# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Dr Matthias Wagner' _publ_contact_author_email Matthias.Wagner@chemie.uni-frankfurt.de _publ_section_title ; Borafluorene Dimethyl Sulphide Adduct: Product of a Unique Ring-Contraction Reaction and Useful Hydroboration Reagent. ; loop_ _publ_author_name A.Das A.Hubner M.Weber M.Bolte H.-W.Lerner M.Wagner # Attachment '- combinedcifs.cif' data_wa1213 _database_code_depnum_ccdc_archive 'CCDC 837677' #TrackingRef '- combinedcifs.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H15 B S' _chemical_formula_sum 'C14 H15 B S' _chemical_formula_weight 226.13 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/c _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 6.9507(13) _cell_length_b 16.302(3) _cell_length_c 22.288(4) _cell_angle_alpha 90.00 _cell_angle_beta 91.155(14) _cell_angle_gamma 90.00 _cell_volume 2524.9(8) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 4149 _cell_measurement_theta_min 3.3 _cell_measurement_theta_max 24.6 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.190 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 960 _exptl_absorpt_coefficient_mu 0.225 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9460 _exptl_absorpt_correction_T_max 0.9735 _exptl_absorpt_process_details 'MULABS (Spek, 2003; Blessing, 1995)' _exptl_special_details ; ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'STOE IPDS II two-circle-diffractometer' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 16340 _diffrn_reflns_av_R_equivalents 0.1351 _diffrn_reflns_av_sigmaI/netI 0.2331 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 3.30 _diffrn_reflns_theta_max 25.02 _reflns_number_total 4445 _reflns_number_gt 1715 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'X-Area (Stoe & Cie, 2001)' _computing_cell_refinement 'X-Area (Stoe & Cie, 2001)' _computing_data_reduction 'X-Area (Stoe & Cie, 2001)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP (Sheldrick, 2008)' _computing_publication_material ? _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^)+(0.0795P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0098(17) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4445 _refine_ls_number_parameters 300 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.2022 _refine_ls_R_factor_gt 0.0911 _refine_ls_wR_factor_ref 0.2382 _refine_ls_wR_factor_gt 0.1933 _refine_ls_goodness_of_fit_ref 0.889 _refine_ls_restrained_S_all 0.889 _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 0.0540(10) 0.8104(5) 0.7967(4) 0.044(2) Uani 1 1 d D . . H1 H 0.059(9) 0.842(4) 0.845(2) 0.053 Uiso 1 1 d D . . S1 S -0.2229(2) 0.79102(11) 0.77964(9) 0.0453(5) Uani 1 1 d . . . C1 C 0.1627(8) 0.7204(4) 0.7919(4) 0.0429(18) Uani 1 1 d . . . C2 C 0.2842(8) 0.7231(4) 0.7438(4) 0.0404(18) Uani 1 1 d . . . C3 C 0.4043(8) 0.6575(4) 0.7286(4) 0.0430(18) Uani 1 1 d . . . H3 H 0.4838 0.6601 0.6944 0.052 Uiso 1 1 calc R . . C4 C 0.4030(9) 0.5883(5) 0.7652(4) 0.058(2) Uani 1 1 d . . . H4 H 0.4855 0.5435 0.7569 0.069 Uiso 1 1 calc R . . C5 C 0.2834(9) 0.5848(4) 0.8132(4) 0.053(2) Uani 1 1 d . . . H5 H 0.2815 0.5366 0.8372 0.063 Uiso 1 1 calc R . . C6 C 0.1639(9) 0.6506(4) 0.8275(4) 0.0454(19) Uani 1 1 d . . . H6 H 0.0838 0.6475 0.8615 0.054 Uiso 1 1 calc R . . C7 C -0.3050(10) 0.7378(5) 0.8430(4) 0.063(2) Uani 1 1 d . . . H7A H -0.2459 0.7613 0.8794 0.094 Uiso 1 1 calc R . . H7B H -0.2697 0.6798 0.8399 0.094 Uiso 1 1 calc R . . H7C H -0.4453 0.7427 0.8449 0.094 Uiso 1 1 calc R . . C8 C -0.3219(10) 0.8897(5) 0.7953(5) 0.071(3) Uani 1 1 d . . . H8A H -0.4622 0.8853 0.7977 0.107 Uiso 1 1 calc R . . H8B H -0.2890 0.9279 0.7631 0.107 Uiso 1 1 calc R . . H8C H -0.2689 0.9099 0.8335 0.107 Uiso 1 1 calc R . . C11 C 0.1436(8) 0.8569(4) 0.7407(3) 0.0373(17) Uani 1 1 d . . . C12 C 0.2740(8) 0.8047(4) 0.7115(3) 0.0384(17) Uani 1 1 d . . . C13 C 0.3802(8) 0.8299(4) 0.6627(3) 0.0424(18) Uani 1 1 d . . . H13 H 0.4700 0.7941 0.6447 0.051 Uiso 1 1 calc R . . C14 C 0.3518(10) 0.9089(5) 0.6410(4) 0.051(2) Uani 1 1 d . . . H14 H 0.4209 0.9271 0.6072 0.061 Uiso 1 1 calc R . . C15 C 0.2235(9) 0.9616(4) 0.6683(4) 0.0468(19) Uani 1 1 d . . . H15 H 0.2068 1.0159 0.6537 0.056 Uiso 1 1 calc R . . C16 C 0.1200(9) 0.9349(4) 0.7169(4) 0.0417(18) Uani 1 1 d . . . H16 H 0.0300 0.9710 0.7345 0.050 Uiso 1 1 calc R . . B1A B 0.5266(10) 0.8130(6) 0.0097(5) 0.051(2) Uani 1 1 d D . . H1A H 0.523(9) 0.847(4) -0.041(2) 0.062 Uiso 1 1 d D . . S1A S 0.2544(2) 0.80233(13) 0.03216(10) 0.0530(6) Uani 1 1 d . . . C1A C 0.6388(9) 0.8583(4) 0.0628(4) 0.0443(19) Uani 1 1 d . . . C2A C 0.7621(8) 0.8009(4) 0.0914(3) 0.0371(16) Uani 1 1 d . . . C3A C 0.8850(9) 0.8250(5) 0.1396(4) 0.050(2) Uani 1 1 d . . . H3A H 0.9732 0.7868 0.1569 0.060 Uiso 1 1 calc R . . C4A C 0.8768(10) 0.9039(5) 0.1616(4) 0.062(2) Uani 1 1 d . . . H4A H 0.9542 0.9192 0.1954 0.074 Uiso 1 1 calc R . . C5A C 0.7551(11) 0.9614(5) 0.1343(4) 0.065(3) Uani 1 1 d . . . H5A H 0.7520 1.0162 0.1488 0.078 Uiso 1 1 calc R . . C6A C 0.6375(9) 0.9379(4) 0.0856(4) 0.050(2) Uani 1 1 d . . . H6A H 0.5542 0.9775 0.0676 0.060 Uiso 1 1 calc R . . C7A C 0.1593(11) 0.9033(6) 0.0200(6) 0.091(4) Uani 1 1 d . . . H7A1 H 0.1968 0.9230 -0.0196 0.136 Uiso 1 1 calc R . . H7A2 H 0.2105 0.9404 0.0510 0.136 Uiso 1 1 calc R . . H7A3 H 0.0186 0.9016 0.0220 0.136 Uiso 1 1 calc R . . C8A C 0.1470(11) 0.7481(7) -0.0304(5) 0.080(3) Uani 1 1 d . . . H8A1 H 0.0065 0.7522 -0.0287 0.119 Uiso 1 1 calc R . . H8A2 H 0.1850 0.6902 -0.0286 0.119 Uiso 1 1 calc R . . H8A3 H 0.1909 0.7722 -0.0680 0.119 Uiso 1 1 calc R . . C11A C 0.6206(9) 0.7210(4) 0.0133(4) 0.0447(18) Uani 1 1 d . . . C12A C 0.7531(8) 0.7214(4) 0.0630(3) 0.0402(17) Uani 1 1 d . . . C13A C 0.8601(9) 0.6502(4) 0.0765(4) 0.0484(19) Uani 1 1 d . . . H13A H 0.9505 0.6505 0.1091 0.058 Uiso 1 1 calc R . . C14A C 0.8345(11) 0.5811(5) 0.0433(4) 0.059(2) Uani 1 1 d . . . H14A H 0.9066 0.5334 0.0532 0.071 Uiso 1 1 calc R . . C15A C 0.7047(11) 0.5788(6) -0.0053(4) 0.065(2) Uani 1 1 d . . . H15A H 0.6879 0.5300 -0.0281 0.078 Uiso 1 1 calc R . . C16A C 0.5993(10) 0.6498(5) -0.0198(4) 0.053(2) Uani 1 1 d . . . H16A H 0.5116 0.6488 -0.0531 0.064 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 0.036(3) 0.032(4) 0.064(6) 0.002(4) 0.003(4) -0.004(3) S1 0.0402(8) 0.0410(11) 0.0546(13) -0.0030(10) 0.0023(8) -0.0011(7) C1 0.035(3) 0.037(4) 0.057(5) -0.002(4) -0.003(3) -0.009(3) C2 0.029(3) 0.034(4) 0.058(5) -0.007(4) 0.000(3) 0.000(3) C3 0.035(3) 0.032(4) 0.062(5) -0.003(4) -0.005(3) 0.002(3) C4 0.042(4) 0.039(5) 0.091(7) -0.001(5) 0.003(4) 0.002(3) C5 0.044(4) 0.028(4) 0.085(7) 0.015(4) -0.005(4) 0.002(3) C6 0.044(3) 0.043(4) 0.049(5) 0.007(4) -0.002(3) -0.005(3) C7 0.051(4) 0.070(6) 0.068(6) 0.029(5) 0.011(4) -0.003(4) C8 0.045(4) 0.049(5) 0.120(9) -0.012(5) 0.004(5) 0.007(3) C11 0.031(3) 0.029(4) 0.052(5) -0.003(3) -0.001(3) -0.003(3) C12 0.031(3) 0.035(4) 0.050(5) -0.009(4) -0.001(3) -0.003(3) C13 0.037(3) 0.043(4) 0.048(5) -0.005(4) 0.007(3) -0.005(3) C14 