data_rh022309_293_final _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C34 H32 B N2 O2' _chemical_formula_weight 511.43 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 P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.0255(5) _cell_length_b 12.1959(7) _cell_length_c 23.8577(14) _cell_angle_alpha 90.00 _cell_angle_beta 100.9030(10) _cell_angle_gamma 90.00 _cell_volume 2578.7(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 4349 _cell_measurement_theta_min 2.30 _cell_measurement_theta_max 24.62 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.317 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1084 _exptl_absorpt_coefficient_mu 0.081 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16274 _diffrn_reflns_av_R_equivalents 0.0309 _diffrn_reflns_av_sigmaI/netI 0.0327 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.88 _diffrn_reflns_theta_max 24.72 _reflns_number_total 4404 _reflns_number_gt 2818 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0485P)^2^+0.3985P] 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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0023(5) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 4404 _refine_ls_number_parameters 355 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0759 _refine_ls_R_factor_gt 0.0374 _refine_ls_wR_factor_ref 0.1073 _refine_ls_wR_factor_gt 0.0905 _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_restrained_S_all 1.037 _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 0.6691(2) 0.32152(17) 0.11008(9) 0.0367(5) Uani 1 1 d . . . O1 O 0.55586(14) 0.24580(10) 0.07807(5) 0.0419(3) Uani 1 1 d . . . O11 O 0.64081(13) 0.42772(10) 0.08295(5) 0.0410(3) Uani 1 1 d . . . N1 N 0.64799(16) 0.32831(12) 0.17342(6) 0.0359(4) Uani 1 1 d . . . N11 N 0.82810(16) 0.28017(12) 0.10941(6) 0.0360(4) Uani 1 1 d . . . C1 C 0.5728(2) 0.25239(15) 0.19775(8) 0.0358(4) Uani 1 1 d . . . C2 C 0.5753(2) 0.24576(16) 0.25769(8) 0.0440(5) Uani 1 1 d . . . H2 H 0.6277 0.2986 0.2817 0.053 Uiso 1 1 calc R . . C3 C 0.5032(2) 0.16448(17) 0.28034(9) 0.0482(5) Uani 1 1 d . . . H3 H 0.5086 0.1629 0.3197 0.058 Uiso 1 1 calc R . . C3A C 0.4193(2) 0.08144(16) 0.24640(8) 0.0440(5) Uani 1 1 d . . . C4 C 0.3488(2) -0.00463(19) 0.26925(10) 0.0563(6) Uani 1 1 d . . . H4 H 0.3546 -0.0084 0.3085 0.068 Uiso 1 1 calc R . . C5 C 0.2704(3) -0.08451(19) 0.23493(11) 0.0635(6) Uani 1 1 d . . . H5 H 0.2258 -0.1420 0.2513 0.076 Uiso 1 1 calc R . . C6 C 0.2580(2) -0.07954(17) 0.17689(11) 0.0578(6) Uani 1 1 d . . . H6 H 0.2036 -0.1334 0.1542 0.069 Uiso 1 1 calc R . . C6A C 0.3263(2) 0.00577(16) 0.15100(9) 0.0467(5) Uani 1 1 d . . . C7 C 0.3173(2) 0.01415(17) 0.09135(9) 0.0530(6) Uani 1 1 d . . . H7 H 0.2598 -0.0366 0.0675 0.064 Uiso 1 1 calc R . . C8 C 0.3908(2) 0.09487(17) 0.06791(9) 0.0489(5) Uani 1 1 d . . . H8 H 0.3820 0.0987 0.0285 0.059 Uiso 1 1 calc R . . C9 C 0.4798(2) 0.17240(15) 0.10287(8) 0.0377(5) Uani 1 1 d . . . C9A C 0.4872(2) 0.17079(14) 0.16194(8) 0.0355(4) Uani 1 1 d . . . C9B C 0.4100(2) 0.08643(15) 0.18626(8) 0.0394(5) Uani 1 1 d . . . C11 C 0.9399(2) 0.34610(15) 0.09733(7) 0.0348(4) Uani 1 1 d . . . C12 C 1.0924(2) 0.31303(16) 0.10221(8) 0.0405(5) Uani 1 1 d . . . H12 H 1.1198 0.2418 0.1136 0.049 Uiso 1 1 calc R . . C13 C 1.1999(2) 0.38378(16) 0.09044(8) 0.0418(5) Uani 1 1 d . . . H13 H 1.2985 0.3588 0.0938 0.050 Uiso 1 1 calc R . . C13A C 1.1668(2) 0.49383(15) 0.07325(7) 0.0362(4) Uani 1 1 d . . . C14 C 1.2753(2) 0.56666(17) 0.06053(8) 0.0451(5) Uani 1 1 d . . . H14 H 1.3742 0.5428 0.0632 0.054 Uiso 1 1 calc R . . C15 C 1.2385(2) 0.67324(17) 0.04415(8) 0.0480(5) Uani 1 1 d . . . H15 H 1.3130 0.7212 0.0371 0.058 Uiso 1 1 calc R . . C16 C 1.0910(2) 0.70869(16) 0.03816(8) 0.0447(5) Uani 1 1 d . . . H16 H 1.0672 0.7805 0.0267 0.054 Uiso 1 1 calc R . . C16A C 0.9758(2) 0.63829(15) 0.04903(7) 0.0366(5) Uani 1 1 d . . . C17 C 0.8224(2) 0.66887(15) 0.04016(8) 0.0418(5) Uani 1 1 d . . . H17 H 0.7947 0.7388 0.0265 0.050 Uiso 1 1 calc R . . C18 C 0.7132(2) 0.59861(15) 0.05113(8) 0.0423(5) Uani 1 1 d . . . H18 H 0.6131 0.6213 0.0452 0.051 Uiso 1 1 calc R . . C19 C 0.7518(2) 0.49286(15) 0.07122(7) 0.0355(4) Uani 1 1 d . . . C19A C 0.9021(2) 0.45620(14) 0.07954(7) 0.0329(4) Uani 1 1 d . . . C19B C 1.0149(2) 0.52955(15) 0.06770(7) 0.0337(4) Uani 1 1 d . . . C20 C 0.7380(2) 0.41242(16) 0.20935(8) 0.0443(5) Uani 1 1 d . . . H20A H 0.8068 0.4455 0.1876 0.053 Uiso 1 1 calc R . . H20B H 0.7986 0.3762 0.2421 0.053 Uiso 1 1 calc R . . C21 C 0.6480(3) 0.50325(18) 0.23091(9) 0.0582(6) Uani 1 1 d . . . H21A H 0.5808 0.4702 0.2534 0.070 Uiso 1 1 calc R . . H21B H 0.7177 0.5500 0.2562 0.070 Uiso 1 1 calc R . . C22 C 0.5583(3) 0.5720(2) 0.18712(11) 0.0825(8) Uani 1 1 d . . . H22A H 0.4839 0.5263 0.1633 0.099 Uiso 1 1 calc R . . H22B H 0.6242 0.6015 0.1631 0.099 Uiso 1 1 calc R . . C23 C 0.4766(3) 0.6675(2) 0.20979(12) 0.0832(8) Uani 1 1 d . . . H23A H 0.4070 0.6393 0.2321 0.125 Uiso 1 1 calc R . . H23B H 0.4225 0.7091 0.1783 0.125 Uiso 1 1 calc R . . H23C H 0.5490 0.7139 0.2332 0.125 Uiso 1 1 calc R . . C24 C 0.8604(2) 0.16582(15) 0.12660(8) 0.0420(5) Uani 1 1 d . . . H24A H 0.7868 0.1416 0.1488 0.050 Uiso 1 1 calc R . . H24B H 0.9591 0.1623 0.1511 0.050 Uiso 1 1 calc R . . C25 C 0.8573(3) 0.08730(16) 0.07667(9) 0.0565(6) Uani 1 1 d . . . H25A H 0.7651 0.0993 0.0490 0.068 Uiso 1 1 calc R . . H25B H 0.9416 0.1039 0.0582 0.068 Uiso 1 1 calc R . . C26 C 0.8656(3) -0.03227(17) 0.09423(12) 0.0673(7) Uani 1 1 d . . . H26A H 0.8900 -0.0755 0.0631 0.081 Uiso 1 1 calc R . . H26B H 0.9475 -0.0411 0.1267 0.081 Uiso 1 1 calc R . . C27 C 0.7239(3) -0.07750(18) 0.10985(10) 0.0671(7) Uani 1 1 d . . . H27A H 0.7031 -0.0396 0.1428 0.101 Uiso 1 1 calc R . . H27B H 0.7370 -0.1542 0.1183 0.101 Uiso 1 1 calc R . . H27C H 0.6411 -0.0676 0.0785 0.101 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 0.0388(13) 