# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _journal_year ? _publ_contact_author_name 'Mark E. Light' _publ_contact_author_email M.E.Light@soton.ac.uk loop_ _publ_author_name 'F.Di Salvo' 'Jose Giner Planas' 'Beatriz Camargo' 'Yolanda Garcia' 'Francesc Teixidor' 'Clara Vinas' ; M.E.Light ; 'Michael B. Hursthouse' data_2010acc0310 _database_code_depnum_ccdc_archive 'CCDC 816749' #TrackingRef '2010acc0310_2a.cif' _chemical_compound_source 'Jose Giner Planas' _database_code_CSD 11AC0310 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C8 H17 B10 N O' _chemical_formula_weight 251.33 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 10.4340(3) _cell_length_b 6.7029(2) _cell_length_c 20.4814(6) _cell_angle_alpha 90.00 _cell_angle_beta 103.747(2) _cell_angle_gamma 90.00 _cell_volume 1391.40(7) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 31104 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.200 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 520 _exptl_absorpt_coefficient_mu 0.063 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9812 _exptl_absorpt_correction_T_max 0.9905 _exptl_absorpt_process_details ; SADABS V2.10 (Sheldrick, G.M., 2003) ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker Nonius FR591 Rotating Anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans to fill the asymmetric unit' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18069 _diffrn_reflns_av_R_equivalents 0.0576 _diffrn_reflns_av_sigmaI/netI 0.0416 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 3.21 _diffrn_reflns_theta_max 27.48 _reflns_number_total 3187 _reflns_number_gt 2387 _reflns_threshold_expression >2\s(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ; Images generated using CrystalMaker: a crystal and molecular structures program for Mac and Windows. CrystalMaker Software Ltd, Oxford, England (www.crystalmaker.com) ; _computing_publication_material 'WINGX (Farrugia, 1998)' _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^ > 2\s(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^)+(0.1007P)^2^+0.5999P] 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 SHELXL _refine_ls_extinction_coef 0.042(8) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3187 _refine_ls_number_parameters 188 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0873 _refine_ls_R_factor_gt 0.0645 _refine_ls_wR_factor_ref 0.1867 _refine_ls_wR_factor_gt 0.1711 _refine_ls_goodness_of_fit_ref 1.062 _refine_ls_restrained_S_all 1.062 _refine_ls_shift/su_max 0.004 _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 O1A O 1.01162(15) -0.0670(3) 0.27964(9) 0.0371(5) Uani 0.854(3) 1 d P A 1 H1A H 1.0651 -0.1618 0.2906 0.056 Uiso 0.854(3) 1 calc PR A 1 C3A C 0.88118(18) -0.1440(3) 0.25879(9) 0.0289(4) Uani 0.854(3) 1 d P A 1 H3A H 0.8874 -0.2928 0.2584 0.035 Uiso 0.854(3) 1 calc PR A 1 O1B O 0.8960(9) -0.3468(15) 0.2593(5) 0.0371(5) Uani 0.146(3) 1 d P A 2 H1B H 0.8232 -0.4015 0.2587 0.056 Uiso 0.146(3) 1 calc PR A 2 C3B C 0.88118(18) -0.1440(3) 0.25879(9) 0.0289(4) Uani 0.146(3) 1 d P A 2 H3B H 0.9703 -0.0803 0.2720 0.035 Uiso 0.146(3) 1 calc PR A 2 N1 N 0.83193(16) 0.1116(3) 0.17066(8) 0.0320(4) Uani 1 1 d . A . C1 C 0.80071(17) -0.0857(3) 0.31057(8) 0.0233(4) Uani 1 1 d . . . C2 C 0.8837(2) -0.0061(3) 0.38548(9) 0.0323(5) Uani 1 1 d . A . H2 H 0.9933 0.0140 0.3976 0.039 Uiso 1 1 calc R . . C4 C 0.81330(18) -0.0769(3) 0.18854(9) 0.0273(4) Uani 1 1 d . . . C5 C 0.7335(2) -0.2088(3) 0.14528(10) 0.0324(5) Uani 1 1 d . A . H5A H 0.7231 -0.3420 0.1590 0.039 Uiso 1 1 calc R . . C6 C 0.6691(2) -0.1450(3) 0.08176(10) 0.0355(5) Uani 1 1 d . . . H6A H 0.6135 -0.2333 0.0514 0.043 Uiso 1 1 calc R A . C7 C 0.6868(2) 0.0489(3) 0.06334(10) 0.0365(5) Uani 1 1 d . A . H7A H 0.6433 0.0973 0.0202 0.044 Uiso 1 1 calc R . . C8 C 0.7690(2) 0.1707(3) 0.10889(10) 0.0363(5) Uani 1 1 d . . . H8A H 0.7817 0.3039 0.0958 0.044 Uiso 1 1 calc R A . B3 B 0.8210(2) -0.2444(3) 0.37810(10) 0.0285(5) Uani 1 1 d . A . H3 H 0.8837 -0.3820 0.3848 0.034 Uiso 1 1 calc R . . B4 B 0.6705(2) -0.2292(3) 0.31696(10) 0.0264(5) Uani 1 1 d . A . H4 H 0.6327 -0.3577 0.2829 0.032 Uiso 1 1 calc R . . B5 B 0.6479(2) 0.0201(3) 0.28846(10) 0.0260(4) Uani 1 1 d . A . H5 H 0.5944 0.0566 0.2356 0.031 Uiso 1 1 calc R . . B6 B 0.7865(2) 0.1600(3) 0.33075(11) 0.0280(5) Uani 1 1 d . A . H6 H 0.8263 0.2876 0.3063 0.034 Uiso 1 1 calc R . . B7 B 0.8110(2) -0.0922(4) 0.44687(11) 0.0326(5) Uani 1 1 d . . . H7 H 0.8661 -0.1286 0.4994 0.039 Uiso 1 1 calc R A . B8 B 0.6718(2) -0.2333(3) 0.40346(11) 0.0303(5) Uani 1 1 d . A . H8 H 0.6335 -0.3637 0.4272 0.036 Uiso 1 1 calc R . . B9 B 0.5641(2) -0.0684(3) 0.34790(11) 0.0281(5) Uani 1 1 d . . . H9 H 0.4545 -0.0901 0.3351 0.034 Uiso 1 1 calc R A . B10 B 0.6364(2) 0.1749(3) 0.35669(11) 0.0294(5) Uani 1 1 d . A . H10 H 0.5751 0.3139 0.3498 0.035 Uiso 1 1 calc R . . B11 B 0.7895(2) 0.1592(4) 0.41768(11) 0.0326(5) Uani 1 1 d . A . H11 H 0.8305 0.2879 0.4510 0.039 Uiso 1 1 calc R . . B12 B 0.6515(2) 0.0173(3) 0.42850(11) 0.0304(5) Uani 1 1 d . A . H12 H 0.5998 0.0526 0.4692 0.036 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 O1A 0.0248(8) 0.0420(10) 0.0445(10) 0.0018(8) 0.0085(7) 0.0042(7) C3A 0.0263(9) 0.0335(10) 0.0277(9) -0.0024(8) 0.0081(7) 0.0041(8) O1B 0.0248(8) 0.0420(10) 0.0445(10) 0.0018(8) 0.0085(7) 0.0042(7) C3B 0.0263(9) 0.0335(10) 0.0277(9) -0.0024(8) 0.0081(7) 0.0041(8) N1 0.0307(9) 0.0368(10) 0.0292(8) -0.0007(7) 0.0086(7) -0.0071(7) C1 0.0233(9) 0.0254(9) 0.0198(8) -0.0013(7) 0.0027(6) 0.0004(7) C2 0.0354(10) 0.0355(11) 0.0247(9) -0.0061(8) 0.0047(8) -0.0022(9) C4 0.0234(9) 0.0356(10) 0.0253(9) -0.0034(8) 0.0105(7) 0.0009(8) C5 0.0400(11) 0.0312(10) 0.0291(10) -0.0051(8) 0.0143(8) -0.0056(8) C6 0.0370(11) 0.0444(12) 0.0262(9) -0.0076(9) 0.0095(8) -0.0105(9) C7 0.0391(11) 0.0466(13) 0.0236(9) -0.0005(9) 0.0073(8) -0.0030(9) C8 0.0429(12) 0.0368(11) 0.0310(10) 0.0018(9) 0.0120(9) -0.0060(9) B3 0.0329(11) 0.0286(11) 0.0229(10) 0.0013(8) 0.0046(8) 0.0015(9) B4 0.0248(10) 0.0267(10) 0.0268(10) 0.0000(8) 0.0043(8) -0.0024(8) B5 0.0239(10) 0.0278(10) 0.0270(10) 0.0021(8) 0.0073(8) 0.0038(8) B6 0.0297(11) 0.0251(10) 0.0312(11) -0.0021(8) 0.0112(9) -0.0008(9) B7 0.0369(12) 0.0380(12) 0.0221(10) -0.0015(9) 0.0057(9) 0.0006(10) B8 0.0360(12) 0.0305(11) 0.0262(10) 0.0008(9) 0.0109(9) -0.0033(9) B9 0.0255(10) 0.0304(11) 0.0301(10) -0.0007(9) 0.0100(8) -0.0006(9) B10 0.0316(11) 0.0267(11) 0.0330(11) -0.0015(9) 0.0142(9) 0.0023(9) B11 0.0353(12) 0.0335(12) 0.0314(11) -0.0076(9) 0.0126(9) -0.0039(10) B12 0.0325(11) 0.0324(11) 0.0290(10) -0.0019(9) 0.0126(9) -0.0009(9) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 O1A C3A 1.423(2) . ? C3A C4 1.513(3) . ? C3A C1 1.551(2) . ? N1 C8 1.340(3) . ? N1 C4 1.343(3) . ? C1 C2 1.660(2) . ? C1 B4 1.695(3) . ? C1 B5 1.705(3) . ? C1 B6 1.712(3) . ? C1 B3 1.718(3) . ? C2 B11 1.714(3) . ? C2 B7 1.715(3) . ? C2 B3 1.719(3) . ? C2 B6 1.727(3) . ? C4 C5 1.381(3) . ? C5 C6 1.383(3) . ? C6 C7 1.378(3) . ? C7 C8 1.376(3) . ? B3 B8 1.756(3) . ? B3 B7 1.762(3) . ? B3 B4 1.763(3) . ? B4 B5 1.767(3) . ? B4 B8 1.769(3) . ? B4 B9 1.770(3) . ? B5 B9 1.762(3) . ? B5 B10 1.767(3) . ? B5 B6 1.768(3) . ? B6 B10 1.773(3) . ? B6 B11 1.773(3) . ? B7 B12 1.776(3) . ? B7 B8 1.783(3) . ? B7 B11 1.784(3) . ? B8 B9 1.781(3) . ? B8 B12 1.784(3) . ? B9 B12 1.781(3) . ? B9 B10 1.788(3) . ? B10 B11 1.782(3) . ? B10 B12 1.787(3) . ? B11 B12 1.782(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 O1A C3A C4 112.08(16) . . ? O1A C3A C1 109.75(15) . . ? C4 C3A C1 111.61(15) . . ? C8 N1 C4 117.76(17) . . ? C3A C1 C2 117.70(15) . . ? C3A C1 B4 118.92(15) . . ? C2 C1 B4 111.24(14) . . ? C3A C1 B5 123.17(14) . . ? C2 C1 B5 111.18(14) . . ? B4 C1 B5 62.64(12) . . ? C3A C1 B6 119.95(15) . . ? C2 C1 B6 61.59(12) . . ? B4 C1 B6 114.24(14) . . ? B5 C1 B6 62.32(12) . . ? C3A C1 B3 114.27(15) . . ? C2 C1 B3 61.14(11) . . ? B4 C1 B3 62.22(12) . . ? B5 C1 B3 113.58(14) . . ? B6 C1 B3 113.74(14) . . ? C1 C2 B11 110.04(15) . . ? C1 C2 B7 110.21(15) . . ? B11 C2 B7 62.71(13) . . ? C1 C2 B3 61.09(11) . . ? B11 C2 B3 113.20(16) . . ? B7 C2 B3 61.75(13) . . ? C1 C2 B6 60.70(11) . . ? B11 C2 B6 62.05(13) . . ? B7 C2 B6 113.54(16) . . ? B3 C2 B6 112.95(15) . . ? N1 C4 C5 122.10(18) . . ? N1 C4 C3A 118.26(17) . . ? C5 C4 C3A 119.63(18) . . ? C4 C5 C6 119.3(2) . . ? C7 C6 C5 118.83(18) . . ? C8 C7 C6 118.47(19) . . ? N1 C8 C7 123.5(2) . . ? C1 B3 C2 57.77(11) . . ? C1 B3 B8 105.27(15) . . ? C2 B3 B8 106.24(15) . . ? C1 B3 B7 105.39(15) . . ? C2 B3 B7 59.02(12) . . ? B8 B3 B7 60.92(13) . . ? C1 B3 B4 58.26(11) . . ? C2 B3 B4 105.34(15) . . ? B8 B3 B4 60.34(12) . . ? B7 B3 B4 108.80(16) . . ? C1 B4 B3 59.53(11) . . ? C1 B4 B5 58.96(11) . . ? B3 B4 B5 108.41(15) . . ? C1 B4 B8 105.70(14) . . ? B3 B4 B8 59.62(12) . . ? B5 B4 B8 108.29(15) . . ? C1 B4 B9 105.33(14) . . ? B3 B4 B9 108.03(15) . . ? B5 B4 B9 59.75(12) . . ? B8 B4 B9 60.44(12) . . ? C1 B5 B9 105.24(14) . . ? C1 B5 B10 105.60(14) . . ? B9 B5 B10 60.87(12) . . ? C1 B5 B4 58.40(11) . . ? B9 B5 B4 60.19(12) . . ? B10 B5 B4 108.83(14) . . ? C1 B5 B6 59.04(11) . . ? B9 B5 B6 108.82(15) . . ? B10 B5 B6 60.18(12) . . ? B4 B5 B6 108.06(14) . . ? C1 B6 C2 57.71(11) . . ? C1 B6 B5 58.63(11) . . ? C2 B6 B5 105.16(15) . . ? C1 B6 B10 105.05(14) . . ? C2 B6 B10 105.42(15) . . ? B5 B6 B10 59.88(12) . . ? C1 B6 B11 104.92(15) . . ? C2 B6 B11 58.60(12) . . ? B5 B6 B11 107.88(15) . . ? B10 B6 B11 60.33(12) . . ? C2 B7 B3 59.23(12) . . ? C2 B7 B12 105.12(15) . . ? B3 B7 B12 107.49(15) . . ? C2 B7 B8 105.21(14) . . ? B3 B7 B8 59.37(12) . . ? B12 B7 B8 60.15(13) . . ? C2 B7 B11 58.60(12) . . ? B3 B7 B11 107.80(15) . . ? B12 B7 B11 60.09(13) . . ? B8 B7 B11 108.11(16) . . ? B3 B8 B4 60.04(12) . . ? B3 B8 B9 107.87(15) . . ? B4 B8 B9 59.81(12) . . ? B3 B8 B7 59.72(12) . . ? B4 B8 B7 107.62(15) . . ? B9 B8 B7 107.77(16) . . ? B3 B8 B12 107.43(15) . . ? B4 B8 B12 107.49(15) . . ? B9 B8 B12 59.94(12) . . ? B7 B8 B12 59.72(13) . . ? B5 B9 B4 60.07(12) . . ? B5 B9 B12 107.65(15) . . ? B4 B9 B12 107.57(15) . . ? B5 B9 B8 108.00(15) . . ? B4 B9 B8 59.75(12) . . ? B12 B9 B8 60.11(12) . . ? B5 B9 B10 59.72(12) . . ? B4 B9 B10 107.83(14) . . ? B12 B9 B10 60.10(12) . . ? B8 B9 B10 108.34(16) . . ? B5 B10 B6 59.94(12) . . ? B5 B10 B11 107.56(15) . . ? B6 B10 B11 59.86(12) . . ? B5 B10 B12 107.14(15) . . ? B6 B10 B12 107.58(15) . . ? B11 B10 B12 59.93(12) . . ? B5 B10 B9 59.41(12) . . ? B6 B10 B9 107.47(15) . . ? B11 B10 B9 107.65(16) . . ? B12 B10 B9 59.76(12) . . ? C2 B11 B6 59.35(12) . . ? C2 B11 B10 105.60(15) . . ? B6 B11 B10 59.82(12) . . ? C2 B11 B12 104.89(16) . . ? B6 B11 B12 107.74(16) . . ? B10 B11 B12 60.17(13) . . ? C2 B11 B7 58.68(12) . . ? B6 B11 B7 108.06(15) . . ? B10 B11 B7 108.14(16) . . ? B12 B11 B7 59.73(13) . . ? B7 B12 B9 108.10(15) . . ? B7 B12 B11 60.18(13) . . ? B9 B12 B11 107.92(15) . . ? B7 B12 B8 60.13(13) . . ? B9 B12 B8 59.95(12) . . ? B11 B12 B8 108.17(15) . . ? B7 B12 B10 108.28(15) . . ? B9 B12 B10 60.14(12) . . ? B11 B12 B10 59.90(13) . . ? B8 B12 B10 108.25(15) . . ? 