0.048(4) 0.049(5) 0.055(6) 0.012(4) -0.003(4) -0.013(3) C15 0.052(4) 0.032(4) 0.057(6) 0.003(4) -0.002(4) -0.006(3) C16 0.042(3) 0.032(4) 0.051(5) -0.009(4) -0.008(4) -0.004(3) B1A 0.036(4) 0.064(6) 0.055(6) 0.006(5) 0.002(4) -0.003(4) S1A 0.0363(8) 0.0631(13) 0.0598(14) 0.0180(11) 0.0024(8) 0.0006(8) C1A 0.040(3) 0.033(4) 0.060(6) 0.006(4) 0.006(3) -0.005(3) C2A 0.030(3) 0.038(4) 0.043(4) 0.005(4) 0.004(3) 0.002(3) C3A 0.043(4) 0.049(5) 0.059(6) 0.003(4) -0.001(4) 0.001(3) C4A 0.057(4) 0.054(5) 0.075(7) -0.013(5) -0.008(4) -0.016(4) C5A 0.072(5) 0.033(4) 0.091(8) -0.013(5) 0.016(5) -0.012(4) C6A 0.044(4) 0.044(5) 0.062(6) -0.005(4) 0.006(4) 0.003(3) C7A 0.046(4) 0.084(7) 0.142(11) 0.050(7) 0.011(5) 0.021(4) C8A 0.055(4) 0.116(8) 0.067(7) 0.001(6) -0.008(4) -0.022(5) C11A 0.040(3) 0.046(4) 0.049(5) 0.001(4) 0.010(3) -0.013(3) C12A 0.037(3) 0.037(4) 0.046(5) -0.004(4) 0.002(3) -0.003(3) C13A 0.043(4) 0.044(4) 0.057(5) 0.003(4) -0.002(3) 0.002(3) C14A 0.061(4) 0.043(5) 0.074(7) -0.010(5) 0.013(5) 0.003(4) C15A 0.064(5) 0.060(6) 0.071(7) -0.017(5) 0.007(5) -0.012(4) C16A 0.049(4) 0.060(5) 0.051(5) 0.002(4) -0.003(4) -0.020(4) _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 C11 1.596(11) . ? B1 C1 1.655(10) . ? B1 S1 1.980(7) . ? B1 H1 1.20(4) . ? S1 C7 1.761(8) . ? S1 C8 1.786(8) . ? C1 C2 1.380(10) . ? C1 C6 1.387(10) . ? C2 C3 1.403(9) . ? C2 C12 1.514(10) . ? C3 C4 1.392(10) . ? C3 H3 0.9500 . ? C4 C5 1.368(12) . ? C4 H4 0.9500 . ? C5 C6 1.397(10) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C11 C16 1.386(9) . ? C11 C12 1.411(9) . ? C12 C13 1.389(10) . ? C13 C14 1.389(10) . ? C13 H13 0.9500 . ? C14 C15 1.387(10) . ? C14 H14 0.9500 . ? C15 C16 1.382(10) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? B1A C1A 1.586(12) . ? B1A C11A 1.638(12) . ? B1A S1A 1.975(8) . ? B1A H1A 1.25(4) . ? S1A C7A 1.792(9) . ? S1A C8A 1.801(9) . ? C1A C6A 1.394(10) . ? C1A C2A 1.413(9) . ? C2A C3A 1.416(9) . ? C2A C12A 1.443(9) . ? C3A C4A 1.378(10) . ? C3A H3A 0.9500 . ? C4A C5A 1.393(11) . ? C4A H4A 0.9500 . ? C5A C6A 1.398(11) . ? C5A H5A 0.9500 . ? C6A H6A 0.9500 . ? C7A H7A1 0.9800 . ? C7A H7A2 0.9800 . ? C7A H7A3 0.9800 . ? C8A H8A1 0.9800 . ? C8A H8A2 0.9800 . ? C8A H8A3 0.9800 . ? C11A C16A 1.383(10) . ? C11A C12A 1.426(10) . ? C12A C13A 1.407(9) . ? C13A C14A 1.358(10) . ? C13A H13A 0.9500 . ? C14A C15A 1.395(12) . ? C14A H14A 0.9500 . ? C15A C16A 1.403(11) . ? C15A H15A 0.9500 . ? C16A H16A 0.9500 . ? 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 C11 B1 C1 100.7(6) . . ? C11 B1 S1 108.6(5) . . ? C1 B1 S1 106.8(4) . . ? C11 B1 H1 120(3) . . ? C1 B1 H1 116(3) . . ? S1 B1 H1 105(3) . . ? C7 S1 C8 98.9(5) . . ? C7 S1 B1 104.8(4) . . ? C8 S1 B1 101.3(4) . . ? C2 C1 C6 118.3(6) . . ? C2 C1 B1 108.0(6) . . ? C6 C1 B1 133.6(7) . . ? C1 C2 C3 122.7(7) . . ? C1 C2 C12 112.0(6) . . ? C3 C2 C12 125.3(7) . . ? C4 C3 C2 117.6(7) . . ? C4 C3 H3 121.2 . . ? C2 C3 H3 121.2 . . ? C5 C4 C3 120.3(7) . . ? C5 C4 H4 119.9 . . ? C3 C4 H4 119.9 . . ? C4 C5 C6 121.3(7) . . ? C4 C5 H5 119.4 . . ? C6 C5 H5 119.4 . . ? C1 C6 C5 119.8(7) . . ? C1 C6 H6 120.1 . . ? C5 C6 H6 120.1 . . ? S1 C7 H7A 109.5 . . ? S1 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? S1 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? S1 C8 H8A 109.5 . . ? S1 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? S1 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C16 C11 C12 116.6(7) . . ? C16 C11 B1 133.5(7) . . ? C12 C11 B1 109.8(6) . . ? C13 C12 C11 122.6(6) . . ? C13 C12 C2 127.7(6) . . ? C11 C12 C2 109.6(6) . . ? C12 C13 C14 118.2(7) . . ? C12 C13 H13 120.9 . . ? C14 C13 H13 120.9 . . ? C15 C14 C13 120.6(7) . . ? C15 C14 H14 119.7 . . ? C13 C14 H14 119.7 . . ? C16 C15 C14 119.9(7) . . ? C16 C15 H15 120.0 . . ? C14 C15 H15 120.0 . . ? C15 C16 C11 121.9(7) . . ? C15 C16 H16 119.0 . . ? C11 C16 H16 119.0 . . ? C1A B1A C11A 101.6(6) . . ? C1A B1A S1A 108.1(6) . . ? C11A B1A S1A 106.8(5) . . ? C1A B1A H1A 118(3) . . ? C11A B1A H1A 117(4) . . ? S1A B1A H1A 105(3) . . ? C7A S1A C8A 100.8(5) . . ? C7A S1A B1A 103.5(4) . . ? C8A S1A B1A 103.4(4) . . ? C6A C1A C2A 117.4(7) . . ? C6A C1A B1A 134.4(7) . . ? C2A C1A B1A 108.2(6) . . ? C1A C2A C3A 120.6(6) . . ? C1A C2A C12A 112.2(6) . . ? C3A C2A C12A 127.1(6) . . ? C4A C3A C2A 120.1(7) . . ? C4A C3A H3A 119.9 . . ? C2A C3A H3A 119.9 . . ? C3A C4A C5A 120.1(7) . . ? C3A C4A H4A 120.0 . . ? C5A C4A H4A 120.0 . . ? C4A C5A C6A 119.7(7) . . ? C4A C5A H5A 120.2 . . ? C6A C5A H5A 120.2 . . ? C1A C6A C5A 122.0(7) . . ? C1A C6A H6A 119.0 . . ? C5A C6A H6A 119.0 . . ? S1A C7A H7A1 109.5 . . ? S1A C7A H7A2 109.5 . . ? H7A1 C7A H7A2 109.5 . . ? S1A C7A H7A3 109.5 . . ? H7A1 C7A H7A3 109.5 . . ? H7A2 C7A H7A3 109.5 . . ? S1A C8A H8A1 109.5 . . ? S1A C8A H8A2 109.5 . . ? H8A1 C8A H8A2 109.5 . . ? S1A C8A H8A3 109.5 . . ? H8A1 C8A H8A3 109.5 . . ? H8A2 C8A H8A3 109.5 . . ? C16A C11A C12A 118.6(7) . . ? C16A C11A B1A 134.8(7) . . ? C12A C11A B1A 106.6(6) . . ? C13A C12A C11A 119.5(6) . . ? C13A C12A C2A 129.0(6) . . ? C11A C12A C2A 111.4(6) . . ? C14A C13A C12A 120.3(7) . . ? C14A C13A H13A 119.9 . . ? C12A C13A H13A 119.9 . . ? C13A C14A C15A 121.4(8) . . ? C13A C14A H14A 119.3 . . ? C15A C14A H14A 119.3 . . ? C14A C15A C16A 118.9(8) . . ? C14A C15A H15A 120.6 . . ? C16A C15A H15A 120.6 . . ? C11A C16A C15A 121.3(7) . . ? C11A C16A H16A 119.4 . . ? C15A C16A H16A 119.4 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C11 B1 S1 C7 178.7(6) . . . . ? C1 B1 S1 C7 70.8(6) . . . . ? C11 B1 S1 C8 -78.9(6) . . . . ? C1 B1 S1 C8 173.3(6) . . . . ? C11 B1 C1 C2 0.9(7) . . . . ? S1 B1 C1 C2 114.3(6) . . . . ? C11 B1 C1 C6 175.7(7) . . . . ? S1 B1 C1 C6 -71.0(9) . . . . ? C6 C1 C2 C3 1.7(10) . . . . ? B1 C1 C2 C3 177.4(6) . . . . ? C6 C1 C2 C12 -176.9(5) . . . . ? B1 C1 C2 C12 -1.2(7) . . . . ? C1 C2 C3 C4 -2.0(9) . . . . ? C12 C2 C3 C4 176.5(6) . . . . ? C2 C3 C4 C5 1.9(10) . . . . ? C3 C4 C5 C6 -1.7(11) . . . . ? C2 C1 C6 C5 -1.3(10) . . . . ? B1 C1 C6 C5 -175.7(7) . . . . ? C4 C5 C6 C1 1.4(11) . . . . ? C1 B1 C11 C16 -179.8(6) . . . . ? S1 B1 C11 C16 68.3(9) . . . . ? C1 B1 C11 C12 -0.3(7) . . . . ? S1 B1 C11 C12 -112.3(5) . . . . ? C16 C11 C12 C13 2.4(9) . . . . ? B1 C11 C12 C13 -177.2(6) . . . . ? C16 C11 C12 C2 179.2(5) . . . . ? B1 C11 C12 C2 -0.4(7) . . . . ? C1 C2 C12 C13 177.6(6) . . . . ? C3 C2 C12 C13 -1.0(10) . . . . ? C1 C2 C12 C11 1.1(7) . . . . ? C3 C2 C12 C11 -177.5(6) . . . . ? C11 C12 C13 C14 -2.0(10) . . . . ? C2 C12 C13 C14 -178.1(6) . . . . ? C12 C13 C14 C15 1.3(10) . . . . ? C13 C14 C15 C16 -1.2(10) . . . . ? C14 C15 C16 C11 1.7(10) . . . . ? C12 C11 C16 C15 -2.3(9) . . . . ? B1 C11 C16 C15 177.2(7) . . . . ? C1A B1A S1A C7A 76.7(7) . . . . ? C11A B1A S1A C7A -174.7(6) . . . . ? C1A B1A S1A C8A -178.5(6) . . . . ? C11A B1A S1A C8A -69.9(6) . . . . ? C11A B1A C1A C6A 178.6(8) . . . . ? S1A B1A C1A C6A -69.2(10) . . . . ? C11A B1A C1A C2A -2.4(8) . . . . ? S1A B1A C1A C2A 109.8(6) . . . . ? C6A