0.0325(12) 0.0404(13) 0.0029(10) 0.0119(10) 0.0033(10) O1 0.0470(8) 0.0420(8) 0.0374(7) 0.0019(6) 0.0101(6) -0.0027(7) O11 0.0369(7) 0.0377(8) 0.0516(8) 0.0100(6) 0.0165(6) 0.0045(6) N1 0.0375(9) 0.0313(9) 0.0406(9) -0.0029(7) 0.0116(7) -0.0022(7) N11 0.0406(9) 0.0313(9) 0.0391(9) 0.0049(7) 0.0153(7) 0.0048(7) C1 0.0364(10) 0.0330(11) 0.0399(11) 0.0015(9) 0.0120(8) 0.0057(9) C2 0.0539(13) 0.0410(12) 0.0389(11) -0.0026(9) 0.0137(9) -0.0011(10) C3 0.0554(13) 0.0504(13) 0.0422(12) 0.0056(10) 0.0176(10) 0.0045(11) C3A 0.0411(12) 0.0439(12) 0.0491(13) 0.0101(10) 0.0141(9) 0.0032(10) C4 0.0539(14) 0.0561(15) 0.0624(14) 0.0177(12) 0.0198(11) 0.0004(12) C5 0.0543(14) 0.0538(15) 0.0843(19) 0.0213(14) 0.0177(13) -0.0074(12) C6 0.0443(13) 0.0426(13) 0.0840(18) 0.0088(12) 0.0061(12) -0.0059(10) C6A 0.0401(12) 0.0388(12) 0.0595(14) 0.0054(10) 0.0050(10) 0.0018(10) C7 0.0487(13) 0.0432(13) 0.0628(15) -0.0037(11) -0.0006(11) -0.0068(11) C8 0.0532(13) 0.0482(13) 0.0421(12) -0.0027(10) 0.0004(10) 0.0018(11) C9 0.0369(11) 0.0332(11) 0.0429(12) 0.0032(9) 0.0069(9) 0.0049(9) C9A 0.0344(10) 0.0317(11) 0.0412(11) 0.0011(8) 0.0095(8) 0.0033(8) C9B 0.0322(10) 0.0350(11) 0.0512(12) 0.0062(9) 0.0086(9) 0.0045(9) C11 0.0396(11) 0.0348(11) 0.0313(10) -0.0002(8) 0.0102(8) 0.0053(9) C12 0.0417(12) 0.0393(12) 0.0414(11) 0.0029(9) 0.0106(9) 0.0108(10) C13 0.0349(11) 0.0496(13) 0.0412(11) -0.0005(9) 0.0084(9) 0.0081(9) C13A 0.0348(10) 0.0426(12) 0.0316(10) -0.0028(9) 0.0069(8) 0.0005(9) C14 0.0364(11) 0.0553(14) 0.0434(12) -0.0022(10) 0.0071(9) -0.0046(10) C15 0.0469(13) 0.0487(14) 0.0495(12) -0.0032(10) 0.0122(10) -0.0130(11) C16 0.0544(13) 0.0365(11) 0.0450(12) -0.0019(9) 0.0139(10) -0.0050(10) C16A 0.0445(12) 0.0346(11) 0.0328(10) -0.0041(8) 0.0128(8) 0.0010(9) C17 0.0523(13) 0.0311(11) 0.0457(12) 0.0035(9) 0.0186(10) 0.0093(10) C18 0.0419(12) 0.0386(12) 0.0503(12) 0.0049(9) 0.0188(9) 0.0103(10) C19 0.0387(11) 0.0341(11) 0.0371(11) 0.0007(8) 0.0158(8) 0.0022(9) C19A 0.0385(11) 0.0314(10) 0.0306(10) -0.0005(8) 0.0112(8) 0.0047(8) C19B 0.0386(11) 0.0347(11) 0.0288(10) -0.0034(8) 0.0091(8) 0.0016(9) C20 0.0479(12) 0.0422(12) 0.0447(12) -0.0042(9) 0.0137(9) -0.0058(10) C21 0.0701(15) 0.0446(13) 0.0597(14) -0.0080(11) 0.0119(12) -0.0033(12) C22 0.093(2) 0.083(2) 0.0663(17) -0.0141(15) 0.0023(14) 0.0280(16) C23 0.092(2) 0.0688(18) 0.088(2) -0.0132(15) 0.0144(16) 0.0260(15) C24 0.0473(12) 0.0348(11) 0.0462(12) 0.0063(9) 0.0149(9) 0.0062(9) C25 0.0738(16) 0.0433(13) 0.0586(14) -0.0016(11) 0.0281(12) 0.0074(11) C26 0.0717(17) 0.0420(14) 0.0891(18) -0.0094(12) 0.0177(14) 0.0103(12) C27 0.0854(18) 0.0494(15) 0.0668(16) 0.0009(12) 0.0152(13) 0.0007(13) _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 O11 1.449(2) . ? B1 O1 1.478(2) . ? B1 N11 1.524(2) . ? B1 N1 1.561(2) . ? O1 C9 1.333(2) . ? O11 C19 1.348(2) . ? N1 C1 1.343(2) . ? N1 C20 1.478(2) . ? N11 C11 1.363(2) . ? N11 C24 1.467(2) . ? C1 C2 1.428(3) . ? C1 