 N1 102.22(12) . . ? C20 B1 N1 116.14(13) . . ? C27 B1 N1 111.74(13) . . ? C7 N1 C8 119.11(14) . . ? C7 N1 B1 117.50(13) . . ? C8 N1 B1 123.18(12) . . ? C1 O1 B1 117.16(13) . . ? O1 C1 C2 120.51(16) . . ? O1 C1 C6 120.37(14) . . ? C2 C1 C6 119.03(16) . . ? C3 C2 C1 119.47(19) . . ? C3 C2 H2 121.9(14) . . ? C1 C2 H2 118.7(14) . . ? C2 C3 C4 121.80(18) . . ? C2 C3 H3 116.1(15) . . ? C4 C3 H3 122.1(15) . . ? C5 C4 C3 119.60(19) . . ? C5 C4 H4 118.5(14) . . ? C3 C4 H4 121.9(14) . . ? C4 C5 C6 119.72(19) . . ? C4 C5 H5 121.7(13) . . ? C6 C5 H5 118.5(13) . . ? C5 C6 C1 120.32(15) . . ? C5 C6 C7 121.91(17) . . ? C1 C6 C7 117.14(15) . . ? N1 C7 C6 121.98(16) . . ? N1 C7 H7 119.5(11) . . ? C6 C7 H7 118.1(11) . . ? C9 C8 C13 122.72(14) . . ? C9 C8 N1 120.77(14) . . ? C13 C8 N1 116.50(14) . . ? C8 C9 C10 116.97(15) . . ? C8 C9 C14 123.88(14) . . ? C10 C9 C14 118.91(15) . . ? C11 C10 C9 121.26(16) . . ? C11 C10 H10 118.5(13) . . ? C9 C10 H10 120.2(13) . . ? C10 C11 C12 120.33(15) . . ? C10 C11 H11 121.2(13) . . ? C12 C11 H11 118.5(13) . . ? C11 C12 C13 120.89(16) . . ? C11 C12 H12 119.8(13) . . ? C13 C12 H12 119.2(13) . . ? C12 C13 C8 117.42(15) . . ? C12 C13 C17 120.45(15) . . ? C8 C13 C17 121.70(14) . . ? C9 C14 C15 113.69(17) . . ? C9 C14 C16 108.64(16) . . ? C15 C14 C16 110.09(17) . . ? C9 C14 H14 109.1(11) . . ? C15 C14 H14 107.8(12) . . ? C16 C14 H14 107.3(12) . . ? C14 C15 H15A 109.7(18) . . ? C14 C15 H15B 110.5(16) . . ? H15A C15 H15B 110(2) . . ? C14 C15 H15C 111.7(15) . . ? H15A C15 H15C 110(2) . . ? H15B C15 H15C 105(2) . . ? C14 C16 H16A 111.9(16) . . ? C14 C16 H16B 107.7(15) . . ? H16A C16 H16B 111(2) . . ? C14 C16 H16C 111.1(14) . . ? H16A C16 H16C 106(2) . . ? H16B C16 H16C 109(2) . . ? C19 C17 C13 114.35(15) . . ? C19 C17 C18 110.14(18) . . ? C13 C17 C18 108.40(16) . . ? C19 C17 H17 107.2(12) . . ? C13 C17 H17 107.8(11) . . ? C18 C17 H17 108.7(12) . . ? C17 C18 H18A 111.1(16) . . ? C17 C18 H18B 110.2(18) . . ? H18A C18 H18B 108(2) . . ? C17 C18 H18C 112.2(15) . . ? H18A C18 H18C 108.0(19) . . ? H18B C18 H18C 107(2) . . ? C17 C19 H19A 111.7(16) . . ? C17 C19 H19B 110.1(13) . . ? H19A C19 H19B 104.8(19) . . ? C17 C19 H19C 113.2(17) . . ? H19A C19 H19C 106(2) . . ? H19B C19 H19C 111(2) . . ? C21 C20 C24 113.14(14) . . ? C21 C20 B1 105.70(14) . . ? C24 C20 B1 112.20(14) . . ? C21 C20 H20 106.0(12) . . ? C24 C20 H20 107.4(12) . . ? B1 C20 H20 112.3(13) . . ? C22 C21 C20 114.87(15) . . ? C22 