C1A C2A C3A -2.7(10) . . . . ? B1A C1A C2A C3A 178.1(6) . . . . ? C6A C1A C2A C12A -179.0(6) . . . . ? B1A C1A C2A C12A 1.8(8) . . . . ? C1A C2A C3A C4A 4.0(11) . . . . ? C12A C2A C3A C4A 179.7(8) . . . . ? C2A C3A C4A C5A -3.5(13) . . . . ? C3A C4A C5A C6A 1.8(13) . . . . ? C2A C1A C6A C5A 1.0(11) . . . . ? B1A C1A C6A C5A 180.0(8) . . . . ? C4A C5A C6A C1A -0.5(12) . . . . ? C1A B1A C11A C16A -177.1(8) . . . . ? S1A B1A C11A C16A 69.7(10) . . . . ? C1A B1A C11A C12A 2.2(8) . . . . ? S1A B1A C11A C12A -111.0(6) . . . . ? C16A C11A C12A C13A 0.8(10) . . . . ? B1A C11A C12A C13A -178.6(6) . . . . ? C16A C11A C12A C2A 178.1(6) . . . . ? B1A C11A C12A C2A -1.3(8) . . . . ? C1A C2A C12A C13A 176.7(7) . . . . ? C3A C2A C12A C13A 0.7(12) . . . . ? C1A C2A C12A C11A -0.3(8) . . . . ? C3A C2A C12A C11A -176.3(7) . . . . ? C11A C12A C13A C14A -1.3(11) . . . . ? C2A C12A C13A C14A -178.1(7) . . . . ? C12A C13A C14A C15A 0.8(12) . . . . ? C13A C14A C15A C16A 0.2(13) . . . . ? C12A C11A C16A C15A 0.2(11) . . . . ? B1A C11A C16A C15A 179.4(8) . . . . ? C14A C15A C16A C11A -0.7(12) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.541 _refine_diff_density_min -0.341 _refine_diff_density_rms 0.081 data_wa1256 _database_code_depnum_ccdc_archive 'CCDC 837678' #TrackingRef '- combinedcifs.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H32 B2 O4' _chemical_formula_sum 'C24 H32 B2 O4' _chemical_formula_weight 406.12 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 Monoclinic _symmetry_space_group_name_H-M P21/n _symmetry_space_group_name_Hall '-P 2yn' 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 11.1036(5) _cell_length_b 11.2005(4) _cell_length_c 19.5494(10) _cell_angle_alpha 90.00 _cell_angle_beta 105.072(4) _cell_angle_gamma 90.00 _cell_volume 2347.64(18) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 36599 _cell_measurement_theta_min 3.7 _cell_measurement_theta_max 26.8 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.51 _exptl_crystal_size_mid 0.49 _exptl_crystal_size_min 0.35 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.149 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 872 _exptl_absorpt_coefficient_mu 0.075 _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 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'STOE IPDS II two-circle-diffractometer' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 34104 _diffrn_reflns_av_R_equivalents 0.0689 _diffrn_reflns_av_sigmaI/netI 0.0290 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 3.64 _diffrn_reflns_theta_max 25.68 _reflns_number_total 4459 _reflns_number_gt 4029 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'X-Area (Stoe & Cie, 2001)' _computing_cell_refinement 'X-Area (Stoe & Cie, 2001)' _computing_data_reduction 'X-Area (Stoe & Cie, 2001)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008) ' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008) ' _computing_molecular_graphics 'XP (Sheldrick, 2008)' _computing_publication_material SHELXL97 _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^)+(0.0707P)^2^+1.8062P] 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 4459 _refine_ls_number_parameters 271 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0637 _refine_ls_R_factor_gt 0.0591 _refine_ls_wR_factor_ref 0.1568 _refine_ls_wR_factor_gt 0.1530 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 1.032 _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 0.38150(19) 0.23774(19) 0.55589(11) 0.0292(4) Uani 1 1 d . . . B2 B 0.22480(18) 0.40337(18) 0.65290(11) 0.0262(4) Uani 1 1 d . . . C1 C 0.47879(16) 0.30378(16) 0.61641(9) 0.0273(4) Uani 1 1 d . . . C2 C 0.48037(15) 0.42833(16) 0.62486(9) 0.0258(4) Uani 1 1 d . . . C3 C 0.58321(17) 0.48248(19) 0.67104(10) 0.0342(4) Uani 1 1 d . . . H3 H 0.5858 0.5670 0.6755 0.041 Uiso 1 1 calc R . . C4 C 0.68125(18) 0.4152(2) 0.71042(11) 0.0415(5) Uani 1 1 d . . . H4 H 0.7508 0.4534 0.7413 0.050 Uiso 1 1 calc R . . C5 C 0.67803(18) 0.2922(2) 0.70476(10) 0.0413(5) Uani 1 1 d . . . H5 H 0.7442 0.2456 0.7326 0.050 Uiso 1 1 calc R . . C6 C 0.57784(17) 0.23736(19) 0.65825(10) 0.0349(4) Uani 1 1 d . . . H6 H 0.5762 0.1528 0.6546 0.042 Uiso 1 1 calc R . . O11 O 0.35030(17) 0.12115(13) 0.55983(8) 0.0538(5) Uani 1 1 d . . . C12 C 0.2500(3) 0.0956(2) 0.49597(13) 0.0565(7) Uani 1 1 d . . . C13 C 0.2690(2) 0.1931(2) 0.44482(11) 0.0478(6) Uani 1 1 d . . . O14 O 0.32622(14) 0.28848(12) 0.49282(7) 0.0417(4) Uani 1 1 d . . . C15 C 0.2635(4) -0.0318(2) 0.47423(16) 0.0822(10) Uani 1 1 d . . . H15A H 0.3431 -0.0412 0.4620 0.123 Uiso 1 1 calc R . . H15B H 0.1948 -0.0516 0.4330 0.123 Uiso 1 1 calc R . . H15C H 0.2614 -0.0853 0.5136 0.123 Uiso 1 1 calc R . . C16 C 0.1258(3) 0.1154(4) 0.51530(17) 0.0812(10) Uani 1 1 d . . . H16A H 0.1200 0.1989 0.5292 0.122 Uiso 1 1 calc R . . H16B H 0.1220 0.0630 0.5548 0.122 Uiso 1 1 calc R . . H16C H 0.0564 0.0969 0.4742 0.122 Uiso 1 1 calc R . . C17 C 0.3682(3) 0.1537(3) 0.40476(14) 0.0663(8) Uani 1 1 d . . . H17A H 0.4422 0.1222 0.4389 0.099 Uiso 1 1 calc R . . H17B H 0.3919 0.2227 0.3803 0.099 Uiso 1 1 calc R . . H17C H 0.3325 0.0917 0.3701 0.099 Uiso 1 1 calc R . . C18 C 0.1569(2) 0.2412(3) 0.39226(13) 0.0571(6) Uani 1 1 d . . . H18A H 0.1830 0.3017 0.3628 0.086 Uiso 1 1 calc R . . H18B H 0.1003 0.2774 0.4173 0.086 Uiso 1 1 calc R . . H18C H 0.1140 0.1761 0.3621 0.086 Uiso 1 1 calc R . . C21 C 0.25321(16) 0.48536(15) 0.59448(9) 0.0255(4) Uani 1 1 d . . . C22 C 0.37363(16) 0.50250(15) 0.58497(9) 0.0253(4) Uani 1 1 d . . . C23 C 0.39188(18) 0.58472(17) 0.53511(10) 0.0316(4) Uani 1 1 d . . . H23 H 0.4736 0.5989 0.5303 0.038 Uiso 1 1 calc R . . C24 C 0.2914(2) 0.64599(18) 0.49246(10) 0.0376(5) Uani 1 1 d . . . H24 H 0.3046 0.7007 0.4580 0.045 Uiso 1 1 calc R . . C25 C 0.17225(19) 0.62779(18) 0.49982(10) 0.0377(5) Uani 1 1 d . . . H25 H 0.1034 0.6689 0.4702 0.045 Uiso 1 1 calc R . . C26 C 0.15431(17) 0.54902(17) 0.55084(10) 0.0318(4) Uani 1 1 d . . . H26 H 0.0725 0.5379 0.5563 0.038 Uiso 1 1 calc R . . O31 O 0.11837(12) 0.33627(13) 0.64074(7) 0.0350(3) Uani 1 1 d . . . C32 C 0.10697(18) 0.29380(19) 0.70948(11) 0.0367(5) Uani 1 1 d . . . O32 O 0.29604(11) 0.39696(11) 0.72104(6) 0.0291(3) Uani 1 1 d . . . C33 C 0.24415(18) 0.30139(17) 0.75589(10) 0.0333(4) Uani 1 1 d . . . C35 C 0.0523(2) 0.1692(2) 0.70048(14) 0.0557(6) Uani 1 1 d . . . H35A H 0.1104 0.1147 0.6862 0.084 Uiso 1 1 calc R . . H35B H -0.0271 0.1700 0.6640 0.084 Uiso 1 1 calc R . . H35C H 0.0382 0.1422 0.7454 0.084 Uiso 1 1 calc R . . C36 C 0.0188(2) 0.3804(2) 0.73208(14) 0.0550(6) Uani 1 1 d . . . H36A H 0.0559 0.4604 0.7379 0.082 Uiso 1 1 calc R . . H36B H 0.0047 0.3539 0.7771 0.082 Uiso 1 1 calc R . . H36C H -0.0608 0.3827 0.6958 0.082 Uiso 1 1 calc R . . C37 C 0.3205(2) 0.19076(19) 0.75164(12) 0.0444(5) Uani 1 1 d . . . H37A H 0.3108 0.1696 0.7019 0.067 Uiso 1 1 calc R . . H37B H 0.2915 0.1245 0.7760 0.067 Uiso 1 1 calc R . . H37C H 0.4086 0.2067 0.7744 0.067 Uiso 1 1 calc R . . C38 C 