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 O1A H1A N1 0.84 1.92 2.748(2) 168.4 2_745 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.637 _refine_diff_density_min -0.381 _refine_diff_density_rms 0.095 _iucr_refine_instruction_details ; TITL 2010acc0310 in P2(1)/c CELL 0.71073 10.4340 6.7029 20.4814 90.000 103.747 90.000 ZERR 4.00 0.0003 0.0002 0.0006 0.000 0.002 0.000 LATT 1 SYMM - X, 1/2 + Y, 1/2 - Z SFAC C H B N O UNIT 32 68 40 4 4 MERG 2 OMIT 1 0 2 OMIT -2 1 7 SHEL 7 0.77 EADP O1A O1B EADP C3A C3B EXYZ C3A C3B HTAB O1A N1_$1 EQIV $1 [ -x+2, y-1/2, -z+1/2 ] FMAP 2 PLAN 20 SIZE 0.15 0.20 0.30 ACTA 55.00 BOND L.S. 8 TEMP -153.00 WGHT 0.100700 0.597000 EXTI 0.042319 FVAR 0.60576 0.86340 PART 1 O1A 5 1.012307 -0.068031 0.279834 21.00000 0.02599 0.04429 = 0.04370 0.00044 0.00911 0.00143 C3A 1 0.881241 -0.144162 0.258827 21.00000 0.02643 0.03348 = 0.02802 -0.00247 0.00818 0.00420 AFIX 13 H3A 2 0.887093 -0.293044 0.258353 21.00000 -1.20000 AFIX 0 PART 2 O1B 5 0.893076 -0.349894 0.260001 -21.00000 0.02599 0.04429 = 0.04370 0.00044 0.00911 0.00143 C3B 1 0.881241 -0.144162 0.258827 -21.00000 0.02643 0.03348 = 0.02802 -0.00247 0.00818 0.00420 AFIX 13 H3B 2 0.970953 -0.082520 0.272158 -21.00000 -1.20000 AFIX 0 PART 0 N1 4 0.831974 0.111615 0.170644 11.00000 0.03084 0.03682 = 0.02943 -0.00050 0.00863 -0.00664 C1 1 0.800663 -0.085585 0.310550 11.00000 0.02346 0.02553 = 0.02009 -0.00127 0.00278 0.00039 C2 1 0.883645 -0.006119 0.385482 11.00000 0.03553 0.03555 = 0.02483 -0.00604 0.00461 -0.00202 AFIX 153 H2 2 0.993319 0.014036 0.397581 11.00000 -1.20000 AFIX 0 C4 1 0.813294 -0.076958 0.188527 11.00000 0.02348 0.03585 = 0.02537 -0.00350 0.01065 0.00067 C5 1 0.733500 -0.208679 0.145251 11.00000 0.03993 0.03132 = 0.02923 -0.00522 0.01443 -0.00591 AFIX 43 H5A 2 0.722963 -0.341796 0.159020 11.00000 -1.20000 AFIX 0 C6 1 0.669178 -0.145129 0.081789 11.00000 0.03707 0.04383 = 0.02642 -0.00742 0.00930 -0.01032 AFIX 43 H6A 2 0.613692 -0.233478 0.051375 11.00000 -1.20000 AFIX 0 C7 1 0.686936 0.048806 0.063371 11.00000 0.03929 0.04687 = 0.02406 -0.00042 0.00762 -0.00342 AFIX 43 H7A 2 0.643509 0.097201 0.020182 11.00000 -1.20000 AFIX 0 C8 1 0.768930 0.170588 0.108931 11.00000 0.04333 0.03721 = 0.03060 0.00184 0.01208 -0.00604 AFIX 43 H8A 2 0.781528 0.303814 0.095911 11.00000 -1.20000 AFIX 0 B3 3 0.821063 -0.244589 0.378157 11.00000 0.03304 0.02872 = 0.02315 0.00154 0.00462 0.00154 AFIX 153 H3 2 0.883696 -0.382227 0.384905 11.00000 -1.20000 AFIX 0 B4 3 0.670531 -0.229047 0.316961 11.00000 0.02458 0.02672 = 0.02680 -0.00012 0.00410 -0.00234 AFIX 153 H4 2 0.632723 -0.357471 0.282824 11.00000 -1.20000 AFIX 0 B5 3 0.647896 0.020107 0.288462 11.00000 0.02366 0.02788 = 0.02708 0.00214 0.00718 0.00389 AFIX 153 H5 2 0.594480 0.056599 0.235638 11.00000 -1.20000 AFIX 0 B6 3 0.786480 0.159981 0.330737 11.00000 0.02982 0.02520 = 0.03140 -0.00199 0.01118 -0.00079 AFIX 153 H6 2 0.826256 0.287591 0.306247 11.00000 -1.20000 AFIX 0 B7 3 0.810999 -0.092165 0.446864 11.00000 0.03703 0.03796 = 0.02230 -0.00145 0.00577 0.00113 AFIX 153 H7 2 0.866075 -0.128587 0.499417 11.00000 -1.20000 AFIX 0 B8 3 0.671853 -0.233212 0.403468 11.00000 0.03598 0.03044 = 0.02639 0.00072 0.01094 -0.00330 AFIX 153 H8 2 0.633588 -0.363710 0.427258 11.00000 -1.20000 AFIX 0 B9 3 0.564124 -0.068393 0.347929 11.00000 0.02563 0.03059 = 0.03015 -0.00067 0.00978 -0.00081 AFIX 153 H9 2 0.454562 -0.090154 0.335134 11.00000 -1.20000 AFIX 0 B10 3 0.636329 0.174811 0.356676 11.00000 0.03168 0.02670 = 0.03311 -0.00162 0.01411 0.00235 AFIX 153 H10 2 0.574976 0.313775 0.349784 11.00000 -1.20000 AFIX 0 B11 3 0.789513 0.159229 0.417733 11.00000 0.03555 0.03369 = 0.03132 -0.00749 0.01255 -0.00371 AFIX 153 H11 2 0.830536 0.287907 0.451068 11.00000 -1.20000 AFIX 0 B12 3 0.651410 0.017453 0.428476 11.00000 0.03262 0.03280 = 0.02894 -0.00197 0.01277 -0.00110 AFIX 153 H12 2 0.599626 0.052816 0.469108 11.00000 -1.20000 HKLF 4 REM 2010acc0310 in P2(1)/c REM R1 = 0.0658 for 2387 Fo > 4sig(Fo) and 0.0885 for all 3187 data REM 186 parameters refined using 0 restraints END WGHT 0.1004 0.7165 REM Highest difference peak 0.683, deepest hole -0.367, 1-sigma level 0.095 Q1 1 0.8356 -0.4023 0.2618 11.00000 0.05 0.68 Q2 1 1.0742 -0.1831 0.2919 11.00000 0.05 0.44 Q3 1 0.9410 -0.3025 0.2574 11.00000 0.05 0.37 Q4 1 0.8911 -0.3355 0.3710 11.00000 0.05 0.27 Q5 1 0.8622 -0.3611 0.3599 11.00000 0.05 0.27 Q6 1 0.9023 -0.4312 0.3324 11.00000 0.05 0.25 Q7 1 0.7811 0.4649 0.3179 11.00000 0.05 0.25 Q8 1 0.7225 -0.4618 0.1794 11.00000 0.05 0.25 Q9 1 0.9585 -0.5453 0.3527 11.00000 0.05 0.24 Q10 1 0.4557 -0.0154 0.3300 11.00000 0.05 0.24 Q11 1 0.9311 -0.4849 0.3668 11.00000 0.05 0.24 Q12 1 0.8594 0.0098 0.1727 11.00000 0.05 0.24 Q13 1 0.8242 -0.4207 0.3135 11.00000 0.05 0.24 Q14 1 0.7996 -0.5061 0.3362 11.00000 0.05 0.23 Q15 1 0.9997 -0.5169 0.4119 11.00000 0.05 0.23 Q16 1 0.5244 -0.0676 0.3474 11.00000 0.05 0.23 Q17 1 0.7364 -0.2558 0.1465 11.00000 0.05 0.23 Q18 1 0.8634 0.4844 0.3134 11.00000 0.05 0.23 Q19 1 0.3242 -0.0535 0.3515 11.00000 0.05 0.23 Q20 1 0.6653 -0.3310 0.2729 11.00000 0.05 0.22 ; # Attachment '2010acc0316_2d.cif' data_2010acc0316 _database_code_depnum_ccdc_archive 'CCDC 816750' #TrackingRef '2010acc0316_2d.cif' _chemical_compound_source 'Jose Giner Planas' _database_code_CSD 0ACC0316 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C8 H17 B10 N O' _chemical_formula_weight 251.33 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 13.0921(3) _cell_length_b 8.7487(2) _cell_length_c 13.6578(4) _cell_angle_alpha 90.00 _cell_angle_beta 118.2650(10) _cell_angle_gamma 90.00 _cell_volume 1377.83(6) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 46802 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description Fragment _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.09 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.212 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 520 _exptl_absorpt_coefficient_mu 0.064 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9943 _exptl_absorpt_correction_T_max 0.9987 _exptl_absorpt_process_details ; SADABS V2.10 (Sheldrick, G.M., 2003) ; _exptl_special_details ; SADABS was used to perform the Absorption correction Parameter refinement on 24822 reflections reduced R(int) from 0.2169 to 0.0846 Ratio of minimum to maximum apparent transmission: 0.849203 The given Tmin and Tmax were generated using the SHELX SIZE command ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker Nonius FR591 Rotating Anode' _diffrn_radiation_monochromator '10cm confocal mirrors' _diffrn_measurement_device_type 'Bruker-Nonius CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans to fill the asymmetric unit' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 30667 _diffrn_reflns_av_R_equivalents 0.1157 _diffrn_reflns_av_sigmaI/netI 0.0506 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.92 _diffrn_reflns_theta_max 25.03 _reflns_number_total 2444 _reflns_number_gt 1853 _reflns_threshold_expression >2\s(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ; Images generated using CrystalMaker: a crystal and molecular structures program for Mac and Windows. CrystalMaker Software Ltd, Oxford, England (www.crystalmaker.com) ; _computing_publication_material 'WINGX (Farrugia, 1998)' _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^ > 2\s(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^)+(0.0531P)^2^+3.3028P] 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 2444 _refine_ls_number_parameters 182 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1128 _refine_ls_R_factor_gt 0.0863 _refine_ls_wR_factor_ref 0.1924 _refine_ls_wR_factor_gt 0.1776 _refine_ls_goodness_of_fit_ref 1.099 _refine_ls_restrained_S_all 1.099 _refine_ls_shift/su_max 0.002 _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 C1 C 0.1436(3) 1.1096(4) 0.8912(3) 0.0231(8) Uani 1 1 d . . . C2 C 0.0866(3) 1.2381(4) 0.9387(3) 0.0285(8) Uani 1 1 d . . . H2 H 0.0415 1.2013 0.9869 0.034 Uiso 1 1 calc R . . C3 C 0.1278(3) 0.9374(4) 0.9092(3) 0.0228(8) Uani 1 1 d . . . H3 H 0.1294 0.8794 0.8469 0.027 Uiso 1 1 calc R . . C4 C 0.2234(3) 0.8734(4) 1.0171(3) 0.0213(7) Uani 1 1 d . . . C5 C 0.3231(3) 0.8091(4) 1.0227(3) 0.0257(8) Uani 1 1 d . . . H5 H 0.3360 0.8114 0.9599 0.031 Uiso 1 1 calc R . . C6 C 0.4035(3) 0.7418(4) 1.1210(3) 0.0294(8) Uani 1 1 d . . . H6 H 0.4719 0.6994 1.1242 0.035 Uiso 1 1 calc R . . C7 C 0.2944(3) 0.7976(4) 1.2067(3) 0.0273(8) Uani 1 1 d . . . H7 H 0.2838 0.7940 1.2709 0.033 Uiso 1 1 calc R . . C8 C 0.2105(3) 0.8688(4) 1.1124(3) 0.0249(8) Uani 1 1 d . . . H8 H 0.1447 0.9141 1.1128 0.030 Uiso 1 1 calc R . . B3 B 0.0173(4) 1.2030(5) 0.7983(3) 0.0288(10) Uani 1 1 d . . . H3A H -0.0697 1.1474 0.7517 0.035 Uiso 1 1 calc R . . B4 B 0.1316(3) 1.1678(5) 0.7671(3) 0.0248(9) Uani 1 1 d . . . H4 H 0.1195 1.0883 0.6982 0.030 Uiso 1 1 calc R . . B5 B 0.2657(3) 1.1778(5) 0.8919(3) 0.0243(9) Uani 1 1 d . . . H5A H 0.3415 1.1047 0.9053 0.029 Uiso 1 1 calc R . . B6 B 0.2358(3) 1.2230(5) 1.0031(3) 0.0249(9) Uani 1 1 d . . . H6A H 0.2909 1.1809 1.0900 0.030 Uiso 1 1 calc R . . B7 B 0.0334(4) 1.3913(5) 0.8507(3) 0.0311(10) Uani 1 1 d . . . H7A H -0.0436 1.4607 0.8385 0.037 Uiso 1 1 calc R . . B8 B 0.0644(4) 1.3499(5) 0.7404(3) 0.0281(9) Uani 1 1 d . . . H8A H 0.0083 1.3929 0.6539 0.034 Uiso 1 1 calc R . . B9 B 0.2178(4) 1.3343(5) 0.7981(3) 0.0266(9) Uani 1 1 d . . . H9 H 0.2633 1.3667 0.7493 0.032 Uiso 1 1 calc R . . B10 B 0.2828(4) 1.3690(5) 0.9440(3) 0.0289(9) Uani 1 1 d . . . H10 H 0.3701 1.4239 0.9914 0.035 Uiso 1 1 calc R . . B11 B 0.1668(4) 1.4039(5) 0.9760(4) 0.0313(10) Uani 1 1 d . . . H11 H 0.1766 1.4814 1.0452 0.038 Uiso 1 1 calc R . . B12 B 0.1569(4) 1.4744(5) 0.8490(4) 0.0316(10) Uani 1 1 d . . . H12 H 0.1617 1.5995 0.8342 0.038 Uiso 1 1 calc R . . N1 N 0.3893(2) 0.7336(3) 1.2120(2) 0.0270(7) Uani 1 1 d . . . O1 O 0.02026(19) 0.9108(3) 0.90382(19) 0.0281(6) Uani 1 1 d . . . H1 H -0.0237 0.8672 0.8436 0.042 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 C1 0.0172(17) 0.0272(19) 0.0239(18) 0.0074(15) 0.0088(14) 0.0039(14) C2 0.031(2) 0.028(2) 0.0298(19) 0.0045(16) 0.0169(16) 0.0050(16) C3 0.0192(17) 0.0272(19) 0.0204(17) 0.0058(15) 