C21 H21A 107.0(12) . . ? C20 C21 H21A 108.4(12) . . ? C22 C21 H21B 107.9(12) . . ? C20 C21 H21B 110.8(12) . . ? H21A C21 H21B 107.6(16) . . ? C21 C22 C23 115.76(15) . . ? C21 C22 H22A 107.7(14) . . ? C23 C22 H22A 108.4(14) . . ? C21 C22 H22B 111.1(12) . . ? C23 C22 H22B 107.7(12) . . ? H22A C22 H22B 105.7(19) . . ? C22 C23 C27 115.38(14) . . ? C22 C23 H23A 106.6(13) . . ? C27 C23 H23A 107.1(13) . . ? C22 C23 H23B 110.4(13) . . ? C27 C23 H23B 110.0(12) . . ? H23A C23 H23B 106.9(17) . . ? C25 C24 C20 115.20(15) . . ? C25 C24 H24A 108.5(13) . . ? C20 C24 H24A 109.7(13) . . ? C25 C24 H24B 110.1(12) . . ? C20 C24 H24B 106.7(12) . . ? H24A C24 H24B 106.2(16) . . ? C26 C25 C24 114.07(16) . . ? C26 C25 H25A 108.5(13) . . ? C24 C25 H25A 112.4(13) . . ? C26 C25 H25B 108.0(12) . . ? C24 C25 H25B 108.7(12) . . ? H25A C25 H25B 104.6(18) . . ? C25 C26 C27 114.67(15) . . ? C25 C26 H26A 109.8(13) . . ? C27 C26 H26A 110.0(13) . . ? C25 C26 H26B 109.7(13) . . ? C27 C26 H26B 107.1(13) . . ? H26A C26 H26B 105.1(18) . . ? C26 C27 C23 112.87(15) . . ? C26 C27 B1 112.06(14) . . ? C23 C27 B1 106.13(14) . . ? C26 C27 H27 106.8(11) . . ? C23 C27 H27 107.1(11) . . ? B1 C27 H27 111.8(11) . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.245 _refine_diff_density_min -0.140 _refine_diff_density_rms 0.037 data_sw080138 _database_code_depnum_ccdc_archive 'CCDC 807115' _publ_section_references ; Bruker (2006). SAINT. Version 7.23A. Bruker AXS Inc., Madison, Wisconsin, USA. Bruker (1999). SMART. Version 5.054. Bruker AXS Inc., Madison, Wisconsin, USA. Sheldrick, G.M. (2008). Acta Cryst. A64, 112-122. Sheldrick, G.M. (2004). SADABS 2004. Bruker AXS Inc., Madison, Wisconsin, USA. ; _publ_section_exptl_refinement ; Hydrogen atoms were found in Fourier difference maps and refined using isotropic thermal paramters. ; _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C21 H18 B N O3' _chemical_formula_sum 'C21 H18 B N O3' _chemical_formula_weight 343.17 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 ' _symmetry_int_tables_number 14 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 16.124(6) _cell_length_b 7.653(3) _cell_length_c 14.192(5) _cell_angle_alpha 90.00 _cell_angle_beta 98.931(5) _cell_angle_gamma 90.00 _cell_volume 1730.0(11) _cell_formula_units_Z 4 _cell_measurement_temperature 173(1) _cell_measurement_reflns_used 5733 _cell_measurement_theta_min 2.5575 _cell_measurement_theta_max 28.2325 _exptl_crystal_description Shard _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.45 _exptl_crystal_size_min 0.075 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.318 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 720 _exptl_absorpt_coefficient_mu 0.087 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9537 _exptl_absorpt_correction_T_max 0.9935 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2004)' _exptl_special_details ; Crystal decay was monitored by repeating the initial 50 frames at the end of the data collection and analyzing duplicate reflections. ; _diffrn_ambient_temperature 173(1) _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_source_type K760 _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker AXS SMART1000/P4' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 11611 _diffrn_reflns_av_R_equivalents 0.0308 _diffrn_reflns_av_sigmaI/netI 0.0341 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.28 _diffrn_reflns_theta_max 27.50 _reflns_number_total 3860 _reflns_number_gt 2745 _reflns_threshold_expression 'I > 2\s(I)' _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL (Sheldrick, 2008)' _computing_publication_material 'Bruker SHELXTL (Sheldrick, 2008)' _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^)+(0.0403P)^2^+0.4779P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3860 _refine_ls_number_parameters 307 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0648 _refine_ls_R_factor_gt 0.0380 _refine_ls_wR_factor_ref 0.1045 _refine_ls_wR_factor_gt 0.0862 _refine_ls_goodness_of_fit_ref 1.076 _refine_ls_restrained_S_all 1.076 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group B1 B 0.19127(11) 0.6572(2) 0.72747(11) 0.0293(4) Uani 1 1 d . . . N1 N 0.22712(7) 0.63038(16) 0.62891(8) 0.0250(3) Uani 1 1 d . . . O1 O 0.12841(7) 0.52547(15) 0.73503(7) 0.0378(3) Uani 1 1 d . . . O2 O 0.15753(6) 0.83568(14) 0.72776(7) 0.0327(3) Uani 1 1 d . . . O3 O 0.26084(6) 0.64885(13) 0.80632(7) 0.0298(3) Uani 1 1 d . . . C1 C 0.08866(9) 0.4329(2) 0.66124(10) 0.0301(3) Uani 1 1 d . . . C2 C 0.01998(10) 0.3303(2) 0.67418(12) 0.0382(4) Uani 1 1 d . . . C3 C -0.01974(11) 0.2313(2) 0.59981(13) 0.0395(4) Uani 1 1 d . . . C4 C 0.00725(10) 0.2304(2) 0.51081(13) 0.0363(4) Uani 1 1 d . . . C5 C 0.07507(10) 0.3309(2) 0.49744(11) 0.0312(3) Uani 1 1 d . . . C6 C 0.11696(9) 0.4329(2) 0.57236(10) 0.0267(3) Uani 1 1 d . . . C7 C 0.18972(9) 0.53301(19) 