0.2580(2) 0.3362(2) 0.83252(11) 0.0498(6) Uani 1 1 d . . . H38A H 0.2079 0.4076 0.8344 0.075 Uiso 1 1 calc R . . H38B H 0.3458 0.3530 0.8554 0.075 Uiso 1 1 calc R . . H38C H 0.2290 0.2705 0.8573 0.075 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 B1 0.0308(10) 0.0290(10) 0.0298(10) 0.0005(8) 0.0111(8) 0.0003(8) B2 0.0229(9) 0.0265(10) 0.0316(10) -0.0003(8) 0.0112(7) 0.0005(7) C1 0.0257(8) 0.0336(9) 0.0247(8) 0.0017(7) 0.0103(7) 0.0003(7) C2 0.0235(8) 0.0339(9) 0.0229(8) -0.0012(7) 0.0112(6) -0.0027(7) C3 0.0296(9) 0.0421(11) 0.0324(9) -0.0070(8) 0.0106(7) -0.0062(8) C4 0.0272(9) 0.0626(14) 0.0322(10) -0.0070(9) 0.0033(8) -0.0052(9) C5 0.0295(10) 0.0627(14) 0.0302(10) 0.0062(9) 0.0053(8) 0.0093(9) C6 0.0344(10) 0.0401(11) 0.0317(9) 0.0041(8) 0.0115(8) 0.0065(8) O11 0.0751(11) 0.0339(8) 0.0404(8) 0.0019(6) -0.0065(8) -0.0102(8) C12 0.0717(17) 0.0458(13) 0.0438(12) -0.0061(10) 0.0001(11) -0.0184(12) C13 0.0574(14) 0.0408(12) 0.0370(11) -0.0066(9) -0.0022(10) -0.0063(10) O14 0.0542(9) 0.0316(7) 0.0323(7) -0.0012(6) -0.0012(6) -0.0049(6) C15 0.132(3) 0.0378(14) 0.0603(17) -0.0099(12) -0.0043(18) -0.0168(16) C16 0.0653(18) 0.117(3) 0.0662(18) -0.0240(18) 0.0258(15) -0.0469(18) C17 0.0625(16) 0.094(2) 0.0450(13) -0.0210(14) 0.0193(12) -0.0108(15) C18 0.0529(14) 0.0634(16) 0.0448(13) -0.0049(11) -0.0055(10) 0.0009(12) C21 0.0270(8) 0.0249(8) 0.0253(8) -0.0018(7) 0.0078(7) -0.0015(7) C22 0.0283(8) 0.0249(8) 0.0244(8) -0.0043(6) 0.0098(7) -0.0030(7) C23 0.0361(10) 0.0304(9) 0.0329(9) -0.0006(7) 0.0175(8) -0.0045(7) C24 0.0517(12) 0.0315(10) 0.0334(10) 0.0068(8) 0.0177(9) 0.0017(9) C25 0.0421(11) 0.0376(11) 0.0326(10) 0.0065(8) 0.0083(8) 0.0085(8) C26 0.0284(9) 0.0347(10) 0.0328(9) 0.0011(8) 0.0087(7) 0.0015(7) O31 0.0287(7) 0.0429(8) 0.0341(7) 0.0064(6) 0.0093(5) -0.0090(6) C32 0.0345(10) 0.0416(11) 0.0385(10) 0.0079(8) 0.0178(8) -0.0066(8) O32 0.0305(6) 0.0299(7) 0.0283(6) 0.0034(5) 0.0103(5) -0.0041(5) C33 0.0372(10) 0.0336(10) 0.0321(9) 0.0080(8) 0.0146(8) -0.0029(8) C35 0.0560(14) 0.0533(14) 0.0609(15) 0.0076(12) 0.0206(12) -0.0237(12) C36 0.0397(12) 0.0685(16) 0.0665(15) 0.0093(12) 0.0312(11) 0.0029(11) C37 0.0505(12) 0.0365(11) 0.0499(12) 0.0134(9) 0.0200(10) 0.0053(9) C38 0.0622(14) 0.0571(14) 0.0334(11) 0.0064(10) 0.0183(10) -0.0034(11) _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 O14 1.351(2) . ? B1 O11 1.358(3) . ? B1 C1 1.565(3) . ? B2 O32 1.363(2) . ? B2 O31 1.368(2) . ? B2 C21 1.560(3) . ? C1 C6 1.401(3) . ? C1 C2 1.404(3) . ? C2 C3 1.397(2) . ? C2 C22 1.491(2) . ? C3 C4 1.382(3) . ? C3 H3 0.9500 . ? C4 C5 1.381(3) . ? C4 H4 0.9500 . ? C5 C6 1.384(3) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? O11 C12 1.469(3) . ? C12 C15 1.508(4) . ? C12 C13 1.532(3) . ? C12 C16 1.538(4) . ? C13 O14 1.454(2) . ? C13 C18 1.493(3) . ? C13 C17 1.572(4) . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C21 C26 1.398(2) . ? C21 C22 1.410(2) . ? C22 C23 1.393(2) . ? C23 C24 1.388(3) . ? C23 H23 0.9500 . ? C24 C25 1.383(3) . ? C24 H24 0.9500 . ? C25 C26 1.384(3) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? O31 C32 1.462(2) . ? C32 C35 1.514(3) . ? C32 C36 1.523(3) . ? C32 C33 1.559(3) . ? O32 C33 1.465(2) . ? C33 C37 1.516(3) . ? C33 C38 1.517(3) . ? C35 H35A 0.9800 . ? C35 H35B 0.9800 . ? C35 H35C 0.9800 . ? C36 H36A 0.9800 . ? C36 H36B 0.9800 . ? C36 H36C 0.9800 . ? C37 H37A 0.9800 . ? C37 H37B 0.9800 . ? C37 H37C 0.9800 . ? C38 H38A 0.9800 . ? C38 H38B 0.9800 . ? C38 H38C 0.9800 . ? 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 O14 B1 O11 113.20(17) . . ? O14 B1 C1 123.46(17) . . ? O11 B1 C1 123.21(17) . . ? O32 B2 O31 113.37(16) . . ? O32 B2 C21 124.75(16) . . ? O31 B2 C21 121.73(16) . . ? C6 C1 C2 118.34(17) . . ? C6 C1 B1 118.23(17) . . ? C2 C1 B1 122.92(16) . . ? C3 C2 C1 119.37(17) . . ? C3 C2 C22 120.09(17) . . ? C1 C2 C22 120.54(15) . . ? C4 C3 C2 121.07(19) . . ? C4 C3 H3 119.5 . . ? C2 C3 H3 119.5 . . ? C5 C4 C3 119.94(18) . . ? C5 C4 H4 120.0 . . ? C3 C4 H4 120.0 . . ? C4 C5 C6 119.67(19) . . ? C4 C5 H5 120.2 . . ? C6 C5 H5 120.2 . . ? C5 C6 C1 121.5(2) . . ? C5 C6 H6 119.3 . . ? C1 C6 H6 119.3 . . ? B1 O11 C12 106.68(17) . . ? O11 C12 C15 108.4(2) . . ? O11 C12 C13 102.34(18) . . ? C15 C12 C13 116.7(2) . . ? O11 C12 C16 107.1(2) . . ? C15 C12 C16 111.5(3) . . ? C13 C12 C16 110.0(2) . . ? O14 C13 C18 108.96(19) . . ? O14 C13 C12 102.32(17) . . ? C18 C13 C12 118.4(2) . . ? O14 C13 C17 106.40(19) . . ? C18 C13 C17 109.0(2) . . ? C12 C13 C17 111.0(2) . . ? B1 O14 C13 107.36(16) . . ? C12 C15 H15A 109.5 . . ? C12 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C12 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C12 C16 H16A 109.5 . . ? C12 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C12 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C13 C17 H17A 109.5 . . ? C13 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C13 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C13 C18 H18A 109.5 . . ? C13 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C13 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C26 C21 C22 118.12(16) . . ? C26 C21 B2 118.07(15) . . ? C22 C21 B2 123.76(15) . . ? C23 C22 C21 119.83(16) . . ? C23 C22 C2 119.59(15) . . ? C21 C22 C2 120.48(15) . . ? C24 C23 C22 120.43(17) . . ? C24 C23 H23 119.8 . . ? C22 C23 H23 119.8 . . ? C25 C24 C23 120.40(17) . . ? C25 C24 H24 119.8 . . ? C23 C24 H24 119.8 . . ? C24 C25 C26 119.33(18) . . ? C24 C25 H25 120.3 . . ? C26 C25 H25 120.3 . . ? C25 C26 C21 121.82(17) . . ? C25 C26 H26 119.1 . . ? C21 C26 H26 119.1 . . ? B2 O31 C32 107.23(14) . . ? O31 C32 C35 108.74(18) . . ? O31 C32 C36 105.98(17) . . ? C35 C32 C36 110.63(19) . . ? O31 C32 C33 102.26(13) . . ? C35 C32 C33 114.79(18) . . ? C36 C32 C33 113.62(18) . . ? B2 O32 C33 107.13(14) . . ? O32 C33 C37 106.16(15) . . ? O32 C33 C38 108.70(16) . . ? C37 C33 C38 110.48(18) . . ? O32 C33 C32 102.24(14) . . ? C37 C33 C32 113.53(18) . . ? C38 C33 C32 114.92(17) . . ? C32 C35 H35A 109.5 . . ? C32 C35 H35B 109.5 . . ? H35A C35 H35B 109.5 . . ? C32 C35 H35C 109.5 . . ? H35A C35 H35C 109.5 . . ? H35B C35 H35C 109.5 . . ? C32 C36 H36A 109.5 . . ? C32 C36 H36B 109.5 . . ? H36A C36 H36B 109.5 . . ? C32 C36 H36C 109.5 . . ? H36A C36 H36C 109.5 . . ? H36B C36 H36C 109.5 . . ? C33 C37 H37A 109.5 . . ? C33 C37 H37B 109.5 . . ? H37A C37 H37B 109.5 . . ? C33 C37 H37C 109.5 . . ? H37A C37 H37C 109.5 . . ? H37B C37 H37C 109.5 . . ? C33 C38 H38A 109.5 . . ? C33 C38 H38B 109.5 . . ? H38A C38 H38B 109.5 . . ? C33 C38 H38C 109.5 . . ? H38A C38 H38C 109.5 . . ? H38B C38 H38C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O14 B1 C1 C6 -144.21(19) . . . . ? O11 B1 C1 C6 31.4(3) . . . . ? O14 B1 C1 C2 27.5(3) . . . . ? O11 B1 C1 C2 -156.94(19) . . . . ? C6 C1 C2 C3 3.9(2) . . . . ? B1 C1 C2 C3 -167.79(16) . . . . ? C6 C1 C2 C22 -176.21(15) . . . . ? B1 C1 C2 C22 12.1(2) . . . . ? C1 C2 C3 C4 -2.4(3) . . . . ? C22 C2 C3 C4 177.73(16) . . . . ? C2 C3 C4 C5 -0.4(3) . . . . ? C3 C4 