0.0080(14) -0.0018(14) C4 0.0224(17) 0.0177(17) 0.0197(17) 0.0022(14) 0.0067(14) -0.0051(14) C5 0.0255(18) 0.0280(19) 0.0209(17) 0.0002(15) 0.0087(15) 0.0018(15) C6 0.0284(19) 0.032(2) 0.0251(19) 0.0026(16) 0.0104(16) 0.0058(16) C7 0.0266(18) 0.031(2) 0.0224(18) 0.0056(15) 0.0098(15) 0.0014(16) C8 0.0209(17) 0.0283(19) 0.0246(18) 0.0036(15) 0.0100(15) 0.0002(15) B3 0.028(2) 0.033(2) 0.026(2) 0.0130(18) 0.0134(18) 0.0088(18) B4 0.024(2) 0.028(2) 0.025(2) 0.0053(17) 0.0131(17) 0.0016(17) B5 0.0222(19) 0.025(2) 0.028(2) -0.0008(17) 0.0138(17) -0.0029(17) B6 0.026(2) 0.023(2) 0.023(2) -0.0014(16) 0.0095(17) -0.0004(17) B7 0.034(2) 0.030(2) 0.032(2) 0.0070(19) 0.018(2) 0.0119(19) B8 0.033(2) 0.026(2) 0.026(2) 0.0073(17) 0.0146(18) 0.0021(18) B9 0.033(2) 0.025(2) 0.028(2) 0.0031(17) 0.0194(19) 0.0012(18) B10 0.035(2) 0.024(2) 0.031(2) 0.0018(18) 0.0176(19) -0.0009(18) B11 0.040(2) 0.026(2) 0.032(2) 0.0001(18) 0.020(2) 0.0059(19) B12 0.042(3) 0.024(2) 0.030(2) 0.0043(18) 0.018(2) 0.0047(19) N1 0.0265(16) 0.0278(17) 0.0215(15) 0.0057(13) 0.0070(13) 0.0027(13) O1 0.0237(13) 0.0331(15) 0.0230(13) -0.0033(11) 0.0074(10) -0.0028(11) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 C1 C3 1.557(5) . ? C1 C2 1.642(5) . ? C1 B5 1.702(5) . ? C1 B4 1.704(5) . ? C1 B3 1.739(5) . ? C1 B6 1.740(5) . ? C2 B7 1.713(5) . ? C2 B3 1.716(5) . ? C2 B11 1.721(6) . ? C2 B6 1.726(5) . ? C3 O1 1.394(4) . ? C3 C4 1.518(4) . ? C4 C5 1.389(5) . ? C4 C8 1.391(5) . ? C5 C6 1.385(5) . ? C6 N1 1.342(4) . ? C7 N1 1.334(4) . ? C7 C8 1.383(5) . ? B3 B8 1.766(6) . ? B3 B4 1.766(5) . ? B3 B7 1.768(6) . ? B4 B9 1.767(6) . ? B4 B8 1.773(6) . ? B4 B5 1.778(6) . ? B5 B9 1.775(6) . ? B5 B6 1.783(5) . ? B5 B10 1.790(6) . ? B6 B10 1.770(6) . ? B6 B11 1.773(6) . ? B7 B8 1.772(6) . ? B7 B11 1.777(6) . ? B7 B12 1.782(6) . ? B8 B12 1.776(6) . ? B8 B9 1.782(6) . ? B9 B12 1.775(6) . ? B9 B10 1.783(6) . ? B10 B11 1.795(6) . ? B10 B12 1.797(6) . ? B11 B12 1.786(6) . ? 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 C3 C1 C2 118.7(3) . . ? C3 C1 B5 122.2(3) . . ? C2 C1 B5 111.1(3) . . ? C3 C1 B4 119.3(3) . . ? C2 C1 B4 110.1(3) . . ? B5 C1 B4 62.9(2) . . ? C3 C1 B3 114.7(3) . . ? C2 C1 B3 60.9(2) . . ? B5 C1 B3 113.9(3) . . ? B4 C1 B3 61.7(2) . . ? C3 C1 B6 120.1(3) . . ? C2 C1 B6 61.3(2) . . ? B5 C1 B6 62.4(2) . . ? B4 C1 B6 113.7(3) . . ? B3 C1 B6 113.4(3) . . ? C1 C2 B7 111.6(3) . . ? C1 C2 B3 62.3(2) . . ? B7 C2 B3 62.1(2) . . ? C1 C2 B11 111.5(3) . . ? B7 C2 B11 62.4(2) . . ? B3 C2 B11 114.0(3) . . ? C1 C2 B6 62.1(2) . . ? B7 C2 B6 113.8(3) . . ? B3 C2 B6 115.3(3) . . ? B11 C2 B6 61.9(2) . . ? O1 C3 C4 109.8(3) . . ? O1 C3 C1 111.1(3) . . ? C4 C3 C1 113.6(3) . . ? C5 C4 C8 117.6(3) . . ? C5 C4 C3 121.6(3) . . ? C8 C4 C3 120.6(3) . . ? C6 C5 C4 119.3(3) . . ? N1 C6 C5 123.0(3) . . ? N1 C7 C8 123.2(3) . . ? C7 C8 C4 119.3(3) . . ? C2 B3 C1 56.8(2) . . ? C2 B3 B8 105.0(3) . . ? C1 B3 B8 104.8(3) . . ? C2 B3 B4 103.9(3) . . ? C1 B3 B4 58.2(2) . . ? B8 B3 B4 60.3(2) . . ? C2 B3 B7 58.9(2) . . ? C1 B3 B7 104.6(3) . . ? B8 B3 B7 60.2(2) . . ? B4 B3 B7 107.9(3) . . ? C1 B4 B3 60.1(2) . . ? C1 B4 B9 105.1(3) . . ? B3 B4 B9 108.5(3) . . ? C1 B4 B8 106.0(3) . . ? B3 B4 B8 59.9(2) . . ? B9 B4 B8 60.5(2) . . ? C1 B4 B5 58.5(2) . . ? B3 B4 B5 108.9(3) . . ? B9 B4 B5 60.1(2) . . ? B8 B4 B5 108.8(3) . . ? C1 B5 B9 104.9(3) . . ? C1 B5 B4 58.6(2) . . ? B9 B5 B4 59.7(2) . . ? C1 B5 B6 59.9(2) . . ? B9 B5 B6 107.4(3) . . ? B4 B5 B6 108.2(3) . . ? C1 B5 B10 105.7(3) . . ? B9 B5 B10 60.0(2) . . ? B4 B5 B10 107.9(3) . . ? B6 B5 B10 59.4(2) . . ? C2 B6 C1 56.6(2) . . ? C2 B6 B10 105.4(3) . . ? C1 B6 B10 104.9(3) . . ? C2 B6 B11 58.9(2) . . ? C1 B6 B11 104.6(3) . . ? B10 B6 B11 60.9(2) . . ? C2 B6 B5 103.6(3) . . ? C1 B6 B5 57.8(2) . . ? B10 B6 B5 60.5(2) . . ? B11 B6 B5 108.4(3) . . ? C2 B7 B3 59.0(2) . . ? C2 B7 B8 104.8(3) . . ? B3 B7 B8 59.8(2) . . ? C2 B7 B11 59.0(2) . . ? B3 B7 B11 108.8(3) . . ? B8 B7 B11 108.4(3) . . ? C2 B7 B12 105.0(3) . . ? B3 B7 B12 108.1(3) . . ? B8 B7 B12 59.9(2) . . ? B11 B7 B12 60.2(2) . . ? B3 B8 B7 60.0(2) . . ? B3 B8 B4 59.9(2) . . ? B7 B8 B4 107.4(3) . . ? B3 B8 B12 108.5(3) . . ? B7 B8 B12 60.3(2) . . ? B4 B8 B12 107.7(3) . . ? B3 B8 B9 107.8(3) . . ? B7 B8 B9 107.7(3) . . ? B4 B8 B9 59.6(2) . . ? B12 B8 B9 59.8(2) . . ? B4 B9 B12 108.0(3) . . ? B4 B9 B5 60.3(2) . . ? B12 B9 B5 108.7(3) . . ? B4 B9 B8 59.9(2) . . ? B12 B9 B8 59.9(2) . . ? B5 B9 B8 108.5(3) . . ? B4 B9 B10 108.7(3) . . ? B12 B9 B10 60.7(2) . . ? B5 B9 B10 60.4(2) . . ? B8 B9 B10 108.8(3) . . ? B6 B10 B9 107.6(3) . . ? B6 B10 B5 60.1(2) . . ? B9 B10 B5 59.6(2) . . ? B6 B10 B11 59.6(2) . . ? B9 B10 B11 106.8(3) . . ? B5 B10 B11 107.1(3) . . ? B6 B10 B12 107.5(3) . . ? B9 B10 B12 59.4(2) . . ? B5 B10 B12 107.1(3) . . ? B11 B10 B12 59.7(2) . . ? C2 B11 B6 59.2(2) . . ? C2 B11 B7 58.6(2) . . ? B6 B11 B7 108.5(3) . . ? C2 B11 B12 104.5(3) . . ? B6 B11 B12 107.9(3) . . ? B7 B11 B12 60.0(2) . . ? C2 B11 B10 104.6(3) . . ? B6 B11 B10 59.5(2) . . ? B7 B11 B10 108.3(3) . . ? B12 B11 B10 60.2(2) . . ? B9 B12 B8 60.3(2) . . ? B9 B12 B7 107.6(3) . . ? B8 B12 B7 59.8(2) . . ? B9 B12 B11 107.6(3) . . ? B8 B12 B11 107.8(3) . . ? B7 B12 B11 59.7(2) . . ? B9 B12 B10 59.9(2) . . ? B8 B12 B10 108.5(3) . . ? B7 B12 B10 108.0(3) . . ? B11 B12 B10 60.1(2) . . ? C7 N1 C6 117.5(3) . . ? 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 N1 0.84 1.84 2.674(4) 176.0 4_575 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.667 _refine_diff_density_min -0.233 _refine_diff_density_rms 0.061 # Attachment '2010acc0319_2c.cif' data_2010acc0319 _database_code_depnum_ccdc_archive 'CCDC 816751' #TrackingRef '2010acc0319_2c.cif' _chemical_compound_source 'Jose Giner Planas' _database_code_CSD 0ACC0319 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C8 H17 B10 N O' _chemical_formula_weight 251.33 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 9.7297(2) _cell_length_b 12.8208(2) _cell_length_c 11.5304(2) _cell_angle_alpha 90.00 _cell_angle_beta 104.9020(10) _cell_angle_gamma 90.00 _cell_volume 1389.96(4) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 27573 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description Fragment _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.201 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 520 _exptl_absorpt_coefficient_mu 0.064 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9874 _exptl_absorpt_correction_T_max 0.9956 _exptl_absorpt_process_details ; SADABS V2.10 (Sheldrick, G.M., 2003) ; _exptl_special_details ; SADABS was used to perform the Absorption correction Parameter refinement on 14609 reflections reduced R(int) from 0.0850 to 0.0417 Ratio of minimum to maximum apparent transmission: 0.912198 The given Tmin and Tmax were generated using the SHELX SIZE command ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker Nonius FR591 Rotating Anode' _diffrn_radiation_monochromator '10cm confocal mirrors' _diffrn_measurement_device_type 'Bruker-Nonius CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans to fill the asymmetric unit' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15768 _diffrn_reflns_av_R_equivalents 0.0414 _diffrn_reflns_av_sigmaI/netI 0.0374 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.92 _diffrn_reflns_theta_max 27.48 _reflns_number_total 3181 _reflns_number_gt 2689 _reflns_threshold_expression >2\s(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ; Images generated using CrystalMaker: a crystal and molecular structures program for Mac and Windows. CrystalMaker Software Ltd, Oxford, England (www.crystalmaker.com) ; _computing_publication_material 'WINGX (Farrugia, 1998)' _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^ > 2\s(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^)+(0.0555P)^2^+1.1711P] 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 3181 _refine_ls_number_parameters 182 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0718 _refine_ls_R_factor_gt 0.0596 _refine_ls_wR_factor_ref 0.1476 _refine_ls_wR_factor_gt 0.1398 _refine_ls_goodness_of_fit_ref 1.063 _refine_ls_restrained_S_all 1.063 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 1.19765(16) 0.17174(12) 0.23407(14) 0.0180(3) Uani 1 1 d . . . C2 C 1.12301(18) 0.15532(14) 0.09108(15) 0.0250(4) Uani 1 1 d . . . H2 H 1.0045 0.1586 0.0566 0.030 Uiso 1 1 calc R . . C3 C 1.09591(17) 0.19594(13) 0.31539(14) 0.0198(3) Uani 1 1 d . . . H3 H 1.0819 0.2732 0.3168 0.024 Uiso 1 1 calc R . . C4 C 1.16026(16) 0.15913(13) 0.44226(15) 0.0190(3) Uani 1 1 d . . . C5 C 1.14819(18) 0.05621(13) 0.47585(15) 0.0220(4) Uani 1 1 d . . . H5 H 1.0988 0.0067 0.4189 0.026 Uiso 1 1 calc R . . C6 C 1.20902(19) 0.02659(15) 0.59324(16) 0.0264(4) Uani 1 1 d . . . H6 H 1.2017 -0.0433 0.6184 0.032 Uiso 1 1 calc R . . C7 C 1.28088(19) 0.10102(16) 0.67343(16) 0.0283(4) Uani 1 1 d . . . H7 H 1.3230 0.0804 0.7539 0.034 Uiso 1 1 calc R . . C8 C 1.23279(17) 0.22798(14) 0.52885(15) 0.0226(4) Uani 1 1 d . . . H8 H 1.2399 0.2987 0.5065 0.027 Uiso 1 1 calc R . . B3 B 1.1930(2) 0.04865(15) 0.17513(18) 0.0240(4) Uani 1 1 d . . . H3A H 1.1300 -0.0176 0.1984 0.029 Uiso 1 1 calc R . . B4 B 1.34911(19) 0.09711(15) 0.27743(17) 0.0211(4) Uani 1 1 d . . . H4 H 1.3909 0.0619 0.3686 0.025 Uiso 1 1 calc R . . B5 B 1.3564(2) 0.23372(15) 0.25341(18) 0.0218(4) Uani 1 1 d . . . H5A H 1.4020 0.2882 0.3295 0.026 Uiso 1 1 calc R . . B6 B 1.2091(2) 0.27055(16) 0.13439(18) 0.0250(4) Uani 1 1 d . . . H6A H 1.1563 0.3486 0.1308 0.030 Uiso 1 1 calc R . . B7 B 1.2126(2) 0.06836(18) 0.02707(19) 0.0299(5) Uani 1 1 d . . . H7A H 1.1624 0.0140 -0.0479 0.036 Uiso 1 1 calc R . . B8 B 1.3612(2) 0.03219(16) 0.14468(19) 0.0258(4) Uani 1 1 d . . . H8A H 1.4113 -0.0467 0.1474 0.031 Uiso 1 1 calc R . . B9 B 1.4638(2) 0.14674(15) 0.19347(17) 0.0223(4) Uani 1 1 d . . . H9 H 1.5823 0.1439 0.2287 0.027 Uiso 1 1 calc R . . B10 B 1.3774(2) 0.25414(16) 0.10615(19) 0.0256(4) Uani 1 1 d . . . H10 H 1.4386 0.3221 0.0843 0.031 Uiso 1 1 calc R . . B11 B 1.2230(2) 0.20511(19) 0.00224(19) 0.0307(5) Uani 1 1 d . . . H11 H 1.1801 0.2401 -0.0889 0.037 Uiso 1 1 calc R . . B12 B 1.3804(2) 0.12900(17) 0.03867(18) 0.0260(4) Uani 1 1 d . . . H12 H 1.4435 0.1142 -0.0283 0.031 Uiso 1 1 calc R . . N1 N 1.29376(16) 0.20036(13) 0.64291(13) 0.0273(4) Uani 1 1 d . . . O1 O 0.96300(12) 0.14870(10) 0.26929(11) 0.0254(3) Uani 1 1 d . . . H1 H 0.9041 0.1938 0.2344 0.038 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 C1 0.0172(7) 0.0186(7) 0.0174(8) 0.0009(6) 0.0029(6) 0.0000(6) C2 0.0212(8) 0.0338(10) 0.0191(8) -0.0007(7) 0.0036(7) 0.0000(7) C3 0.0176(8) 0.0204(8) 0.0212(8) 0.0014(6) 0.0048(6) 0.0008(6) C4 