0.56104(10) 0.0254(3) Uani 1 1 d . . . C8 C 0.30539(9) 0.71846(19) 0.61825(9) 0.0251(3) Uani 1 1 d . . . C9 C 0.30334(9) 0.8870(2) 0.58090(10) 0.0288(3) Uani 1 1 d . . . C10 C 0.38061(11) 0.9673(2) 0.57667(12) 0.0374(4) Uani 1 1 d . . . C11 C 0.45530(11) 0.8833(3) 0.60815(12) 0.0427(4) Uani 1 1 d . . . C12 C 0.45499(10) 0.7141(3) 0.64328(11) 0.0385(4) Uani 1 1 d . . . C13 C 0.37999(9) 0.6278(2) 0.64830(10) 0.0300(3) Uani 1 1 d . . . C14 C 0.22309(11) 0.9799(3) 0.54245(13) 0.0372(4) Uani 1 1 d . . . C15 C 0.37990(12) 0.4416(2) 0.68273(13) 0.0391(4) Uani 1 1 d . . . C16 C 0.21509(10) 0.9290(2) 0.78843(10) 0.0304(3) Uani 1 1 d . . . C21 C 0.21764(12) 1.1062(2) 0.80423(12) 0.0400(4) Uani 1 1 d . . . C20 C 0.28515(13) 1.1720(3) 0.86778(12) 0.0455(5) Uani 1 1 d . . . C19 C 0.34652(12) 1.0625(3) 0.91316(12) 0.0433(4) Uani 1 1 d . . . C18 C 0.34381(10) 0.8817(2) 0.89707(11) 0.0349(4) Uani 1 1 d . . . C17 C 0.27698(9) 0.8184(2) 0.83461(10) 0.0287(3) Uani 1 1 d . . . H21 H 0.1740(12) 1.179(3) 0.7713(13) 0.049(5) Uiso 1 1 d . . . H18 H 0.3870(10) 0.802(2) 0.9283(12) 0.037(5) Uiso 1 1 d . . . H20 H 0.2900(12) 1.299(3) 0.8798(13) 0.055(6) Uiso 1 1 d . . . H19 H 0.3929(11) 1.115(2) 0.9566(13) 0.046(5) Uiso 1 1 d . . . H5 H 0.0963(10) 0.333(2) 0.4361(13) 0.041(5) Uiso 1 1 d . . . H4 H -0.0216(11) 0.160(2) 0.4598(12) 0.041(5) Uiso 1 1 d . . . H3 H -0.0664(11) 0.161(2) 0.6097(12) 0.040(5) Uiso 1 1 d . . . H2 H 0.0014(11) 0.332(2) 0.7370(13) 0.047(5) Uiso 1 1 d . . . H7 H 0.2133(9) 0.5248(19) 0.5011(11) 0.026(4) Uiso 1 1 d . . . H12 H 0.5069(12) 0.655(2) 0.6631(12) 0.045(5) Uiso 1 1 d . . . H10 H 0.3803(11) 1.086(3) 0.5501(13) 0.047(5) Uiso 1 1 d . . . H11 H 0.5100(12) 0.938(3) 0.6068(13) 0.053(5) Uiso 1 1 d . . . H14A H 0.1764(14) 0.950(3) 0.5737(16) 0.073(7) Uiso 1 1 d . . . H14B H 0.2046(14) 0.958(3) 0.4731(18) 0.083(7) Uiso 1 1 d . . . H14C H 0.2319(15) 1.105(4) 0.5463(18) 0.096(9) Uiso 1 1 d . . . H15A H 0.3602(12) 0.436(3) 0.7427(14) 0.056(6) Uiso 1 1 d . . . H15B H 0.4361(13) 0.394(3) 0.6917(14) 0.060(6) Uiso 1 1 d . . . H15C H 0.3427(13) 0.361(3) 0.6346(14) 0.060(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 B1 0.0294(9) 0.0358(10) 0.0243(8) 0.0008(7) 0.0089(7) 0.0008(8) N1 0.0236(6) 0.0271(7) 0.0250(6) 0.0023(5) 0.0065(5) 0.0007(5) O1 0.0377(6) 0.0486(7) 0.0295(5) -0.0024(5) 0.0129(5) -0.0124(6) O2 0.0311(6) 0.0397(7) 0.0279(5) -0.0005(4) 0.0071(4) 0.0070(5) O3 0.0337(6) 0.0308(6) 0.0252(5) 