C5 C6 1.6(3) . . . . ? C4 C5 C6 C1 0.0(3) . . . . ? C2 C1 C6 C5 -2.8(3) . . . . ? B1 C1 C6 C5 169.30(17) . . . . ? O14 B1 O11 C12 -8.5(3) . . . . ? C1 B1 O11 C12 175.54(19) . . . . ? B1 O11 C12 C15 146.5(2) . . . . ? B1 O11 C12 C13 22.6(3) . . . . ? B1 O11 C12 C16 -93.1(2) . . . . ? O11 C12 C13 O14 -27.8(2) . . . . ? C15 C12 C13 O14 -145.9(2) . . . . ? C16 C12 C13 O14 85.7(2) . . . . ? O11 C12 C13 C18 -147.5(2) . . . . ? C15 C12 C13 C18 94.4(3) . . . . ? C16 C12 C13 C18 -34.0(3) . . . . ? O11 C12 C13 C17 85.4(2) . . . . ? C15 C12 C13 C17 -32.7(3) . . . . ? C16 C12 C13 C17 -161.1(2) . . . . ? O11 B1 O14 C13 -10.7(2) . . . . ? C1 B1 O14 C13 165.32(18) . . . . ? C18 C13 O14 B1 150.1(2) . . . . ? C12 C13 O14 B1 24.0(2) . . . . ? C17 C13 O14 B1 -92.6(2) . . . . ? O32 B2 C21 C26 -135.74(19) . . . . ? O31 B2 C21 C26 39.5(2) . . . . ? O32 B2 C21 C22 41.7(3) . . . . ? O31 B2 C21 C22 -143.09(18) . . . . ? C26 C21 C22 C23 2.6(2) . . . . ? B2 C21 C22 C23 -174.87(16) . . . . ? C26 C21 C22 C2 -173.89(16) . . . . ? B2 C21 C22 C2 8.7(3) . . . . ? C3 C2 C22 C23 64.4(2) . . . . ? C1 C2 C22 C23 -115.54(19) . . . . ? C3 C2 C22 C21 -119.17(18) . . . . ? C1 C2 C22 C21 60.9(2) . . . . ? C21 C22 C23 C24 -2.9(3) . . . . ? C2 C22 C23 C24 173.55(17) . . . . ? C22 C23 C24 C25 1.2(3) . . . . ? C23 C24 C25 C26 0.9(3) . . . . ? C24 C25 C26 C21 -1.2(3) . . . . ? C22 C21 C26 C25 -0.5(3) . . . . ? B2 C21 C26 C25 177.06(17) . . . . ? O32 B2 O31 C32 8.9(2) . . . . ? C21 B2 O31 C32 -166.83(16) . . . . ? B2 O31 C32 C35 -144.20(18) . . . . ? B2 O31 C32 C36 96.84(19) . . . . ? B2 O31 C32 C33 -22.41(19) . . . . ? O31 B2 O32 C33 10.1(2) . . . . ? C21 B2 O32 C33 -174.36(16) . . . . ? B2 O32 C33 C37 96.15(18) . . . . ? B2 O32 C33 C38 -144.99(17) . . . . ? B2 O32 C33 C32 -23.07(18) . . . . ? O31 C32 C33 O32 27.27(18) . . . . ? C35 C32 C33 O32 144.81(17) . . . . ? C36 C32 C33 O32 -86.46(19) . . . . ? O31 C32 C33 C37 -86.64(18) . . . . ? C35 C32 C33 C37 30.9(2) . . . . ? C36 C32 C33 C37 159.63(18) . . . . ? O31 C32 C33 C38 144.81(17) . . . . ? C35 C32 C33 C38 -97.6(2) . . . . ? C36 C32 C33 C38 31.1(2) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.766 _refine_diff_density_min -0.322 _refine_diff_density_rms 0.051 data_wa1222 _database_code_depnum_ccdc_archive 'CCDC 837679' #TrackingRef '- combinedcifs.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H10 B2 O3' _chemical_formula_sum 'C12 H10 B2 O3' _chemical_formula_weight 223.82 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 Monoclinic _symmetry_space_group_name_H-M P21/c _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 10.130(2) _cell_length_b 7.2521(15) _cell_length_c 15.992(3) _cell_angle_alpha 90.00 _cell_angle_beta 105.63(3) _cell_angle_gamma 90.00 _cell_volume 1131.4(4) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 5702 _cell_measurement_theta_min 3.5 _cell_measurement_theta_max 2.59 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.314 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 464 _exptl_absorpt_coefficient_mu 0.090 _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 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'STOE IPDS II two-circle-diffractometer' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 7543 _diffrn_reflns_av_R_equivalents 0.1062 _diffrn_reflns_av_sigmaI/netI 0.0750 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.50 _diffrn_reflns_theta_max 25.61 _reflns_number_total 2114 _reflns_number_gt 1564 _reflns_threshold_expression >2\s(I) _computing_data_collection 'X-Area (Stoe & Cie, 2001)' _computing_cell_refinement 'X-Area (Stoe & Cie, 2001)' _computing_data_reduction 'X-Area (Stoe & Cie, 2001)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP (Sheldrick, 2008)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0662P)^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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.026(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2114 _refine_ls_number_parameters 163 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0684 _refine_ls_R_factor_gt 0.0488 _refine_ls_wR_factor_ref 0.1186 _refine_ls_wR_factor_gt 0.1106 _refine_ls_goodness_of_fit_ref 0.953 _refine_ls_restrained_S_all 0.953 _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 0.16681(19) 0.1339(3) 0.68625(13) 0.0227(4) Uani 1 1 d . . . B2 B 0.14795(18) 0.4759(3) 0.67944(14) 0.0234(4) Uani 1 1 d . . . O1 O 0.09160(13) -0.01372(18) 0.69991(9) 0.0288(3) Uani 1 1 d . . . H1 H 0.028(3) 0.030(5) 0.727(2) 0.071(9) Uiso 1 1 d . . . O2 O 0.11113(13) 0.61135(19) 0.72785(9) 0.0289(3) Uani 1 1 d . . . H2 H 0.113(3) 0.742(5) 0.714(2) 0.065(8) Uiso 1 1 d . . . O3 O 0.13008(12) 0.30368(18) 0.70925(9) 0.0268(3) Uani 1 1 d . . . C1 C 0.29807(17) 0.1022(3) 0.65424(12) 0.0237(4) Uani 1 1 d . . . C2 C 0.34536(17) 0.2263(3) 0.60074(12) 0.0255(4) Uani 1 1 d . . . C3 C 0.47421(19) 0.1911(3) 0.58642(14) 0.0335(5) Uani 1 1 d . . . H3 H 0.5091 0.2745 0.5518 0.040 Uiso 1 1 calc R . . C4 C 0.55129(19) 0.0387(3) 0.62122(15) 0.0386(5) Uani 1 1 d . . . H4 H 0.6381 0.0196 0.6106 0.046 Uiso 1 1 calc R . . C5 C 0.50355(19) -0.0858(3) 0.67112(15) 0.0369(5) Uani 1 1 d . . . H5 H 0.5556 -0.1922 0.6940 0.044 Uiso 1 1 calc R . . C6 C 0.37754(19) -0.0527(3) 0.68744(13) 0.0300(4) Uani 1 1 d . . . H6 H 0.3444 -0.1378 0.7222 0.036 Uiso 1 1 calc R . . C11 C 0.18845(16) 0.5110(3) 0.59315(12) 0.0238(4) Uani 1 1 d . . . C12 C 0.26739(16) 0.3904(3) 0.55568(12) 0.0249(4) Uani 1 1 d . . . C13 C 0.2777(2) 0.4299(3) 0.47200(14) 0.0343(5) Uani 1 1 d . . . H13 H 0.3260 0.3467 0.4450 0.041 Uiso 1 1 calc R . . C14 C 0.2198(2) 0.5864(3) 0.42728(14) 0.0376(5) Uani 1 1 d . . . H14 H 0.2282 0.6091 0.3704 0.045 Uiso 1 1 calc R . . C15 C 0.14956(19) 0.7099(3) 0.46548(13) 0.0349(5) Uani 1 1 d . . . H15 H 0.1132 0.8204 0.4364 0.042 Uiso 1 1 calc R . . C16 C 0.13315(18) 0.6700(3) 0.54635(13) 0.0294(4) Uani 1 1 d . . . H16 H 0.0824 0.7533 0.5715 0.035 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 0.0309(9) 0.0158(10) 0.0226(10) 0.0001(8) 0.0092(8) 0.0004(7) B2 0.0226(8) 0.0168(10) 0.0319(11) -0.0016(8) 0.0092(8) -0.0010(7) O1 0.0388(7) 0.0150(7) 0.0397(8) 0.0003(6) 0.0232(6) -0.0005(5) O2 0.0393(7) 0.0149(7) 0.0391(8) -0.0010(6) 0.0219(6) 0.0005(5) O3 0.0359(6) 0.0165(7) 0.0342(7) 0.0002(5) 0.0202(5) -0.0006(5) C1 0.0281(8) 0.0198(10) 0.0244(9) -0.0026(7) 0.0092(7) -0.0009(7) C2 0.0288(8) 0.0255(10) 0.0245(9) -0.0031(8) 0.0109(7) -0.0016(7) C3 0.0327(9) 0.0348(12) 0.0377(11) -0.0020(9) 0.0177(8) -0.0001(8) C4 0.0280(9) 0.0427(13) 0.0486(13) -0.0024(10) 0.0166(9) 0.0058(9) C5 0.0339(9) 0.0337(12) 0.0429(12) -0.0007(10) 0.0098(8) 0.0098(8) C6 0.0349(9) 0.0239(10) 0.0326(10) -0.0002(8) 0.0112(8) 0.0031(8) C11 0.0262(8) 0.0184(10) 0.0272(10) -0.0005(7) 0.0081(7) -0.0036(6) C12 0.0261(8) 0.0230(10) 0.0278(10) -0.0005(8) 0.0109(7) -0.0050(7) C13 0.0395(10) 0.0367(13) 0.0304(11) -0.0010(9) 0.0158(8) -0.0036(8) C14 0.0434(10) 0.0450(14) 0.0259(10) 0.0061(9) 0.0120(8) -0.0083(9) C15 0.0380(10) 0.0313(12) 0.0319(10) 0.0081(9) 0.0031(8) -0.0060(8) C16 0.0316(9) 0.0218(10) 0.0347(10) 0.0016(8) 0.0088(8) -0.0038(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 O3 1.365(2) . ? B1 O1 1.365(2) . ? B1 C1 1.565(3) . ? B2 O2 1.363(2) . ? B2 O3 1.366(2) . ? B2 C11 1.563(3) . ? O1 H1 0.92(3) . ? O2 H2 0.97(4) . ? C1 C6 1.401(3) . ? C1 C2 1.411(3) . ? C2 C3 1.408(3) . ? C2 C12 1.501(3) . ? C3 C4 1.381(3) . ? C3 H3 0.9500 . ? C4 C5 1.376(3) . ? C4 H4 0.9500 . ? C5 C6 1.391(3) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C11 C16 1.406(3) . ? C11 C12 1.422(3) . ? C12 C13 1.400(3) . ? C13 C14 1.385(3) . ? C13 H13 0.9500 . ? C14 C15 1.384(3) . ? C14 H14 0.9500 . ? C15 C16 1.378(3) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? 