C9A 1.438(3) . ? C2 C3 1.353(3) . ? C3 C3A 1.422(3) . ? C3A C4 1.391(3) . ? C3A C9B 1.422(3) . ? C4 C5 1.378(3) . ? C5 C6 1.369(3) . ? C6 C6A 1.410(3) . ? C6A C7 1.414(3) . ? C6A C9B 1.417(3) . ? C7 C8 1.365(3) . ? C8 C9 1.407(3) . ? C9 C9A 1.398(2) . ? C9A C9B 1.426(2) . ? C11 C12 1.417(2) . ? C11 C19A 1.430(2) . ? C12 C13 1.367(3) . ? C13 C13A 1.419(3) . ? C13A C14 1.397(2) . ? C13A C19B 1.420(2) . ? C14 C15 1.380(3) . ? C15 C16 1.381(3) . ? C16 C16A 1.410(3) . ? C16A C17 1.410(2) . ? C16A C19B 1.422(3) . ? C17 C18 1.368(3) . ? C18 C19 1.397(2) . ? C19 C19A 1.406(2) . ? C19A C19B 1.424(2) . ? C20 C21 1.519(3) . ? C21 C22 1.460(3) . ? C22 C23 1.530(3) . ? C24 C25 1.525(3) . ? C25 C26 1.515(3) . ? C26 C27 1.503(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 O11 B1 O1 106.35(15) . . ? O11 B1 N11 112.21(15) . . ? O1 B1 N11 110.39(15) . . ? O11 B1 N1 109.97(15) . . ? O1 B1 N1 109.52(14) . . ? N11 B1 N1 108.39(15) . . ? C9 O1 B1 123.66(15) . . ? C19 O11 B1 122.97(14) . . ? C1 N1 C20 119.68(15) . . ? C1 N1 B1 123.10(15) . . ? C20 N1 B1 116.37(14) . . ? C11 N11 C24 120.27(15) . . ? C11 N11 B1 122.91(15) . . ? C24 N11 B1 116.69(14) . . ? N1 C1 C2 123.94(17) . . ? N1 C1 C9A 118.62(16) . . ? C2 C1 C9A 117.42(16) . . ? C3 C2 C1 121.58(19) . . ? C2 C3 C3A 122.58(19) . . ? C4 C3A C3 123.2(2) . . ? C4 C3A C9B 118.9(2) . . ? C3 C3A C9B 117.87(17) . . ? C5 C4 C3A 121.5(2) . . ? C6 C5 C4 120.3(2) . . ? C5 C6 C6A 121.1(2) . . ? C6 C6A C7 123.2(2) . . ? C6 C6A C9B 118.7(2) . . ? C7 C6A C9B 118.05(18) . . ? C8 C7 C6A 121.66(19) . . ? C7 C8 C9 120.59(19) . . ? O1 C9 C9A 121.75(17) . . ? O1 C9 C8 118.18(17) . . ? C9A C9 C8 120.06(17) . . ? C9 C9A C9B 119.10(17) . . ? C9 C9A C1 120.46(16) . . ? C9B C9A C1 120.44(17) . . ? C6A C9B C3A 119.49(17) . . ? C6A C9B C9A 120.42(18) . . ? C3A C9B C9A 120.08(18) . . ? N11 C11 C12 124.12(16) . . ? N11 C11 C19A 118.14(16) . . ? C12 C11 C19A 117.73(16) . . ? C13 C12 C11 121.29(18) . . ? C12 C13 C13A 122.54(18) . . ? C14 C13A C13 123.13(18) . . ? C14 C13A C19B 119.22(17) . . ? C13 C13A C19B 117.63(17) . . ? C15 C14 C13A 121.30(19) . . ? C14 C15 C16 119.99(19) . . ? C15 C16 C16A 121.36(19) . . ? C16 C16A C17 123.26(17) . . ? C16 C16A C19B 118.50(17) . . ? C17 C16A C19B 118.19(17) . . ? C18 C17 C16A 121.86(18) . . ? C17 C18 C19 120.15(18) . . ? O11 C19 C18 117.94(16) . . ? O11 C19 C19A 121.19(16) . . ? C18 C19 C19A 120.86(17) . . ? C19 C19A C19B 118.66(16) . . ? C19 C19A C11 120.69(16) . . ? C19B C19A C11 120.60(16) . . ? C13A C19B C16A 119.58(17) . . ? C13A C19B C19A 120.19(16) . . ? C16A C19B C19A 120.21(16) . . ? N1 C20 C21 115.60(16) . . ? C22 C21 C20 115.87(19) . . ? C21 C22 C23 115.0(2) . . ? N11 C24 C25 113.90(15) . . ? C26 C25 C24 113.31(18) . . ? C27 C26 C25 115.0(2) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 24.72 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.294 _refine_diff_density_min -0.176 _refine_diff_density_rms 0.035