0.0007(4) 0.0060(4) 0.0027(5) C1 0.0274(8) 0.0314(8) 0.0321(8) 0.0035(6) 0.0063(6) -0.0003(7) C2 0.0318(9) 0.0458(11) 0.0381(9) 0.0093(7) 0.0089(7) -0.0043(8) C3 0.0296(9) 0.0370(10) 0.0517(10) 0.0108(8) 0.0057(8) -0.0061(8) C4 0.0314(9) 0.0304(9) 0.0455(9) 0.0005(7) 0.0005(7) -0.0032(7) C5 0.0285(8) 0.0298(8) 0.0353(8) 0.0009(6) 0.0044(6) 0.0041(7) C6 0.0237(7) 0.0254(8) 0.0313(7) 0.0034(6) 0.0051(6) 0.0036(6) C7 0.0252(7) 0.0266(8) 0.0250(7) 0.0020(6) 0.0060(6) 0.0049(6) C8 0.0243(7) 0.0298(8) 0.0223(7) -0.0025(6) 0.0067(5) -0.0015(6) C9 0.0320(8) 0.0304(8) 0.0251(7) -0.0006(6) 0.0081(6) -0.0010(7) C10 0.0414(10) 0.0356(10) 0.0367(9) -0.0005(7) 0.0110(7) -0.0087(8) C11 0.0310(9) 0.0580(12) 0.0402(9) -0.0030(8) 0.0088(7) -0.0145(9) C12 0.0257(8) 0.0566(12) 0.0329(8) -0.0005(8) 0.0036(7) 0.0013(8) C13 0.0285(8) 0.0382(9) 0.0240(7) -0.0011(6) 0.0060(6) 0.0032(7) C14 0.0385(10) 0.0354(10) 0.0387(9) 0.0087(7) 0.0094(8) 0.0053(8) C15 0.0388(10) 0.0415(10) 0.0379(9) 0.0062(8) 0.0088(8) 0.0127(9) C16 0.0347(8) 0.0354(9) 0.0237(7) 0.0006(6) 0.0128(6) 0.0024(7) C21 0.0556(11) 0.0350(10) 0.0338(8) 0.0036(7) 0.0206(8) 0.0078(9) C20 0.0706(13) 0.0337(10) 0.0387(9) -0.0046(8) 0.0288(9) -0.0111(10) C19 0.0514(11) 0.0487(11) 0.0338(9) -0.0076(8) 0.0192(8) -0.0185(10) C18 0.0344(9) 0.0457(10) 0.0264(7) -0.0007(7) 0.0105(7) -0.0039(8) C17 0.0338(8) 0.0313(8) 0.0236(7) -0.0003(6) 0.0123(6) -0.0006(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 B1 O1 1.445(2) . ? B1 O3 1.458(2) . ? B1 O2 1.471(2) . ? B1 N1 1.6074(19) . ? N1 C7 1.2907(18) . ? N1 C8 1.4592(18) . ? O1 C1 1.3419(19) . ? O2 C16 1.3657(19) . ? O3 C17 1.3711(19) . ? C1 C2 1.393(2) . ? C1 C6 1.406(2) . ? C2 C3 1.374(2) . ? C2 H2 0.983(19) . ? C3 C4 1.398(2) . ? C3 H3 0.956(18) . ? C4 C5 1.374(2) . ? C4 H4 0.961(17) . ? C5 C6 1.405(2) . ? C5 H5 0.983(18) . ? C6 C7 1.431(2) . ? C7 H7 0.986(15) . ? C8 C9 1.393(2) . ? C8 C13 1.397(2) . ? C9 C10 1.399(2) . ? C9 C14 1.503(2) . ? C10 C11 1.377(3) . ? C10 H10 0.984(19) . ? C11 C12 1.388(3) . ? C11 H11 0.98(2) . ? C12 C13 1.390(2) . ? C12 H12 0.956(18) . ? C13 C15 1.507(2) . ? C14 H14A 0.96(2) . ? C14 H14B 1.00(3) . ? C14 H14C 0.97(3) . ? C15 H15A 0.95(2) . ? C15 H15B 0.97(2) . ? C15 H15C 1.04(2) . ? C16 C21 1.374(2) . ? C16 C17 1.393(2) . ? C21 C20 1.395(3) . ? C21 H21 0.960(19) . ? C20 C19 1.378(3) . ? C20 H20 0.99(2) . ? C19 C18 1.402(3) . ? C19 H19 0.979(18) . ? C18 C17 1.373(2) . ? C18 H18 0.978(17) . ? 