0.0143(7) 0.0225(8) 0.0211(8) -0.0005(6) 0.0065(6) 0.0008(6) C5 0.0203(8) 0.0241(8) 0.0215(8) -0.0006(7) 0.0052(6) -0.0017(6) C6 0.0252(9) 0.0275(9) 0.0265(9) 0.0067(7) 0.0067(7) -0.0013(7) C7 0.0221(9) 0.0402(11) 0.0211(8) 0.0033(8) 0.0031(7) -0.0005(7) C8 0.0201(8) 0.0235(8) 0.0247(8) -0.0018(7) 0.0068(7) -0.0010(6) B3 0.0249(10) 0.0190(9) 0.0287(10) -0.0032(8) 0.0078(8) -0.0023(7) B4 0.0177(9) 0.0210(9) 0.0246(9) 0.0029(7) 0.0053(7) 0.0037(7) B5 0.0182(9) 0.0212(9) 0.0264(10) -0.0020(7) 0.0066(7) -0.0031(7) B6 0.0247(10) 0.0244(10) 0.0274(10) 0.0086(8) 0.0094(8) 0.0037(8) B7 0.0265(10) 0.0379(12) 0.0256(10) -0.0107(9) 0.0073(8) -0.0027(9) B8 0.0265(10) 0.0218(9) 0.0306(10) -0.0033(8) 0.0098(8) 0.0008(8) B9 0.0193(9) 0.0238(9) 0.0241(9) -0.0005(8) 0.0063(7) 0.0001(7) B10 0.0261(10) 0.0238(10) 0.0304(10) 0.0058(8) 0.0138(8) 0.0016(7) B11 0.0267(10) 0.0445(13) 0.0218(10) 0.0086(9) 0.0078(8) 0.0052(9) B12 0.0243(10) 0.0318(11) 0.0230(10) 0.0004(8) 0.0080(8) 0.0003(8) N1 0.0225(7) 0.0343(9) 0.0240(8) -0.0045(6) 0.0040(6) -0.0032(6) O1 0.0173(6) 0.0288(7) 0.0283(7) 0.0048(5) 0.0025(5) 0.0003(5) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 C1 C3 1.560(2) . ? C1 C2 1.635(2) . ? C1 B5 1.700(2) . ? C1 B3 1.714(2) . ? C1 B4 1.720(2) . ? C1 B6 1.733(2) . ? C2 B7 1.696(3) . ? C2 B11 1.708(3) . ? C2 B6 1.708(3) . ? C2 B3 1.713(3) . ? C3 O1 1.403(2) . ? C3 C4 1.511(2) . ? C4 C8 1.383(2) . ? C4 C5 1.389(2) . ? C5 C6 1.384(2) . ? C6 C7 1.386(3) . ? C7 N1 1.336(3) . ? C8 N1 1.344(2) . ? B3 B8 1.772(3) . ? B3 B4 1.778(3) . ? B3 B7 1.784(3) . ? B4 B8 1.773(3) . ? B4 B9 1.773(3) . ? B4 B5 1.778(3) . ? B5 B6 1.775(3) . ? B5 B10 1.781(3) . ? B5 B9 1.785(3) . ? B6 B10 1.763(3) . ? B6 B11 1.775(3) . ? B7 B8 1.771(3) . ? B7 B12 1.782(3) . ? B7 B11 1.784(3) . ? B8 B9 1.784(3) . ? B8 B12 1.785(3) . ? B9 B12 1.775(3) . ? B9 B10 1.784(3) . ? B10 B11 1.778(3) . ? B10 B12 1.787(3) . ? B11 B12 1.772(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 C3 C1 C2 116.47(13) . . ? C3 C1 B5 121.60(13) . . ? C2 C1 B5 110.20(13) . . ? C3 C1 B3 117.75(13) . . ? C2 C1 B3 61.46(11) . . ? B5 C1 B3 114.36(13) . . ? C3 C1 B4 124.39(13) . . ? C2 C1 B4 110.28(13) . . ? B5 C1 B4 62.62(11) . . ? B3 C1 B4 62.37(11) . . ? C3 C1 B6 114.34(13) . . ? C2 C1 B6 60.86(11) . . ? B5 C1 B6 62.24(11) . . ? B3 C1 B6 114.17(13) . . ? B4 C1 B6 113.77(13) . . ? C1 C2 B7 112.25(14) . . ? C1 C2 B11 112.51(14) . . ? B7 C2 B11 63.19(13) . . ? C1 C2 B6 62.40(11) . . ? B7 C2 B6 115.31(14) . . ? B11 C2 B6 62.61(12) . . ? C1 C2 B3 61.54(10) . . ? B7 C2 B3 63.08(12) . . ? B11 C2 B3 115.63(14) . . ? B6 C2 B3 115.55(13) . . ? O1 C3 C4 110.12(13) . . ? O1 C3 C1 110.61(13) . . ? C4 C3 C1 110.54(13) . . ? C8 C4 C5 117.99(16) . . ? C8 C4 C3 120.47(15) . . ? C5 C4 C3 121.53(15) . . ? C6 C5 C4 119.21(16) . . ? C5 C6 C7 118.62(17) . . ? N1 C7 C6 123.09(16) . . ? N1 C8 C4 123.59(16) . . ? C2 B3 C1 57.00(10) . . ? C2 B3 B8 103.67(14) . . ? C1 B3 B8 104.89(13) . . ? C2 B3 B4 104.12(13) . . ? C1 B3 B4 58.98(10) . . ? B8 B3 B4 59.91(11) . . ? C2 B3 B7 58.01(11) . . ? C1 B3 B7 104.52(14) . . ? B8 B3 B7 59.75(12) . . ? B4 B3 B7 107.61(14) . . ? C1 B4 B8 104.61(13) . . ? C1 B4 B9 104.73(13) . . ? B8 B4 B9 60.41(11) . . ? C1 B4 B5 58.15(10) . . ? B8 B4 B5 108.29(14) . . ? B9 B4 B5 60.34(11) . . ? C1 B4 B3 58.66(10) . . ? B8 B4 B3 59.87(11) . . ? B9 B4 B3 108.26(14) . . ? B5 B4 B3 107.61(13) . . ? C1 B5 B6 59.79(10) . . ? C1 B5 B4 59.23(10) . . ? B6 B5 B4 109.01(13) . . ? C1 B5 B10 105.47(13) . . ? B6 B5 B10 59.43(11) . . ? B4 B5 B10 108.21(14) . . ? C1 B5 B9 105.07(13) . . ? B6 B5 B9 107.69(14) . . ? B4 B5 B9 59.71(11) . . ? B10 B5 B9 60.04(11) . . ? C2 B6 C1 56.74(10) . . ? C2 B6 B10 104.58(14) . . ? C1 B6 B10 104.86(13) . . ? C2 B6 B5 103.53(13) . . ? C1 B6 B5 57.97(10) . . ? B10 B6 B5 60.45(11) . . ? C2 B6 B11 58.68(12) . . ? C1 B6 B11 104.83(14) . . ? B10 B6 B11 60.34(12) . . ? B5 B6 B11 108.25(14) . . ? C2 B7 B8 104.39(14) . . ? C2 B7 B12 104.11(15) . . ? B8 B7 B12 60.32(12) . . ? C2 B7 B3 58.91(11) . . ? B8 B7 B3 59.79(12) . . ? B12 B7 B3 108.12(14) . . ? C2 B7 B11 58.71(12) . . ? B8 B7 B11 108.13(15) . . ? B12 B7 B11 59.61(12) . . ? B3 B7 B11 108.50(14) . . ? B7 B8 B3 60.46(12) . . ? B7 B8 B4 108.42(14) . . ? B3 B8 B4 60.22(11) . . ? B7 B8 B9 107.86(15) . . ? B3 B8 B9 108.07(13) . . ? B4 B8 B9 59.81(11) . . ? B7 B8 B12 60.15(12) . . ? B3 B8 B12 108.50(14) . . ? B4 B8 B12 107.86(14) . . ? B9 B8 B12 59.66(11) . . ? B4 B9 B12 108.27(13) . . ? B4 B9 B10 108.28(13) . . ? B12 B9 B10 60.26(12) . . ? B4 B9 B8 59.78(11) . . ? B12 B9 B8 60.21(11) . . ? B10 B9 B8 108.24(14) . . ? B4 B9 B5 59.95(11) . . ? B12 B9 B5 107.90(13) . . ? B10 B9 B5 59.88(11) . . ? B8 B9 B5 107.48(13) . . ? B6 B10 B11 60.17(12) . . ? B6 B10 B5 60.11(11) . . ? B11 B10 B5 107.84(14) . . ? B6 B10 B9 108.26(13) . . ? B11 B10 B9 107.54(14) . . ? B5 B10 B9 60.08(11) . . ? B6 B10 B12 107.90(14) . . ? B11 B10 B12 59.64(12) . . ? B5 B10 B12 107.57(14) . . ? B9 B10 B12 59.63(11) . . ? C2 B11 B12 104.05(14) . . ? C2 B11 B6 58.71(11) . . ? B12 B11 B6 107.99(14) . . ? C2 B11 B10 103.95(14) . . ? B12 B11 B10 60.42(12) . . ? B6 B11 B10 59.49(12) . . ? C2 B11 B7 58.09(12) . . ? B12 B11 B7 60.15(12) . . ? B6 B11 B7 107.86(14) . . ? B10 B11 B7 108.22(15) . . ? B11 B12 B9 108.16(14) . . ? B11 B12 B7 60.23(13) . . ? B9 B12 B7 107.74(14) . . ? B11 B12 B8 107.99(14) . . ? B9 B12 B8 60.13(11) . . ? B7 B12 B8 59.53(12) . . ? B11 B12 B10 59.94(12) . . ? B9 B12 B10 60.10(11) . . ? B7 B12 B10 107.90(14) . . ? B8 B12 B10 108.06(14) . . ? C7 N1 C8 117.48(15) . . ? 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 N1 0.84 1.88 2.7104(19) 170.9 4_565 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.349 _refine_diff_density_min -0.281 _refine_diff_density_rms 0.051 # Attachment '2010acc0320_2e.cif' data_2010acc0320 _database_code_depnum_ccdc_archive 'CCDC 816752' #TrackingRef '2010acc0320_2e.cif' _chemical_compound_source 'Jose Giner Planas' _database_code_CSD 0ACC0320 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_absolute_configuration unk _chemical_formula_moiety ? _chemical_formula_sum 'C12 H19 B10 N O' _chemical_formula_weight 301.38 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 Monoclinic _symmetry_space_group_name_H-M P2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 7.2182(2) _cell_length_b 19.7365(4) _cell_length_c 11.3467(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.4040(10) _cell_angle_gamma 90.00 _cell_volume 1616.43(7) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 36927 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.238 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 624 _exptl_absorpt_coefficient_mu 0.066 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9869 _exptl_absorpt_correction_T_max 0.9954 _exptl_absorpt_process_details ; SADABS V2.10 (Sheldrick, G.M., 2003) ; _exptl_special_details ; SADABS was used to perform the Absorption correction Parameter refinement on 16093 reflections reduced R(int) from 0.1554 to 0.0615 Ratio of minimum to maximum apparent transmission: 0.822942 The given Tmin and Tmax were generated using the SHELX SIZE command ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker Nonius FR591 Rotating Anode' _diffrn_radiation_monochromator '10cm confocal mirrors' _diffrn_measurement_device_type 'Bruker-Nonius CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans to fill the asymmetric unit' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15597 _diffrn_reflns_av_R_equivalents 0.0548 _diffrn_reflns_av_sigmaI/netI 0.0494 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.00 _diffrn_reflns_theta_max 27.48 _reflns_number_total 3793 _reflns_number_gt 3494 _reflns_threshold_expression >2\s(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ; Images generated using CrystalMaker: a crystal and molecular structures program for Mac and Windows. CrystalMaker Software Ltd, Oxford, England (www.crystalmaker.com) ; _computing_publication_material 'WINGX (Farrugia, 1998)' _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^ > 2\s(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. The crystal was a pseudo merohedral twin, TWINLAW used: (1 0 0 0 -1 0 0 0 -1), BASF= ca 17% ; _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^)+(0.0294P)^2^+1.0735P] 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 3793 _refine_ls_number_parameters 436 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0619 _refine_ls_R_factor_gt 0.0540 _refine_ls_wR_factor_ref 0.1231 _refine_ls_wR_factor_gt 0.1172 _refine_ls_goodness_of_fit_ref 1.157 _refine_ls_restrained_S_all 1.157 _refine_ls_shift/su_max 0.002 _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 C101 C 0.7160(5) 0.43338(19) -0.0763(3) 0.0181(7) Uani 1 1 d . . . C102 C 0.6527(6) 0.4213(2) -0.2145(3) 0.0221(8) Uani 1 1 d . . . H102 H 0.5309 0.4490 -0.2527 0.027 Uiso 1 1 calc R . . C103 C 0.5990(5) 0.4858(2) -0.0079(3) 0.0201(8) Uani 1 1 d . . . H103 H 0.6700 0.5293 -0.0043 0.024 Uiso 1 1 calc R . . C104 C 0.5624(5) 0.46234(19) 0.1185(3) 0.0195(8) Uani 1 1 d . . . C105 C 0.6971(6) 0.4709(2) 0.2080(3) 0.0229(8) Uani 1 1 d . . . H105 H 0.8159 0.4889 0.1909 0.027 Uiso 1 1 calc R . . C106 C 0.6512(6) 0.4525(2) 0.3201(4) 0.0241(9) Uani 1 1 d . . . H106 H 0.7373 0.4586 0.3829 0.029 Uiso 1 1 calc R . . C107 C 0.4746(5) 0.42432(19) 0.3421(3) 0.0210(8) Uani 1 1 d . . . C108 C 0.4148(6) 0.4050(2) 0.4567(4) 0.0269(9) Uani 1 1 d . . . H108 H 0.4951 0.4108 0.5226 0.032 Uiso 1 1 calc R . . C109 C 0.2431(7) 0.3781(2) 0.4718(4) 0.0307(10) Uani 1 1 d . . . H109 H 0.2036 0.3655 0.5484 0.037 Uiso 1 1 calc R . . C110 C 0.1239(7) 0.3690(2) 0.3748(4) 0.0324(10) Uani 1 1 d . . . H110 H 0.0048 0.3498 0.3866 0.039 Uiso 1 1 calc R . . C111 C 0.1758(6) 0.3872(2) 0.2639(4) 0.0289(9) Uani 1 1 d . . . H111 H 0.0931 0.3808 0.1994 0.035 Uiso 1 1 calc R . . C112 C 0.3522(6) 0.4155(2) 0.2452(3) 0.0218(8) Uani 1 1 d . . . B103 B 0.6076(7) 0.3586(2) -0.1133(4) 0.0229(9) Uani 1 1 d . . . H10A H 0.4663 0.3434 -0.0830 0.028 Uiso 1 1 calc R . . B104 B 0.8040(6) 0.3601(2) -0.0168(4) 0.0213(9) Uani 1 1 d . . . H104 H 0.7925 0.3450 0.0780 0.026 Uiso 1 1 calc R . . B105 B 0.9501(6) 0.4282(2) -0.0614(4) 0.0219(9) Uani 1 1 d . . . H10B H 1.0329 0.4580 0.0043 0.026 Uiso 1 1 calc R . . B106 B 0.8520(7) 0.4674(2) -0.1872(4) 0.0225(9) Uani 1 1 d . . . H10C H 0.8691 0.5228 -0.2051 0.027 Uiso 1 1 calc R . . B107 B 0.6894(7) 0.3398(2) -0.2580(4) 0.0261(10) Uani 1 1 d . . . H107 H 0.6013 0.3116 -0.3231 0.031 Uiso 1 1 calc R . . B108 B 0.7923(7) 0.2999(2) -0.1323(4) 0.0245(10) Uani 1 1 d . . . H10D H 0.7736 0.2445 -0.1145 0.029 Uiso 1 1 calc R . . B109 B 1.0049(7) 0.3427(2) -0.0999(4) 0.0244(10) Uani 1 1 d . . . H10E H 1.1268 0.3156 -0.0605 0.029 Uiso 1 1 calc R . . B110 B 1.0330(7) 0.4091(2) -0.2055(4) 0.0238(9) Uani 1 1 d . . . H11A H 1.1733 0.4256 -0.2356 0.029 Uiso 1 1 calc R . . B111 B 0.8397(7) 0.4069(2) -0.3029(4) 0.0246(9) Uani 1 1 d . . . H11B H 0.8496 0.4225 -0.3976 0.029 Uiso 1 1 calc R . . B112 B 0.9353(7) 0.3299(2) -0.2495(4) 0.0257(10) Uani 1 1 d . . . H112 H 1.0111 0.2942 -0.3089 0.031 Uiso 1 1 calc R . . N101 N 0.3988(5) 0.43582(16) 0.1339(3) 0.0212(7) Uani 1 1 d . . . O101 O 0.4306(4) 0.49807(15) -0.0669(3) 0.0269(6) Uani 1 1 d . . . H101 H 0.3480 0.4727 -0.0393 0.040 Uiso 1 1 calc R . . C201 C -0.2094(6) 0.1177(2) 0.4796(3) 0.0203(8) Uani 1 1 d . . . C202 C -0.1518(6) 0.1337(2) 0.3423(3) 0.0228(8) Uani 1 1 d . . . H202 H -0.0279 0.1087 0.3026 0.027 Uiso 1 1 calc R . . C203 C -0.0851(6) 0.0663(2) 0.5459(4) 0.0243(9) Uani 1 1 d . . . H203 H -0.1507 0.0216 0.5462 0.029 Uiso 1 1 calc R . . C204 C -0.0536(6) 0.08760(19) 0.6738(3) 0.0216(8) Uani 1 1 d . . . C205 C -0.1902(6) 0.0774(2) 0.7609(4) 0.0235(8) Uani 1 1 d . . . H205 H -0.3067 0.0580 0.7411 0.028 Uiso 1 1 calc R . . C206 C -0.1507(6) 0.0961(2) 0.8739(4) 0.0243(8) Uani 1 1 d . . . H206 H -0.2393 0.0892 0.9342 0.029 Uiso 1 1 calc R . . C207 C 0.0222(6) 0.1259(2) 0.9011(4) 0.0231(8) Uani 1 1 d . . . C208 C 0.0725(6) 0.1468(2) 1.0166(4) 0.0259(9) Uani 1 1 d . . . H208 H -0.0121 0.1412 1.0796 0.031 Uiso 1 1 calc R . . C209 C 0.2433(7) 0.1752(2) 1.0373(4) 0.0298(10) Uani 1 1 d . . . H209 H 0.2763 0.1893 1.1147 0.036 Uiso 1 1 calc R . . C210 C 0.3700(6) 0.1836(2) 0.9444(4) 0.0305(10) Uani 1 1 d . . . H210 H 0.4880 0.2030 0.9602 0.037 Uiso 1 1 calc R . . C211 C 0.3259(6) 0.1642(2) 0.8323(4) 0.0283(9) Uani 1 1 d . . . H211 H 0.4129 0.1700 0.7707 0.034 Uiso 1 1 calc R . . C212 C 0.1505(6) 0.1356(2) 0.8083(3) 0.0232(8) Uani 1 1 d . . . B203 B -0.1113(6) 0.1951(2) 0.4469(4) 0.0197(9) Uani 1 1 d . . . H20A H 0.0286 0.2120 0.4784 0.024 Uiso 1 1 calc R . . B204 B -0.3036(6) 0.1879(2) 0.5427(4) 0.0191(8) Uani 1 1 d . . . H204 H -0.2910 0.2009 0.6385 0.023 Uiso 1 1 calc R . . B205 B -0.4447(6) 0.1194(2) 0.4936(4) 0.0224(9) Uani 1 1 d . . . H20B H -0.5241 0.0873 0.5570 0.027 Uiso 1 1 calc R . . B206 B -0.3420(7) 0.0839(2) 0.3654(4) 0.0245(10) Uani 1 1 d . . . H20C H -0.3516 0.0286 0.3439 0.029 Uiso 1 1 calc R . . B207 B -0.1968(7) 0.2149(2) 0.3043(4) 0.0241(9) Uani 1 1 d . . . H207 H -0.1125 0.2456 0.2414 0.029 Uiso 1 1 calc R . . B208 B -0.3005(7) 0.2506(2) 0.4306(4) 0.0237(9) Uani 1 1 d . . . H20D H -0.2869 0.3059 0.4513 0.028 Uiso 1 1 calc R . . B209 B -0.5097(7) 0.2045(2) 0.4611(4) 0.0248(10) Uani 1 1 d . . . H20E H -0.6333 0.2291 0.5022 0.030 Uiso 1 1 calc R . . B210 B -0.5323(7) 0.1397(3) 0.3503(4) 0.0266(10) Uani 1 1 d . . . H21A H -0.6710 0.1216 0.3186 0.032 Uiso 1 1 calc R . . B211 B -0.3393(7) 0.1466(2) 0.2540(4) 0.0247(9) Uani 1 1 d . . . H21B H -0.3485 0.1328 0.1584 0.030 Uiso 1 1 calc R . . B212 B -0.4428(7) 0.2213(2) 0.3120(4) 0.0265(10) Uani 1 1 d . . . H212 H -0.5233 0.2572 0.2548 0.032 Uiso 1 1 calc R . . N201 N 0.1091(5) 0.11567(17) 0.6945(3) 0.0241(7) Uani 1 1 d . . . O201 O 0.0832(4) 0.05748(16) 0.4884(3) 0.0301(7) Uani 1 1 d . . . H201 H 0.1660 0.0798 0.5234 0.045 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 C101 0.0146(17) 0.0190(18) 0.0207(17) 0.0005(15) 0.0005(14) -0.0002(14) C102 0.026(2) 0.0232(19) 0.0177(17) -0.0023(16) -0.0006(15) -0.0003(17) C103 0.0189(19) 0.0204(19) 0.0211(18) -0.0001(15) 0.0007(15) -0.0005(15) C104 0.0182(18) 0.0182(18) 0.0221(18) -0.0025(15) 0.0022(15) 0.0011(15) C105 0.022(2) 0.023(2) 0.0245(19) -0.0040(15) 0.0033(16) -0.0030(16) C106 0.025(2) 0.024(2) 0.0227(19) -0.0054(15) -0.0010(16) 0.0003(17) C107 0.0208(19) 0.0177(17) 0.0245(18) 0.0005(15) 0.0031(15) 0.0022(15) C108 0.030(2) 0.026(2) 0.024(2) 0.0020(17) -0.0001(17) 0.0097(18) C109 0.036(3) 0.026(2) 0.031(2) 0.0057(18) 0.0122(19) 0.0033(19) C110 0.029(2) 0.030(2) 0.038(2) 0.001(2) 0.009(2) -0.0029(19) C111 0.023(2) 0.030(2) 0.034(2) 0.0028(17) -0.0010(18) -0.0014(18) C112 0.023(2) 0.0184(18) 0.0238(18) -0.0008(15) 0.0041(16) 0.0021(15) B103 0.026(2) 0.016(2) 0.026(2) -0.0012(18) 0.0024(19) -0.0020(17) B104 0.022(2) 0.018(2) 0.024(2) 0.0049(17) 0.0003(18) 0.0017(17) B105 0.019(2) 0.023(2) 0.023(2) -0.0010(18) -0.0025(17) -0.0028(18) B106 0.027(2) 0.023(2) 0.0173(19) 0.0021(17) 0.0025(17) -0.0032(19) B107 0.031(3) 0.022(2) 0.026(2) -0.0061(18) 0.004(2) -0.0008(19) B108 0.022(2) 0.020(2) 0.032(2) -0.0005(19) 0.0064(19) -0.0016(18) B109 0.023(2) 0.022(2) 0.028(2) 0.0035(18) 0.0072(19) 0.0032(18) B110 0.020(2) 0.026(2) 0.025(2) -0.0005(18) 0.0056(18) -0.0018(18) B111 0.026(2) 0.026(2) 0.021(2) -0.0039(18) 0.0051(18) 0.0003(19) B112 0.024(2) 0.023(2) 0.029(2) -0.0022(19) 0.009(2) 0.0029(18) N101 0.0217(17) 0.0193(16) 0.0225(15) -0.0005(13) -0.0022(13) 0.0030(13) O101 0.0242(15) 0.0301(16) 0.0263(14) 0.0022(12) 0.0009(12) 0.0075(13) C201 0.022(2) 0.0203(18) 0.0182(17) -0.0042(15) 0.0001(15) 0.0029(16) C202 0.029(2) 0.0203(19) 0.0194(17) -0.0038(15) 0.0034(16) -0.0015(16) C203 0.027(2) 0.0196(19) 0.026(2) -0.0024(16) -0.0010(17) 0.0032(16) C204 0.024(2) 0.0153(17) 0.0256(19) 0.0025(15) -0.0020(16) 0.0031(15) C205 0.022(2) 0.0210(19) 0.028(2) 0.0044(16) 0.0037(17) -0.0022(16) C206 0.022(2) 0.024(2) 0.027(2) 0.0047(16) 0.0026(17) 0.0011(16) C207 0.025(2) 0.0194(19) 0.0247(19) 0.0046(16) 0.0016(16) 0.0046(16) C208 0.028(2) 0.027(2) 0.023(2) 0.0030(16) 0.0004(17) 0.0005(18) C209 0.039(3) 0.026(2) 0.024(2) -0.0016(17) -0.0060(18) 0.0012(19) C210 0.025(2) 0.029(2) 0.038(2) 0.0030(19) -0.0080(19) -0.0048(18) C211 0.023(2) 0.028(2) 0.033(2) 0.0053(18) 0.0032(18) 0.0008(17) C212 0.021(2) 0.0199(19) 0.028(2) 0.0025(16) -0.0022(16) 0.0030(15) B203 0.018(2) 0.022(2) 0.0197(19) -0.0016(16) 0.0003(17) -0.0007(16) B204 0.019(2) 0.0169(19) 0.022(2) -0.0018(16) 0.0002(17) -0.0006(16) B205 0.014(2) 0.025(2) 0.028(2) 0.0010(18) -0.0027(18) -0.0028(17) B206 0.026(2) 0.021(2) 0.027(2) -0.0025(18) -0.0073(19) -0.0004(19) B207 0.026(2) 0.024(2) 0.023(2) 0.0002(17) 0.0035(19) -0.0014(19) B208 0.022(2) 0.021(2) 0.028(2) 0.0036(18) 0.0021(19) -0.0002(17) B209 0.017(2) 0.027(2) 0.031(2) 0.0034(19) 0.0027(19) 0.0003(18) B210 0.024(2) 0.028(2) 0.028(2) 0.000(2) -0.0049(19) -0.002(2) B211 0.024(2) 0.027(2) 0.022(2) -0.0021(18) -0.0029(19) -0.005(2) B212 0.025(2) 0.028(2) 0.026(2) 0.0031(19) -0.0038(19) -0.001(2) N201 0.0240(18) 0.0232(17) 0.0252(17) 0.0031(14) 0.0036(14) 0.0027(14) O201 0.0253(16) 0.0346(17) 0.0305(16) -0.0050(13) 0.0027(13) 0.0073(13) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 C101 C103 1.548(5) . ? C101 C102 1.647(5) . ? C101 B105 1.700(6) . ? C101 B104 1.716(6) . ? C101 B103 1.722(6) . ? C101 B106 1.736(6) . ? C102 B107 1.703(6) . ? C102 B111 1.712(6) . ? C102 B103 1.721(6) . ? C102 B106 1.728(6) . ? C103 O101 1.405(5) . ? C103 C104 1.532(5) . ? C104 N101 1.304(5) . ? C104 C105 1.412(6) . ? C105 C106 1.366(6) . ? C106 C107 1.415(6) . ? C107 C112 1.416(6) . ? C107 C108 1.425(5) . ? C108 C109 1.360(6) . ? C109 C110 1.404(7) . ? C110 C111 1.363(6) . ? C111 C112 1.408(6) . ? C112 N101 1.369(5) . ? B103 B108 1.780(7) . ? B103 B104 1.786(7) . ? B103 B107 1.787(6) . ? B104 B109 1.769(7) . ? B104 B108 1.772(7) . ? B104 B105 1.783(6) . ? B105 B106 1.767(6) . ? B105 B110 1.785(6) . ? B105 B109 1.787(7) . ? B106 B110 1.754(7) . ? B106 B111 1.775(6) . ? B107 B108 1.787(7) . ? B107 B112 1.787(7) . ? B107 B111 1.788(7) . ? B108 B109 1.788(7) . ? B108 B112 1.790(7) . ? B109 B112 1.785(7) . ? B109 B110 1.787(7) . ? B110 B111 1.774(7) . ? B110 B112 1.783(7) . ? B111 B112 1.774(7) . ? C201 C203 1.546(6) . ? C201 C202 1.646(5) . ? C201 B204 1.704(6) . ? C201 B205 1.707(6) . ? C201 B203 1.725(6) . ? C201 B206 1.738(6) . ? C202 B207 1.690(6) . ? C202 B211 1.697(6) . ? C202 B206 1.710(6) . ? C202 B203 1.719(6) . ? C203 O201 1.394(5) . ? C203 C204 1.527(5) . ? C204 N201 1.318(5) . ? C204 C205 1.415(6) . ? C205 C206 1.362(6) . ? C206 C207 1.412(6) . ? C207 C208 1.419(6) . ? C207 C212 1.420(6) . ? C208 C209 1.373(6) . ? C209 C210 1.410(6) . ? C210 C211 1.363(6) . ? C211 C212 1.411(6) . ? C212 N201 1.380(5) . ? B203 B208 1.760(6) . ? B203 B207 1.772(6) . ? B203 B204 1.775(6) . ? B204 B208 1.775(6) . ? B204 B209 1.777(7) . ? B204 B205 1.779(6) . ? B205 B206 1.782(7) . ? B205 B209 1.782(7) . ? B205 B210 1.786(7) . ? B206 B210 1.768(7) . ? B206 B211 1.770(7) . ? B207 B208 1.768(7) . ? B207 B212 1.783(7) . ? B207 B211 1.786(7) . ? B208 B212 1.783(7) . ? B208 B209 1.799(7) . ? B209 B212 1.794(7) . ? B209 B210 1.801(7) . ? B210 B211 1.782(7) . ? B210 B212 1.791(7) . ? B211 B212 1.781(7) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C103 C101 C102 115.2(3) . . ? C103 C101 B105 122.4(3) . . ? C102 C101 B105 110.8(3) . . ? C103 C101 B104 124.6(3) . . ? C102 C101 B104 110.6(3) . . ? B105 C101 B104 62.9(3) . . ? C103 C101 B103 116.6(3) . . ? C102 C101 B103 61.4(2) . . ? B105 C101 B103 114.9(3) . . ? B104 C101 B103 62.6(3) . . ? C103 C101 B106 114.7(3) . . ? C102 C101 B106 61.3(2) . . ? B105 C101 B106 61.9(3) . . ? B104 C101 B106 113.6(3) . . ? B103 C101 B106 114.4(3) . . ? C101 C102 B107 111.7(3) . . ? C101 C102 B111 111.5(3) . . ? B107 C102 B111 63.2(3) . . ? C101 C102 B103 61.4(2) . . ? B107 C102 B103 62.9(3) . . ? B111 C102 B103 115.2(3) . . ? C101 C102 B106 61.9(2) . . ? B107 C102 B106 114.7(3) . . ? B111 C102 B106 62.1(3) . . ? B103 C102 B106 114.8(3) . . ? O101 C103 C104 110.1(3) . . ? O101 C103 C101 110.5(3) . . ? C104 C103 C101 111.5(3) . . ? N101 C104 C105 124.9(4) . . ? N101 C104 C103 114.1(3) . . ? C105 C104 C103 121.0(3) . . ? C106 C105 C104 117.9(4) . . ? C105 C106 C107 119.6(4) . . ? C106 C107 C112 118.0(4) . . ? C106 C107 C108 123.0(4) . . ? C112 C107 C108 119.0(4) . . ? C109 C108 C107 120.1(4) . . ? C108 C109 C110 120.4(4) . . ? C111 C110 C109 121.2(4) . . ? C110 C111 C112 119.9(4) . . ? N101 C112 C111 118.9(4) . . ? N101 C112 C107 121.6(4) . . ? C111 C112 C107 119.5(4) . . ? C102 B103 C101 57.2(2) . . ? C102 B103 B108 104.0(3) . . ? C101 B103 B108 104.4(3) . . ? C102 B103 B104 104.1(3) . . ? C101 B103 B104 58.5(2) . . ? B108 B103 B104 59.6(3) . . ? C102 B103 B107 58.1(2) . . ? C101 B103 B107 104.4(3) . . ? B108 B103 B107 60.1(3) . . ? B104 B103 B107 107.5(3) . . ? C101 B104 B109 104.8(3) . . ? C101 B104 B108 105.0(3) . . ? B109 B104 B108 60.7(3) . . ? C101 B104 B105 58.1(2) . . ? B109 B104 B105 60.4(3) . . ? B108 B104 B105 108.7(3) . . ? C101 B104 B103 58.9(2) . . ? B109 B104 B103 108.6(3) . . ? B108 B104 B103 60.1(3) . . ? B105 B104 B103 107.9(3) . . ? C101 B105 B106 60.1(2) . . ? C101 B105 