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 O3 B1 O1 117.38(16) . . ? O3 B1 C1 122.54(16) . . ? O1 B1 C1 119.79(17) . . ? O2 B2 O3 112.22(17) . . ? O2 B2 C11 124.14(17) . . ? O3 B2 C11 123.22(17) . . ? B1 O1 H1 107(2) . . ? B2 O2 H2 123.0(18) . . ? B1 O3 B2 131.25(15) . . ? C6 C1 C2 119.14(16) . . ? C6 C1 B1 116.49(16) . . ? C2 C1 B1 124.16(17) . . ? C3 C2 C1 117.64(18) . . ? C3 C2 C12 117.17(17) . . ? C1 C2 C12 125.17(15) . . ? C4 C3 C2 121.9(2) . . ? C4 C3 H3 119.1 . . ? C2 C3 H3 119.1 . . ? C5 C4 C3 120.65(17) . . ? C5 C4 H4 119.7 . . ? C3 C4 H4 119.7 . . ? C4 C5 C6 118.65(19) . . ? C4 C5 H5 120.7 . . ? C6 C5 H5 120.7 . . ? C5 C6 C1 122.00(19) . . ? C5 C6 H6 119.0 . . ? C1 C6 H6 119.0 . . ? C16 C11 C12 117.94(17) . . ? C16 C11 B2 116.22(16) . . ? C12 C11 B2 125.68(16) . . ? C13 C12 C11 118.21(18) . . ? C13 C12 C2 117.12(17) . . ? C11 C12 C2 124.63(16) . . ? C14 C13 C12 122.1(2) . . ? C14 C13 H13 119.0 . . ? C12 C13 H13 119.0 . . ? C15 C14 C13 119.93(19) . . ? C15 C14 H14 120.0 . . ? C13 C14 H14 120.0 . . ? C16 C15 C14 119.0(2) . . ? C16 C15 H15 120.5 . . ? C14 C15 H15 120.5 . . ? C15 C16 C11 122.69(19) . . ? C15 C16 H16 118.7 . . ? C11 C16 H16 118.7 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 B1 O3 B2 -154.30(17) . . . . ? C1 B1 O3 B2 31.8(3) . . . . ? O2 B2 O3 B1 -172.15(17) . . . . ? C11 B2 O3 B1 15.0(3) . . . . ? O3 B1 C1 C6 137.02(19) . . . . ? O1 B1 C1 C6 -36.7(2) . . . . ? O3 B1 C1 C2 -37.7(3) . . . . ? O1 B1 C1 C2 148.63(18) . . . . ? C6 C1 C2 C3 -2.6(3) . . . . ? B1 C1 C2 C3 171.96(18) . . . . ? C6 C1 C2 C12 175.59(18) . . . . ? B1 C1 C2 C12 -9.9(3) . . . . ? C1 C2 C3 C4 1.6(3) . . . . ? C12 C2 C3 C4 -176.74(19) . . . . ? C2 C3 C4 C5 0.5(3) . . . . ? C3 C4 C5 C6 -1.5(3) . . . . ? C4 C5 C6 C1 0.4(3) . . . . ? C2 C1 C6 C5 1.7(3) . . . . ? B1 C1 C6 C5 -173.29(18) . . . . ? O2 B2 C11 C16 -26.1(2) . . . . ? O3 B2 C11 C16 145.96(17) . . . . ? O2 B2 C11 C12 158.64(17) . . . . ? O3 B2 C11 C12 -29.3(3) . . . . ? C16 C11 C12 C13 -4.3(2) . . . . ? B2 C11 C12 C13 170.92(17) . . . . ? C16 C11 C12 C2 173.37(17) . . . . ? B2 C11 C12 C2 -11.4(3) . . . . ? C3 C2 C12 C13 36.3(2) . . . . ? C1 C2 C12 C13 -141.86(19) . . . . ? C3 C2 C12 C11 -141.37(19) . . . . ? C1 C2 C12 C11 40.5(3) . . . . ? C11 C12 C13 C14 3.4(3) . . . . ? C2 C12 C13 C14 -174.44(18) . . . . ? C12 C13 C14 C15 0.3(3) . . . . ? C13 C14 C15 C16 -3.0(3) . . . . ? C14 C15 C16 C11 2.0(3) . . . . ? C12 C11 C16 C15 1.7(3) . . . . ? B2 C11 C16 C15 -173.93(16) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1 O2 0.92(3) 1.85(3) 2.7665(19) 174(3) 2_546 O2 H2 O1 0.97(4) 1.80(4) 2.754(2) 169(3) 1_565 _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.258 _refine_diff_density_min -0.224 _refine_diff_density_rms 0.058 data_wa1220 _database_code_depnum_ccdc_archive 'CCDC 837680' #TrackingRef '- combinedcifs.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H34 B2 Li2 O2' _chemical_formula_sum 'C20 H34 B2 Li2 O2' _chemical_formula_weight 341.97 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' Li Li -0.0003 0.0001 '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 C2/c _symmetry_space_group_name_Hall '-C 2yc' 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 11.229(3) _cell_length_b 12.210(2) _cell_length_c 15.985(4) _cell_angle_alpha 90.00 _cell_angle_beta 92.907(19) _cell_angle_gamma 90.00 _cell_volume 2188.8(9) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 3185 _cell_measurement_theta_min 3.5 _cell_measurement_theta_max 25.8 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.038 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 744 _exptl_absorpt_coefficient_mu 0.061 _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 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'STOE IPDS II two-circle-diffractometer' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 6821 _diffrn_reflns_av_R_equivalents 0.0731 _diffrn_reflns_av_sigmaI/netI 0.0819 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.48 _diffrn_reflns_theta_max 25.02 _reflns_number_total 1930 _reflns_number_gt 1230 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'X-Area (Stoe & Cie, 2001)' _computing_cell_refinement 'X-Area (Stoe & Cie, 2001)' _computing_data_reduction 'X-Area (Stoe & Cie, 2001)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008) ' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008) ' _computing_molecular_graphics 'XP (Sheldrick, 2008)' _computing_publication_material SHELXL97 _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^)+(0.1515P)^2^+5.3867P] 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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1930 _refine_ls_number_parameters 133 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1393 _refine_ls_R_factor_gt 0.1046 _refine_ls_wR_factor_ref 0.3036 _refine_ls_wR_factor_gt 0.2866 _refine_ls_goodness_of_fit_ref 1.059 _refine_ls_restrained_S_all 1.059 _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 Li1 Li 0.6085(7) 0.4825(7) 0.1923(5) 0.0382(19) Uani 1 1 d . . . B1 B 0.6110(5) 0.5306(4) 0.3388(3) 0.0290(12) Uani 1 1 d . . . H1A H 0.656(6) 0.503(5) 0.404(4) 0.08(2) Uiso 1 1 d . . . H1B H 0.670(4) 0.556(4) 0.285(3) 0.041(14) Uiso 1 1 d . . . H1C H 0.559(4) 0.447(4) 0.314(3) 0.039(14) Uiso 1 1 d . . . C1 C 0.5175(4) 0.6287(3) 0.3540(3) 0.0248(10) Uani 1 1 d . . . C2 C 0.4790(4) 0.7083(3) 0.2942(3) 0.0255(10) Uani 1 1 d . . . C3 C 0.4038(4) 0.7943(4) 0.3156(3) 0.0327(11) Uani 1 1 d . . . H3A H 0.3793 0.8468 0.2744 0.039 Uiso 1 1 calc R . . C4 C 0.3644(4) 0.8041(4) 0.3962(3) 0.0376(12) Uani 1 1 d . . . H4 H 0.3139 0.8630 0.4101 0.045 Uiso 1 1 calc R . . C5 C 0.3996(4) 0.7272(4) 0.4560(3) 0.0371(12) Uani 1 1 d . . . H5 H 0.3728 0.7331 0.5113 0.045 Uiso 1 1 calc R . . C6 C 0.4733(4) 0.6421(4) 0.4355(3) 0.0308(11) Uani 1 1 d . . . H6 H 0.4958 0.5901 0.4776 0.037 Uiso 1 1 calc R . . C21 C 0.6097(5) 0.2343(5) 0.1719(4) 0.0546(16) Uani 1 1 d . . . H21A H 0.6412 0.2441 0.2297 0.082 Uiso 1 1 calc R . . H21B H 0.5979 0.1561 0.1605 0.082 Uiso 1 1 calc R . . H21C H 0.5332 0.2727 0.1642 0.082 Uiso 1 1 calc R . . C22 C 0.6957(5) 0.2800(4) 0.1132(4) 0.0445(13) Uani 1 1 d . . . H22A H 0.7719 0.2392 0.1186 0.053 Uiso 1 1 calc R . . H22B