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 O1 B1 O3 112.17(13) . . ? O1 B1 O2 112.56(13) . . ? O3 B1 O2 106.22(13) . . ? O1 B1 N1 109.07(12) . . ? O3 B1 N1 108.95(12) . . ? O2 B1 N1 107.71(12) . . ? C7 N1 C8 120.04(12) . . ? C7 N1 B1 122.25(12) . . ? C8 N1 B1 117.70(11) . . ? C1 O1 B1 124.45(12) . . ? C16 O2 B1 105.80(12) . . ? C17 O3 B1 105.77(12) . . ? O1 C1 C2 119.20(14) . . ? O1 C1 C6 121.18(13) . . ? C2 C1 C6 119.57(14) . . ? C3 C2 C1 119.66(15) . . ? C3 C2 H2 122.2(11) . . ? C1 C2 H2 118.1(11) . . ? C2 C3 C4 121.56(16) . . ? C2 C3 H3 118.9(10) . . ? C4 C3 H3 119.5(10) . . ? C5 C4 C3 119.19(16) . . ? C5 C4 H4 120.7(11) . . ? C3 C4 H4 120.1(11) . . ? C4 C5 C6 120.40(15) . . ? C4 C5 H5 121.6(10) . . ? C6 C5 H5 118.0(10) . . ? C5 C6 C1 119.61(14) . . ? C5 C6 C7 121.25(13) . . ? C1 C6 C7 119.11(13) . . ? N1 C7 C6 121.43(13) . . ? N1 C7 H7 118.9(9) . . ? C6 C7 H7 119.7(9) . . ? C9 C8 C13 122.99(14) . . ? C9 C8 N1 119.83(13) . . ? C13 C8 N1 117.17(13) . . ? C8 C9 C10 117.03(14) . . ? C8 C9 C14 122.99(14) . . ? C10 C9 C14 119.94(15) . . ? C11 C10 C9 121.40(16) . . ? C11 C10 H10 120.5(11) . . ? C9 C10 H10 118.1(11) . . ? C10 C11 C12 120.02(16) . . ? C10 C11 H11 122.5(11) . . ? C12 C11 H11 117.5(11) . . ? C11 C12 C13 120.91(16) . . ? C11 C12 H12 119.8(11) . . ? C13 C12 H12 119.2(11) . . ? C12 C13 C8 117.60(15) . . ? C12 C13 C15 120.73(15) . . ? C8 C13 C15 121.65(14) . . ? C9 C14 H14A 114.5(13) . . ? C9 C14 H14B 112.8(13) . . ? H14A C14 H14B 106.2(18) . . ? C9 C14 H14C 109.7(15) . . ? H14A C14 H14C 109(2) . . ? H14B C14 H14C 104.0(19) . . ? C13 C15 H15A 110.5(12) . . ? C13 C15 H15B 110.6(12) . . ? H15A C15 H15B 107.5(16) . . ? C13 C15 H15C 112.4(11) . . ? H15A C15 H15C 108.6(16) . . ? H15B C15 H15C 107.1(16) . . ? O2 C16 C21 128.27(15) . . ? O2 C16 C17 110.22(14) . . ? C21 C16 C17 121.49(15) . . ? C16 C21 C20 117.51(17) . . ? C16 C21 H21 119.5(12) . . ? C20 C21 H21 123.0(11) . . ? C19 C20 C21 120.97(18) . . ? C19 C20 H20 119.1(11) . . ? C21 C20 H20 120.0(11) . . ? C20 C19 C18 121.47(18) . . ? C20 C19 H19 117.7(11) . . ? C18 C19 H19 120.8(11) . . ? C17 C18 C19 117.07(17) . . ? C17 C18 H18 120.3(10) . . ? C19 C18 H18 122.6(10) . . ? O3 C17 C18 128.12(15) . . ? O3 C17 C16 110.37(13) . . ? C18 C17 C16 121.49(15) . . ? _diffrn_measured_fraction_theta_max 0.973 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.196 _refine_diff_density_min -0.192 _refine_diff_density_rms 0.037