B104 59.0(2) . . ? B106 B105 B104 109.0(3) . . ? C101 B105 B110 105.1(3) . . ? B106 B105 B110 59.2(3) . . ? B104 B105 B110 107.7(3) . . ? C101 B105 B109 104.7(3) . . ? B106 B105 B109 107.7(3) . . ? B104 B105 B109 59.4(3) . . ? B110 B105 B109 60.0(3) . . ? C102 B106 C101 56.8(2) . . ? C102 B106 B110 104.7(3) . . ? C101 B106 B110 104.9(3) . . ? C102 B106 B105 104.0(3) . . ? C101 B106 B105 58.0(2) . . ? B110 B106 B105 60.9(3) . . ? C102 B106 B111 58.5(2) . . ? C101 B106 B111 104.5(3) . . ? B110 B106 B111 60.3(3) . . ? B105 B106 B111 108.7(3) . . ? C102 B107 B108 104.5(3) . . ? C102 B107 B103 59.0(2) . . ? B108 B107 B103 59.8(3) . . ? C102 B107 B112 104.1(3) . . ? B108 B107 B112 60.1(3) . . ? B103 B107 B112 107.9(3) . . ? C102 B107 B111 58.7(2) . . ? B108 B107 B111 107.7(3) . . ? B103 B107 B111 108.3(3) . . ? B112 B107 B111 59.5(3) . . ? B104 B108 B103 60.4(3) . . ? B104 B108 B107 108.2(3) . . ? B103 B108 B107 60.1(3) . . ? B104 B108 B109 59.6(3) . . ? B103 B108 B109 108.0(3) . . ? B107 B108 B109 107.8(3) . . ? B104 B108 B112 107.6(3) . . ? B103 B108 B112 108.1(3) . . ? B107 B108 B112 60.0(3) . . ? B109 B108 B112 59.8(3) . . ? B104 B109 B112 108.0(3) . . ? B104 B109 B105 60.2(3) . . ? B112 B109 B105 107.7(3) . . ? B104 B109 B110 108.2(3) . . ? B112 B109 B110 59.9(3) . . ? B105 B109 B110 59.9(3) . . ? B104 B109 B108 59.7(3) . . ? B112 B109 B108 60.2(3) . . ? B105 B109 B108 107.8(3) . . ? B110 B109 B108 108.1(3) . . ? B106 B110 B111 60.4(3) . . ? B106 B110 B112 108.3(3) . . ? B111 B110 B112 59.8(3) . . ? B106 B110 B105 59.9(3) . . ? B111 B110 B105 108.0(3) . . ? B112 B110 B105 107.9(3) . . ? B106 B110 B109 108.2(3) . . ? B111 B110 B109 107.9(3) . . ? B112 B110 B109 60.0(3) . . ? B105 B110 B109 60.0(3) . . ? C102 B111 B112 104.4(3) . . ? C102 B111 B110 104.5(3) . . ? B112 B111 B110 60.3(3) . . ? C102 B111 B106 59.4(2) . . ? B112 B111 B106 107.8(3) . . ? B110 B111 B106 59.2(3) . . ? C102 B111 B107 58.2(3) . . ? B112 B111 B107 60.2(3) . . ? B110 B111 B107 108.4(3) . . ? B106 B111 B107 108.3(3) . . ? B111 B112 B110 59.8(3) . . ? B111 B112 B109 108.0(3) . . ? B110 B112 B109 60.1(3) . . ? B111 B112 B107 60.3(3) . . ? B110 B112 B107 108.0(3) . . ? B109 B112 B107 108.0(3) . . ? B111 B112 B108 108.2(3) . . ? B110 B112 B108 108.1(3) . . ? B109 B112 B108 60.0(3) . . ? B107 B112 B108 59.9(3) . . ? C104 N101 C112 118.0(3) . . ? C203 C201 C202 115.9(3) . . ? C203 C201 B204 124.1(3) . . ? C202 C201 B204 110.2(3) . . ? C203 C201 B205 122.8(3) . . ? C202 C201 B205 110.0(3) . . ? B204 C201 B205 62.9(3) . . ? C203 C201 B203 116.6(3) . . ? C202 C201 B203 61.3(2) . . ? B204 C201 B203 62.3(2) . . ? B205 C201 B203 114.4(3) . . ? C203 C201 B206 115.2(3) . . ? C202 C201 B206 60.6(2) . . ? B204 C201 B206 114.0(3) . . ? B205 C201 B206 62.3(3) . . ? B203 C201 B206 113.8(3) . . ? C201 C202 B207 112.0(3) . . ? C201 C202 B211 112.5(3) . . ? B207 C202 B211 63.6(3) . . ? C201 C202 B206 62.4(3) . . ? B207 C202 B206 115.6(3) . . ? B211 C202 B206 62.6(3) . . ? C201 C202 B203 61.6(2) . . ? B207 C202 B203 62.6(3) . . ? B211 C202 B203 115.7(3) . . ? B206 C202 B203 115.6(3) . . ? O201 C203 C204 110.8(3) . . ? O201 C203 C201 111.0(3) . . ? C204 C203 C201 111.3(3) . . ? N201 C204 C205 124.0(4) . . ? N201 C204 C203 114.3(4) . . ? C205 C204 C203 121.7(4) . . ? C206 C205 C204 118.4(4) . . ? C205 C206 C207 119.9(4) . . ? C206 C207 C208 122.9(4) . . ? C206 C207 C212 118.3(4) . . ? C208 C207 C212 118.8(4) . . ? C209 C208 C207 120.0(4) . . ? C208 C209 C210 120.4(4) . . ? C211 C210 C209 121.1(4) . . ? C210 C211 C212 119.7(4) . . ? N201 C212 C211 118.9(4) . . ? N201 C212 C207 121.1(4) . . ? C211 C212 C207 120.0(4) . . ? C202 B203 C201 57.1(2) . . ? C202 B203 B208 103.8(3) . . ? C201 B203 B208 104.8(3) . . ? C202 B203 B207 57.9(2) . . ? C201 B203 B207 104.5(3) . . ? B208 B203 B207 60.1(3) . . ? C202 B203 B204 103.7(3) . . ? C201 B203 B204 58.2(2) . . ? B208 B203 B204 60.3(2) . . ? B207 B203 B204 107.9(3) . . ? C201 B204 B203 59.4(2) . . ? C201 B204 B208 105.0(3) . . ? B203 B204 B208 59.4(3) . . ? C201 B204 B209 105.5(3) . . ? B203 B204 B209 108.8(3) . . ? B208 B204 B209 60.8(3) . . ? C201 B204 B205 58.7(2) . . ? B203 B204 B205 108.5(3) . . ? B208 B204 B205 108.4(3) . . ? B209 B204 B205 60.2(3) . . ? C201 B205 B204 58.5(2) . . ? C201 B205 B206 59.7(2) . . ? B204 B205 B206 108.3(3) . . ? C201 B205 B209 105.1(3) . . ? B204 B205 B209 59.9(3) . . ? B206 B205 B209 108.2(3) . . ? C201 B205 B210 105.4(3) . . ? B204 B205 B210 108.2(3) . . ? B206 B205 B210 59.4(3) . . ? B209 B205 B210 60.6(3) . . ? C202 B206 C201 57.0(2) . . ? C202 B206 B210 104.5(3) . . ? C201 B206 B210 104.8(3) . . ? C202 B206 B211 58.4(3) . . ? C201 B206 B211 104.8(3) . . ? B210 B206 B211 60.5(3) . . ? C202 B206 B205 103.7(3) . . ? C201 B206 B205 58.0(2) . . ? B210 B206 B205 60.4(3) . . ? B211 B206 B205 108.3(3) . . ? C202 B207 B208 104.7(3) . . ? C202 B207 B203 59.5(2) . . ? B208 B207 B203 59.6(3) . . ? C202 B207 B212 104.1(3) . . ? B208 B207 B212 60.3(3) . . ? B203 B207 B212 108.1(3) . . ? C202 B207 B211 58.4(3) . . ? B208 B207 B211 108.3(3) . . ? B203 B207 B211 108.8(3) . . ? B212 B207 B211 59.9(3) . . ? B203 B208 B207 60.3(3) . . ? B203 B208 B204 60.3(3) . . ? B207 B208 B204 108.1(3) . . ? B203 B208 B212 108.6(3) . . ? B207 B208 B212 60.3(3) . . ? B204 B208 B212 107.7(3) . . ? B203 B208 B209 108.4(3) . . ? B207 B208 B209 108.4(3) . . ? B204 B208 B209 59.6(3) . . ? B212 B208 B209 60.1(3) . . ? B204 B209 B205 60.0(2) . . ? B204 B209 B212 107.2(3) . . ? B205 B209 B212 107.3(3) . . ? B204 B209 B208 59.5(3) . . ? B205 B209 B208 107.3(3) . . ? B212 B209 B208 59.5(3) . . ? B204 B209 B210 107.7(3) . . ? B205 B209 B210 59.8(3) . . ? B212 B209 B210 59.8(3) . . ? B208 B209 B210 107.3(3) . . ? B206 B210 B211 59.8(3) . . ? B206 B210 B205 60.2(3) . . ? B211 B210 B205 107.6(3) . . ? B206 B210 B212 107.6(3) . . ? B211 B210 B212 59.8(3) . . ? B205 B210 B212 107.2(3) . . ? B206 B210 B209 108.0(3) . . ? B211 B210 B209 107.8(3) . . ? B205 B210 B209 59.6(3) . . ? B212 B210 B209 59.9(3) . . ? C202 B211 B206 59.1(3) . . ? C202 B211 B212 103.9(3) . . ? B206 B211 B212 108.0(3) . . ? C202 B211 B210 104.4(3) . . ? B206 B211 B210 59.7(3) . . ? B212 B211 B210 60.3(3) . . ? C202 B211 B207 58.0(3) . . ? B206 B211 B207 108.0(3) . . ? B212 B211 B207 60.0(3) . . ? B210 B211 B207 108.2(3) . . ? B211 B212 B207 60.2(3) . . ? B211 B212 B208 107.9(3) . . ? B207 B212 B208 59.4(3) . . ? B211 B212 B210 59.9(3) . . ? B207 B212 B210 108.0(3) . . ? B208 B212 B210 108.4(3) . . ? B211 B212 B209 108.2(3) . . ? B207 B212 B209 107.9(3) . . ? B208 B212 B209 60.4(3) . . ? B210 B212 B209 60.3(3) . . ? C204 N201 C212 118.2(3) . . ? 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 O101 H101 N101 0.84 2.13 2.600(4) 115.5 . O201 H201 N201 0.84 2.11 2.611(5) 117.9 . _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.235 _refine_diff_density_min -0.230 _refine_diff_density_rms 0.051 # Attachment '2010acc0322_2f.cif' data_2010acc0322 _database_code_depnum_ccdc_archive 'CCDC 816753' #TrackingRef '2010acc0322_2f.cif' _chemical_compound_source 'Jose Giner Planas' _database_code_CSD 0ACC0322 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H19 B10 N O' _chemical_formula_weight 301.38 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 0.0016 '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 C2/c 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 25.8502(4) _cell_length_b 9.7968(2) _cell_length_c 12.8393(2) _cell_angle_alpha 90.00 _cell_angle_beta 96.4100(10) _cell_angle_gamma 90.00 _cell_volume 3231.22(10) _cell_formula_units_Z 8 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 23727 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description Fragment _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.239 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1248 _exptl_absorpt_coefficient_mu 0.066 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9855 _exptl_absorpt_correction_T_max 0.9882 _exptl_absorpt_process_details ; SADABS V2.10 (Sheldrick, G.M., 2003) ; _exptl_special_details ; ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker Nonius FR591 Rotating Anode' _diffrn_radiation_monochromator '10cm confocal mirrors' _diffrn_measurement_device_type 'Bruker-Nonius CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans to fill the asymmetric unit' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15346 _diffrn_reflns_av_R_equivalents 0.0463 _diffrn_reflns_av_sigmaI/netI 0.0359 _diffrn_reflns_limit_h_min -30 _diffrn_reflns_limit_h_max 30 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.16 _diffrn_reflns_theta_max 25.03 _reflns_number_total 2848 _reflns_number_gt 2407 _reflns_threshold_expression >2\s(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ; Images generated using CrystalMaker: a crystal and molecular structures program for Mac and Windows. CrystalMaker Software Ltd, Oxford, England (www.crystalmaker.com) ; _computing_publication_material 'WINGX (Farrugia, 1998)' _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^ > 2\s(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^)+(0.0723P)^2^+7.1722P] 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 2848 _refine_ls_number_parameters 218 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0669 _refine_ls_R_factor_gt 0.0553 _refine_ls_wR_factor_ref 0.1516 _refine_ls_wR_factor_gt 0.1406 _refine_ls_goodness_of_fit_ref 0.998 _refine_ls_restrained_S_all 0.998 _refine_ls_shift/su_max 0.020 _refine_ls_shift/su_mean 0.004 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.13868(6) 0.18568(15) 0.20831(11) 0.0257(4) Uani 1 1 d . . . H1 H 0.1198 0.1314 0.1704 0.039 Uiso 1 1 calc R . . N1 N 0.10494(7) -0.00299(17) 0.55975(14) 0.0230(4) Uani 1 1 d . . . C1 C 0.13828(7) 0.3818(2) 0.31483(14) 0.0165(4) Uani 1 1 d . . . C2 C 0.18637(8) 0.4275(2) 0.24691(16) 0.0220(5) Uani 1 1 d . . . H2 H 0.1971 0.3621 0.1810 0.026 Uiso 1 1 calc R . . C3 C 0.10955(7) 0.2464(2) 0.28054(15) 0.0187(4) Uani 1 1 d . . . H3 H 0.0740 0.2684 0.2454 0.022 Uiso 1 1 calc R . . C4 C 0.10449(7) 0.1553(2) 0.37555(15) 0.0179(4) Uani 1 1 d . . . C5 C 0.14120(8) 0.0562(2) 0.40106(16) 0.0208(5) Uani 1 1 d . . . H5 H 0.1674 0.0392 0.3565 0.025 Uiso 1 1 calc R . . C6 C 0.13988(8) -0.0202(2) 0.49351(17) 0.0223(5) Uani 1 1 d . . . H6 H 0.1657 -0.0883 0.5092 0.027 Uiso 1 1 calc R . . C7 C 0.06654(7) 0.0919(2) 0.53456(15) 0.0201(4) Uani 1 1 d . . . C8 C 0.02870(8) 0.1090(2) 0.60510(16) 0.0261(5) Uani 1 1 d . . . H8 H 0.0309 0.0566 0.6677 0.031 Uiso 1 1 calc R . . C9 C -0.01093(8) 0.2001(2) 0.58375(18) 0.0291(5) Uani 1 1 d . . . H9 H -0.0359 0.2119 0.6319 0.035 Uiso 1 1 calc R . . C10 C -0.01489(8) 0.2769(2) 0.49032(18) 0.0279(5) Uani 1 1 d . . . H10 H -0.0431 0.3385 0.4750 0.033 Uiso 1 1 calc R . . C11 C 0.02147(8) 0.2634(2) 0.42175(16) 0.0223(5) Uani 1 1 d . . . H11 H 0.0183 0.3165 0.3594 0.027 Uiso 1 1 calc R . . C12 C 0.06390(7) 0.17198(19) 0.44143(15) 0.0183(4) Uani 1 1 d . . . B3 B 0.20168(8) 0.3665(2) 0.37196(18) 0.0208(5) Uani 1 1 d . . . H3A H 0.2215 0.2670 0.3927 0.025 Uiso 1 1 calc R . . B4 B 0.15147(9) 0.4324(2) 0.44188(17) 0.0188(5) Uani 1 1 d . . . H4 H 0.1382 0.3764 0.5102 0.023 Uiso 1 1 calc R . . B5 B 0.10690(9) 0.5238(2) 0.35194(18) 0.0206(5) Uani 1 1 d . . . H5A H 0.0644 0.5278 0.3611 0.025 Uiso 1 1 calc R . . B6 B 0.12914(9) 0.5154(2) 0.22589(18) 0.0218(5) Uani 1 1 d . . . H6A H 0.1019 0.5121 0.1518 0.026 Uiso 1 1 calc R . . B7 B 0.23504(9) 0.5074(3) 0.32235(19) 0.0239(5) Uani 1 1 d . . . H7 H 0.2773 0.5006 0.3110 0.029 Uiso 1 1 calc R . . B8 B 0.21301(9) 0.5158(2) 0.44913(19) 0.0236(5) Uani 1 1 d . . . H8A H 0.2407 0.5160 0.5227 0.028 Uiso 1 1 calc R . . B9 B 0.15429(9) 0.6137(2) 0.43703(19) 0.0230(5) Uani 1 1 d . . . H9A H 0.1433 0.6787 0.5029 0.028 Uiso 1 1 calc R . . B10 B 0.14019(10) 0.6653(2) 0.30276(19) 0.0251(5) Uani 1 1 d . . . H10A H 0.1199 0.7636 0.2800 0.030 Uiso 1 1 calc R . . B11 B 0.19043(10) 0.5995(3) 0.23340(19) 0.0252(5) Uani 1 1 d . . . H11A H 0.2035 0.6535 0.1640 0.030 Uiso 1 1 calc R . . B12 B 0.20614(10) 0.6603(2) 0.36328(18) 0.0241(5) Uani 1 1 d . . . H12 H 0.2294 0.7557 0.3806 0.029 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0295(8) 0.0267(8) 0.0220(8) -0.0093(6) 0.0078(6) -0.0062(6) N1 0.0229(9) 0.0212(9) 0.0245(9) 0.0024(7) 0.0016(7) -0.0009(7) C1 0.0169(9) 0.0193(10) 0.0135(9) -0.0001(8) 0.0033(7) -0.0009(8) C2 0.0217(10) 0.0261(11) 0.0195(10) -0.0037(9) 0.0073(8) -0.0059(9) C3 0.0186(9) 0.0200(10) 0.0176(10) -0.0038(8) 0.0026(7) -0.0021(8) C4 0.0189(10) 0.0174(10) 0.0168(10) -0.0038(8) -0.0003(8) -0.0053(8) C5 0.0205(10) 0.0184(10) 0.0236(11) -0.0029(8) 0.0032(8) -0.0008(8) C6 0.0204(10) 0.0158(10) 0.0305(12) -0.0004(8) 0.0016(8) 0.0021(8) C7 0.0206(10) 0.0186(10) 0.0212(10) -0.0001(8) 0.0022(8) -0.0019(8) C8 0.0310(11) 0.0273(12) 0.0208(11) 0.0032(9) 0.0068(9) -0.0040(9) C9 0.0258(11) 0.0317(12) 0.0320(12) 0.0005(10) 0.0127(9) 0.0008(9) C10 0.0211(10) 0.0266(11) 0.0371(13) 0.0014(10) 0.0084(9) 0.0037(9) C11 0.0207(10) 0.0221(11) 0.0239(11) 0.0038(9) 0.0025(8) -0.0023(8) C12 0.0177(9) 0.0179(10) 0.0190(10) -0.0023(8) 0.0008(8) -0.0039(8) B3 0.0170(11) 0.0241(12) 0.0211(12) -0.0018(10) 0.0008(9) -0.0026(9) B4 0.0235(11) 0.0176(11) 0.0152(11) -0.0019(9) 0.0023(9) -0.0037(9) B5 0.0214(11) 0.0183(11) 0.0230(12) 0.0000(9) 0.0064(9) 0.0001(9) B6 0.0233(12) 0.0233(12) 0.0189(12) 0.0041(10) 0.0032(9) -0.0026(9) B7 0.0220(12) 0.0259(12) 0.0247(13) -0.0041(10) 0.0066(10) -0.0071(10) B8 0.0232(12) 0.0248(13) 0.0225(12) -0.0029(10) 0.0018(9) -0.0069(10) B9 0.0292(12) 0.0191(12) 0.0218(12) -0.0038(9) 0.0074(10) -0.0059(10) B10 0.0296(13) 0.0195(12) 0.0266(13) 0.0022(10) 0.0054(10) -0.0020(10) B11 0.0306(13) 0.0251(13) 0.0207(12) -0.0012(10) 0.0061(10) -0.0090(10) B12 0.0290(12) 0.0243(12) 0.0197(12) -0.0038(10) 0.0058(10) -0.0062(10) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C3 1.392(2) . ? N1 C6 1.319(3) . ? N1 C7 1.372(3) . ? C1 C3 1.559(3) . ? C1 C2 1.658(3) . ? C1 B4 1.702(3) . ? C1 B5 1.705(3) . ? C1 B3 1.726(3) . ? C1 B6 1.735(3) . ? C2 B7 1.692(3) . ? C2 B11 1.699(3) . ? C2 B6 1.707(3) . ? C2 B3 1.717(3) . ? C3 C4 1.529(3) . ? C4 C5 1.371(3) . ? C4 C12 1.429(3) . ? C5 C6 1.407(3) . ? C7 C8 1.415(3) . ? C7 C12 1.425(3) . ? C8 C9 1.363(3) . ? C9 C10 1.410(3) . ? C10 C11 1.364(3) . ? C11 C12 1.417(3) . ? B3 B8 1.772(3) . ? B3 B7 1.782(3) . ? B3 B4 1.779(3) . ? B4 B5 1.779(3) . ? B4 B8 1.782(3) . ? B4 B9 1.780(3) . ? B5 B9 1.781(3) . ? B5 B10 1.784(3) . ? B5 B6 1.779(3) . ? B6 B10 1.775(3) . ? B6 B11 1.779(3) . ? B7 B11 1.776(4) . ? B7 B12 1.780(3) . ? B7 B8 1.785(3) . ? B8 B9 1.788(3) . ? B8 B12 1.791(3) . ? B9 B12 1.785(3) . ? B9 B10 1.794(3) . ? B10 B11 1.776(3) . ? B10 B12 1.793(4) . ? B11 B12 1.774(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 C6 N1 C7 117.65(18) . . ? C3 C1 C2 116.27(15) . . ? C3 C1 B4 123.78(15) . . ? C2 C1 B4 110.11(15) . . ? C3 C1 B5 123.12(16) . . ? C2 C1 B5 109.56(15) . . ? B4 C1 B5 62.96(13) . . ? C3 C1 B3 116.51(16) . . ? C2 C1 B3 60.97(12) . . ? B4 C1 B3 62.54(12) . . ? B5 C1 B3 114.25(15) . . ? C3 C1 B6 115.46(15) . . ? C2 C1 B6 60.35(12) . . ? B4 C1 B6 114.15(15) . . ? B5 C1 B6 62.26(13) . . ? B3 C1 B6 113.46(15) . . ? C1 C2 B7 112.16(15) . . ? C1 C2 B11 112.34(16) . . ? B7 C2 B11 63.18(14) . . ? C1 C2 B6 62.08(12) . . ? B7 C2 B6 115.67(17) . . ? B11 C2 B6 62.98(14) . . ? C1 C2 B3 61.47(12) . . ? B7 C2 B3 63.03(13) . . ? B11 C2 B3 115.46(16) . . ? B6 C2 B3 115.36(15) . . ? O1 C3 C4 112.49(16) . . ? O1 C3 C1 106.00(15) . . ? C4 C3 C1 110.61(15) . . ? C5 C4 C12 118.29(18) . . ? C5 C4 C3 119.04(17) . . ? C12 C4 C3 122.63(17) . . ? C4 C5 C6 119.78(19) . . ? N1 C6 C5 124.00(19) . . ? N1 C7 C8 117.56(18) . . ? N1 C7 C12 122.42(18) . . ? C8 C7 C12 120.01(18) . . ? C9 C8 C7 120.4(2) . . ? C8 C9 C10 120.13(19) . . ? C11 C10 C9 120.5(2) . . ? C10 C11 C12 121.43(19) . . ? C11 C12 C7 117.46(17) . . ? C11 C12 C4 124.88(18) . . ? C7 C12 C4 117.66(18) . . ? C2 B3 C1 57.56(11) . . ? C2 B3 B8 104.02(16) . . ? C1 B3 B8 104.84(16) . . ? C2 B3 B7 57.79(12) . . ? C1 B3 B7 104.81(16) . . ? B8 B3 B7 60.31(13) . . ? C2 B3 B4 103.93(16) . . ? C1 B3 B4 58.09(11) . . ? B8 B3 B4 60.23(12) . . ? B7 B3 B4 108.01(16) . . ? C1 B4 B5 58.59(12) . . ? C1 B4 B3 59.37(12) . . ? B5 B4 B3 108.11(15) . . ? C1 B4 B8 105.40(15) . . ? B5 B4 B8 108.20(16) . . ? B3 B4 B8 59.69(13) . . ? C1 B4 B9 105.17(15) . . ? B5 B4 B9 60.05(13) . . ? B3 B4 B9 108.00(16) . . ? B8 B4 B9 60.25(13) . . ? C1 B5 B4 58.45(12) . . ? C1 B5 B9 105.01(16) . . ? B4 B5 B9 59.99(13) . . ? C1 B5 B10 105.78(15) . . ? B4 B5 B10 108.55(16) . . ? B9 B5 B10 60.44(13) . . ? C1 B5 B6 59.71(12) . . ? B4 B5 B6 108.39(16) . . ? B9 B5 B6 108.13(16) . . ? B10 B5 B6 59.77(13) . . ? C2 B6 C1 57.57(12) . . ? C2 B6 B10 104.28(16) . . ? C1 B6 B10 104.87(16) . . ? C2 B6 B11 58.30(13) . . ? C1 B6 B11 105.00(16) . . ? B10 B6 B11 59.94(13) . . ? C2 B6 B5 104.01(16) . . ? C1 B6 B5 58.03(12) . . ? B10 B6 B5 60.26(13) . . ? B11 B6 B5 107.78(16) . . ? C2 B7 B11 58.61(13) . . ? C2 B7 B12 104.40(17) . . ? B11 B7 B12 59.87(14) . . ? C2 B7 B3 59.19(12) . . ? B11 B7 B3 108.54(16) . . ? B12 B7 B3 108.08(16) . . ? C2 B7 B8 104.53(16) . . ? B11 B7 B8 108.19(17) . . ? B12 B7 B8 60.30(13) . . ? B3 B7 B8 59.58(13) . . ? B3 B8 B4 60.08(12) . . ? B3 B8 B7 60.11(13) . . ? B4 B8 B7 107.75(16) . . ? B3 B8 B9 107.97(16) . . ? B4 B8 B9 59.82(13) . . ? B7 B8 B9 107.45(17) . . ? B3 B8 B12 108.02(16) . . ? B4 B8 B12 107.70(17) . . ? B7 B8 B12 59.69(13) . . ? B9 B8 B12 59.83(13) . . ? B5 B9 B12 107.87(16) . . ? B5 B9 B4 59.96(12) . . ? B12 B9 B4 108.06(16) . . ? B5 B9 B8 107.88(16) . . ? B12 B9 B8 60.17(13) . . ? B4 B9 B8 59.93(13) . . ? B5 B9 B10 59.87(13) . . ? B12 B9 B10 60.14(13) . . ? B4 B9 B10 108.06(16) . . ? B8 B9 B10 108.30(16) . . ? B11 B10 B6 60.14(13) . . ? B11 B10 B5 107.70(17) . . ? B6 B10 B5 59.96(13) . . ? B11 B10 B9 107.35(17) . . ? B6 B10 B9 107.69(16) . . ? B5 B10 B9 59.69(13) . . ? B11 B10 B12 59.63(13) . . ? B6 B10 B12 107.72(17) . . ? B5 B10 B12 107.34(17) . . ? B9 B10 B12 59.65(13) . . ? C2 B11 B12 104.32(17) . . ? C2 B11 B7 58.21(13) . . ? B12 B11 B7 60.16(14) . . ? C2 B11 B10 104.59(16) . . ? B12 B11 B10 60.69(14) . . ? B7 B11 B10 108.71(17) . . ? C2 B11 B6 58.72(13) . . ? B12 B11 B6 108.39(16) . . ? B7 B11 B6 108.03(16) . . ? B10 B11 B6 59.92(13) . . ? B11 B12 B7 59.97(14) . . ? B11 B12 B9 107.83(17) . . ? B7 B12 B9 107.84(16) . . ? B11 B12 B8 108.05(17) . . ? B7 B12 B8 60.01(13) . . ? B9 B12 B8 60.00(13) . . ? B11 B12 B10 59.69(14) . . ? B7 B12 B10 107.77(17) . . ? B9 B12 B10 60.20(13) . . ? B8 B12 B10 108.21(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 N1 0.84 1.90 2.689(2) 155.0 6 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.423 _refine_diff_density_min -0.327 _refine_diff_density_rms 0.050 # Attachment '2010acc0643_1c.cif' data_2010acc0643 _database_code_depnum_ccdc_archive 'CCDC 816754' #TrackingRef '2010acc0643_1c.cif' _chemical_compound_source 'Jose Giner Planas' _database_code_CSD 10AC0643 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common TPMec018_I _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C9 H19 B10 N O' _chemical_formula_weight 265.35 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 9.8268(2) _cell_length_b 13.4445(4) _cell_length_c 11.3957(3) _cell_angle_alpha 90.00 _cell_angle_beta 105.640(2) _cell_angle_gamma 90.00 _cell_volume 1449.81(6) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 10720 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description Fragment _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.216 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 552 _exptl_absorpt_coefficient_mu 0.064 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9872 _exptl_absorpt_correction_T_max 0.9961 _exptl_absorpt_process_details ; SADABS V2.10 (Sheldrick, G.M., 2003) ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker Nonius FR591 Rotating Anode' _diffrn_radiation_monochromator '10cm confocal mirrors' _diffrn_measurement_device_type 'Bruker-Nonius CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans to fill the asymmetric unit' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15492 _diffrn_reflns_av_R_equivalents 0.0514 _diffrn_reflns_av_sigmaI/netI 0.0475 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.20 _diffrn_reflns_theta_max 27.48 _reflns_number_total 3301 _reflns_number_gt 2576 _reflns_threshold_expression >2\s(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ; Images generated using CrystalMaker: a crystal and molecular structures program for Mac and Windows. CrystalMaker Software Ltd, Oxford, England (www.crystalmaker.com) ; _computing_publication_material 'WINGX (Farrugia, 1998)' _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^ > 2\s(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. Every hydrogen atom was clearly visible in the difference map. All C-H and B-H hydrogens were placed in idealised positions and refined using a riding model, the CH3 torsion angle was allowed to refine. The OH hydrogen was freely refined. ; _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^)+(0.0766P)^2^+1.2731P] 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 3301 _refine_ls_number_parameters 195 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0880 _refine_ls_R_factor_gt 