H 0.6631 0.2729 0.0548 0.053 Uiso 1 1 calc R . . O23 O 0.7159(3) 0.3939(3) 0.1332(2) 0.0349(9) Uani 1 1 d . . . C24 C 0.8080(5) 0.4380(5) 0.0838(3) 0.0477(14) Uani 1 1 d . . . H24A H 0.7763 0.4508 0.0257 0.057 Uiso 1 1 calc R . . H24B H 0.8749 0.3853 0.0821 0.057 Uiso 1 1 calc R . . C25 C 0.8513(5) 0.5430(5) 0.1215(4) 0.0574(16) Uani 1 1 d . . . H25A H 0.7851 0.5953 0.1222 0.086 Uiso 1 1 calc R . . H25B H 0.9146 0.5730 0.0883 0.086 Uiso 1 1 calc R . . H25C H 0.8826 0.5299 0.1790 0.086 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 Li1 0.039(4) 0.040(4) 0.036(4) -0.008(3) 0.003(3) 0.009(3) B1 0.030(3) 0.030(3) 0.026(3) 0.000(2) -0.002(2) 0.004(2) C1 0.027(2) 0.023(2) 0.024(2) -0.0038(16) 0.0031(17) 0.0003(17) C2 0.027(2) 0.024(2) 0.026(2) -0.0032(17) 0.0031(17) -0.0008(16) C3 0.035(3) 0.027(2) 0.036(3) 0.0000(19) 0.001(2) 0.0042(18) C4 0.038(3) 0.035(3) 0.041(3) -0.007(2) 0.009(2) 0.005(2) C5 0.041(3) 0.042(3) 0.029(3) -0.004(2) 0.011(2) 0.002(2) C6 0.039(3) 0.031(2) 0.023(2) 0.0036(18) 0.0079(18) -0.0005(19) C21 0.046(3) 0.040(3) 0.078(4) -0.004(3) 0.009(3) 0.001(2) C22 0.044(3) 0.041(3) 0.048(3) -0.013(2) -0.004(2) 0.012(2) O23 0.0336(17) 0.0376(18) 0.0341(18) -0.0029(14) 0.0085(14) 0.0046(14) C24 0.040(3) 0.070(4) 0.034(3) 0.006(3) 0.013(2) 0.005(3) C25 0.046(3) 0.052(3) 0.075(4) 0.012(3) 0.012(3) -0.001(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Li1 O23 1.906(8) . ? Li1 C1 2.373(9) 2_655 ? Li1 B1 2.414(10) . ? Li1 B1 2.558(10) 2_655 ? Li1 Li1 3.130(17) 2_655 ? Li1 H1B 1.84(5) . ? Li1 H1C 2.09(5) . ? B1 C1 1.620(6) . ? B1 Li1 2.558(10) 2_655 ? B1 H1A 1.18(7) . ? B1 H1B 1.15(5) . ? B1 H1C 1.23(5) . ? C1 C2 1.415(6) . ? C1 C6 1.427(6) . ? C1 Li1 2.373(9) 2_655 ? C2 C3 1.401(6) . ? C2 C2 1.513(9) 2_655 ? C3 C4 1.388(7) . ? C3 H3A 0.9500 . ? C4 C5 1.383(7) . ? C4 H4 0.9500 . ? C5 C6 1.379(6) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C21 C22 1.489(8) . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 O23 1.442(6) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? O23 C24 1.438(6) . ? C24 C25 1.488(9) . ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? 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 O23 Li1 C1 130.9(4) . 2_655 ? O23 Li1 B1 130.0(4) . . ? C1 Li1 B1 95.6(3) 2_655 . ? O23 Li1 B1 131.4(4) . 2_655 ? C1 Li1 B1 38.13(19) 2_655 2_655 ? B1 Li1 B1 95.6(3) . 2_655 ? O23 Li1 Li1 145.4(3) . 2_655 ? C1 Li1 Li1 73.4(3) 2_655 2_655 ? B1 Li1 Li1 53.1(3) . 2_655 ? B1 Li1 Li1 49.0(3) 2_655 2_655 ? O23 Li1 H1B 117.2(16) . . ? C1 Li1 H1B 94.4(16) 2_655 . ? B1 Li1 H1B 27.4(16) . . ? B1 Li1 H1B 111.3(16) 2_655 . ? Li1 Li1 H1B 78.2(17) 2_655 . ? O23 Li1 H1C 123.1(14) . . ? C1 Li1 H1C 105.3(14) 2_655 . ? B1 Li1 H1C 30.6(13) . . ? B1 Li1 H1C 86.0(14) 2_655 . ? Li1 Li1 H1C 37.1(14) 2_655 . ? H1B Li1 H1C 57(2) . . ? C1 B1 Li1 110.4(3) . . ? C1 B1 Li1 64.7(3) . 2_655 ? Li1 B1 Li1 78.0(4) . 2_655 ? C1 B1 H1A 109(3) . . ? Li1 B1 H1A 140(3) . . ? Li1 B1 H1A 118(3) 2_655 . ? C1 B1 H1B 108(3) . . ? Li1 B1 H1B 47(3) . . ? Li1 B1 H1B 120(3) 2_655 . ? H1A B1 H1B 120(4) . . ? C1 B1 H1C 111(2) . . ? Li1 B1 H1C 60(2) . . ? Li1 B1 H1C 47(2) 2_655 . ? H1A B1 H1C 103(4) . . ? H1B B1 H1C 105(3) . . ? C2 C1 C6 115.5(4) . . ? C2 C1 B1 125.8(4) . . ? C6 C1 B1 118.6(4) . . ? C2 C1 Li1 98.6(3) . 2_655 ? C6 C1 Li1 98.2(3) . 2_655 ? B1 C1 Li1 77.2(3) . 2_655 ? C3 C2 C1 121.1(4) . . ? C3 C2 C2 116.7(3) . 2_655 ? C1 C2 C2 122.2(3) . 2_655 ? C4 C3 C2 121.0(4) . . ? C4 C3 H3A 119.5 . . ? C2 C3 H3A 119.5 . . ? C5 C4 C3 119.4(4) . . ? C5 C4 H4 120.3 . . ? C3 C4 H4 120.3 . . ? C6 C5 C4 120.0(4) . . ? C6 C5 H5 120.0 . . ? C4 C5 H5 120.0 . . ? C5 C6 C1 123.0(4) . . ? C5 C6 H6 118.5 . . ? C1 C6 H6 118.5 . . ? C22 C21 H21A 109.5 . . ? C22 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C22 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? O23 C22 C21 108.8(4) . . ? O23 C22 H22A 109.9 . . ? C21 C22 H22A 109.9 . . ? O23 C22 H22B 109.9 . . ? C21 C22 H22B 109.9 . . ? H22A C22 H22B 108.3 . . ? C24 O23 C22 110.4(4) . . ? C24 O23 Li1 123.4(4) . . ? C22 O23 Li1 124.1(4) . . ? O23 C24 C25 109.2(5) . . ? O23 C24 H24A 109.8 . . ? C25 C24 H24A 109.8 . . ? O23 C24 H24B 109.8 . . ? C25 C24 H24B 109.8 . . ? H24A C24 H24B 108.3 . . ? C24 C25 H25A 109.5 . . ? C24 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C24 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O23 Li1 B1 C1 167.5(5) . . . . ? C1 Li1 B1 C1 7.4(5) 2_655 . . . ? B1 Li1 B1 C1 -30.9(5) 2_655 . . . ? Li1 Li1 B1 C1 -56.9(3) 2_655 . . . ? O23 Li1 B1 Li1 -135.5(4) . . . 2_655 ? C1 Li1 B1 Li1 64.4(4) 2_655 . . 2_655 ? B1 Li1 B1 Li1 26.1(4) 2_655 . . 2_655 ? Li1 B1 C1 C2 -26.4(6) . . . . ? Li1 B1 C1 C2 -91.4(4) 2_655 . . . ? Li1 B1 C1 C6 157.4(4) . . . . ? Li1 B1 C1 C6 92.4(4) 2_655 . . . ? Li1 B1 C1 Li1 65.0(4) . . . 2_655 ? C6 C1 C2 C3 0.7(6) . . . . ? B1 C1 C2 C3 -175.6(4) . . . . ? Li1 C1 C2 C3 104.1(4) 2_655 . . . ? C6 C1 C2 C2 177.8(4) . . . 2_655 ? B1 C1 C2 C2 1.5(7) . . . 2_655 ? Li1 C1 C2 C2 -78.8(5) 2_655 . . 2_655 ? C1 C2 C3 C4 -0.1(7) . . . . ? C2 C2 C3 C4 -177.3(5) 2_655 . . . ? C2 C3 C4 C5 -0.4(7) . . . . ? C3 C4 C5 C6 0.2(7) . . . . ? C4 C5 C6 C1 0.4(7) . . . . ? C2 C1 C6 C5 -0.9(6) . . . . ? B1 C1 C6 C5 175.7(4) . . . . ? Li1 C1 C6 C5 -104.5(5) 2_655 . . . ? C21 C22 O23 C24 173.9(4) . . . . ? C21 C22 O23 Li1 -22.0(6) . . . . ? C1 Li1 O23 C24 53.0(7) 2_655 . . . ? B1 Li1 O23 C24 -100.4(6) . . . . ? B1 Li1 O23 C24 104.4(6) 2_655 . . . ? Li1 Li1 O23 C24 179.2(8) 2_655 . . . ? C1 Li1 O23 C22 -109.1(6) 2_655 . . . ? B1 Li1 O23 C22 97.6(6) . . . . ? B1 Li1 O23 C22 -57.6(7) 2_655 . . . ? Li1 Li1 O23 C22 17.1(11) 2_655 . . . ? C22 O23 C24 C25 -163.9(4) . . . . ? Li1 O23 C24 C25 31.9(6) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.318 _refine_diff_density_min -0.296 _refine_diff_density_rms 0.083 data_wa1273 _database_code_depnum_ccdc_archive 'CCDC 837681' #TrackingRef '- combinedcifs.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H12 B2' _chemical_formula_sum 'C12 H12 B2' _chemical_formula_weight 177.84 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/c _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.4074(12) _cell_length_b 14.8970(14) _cell_length_c 7.1428(10) _cell_angle_alpha 90.00 _cell_angle_beta 99.524(11) _cell_angle_gamma 90.00 _cell_volume 987.2(2) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 6878 _cell_measurement_theta_min 3.5 _cell_measurement_theta_max 26.6 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.41 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.32 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.197 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 376 _exptl_absorpt_coefficient_mu 0.064 _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 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'STOE IPDS II two-circle-diffractometer' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 12161 _diffrn_reflns_av_R_equivalents 0.0688 _diffrn_reflns_av_sigmaI/netI 0.0840 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 3.51 _diffrn_reflns_theta_max 26.44 _reflns_number_total 2012 _reflns_number_gt 1459 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'X-Area (Stoe & Cie, 2001)' _computing_cell_refinement 'X-Area (Stoe & Cie, 2001)' _computing_data_reduction 'X-Area (Stoe & Cie, 2001)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008) ' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008) ' _computing_molecular_graphics 'XP (Sheldrick, 2008)' _computing_publication_material SHELXL97 _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^)+(0.0676P)^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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.068(9) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2012 _refine_ls_number_parameters 144 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0719 _refine_ls_R_factor_gt 0.0494 _refine_ls_wR_factor_ref 0.1280 _refine_ls_wR_factor_gt 0.1180 _refine_ls_goodness_of_fit_ref 0.954 _refine_ls_restrained_S_all 0.954 _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 0.87212(17) 0.17965(11) 0.1948(2) 0.0262(4) Uani 1 1 d . . . H1A H 0.8065(16) 0.1390(11) 0.310(2) 0.029(4) Uiso 1 1 d . . . H1B H 0.984(2) 0.1544(13) 0.224(3) 0.048(5) Uiso 1 1 d . . . B2 B 0.71732(18) 0.11198(11) 0.1641(2) 0.0277(4) Uani 1 1 d . . . H2B H 0.7175(17) 0.0376(12) 0.170(2) 0.035(4) Uiso 1 1 d . . . H2A H 0.8034(18) 0.1372(12) 0.057(2) 0.035(4) Uiso 1 1 d . . . C1 C 0.83848(13) 0.28188(9) 0.18372(18) 0.0239(3) Uani 1 1 d . . . C2 C 0.69702(14) 0.31840(9) 0.14873(17) 0.0229(3) Uani 1 1 d . . . C3 C 0.68373(16) 0.41240(10) 0.1443(2) 0.0297(4) Uani 1 1 d . . . H3 H 0.5901 0.4382 0.1229 0.036 Uiso 1 1 calc R . . C4 C 0.80253(17) 0.46866(10) 0.1702(2) 0.0343(4) Uani 1 1 d . . . H4 H 0.7893 0.5319 0.1651 0.041 Uiso 1 1 calc R . . C5 C 0.94083(16) 0.43317(11) 0.2036(2) 0.0342(4) Uani 1 1 d . . . H5 H 1.0228 0.4714 0.2213 0.041 Uiso 1 1 calc R . . C6 C 0.95666(15) 0.34110(10) 0.2105(2) 0.0301(4) Uani 1 1 d . . . H6 H 1.0512 0.3167 0.2343 0.036 Uiso 1 1 calc R . . C11 C 0.57371(14) 0.16590(10) 0.12514(18) 0.0246(3) Uani 1 1 d . . . C12 C 0.56565(14) 0.26057(10) 0.11542(18) 0.0235(3) Uani 1 1 d . . . C13 C 0.42843(15) 0.30017(11) 0.0712(2) 0.0297(4) Uani 1 1 d . . . H13 H 0.4211 0.3637 0.0646 0.036 Uiso 1 1 calc R . . C14 C 0.30401(15) 0.24929(12) 0.0373(2) 0.0339(4) Uani 1 1 d . . . H14 H 0.2131 0.2781 0.0063 0.041 Uiso 1 1 calc R . . C15 C 0.31112(16) 0.15655(12) 0.0482(2) 0.0340(4) Uani 1 1 d . . . H15 H 0.2258 0.1213 0.0256 0.041 Uiso 1 1 calc R . . C16 C 0.44497(15) 0.11631(11) 0.0927(2) 0.0308(4) Uani 1 1 d . . . H16 H 0.4500 0.0527 0.1017 0.037 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 0.0225(7) 0.0267(8) 0.0285(8) -0.0006(6) 0.0016(6) 0.0027(6) B2 0.0294(8) 0.0231(8) 0.0294(8) -0.0017(6) 0.0017(6) -0.0008(6) C1 0.0220(7) 0.0253(8) 0.0242(6) -0.0005(5) 0.0031(5) -0.0010(5) C2 0.0233(7) 0.0237(7) 0.0215(6) -0.0002(5) 0.0031(5) 0.0010(5) C3 0.0281(7) 0.0249(8) 0.0358(8) -0.0016(6) 0.0043(6) 0.0026(5) C4 0.0400(8) 0.0213(7) 0.0416(9) -0.0019(6) 0.0062(6) -0.0021(6) C5 0.0317(7) 0.0315(8) 0.0389(8) -0.0021(7) 0.0040(6) -0.0098(7) C6 0.0229(7) 0.0334(8) 0.0333(8) -0.0010(6) 0.0029(6) -0.0022(6) C11 0.0245(7) 0.0252(8) 0.0239(7) -0.0026(5) 0.0036(5) -0.0017(5) C12 0.0221(7) 0.0277(7) 0.0210(6) -0.0001(5) 0.0037(5) 0.0015(5) C13 0.0242(7) 0.0314(8) 0.0331(8) 0.0005(6) 0.0040(5) 0.0029(6) C14 0.0191(7) 0.0459(10) 0.0360(8) 0.0004(7) 0.0029(6) 0.0021(6) C15 0.0240(7) 0.0436(10) 0.0337(8) 0.0000(7) 0.0024(6) -0.0083(6) C16 0.0298(8) 0.0299(8) 0.0323(8) -0.0016(6) 0.0038(6) -0.0071(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 C1 1.555(2) . ? B1 B2 1.755(2) . ? B1 H1A 1.262(15) . ? B1 H1B 1.10(2) . ? B1 H2A 1.256(17) . ? B2 C11 1.557(2) . ? B2 H1A 1.289(15) . ? B2 H2B 1.108(18) . ? B2 H2A 1.259(16) . ? C1 C6 1.4073(19) . ? C1 C2 1.4210(18) . ? C2 C3 1.406(2) . ? C2 C12 1.4929(18) . ? C3 C4 1.385(2) . ? C3 H3 0.9500 . ? C4 C5 1.388(2) . ? C4 H4 0.9500 . ? C5 C6 1.380(2) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C11 C16 1.4048(19) . ? C11 C12 1.4134(19) . ? C12 C13 1.4068(19) . ? C13 C14 1.382(2) . ? C13 H13 0.9500 . ? C14 C15 1.385(2) . ? C14 H14 0.9500 . ? C15 C16 1.383(2) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? 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 C1 B1 B2 113.49(12) . . ? C1 B1 H1A 112.7(7) . . ? B2 B1 H1A 47.2(7) . . ? C1 B1 H1B 121.5(10) . . ? B2 B1 H1B 125.0(10) . . ? H1A B1 H1B 105.4(12) . . ? C1 B1 H2A 112.3(8) . . ? B2 B1 H2A 45.8(7) . . ? H1A B1 H2A 91.4(10) . . ? H1B B1 H2A 109.2(12) . . ? C11 B2 B1 113.81(12) . . ? C11 B2 H1A 114.4(7) . . ? B1 B2 H1A 45.9(7) . . ? C11 B2 H2B 121.2(9) . . ? B1 B2 H2B 125.0(9) . . ? H1A B2 H2B 106.4(11) . . ? C11 B2 H2A 111.3(8) . . ? B1 B2 H2A 45.7(8) . . ? H1A B2 H2A 90.0(10) . . ? H2B B2 H2A 109.0(11) . . ? C6 C1 C2 118.67(13) . . ? C6 C1 B1 117.23(12) . . ? C2 C1 B1 124.10(12) . . ? C3 C2 C1 117.55(12) . . ? C3 C2 C12 120.20(12) . . ? C1 C2 C12 122.25(12) . . ? C4 C3 C2 122.22(14) . . ? C4 C3 H3 118.9 . . ? C2 C3 H3 118.9 . . ? C3 C4 C5 120.36(14) . . ? C3 C4 H4 119.8 . . ? C5 C4 H4 119.8 . . ? C6 C5 C4 118.51(13) . . ? C6 C5 H5 120.7 . . ? C4 C5 H5 120.7 . . ? C5 C6 C1 122.70(13) . . ? C5 C6 H6 118.7 . . ? C1 C6 H6 118.7 . . ? C16 C11 C12 118.61(13) . . ? C16 C11 B2 117.21(13) . . ? C12 C11 B2 124.16(12) . . ? C13 C12 C11 117.99(13) . . ? C13 C12 C2 119.90(13) . . ? C11 C12 C2 122.12(12) . . ? C14 C13 C12 121.90(15) . . ? C14 C13 H13 119.0 . . ? C12 C13 H13 119.0 . . ? C13 C14 C15 120.38(14) . . ? C13 C14 H14 119.8 . . ? C15 C14 H14 119.8 . . ? C16 C15 C14 118.62(14) . . ? C16 C15 H15 120.7 . . ? C14 C15 H15 120.7 . . ? C15 C16 C11 122.49(15) . . ? C15 C16 H16 118.8 . . ? C11 C16 H16 118.8 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 B1 B2 C11 1.71(17) . . . . ? B2 B1 C1 C6 178.84(12) . . . . ? B2 B1 C1 C2 -1.09(18) . . . . ? C6 C1 C2 C3 -0.45(18) . . . . ? B1 C1 C2 C3 179.48(12) . . . . ? C6 C1 C2 C12 178.92(12) . . . . ? B1 C1 C2 C12 -1.16(19) . . . . ? C1 C2 C3 C4 0.8(2) . . . . ? C12 C2 C3 C4 -178.53(13) . . . . ? C2 C3 C4 C5 -0.6(2) . . . . ? C3 C4 C5 C6 -0.1(2) . . . . ? C4 C5 C6 C1 0.5(2) . . . . ? C2 C1 C6 C5 -0.2(2) . . . . ? B1 C1 C6 C5 179.88(13) . . . . ? B1 B2 C11 C16 177.96(12) . . . . ? B1 B2 C11 C12 -0.21(18) . . . . ? C16 C11 C12 C13 -0.77(18) . . . . ? B2 C11 C12 C13 177.38(13) . . . . ? C16 C11 C12 C2 179.74(12) . . . . ? B2 C11 C12 C2 -2.11(19) . . . . ? C3 C2 C12 C13 2.80(18) . . . . ? C1 C2 C12 C13 -176.55(12) . . . . ? C3 C2 C12 C11 -177.72(13) . . . . ? C1 C2 C12 C11 2.93(18) . . . . ? C11 C12 C13 C14 -0.2(2) . . . . ? C2 C12 C13 C14 179.29(12) . . . . ? C12 C13 C14 C15 0.8(2) . . . . ? C13 C14 C15 C16 -0.3(2) . . . . ? C14 C15 C16 C11 -0.7(2) . . . . ? C12 C11 C16 C15 1.2(2) . . . . ? B2 C11 C16 C15 -177.03(13) . . . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.165 _refine_diff_density_min -0.264 _refine_diff_density_rms 0.049