0.0640 _refine_ls_wR_factor_ref 0.1729 _refine_ls_wR_factor_gt 0.1541 _refine_ls_goodness_of_fit_ref 1.057 _refine_ls_restrained_S_all 1.057 _refine_ls_shift/su_max 0.029 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.04467(15) 0.14162(12) 0.24319(13) 0.0260(4) Uani 1 1 d . . . H901 H 0.112(3) 0.190(2) 0.284(3) 0.055(9) Uiso 1 1 d . . . N1 N -0.27808(18) 0.21363(15) -0.13216(16) 0.0283(4) Uani 1 1 d . . . C1 C -0.1874(2) 0.16037(14) 0.28171(16) 0.0177(4) Uani 1 1 d . . . C2 C -0.2066(2) 0.24191(15) 0.38776(17) 0.0201(4) Uani 1 1 d . . . C3 C -0.1274(2) 0.33960(15) 0.40398(19) 0.0253(4) Uani 1 1 d . . . H3A H -0.0261 0.3267 0.4176 0.038 Uiso 1 1 calc R . . H3B H -0.1431 0.3751 0.4743 0.038 Uiso 1 1 calc R . . H3C H -0.1615 0.3802 0.3305 0.038 Uiso 1 1 calc R . . C4 C -0.0864(2) 0.18934(15) 0.20209(17) 0.0193(4) Uani 1 1 d . . . H4 H -0.0706 0.2629 0.2080 0.023 Uiso 1 1 calc R . . C5 C -0.15070(19) 0.16232(15) 0.06936(17) 0.0192(4) Uani 1 1 d . . . C6 C -0.1393(2) 0.06662(16) 0.02676(18) 0.0234(4) Uani 1 1 d . . . H6 H -0.0917 0.0162 0.0809 0.028 Uiso 1 1 calc R . . C7 C -0.1981(2) 0.04551(17) -0.09564(19) 0.0278(5) Uani 1 1 d . . . H7 H -0.1915 -0.0193 -0.1268 0.033 Uiso 1 1 calc R . . C8 C -0.2664(2) 0.12118(19) -0.17129(18) 0.0297(5) Uani 1 1 d . . . H8 H -0.3070 0.1067 -0.2550 0.036 Uiso 1 1 calc R . . C9 C -0.2195(2) 0.23331(16) -0.01351(18) 0.0240(4) Uani 1 1 d . . . H9 H -0.2257 0.2992 0.0148 0.029 Uiso 1 1 calc R . . B3 B -0.1097(2) 0.13585(17) 0.4343(2) 0.0218(5) Uani 1 1 d . . . H3 H 0.0071 0.1350 0.4771 0.026 Uiso 1 1 calc R . . B4 B -0.1961(2) 0.04175(17) 0.3316(2) 0.0214(5) Uani 1 1 d . . . H4A H -0.1361 -0.0222 0.3069 0.026 Uiso 1 1 calc R . . B5 B -0.3419(2) 0.09682(17) 0.2235(2) 0.0198(4) Uani 1 1 d . . . H5 H -0.3786 0.0687 0.1276 0.024 Uiso 1 1 calc R . . B6 B -0.3429(2) 0.22527(17) 0.2576(2) 0.0205(5) Uani 1 1 d . . . H6A H -0.3779 0.2829 0.1847 0.025 Uiso 1 1 calc R . . B7 B -0.2305(3) 0.18174(17) 0.5122(2) 0.0229(5) Uani 1 1 d . . . H7A H -0.1934 0.2105 0.6077 0.027 Uiso 1 1 calc R . . B8 B -0.2269(3) 0.05296(18) 0.4784(2) 0.0247(5) Uani 1 1 d . . . H8A H -0.1882 -0.0042 0.5513 0.030 Uiso 1 1 calc R . . B9 B -0.3710(3) 0.02919(18) 0.3478(2) 0.0241(5) Uani 1 1 d . . . H9A H -0.4274 -0.0440 0.3349 0.029 Uiso 1 1 calc R . . B10 B -0.4624(2) 0.14343(18) 0.3012(2) 0.0238(5) Uani 1 1 d . . . H10 H -0.5790 0.1461 0.2573 0.029 Uiso 1 1 calc R . . B11 B -0.3747(2) 0.23766(18) 0.4032(2) 0.0239(5) Uani 1 1 d . . . H11 H -0.4326 0.3034 0.4264 0.029 Uiso 1 1 calc R . . B12 B -0.3920(3) 0.11651(18) 0.4592(2) 0.0250(5) Uani 1 1 d . . . H12 H -0.4624 0.1013 0.5197 0.030 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0199(7) 0.0308(8) 0.0263(7) -0.0027(6) 0.0045(6) 0.0030(6) N1 0.0221(9) 0.0406(11) 0.0225(9) 0.0057(8) 0.0064(7) 0.0008(8) C1 0.0202(9) 0.0166(9) 0.0159(8) -0.0014(7) 0.0044(7) 0.0005(7) C2 0.0241(10) 0.0194(9) 0.0183(9) -0.0012(7) 0.0082(8) 0.0013(8) C3 0.0307(11) 0.0197(10) 0.0281(10) -0.0038(8) 0.0125(9) -0.0031(8) C4 0.0184(9) 0.0204(10) 0.0196(9) -0.0003(7) 0.0059(7) -0.0001(7) C5 0.0167(9) 0.0235(10) 0.0192(9) 0.0008(7) 0.0080(7) -0.0020(7) C6 0.0229(10) 0.0263(11) 0.0220(10) -0.0012(8) 0.0079(8) -0.0006(8) C7 0.0263(11) 0.0326(12) 0.0257(10) -0.0068(9) 0.0093(8) -0.0030(9) C8 0.0225(10) 0.0495(14) 0.0176(9) -0.0030(9) 0.0064(8) -0.0038(10) C9 0.0206(10) 0.0300(11) 0.0227(10) 0.0037(8) 0.0081(8) 0.0015(8) B3 0.0240(11) 0.0211(11) 0.0193(10) 0.0011(8) 0.0044(8) 0.0015(9) B4 0.0248(11) 0.0188(11) 0.0216(10) 0.0014(8) 0.0079(9) 0.0012(9) B5 0.0197(10) 0.0207(11) 0.0192(10) 0.0019(8) 0.0057(8) -0.0017(8) B6 0.0198(11) 0.0215(11) 0.0208(10) 0.0013(8) 0.0062(8) 0.0024(8) B7 0.0294(12) 0.0235(11) 0.0172(10) -0.0002(8) 0.0088(9) -0.0019(9) B8 0.0320(12) 0.0228(11) 0.0193(10) 0.0036(9) 0.0069(9) -0.0005(9) B9 0.0286(12) 0.0235(11) 0.0224(11) 0.0002(9) 0.0106(9) -0.0045(9) B10 0.0217(11) 0.0281(12) 0.0233(11) 0.0011(9) 0.0091(9) -0.0008(9) B11 0.0240(11) 0.0244(12) 0.0267(11) -0.0001(9) 0.0130(9) 0.0021(9) B12 0.0278(12) 0.0264(12) 0.0230(11) -0.0002(9) 0.0106(9) -0.0023(10) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C4 1.401(2) . ? N1 C8 1.336(3) . ? N1 C9 1.345(3) . ? C1 C4 1.564(3) . ? C1 C2 1.680(3) . ? C1 B4 1.703(3) . ? C1 B5 1.712(3) . ? C1 B6 1.716(3) . ? C1 B3 1.732(3) . ? C2 C3 1.513(3) . ? C2 B7 1.703(3) . ? C2 B11 1.709(3) . ? C2 B3 1.717(3) . ? C2 B6 1.724(3) . ? C4 C5 1.518(3) . ? C5 C9 1.384(3) . ? C5 C6 1.390(3) . ? C6 C7 1.388(3) . ? C7 C8 1.385(3) . ? B3 B8 1.770(3) . ? B3 B7 1.773(3) . ? B3 B4 1.776(3) . ? B4 B5 1.779(3) . ? B4 B8 1.785(3) . ? B4 B9 1.785(3) . ? B5 B9 1.770(3) . ? B5 B6 1.771(3) . ? B5 B10 1.773(3) . ? B6 B10 1.776(3) . ? B6 B11 1.777(3) . ? B7 B12 1.771(3) . ? B7 B8 1.776(3) . ? B7 B11 1.780(3) . ? B8 B9 1.785(3) . ? B8 B12 1.794(3) . ? B9 B12 1.781(3) . ? B9 B10 1.786(3) . ? B10 B11 1.777(3) . ? B10 B12 1.783(3) . ? B11 B12 1.774(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 C8 N1 C9 117.82(19) . . ? C4 C1 C2 117.83(15) . . ? C4 C1 B4 121.58(15) . . ? C2 C1 B4 110.21(14) . . ? C4 C1 B5 122.34(15) . . ? C2 C1 B5 110.16(14) . . ? B4 C1 B5 62.81(12) . . ? C4 C1 B6 117.23(15) . . ? C2 C1 B6 61.02(12) . . ? B4 C1 B6 114.03(15) . . ? B5 C1 B6 62.21(12) . . ? C4 C1 B3 116.91(15) . . ? C2 C1 B3 60.43(12) . . ? B4 C1 B3 62.26(12) . . ? B5 C1 B3 113.50(15) . . ? B6 C1 B3 112.96(15) . . ? C3 C2 C1 120.04(16) . . ? C3 C2 B7 119.52(16) . . ? C1 C2 B7 110.89(15) . . ? C3 C2 B11 119.78(17) . . ? C1 C2 B11 110.57(15) . . ? B7 C2 B11 62.91(13) . . ? C3 C2 B3 117.32(17) . . ? C1 C2 B3 61.30(12) . . ? B7 C2 B3 62.46(13) . . ? B11 C2 B3 114.29(16) . . ? C3 C2 B6 118.21(16) . . ? C1 C2 B6 60.53(11) . . ? B7 C2 B6 113.93(16) . . ? B11 C2 B6 62.35(13) . . ? B3 C2 B6 113.29(15) . . ? O1 C4 C5 108.77(15) . . ? O1 C4 C1 111.23(15) . . ? C5 C4 C1 111.06(15) . . ? C9 C5 C6 118.06(18) . . ? C9 C5 C4 120.70(18) . . ? C6 C5 C4 121.22(17) . . ? C7 C6 C5 119.3(2) . . ? C8 C7 C6 118.4(2) . . ? N1 C8 C7 123.14(19) . . ? N1 C9 C5 123.2(2) . . ? C2 B3 C1 58.28(11) . . ? C2 B3 B8 105.17(16) . . ? C1 B3 B8 105.11(15) . . ? C2 B3 B7 58.36(12) . . ? C1 B3 B7 105.24(15) . . ? B8 B3 B7 60.17(13) . . ? C2 B3 B4 105.15(15) . . ? C1 B3 B4 58.07(12) . . ? B8 B3 B4 60.45(13) . . ? B7 B3 B4 108.19(16) . . ? C1 B4 B3 59.67(12) . . ? C1 B4 B5 58.84(12) . . ? B3 B4 B5 108.20(16) . . ? C1 B4 B8 105.69(15) . . ? B3 B4 B8 59.60(13) . . ? B5 B4 B8 107.79(16) . . ? C1 B4 B9 105.03(15) . . ? B3 B4 B9 107.56(16) . . ? B5 B4 B9 59.54(13) . . ? B8 B4 B9 60.00(13) . . ? C1 B5 B9 105.31(15) . . ? C1 B5 B6 59.00(12) . . ? B9 B5 B6 108.30(16) . . ? C1 B5 B10 105.79(15) . . ? B9 B5 B10 60.56(13) . . ? B6 B5 B10 60.13(13) . . ? C1 B5 B4 58.35(12) . . ? B9 B5 B4 60.39(13) . . ? B6 B5 B4 107.76(15) . . ? B10 B5 B4 108.85(15) . . ? C1 B6 C2 58.46(11) . . ? C1 B6 B5 58.79(12) . . ? C2 B6 B5 105.45(15) . . ? C1 B6 B10 105.53(16) . . ? C2 B6 B10 104.99(15) . . ? B5 B6 B10 60.01(13) . . ? C1 B6 B11 105.76(15) . . ? C2 B6 B11 58.41(12) . . ? B5 B6 B11 107.99(16) . . ? B10 B6 B11 60.02(13) . . ? C2 B7 B12 105.26(15) . . ? C2 B7 B3 59.17(12) . . ? B12 B7 B3 108.43(16) . . ? C2 B7 B8 105.51(15) . . ? B12 B7 B8 60.78(14) . . ? B3 B7 B8 59.81(13) . . ? C2 B7 B11 58.72(12) . . ? B12 B7 B11 59.94(13) . . ? B3 B7 B11 108.19(15) . . ? B8 B7 B11 108.61(16) . . ? B3 B8 B7 60.01(13) . . ? B3 B8 B4 59.95(13) . . ? B7 B8 B4 107.68(16) . . ? B3 B8 B9 107.84(16) . . ? B7 B8 B9 107.30(17) . . ? B4 B8 B9 60.01(13) . . ? B3 B8 B12 107.55(16) . . ? B7 B8 B12 59.47(13) . . ? B4 B8 B12 107.57(16) . . ? B9 B8 B12 59.69(13) . . ? B5 B9 B12 107.84(16) . . ? B5 B9 B8 108.20(16) . . ? B12 B9 B8 60.42(13) . . ? B5 B9 B4 60.07(12) . . ? B12 B9 B4 108.13(16) . . ? B8 B9 B4 59.99(13) . . ? B5 B9 B10 59.81(13) . . ? B12 B9 B10 59.98(13) . . ? B8 B9 B10 108.45(17) . . ? B4 B9 B10 108.00(16) . . ? B5 B10 B6 59.86(12) . . ? B5 B10 B11 107.88(16) . . ? B6 B10 B11 60.03(13) . . ? B5 B10 B12 107.61(16) . . ? B6 B10 B12 107.60(16) . . ? B11 B10 B12 59.78(13) . . ? B5 B10 B9 59.63(12) . . ? B6 B10 B9 107.35(16) . . ? B11 B10 B9 107.58(16) . . ? B12 B10 B9 59.87(13) . . ? C2 B11 B12 104.86(16) . . ? C2 B11 B6 59.24(12) . . ? B12 B11 B6 107.93(16) . . ? C2 B11 B10 105.57(15) . . ? B12 B11 B10 60.29(13) . . ? B6 B11 B10 59.94(13) . . ? C2 B11 B7 58.38(12) . . ? B12 B11 B7 59.77(13) . . ? B6 B11 B7 107.71(16) . . ? B10 B11 B7 108.05(16) . . ? B7 B12 B11 60.28(13) . . ? B7 B12 B9 107.69(16) . . ? B11 B12 B9 107.93(16) . . ? B7 B12 B10 108.18(16) . . ? B11 B12 B10 59.93(13) . . ? B9 B12 B10 60.16(13) . . ? B7 B12 B8 59.75(13) . . ? B11 B12 B8 108.06(16) . . ? B9 B12 B8 59.89(13) . . ? B10 B12 B8 108.18(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 H901 N1 0.95(3) 1.79(3) 2.740(2) 173(3) 4_666 _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.315 _refine_diff_density_min -0.245 _refine_diff_density_rms 0.055 _iucr_refine_instruction_details ; TITL 2010acc0643 in P2(1)/n CELL 0.71073 9.8268 13.4445 11.3957 90.000 105.640 90.000 ZERR 4.00 0.0002 0.0004 0.0003 0.000 0.002 0.000 LATT 1 SYMM 1/2 - X, 1/2 + Y, 1/2 - Z SFAC C H B N O UNIT 36 76 40 4 4 MERG 2 SHEL 7 0.77 OMIT 0 2 0 ACTA 55 TEMP -153 SIZE 0.2 0.13 0.06 FMAP 2 HTAB O1 N1_$1 EQIV $1 [ x+1/2, -y+1/2, z+1/2 ] PLAN 20 BOND L.S. 4 WGHT 0.076600 1.273100 FVAR 0.80390 O1 5 0.044669 0.141619 0.243187 11.00000 0.01994 0.03075 = 0.02626 -0.00274 0.00453 0.00303 H901 2 0.112290 0.189854 0.283906 11.00000 0.05471 N1 4 -0.278080 0.213625 -0.132159 11.00000 0.02214 0.04058 = 0.02248 0.00569 0.00645 0.00081 C1 1 -0.187437 0.160369 0.281710 11.00000 0.02023 0.01658 = 0.01592 -0.00142 0.00443 0.00047 C2 1 -0.206627 0.241911 0.387761 11.00000 0.02409 0.01939 = 0.01831 -0.00118 0.00818 0.00132 C3 1 -0.127375 0.339597 0.403977 11.00000 0.03066 0.01973 = 0.02809 -0.00383 0.01249 -0.00313 AFIX 137 H3A 2 -0.026137 0.326730 0.417631 11.00000 -1.50000 H3B 2 -0.143110 0.375106 0.474277 11.00000 -1.50000 H3C 2 -0.161533 0.380245 0.330528 11.00000 -1.50000 AFIX 0 C4 1 -0.086367 0.189339 0.202092 11.00000 0.01839 0.02043 = 0.01957 -0.00034 0.00587 -0.00007 AFIX 13 H4 2 -0.070612 0.262864 0.207951 11.00000 -1.20000 AFIX 0 C5 1 -0.150698 0.162323 0.069363 11.00000 0.01671 0.02351 = 0.01920 0.00084 0.00799 -0.00196 C6 1 -0.139283 0.066623 0.026762 11.00000 0.02286 0.02630 = 0.02202 -0.00125 0.00793 -0.00062 AFIX 43 H6 2 -0.091749 0.016218 0.080885 11.00000 -1.20000 AFIX 0 C7 1 -0.198055 0.045513 -0.095643 11.00000 0.02629 0.03261 = 0.02568 -0.00679 0.00927 -0.00302 AFIX 43 H7 2 -0.191541 -0.019331 -0.126807 11.00000 -1.20000 AFIX 0 C8 1 -0.266419 0.121180 -0.171294 11.00000 0.02246 0.04954 = 0.01764 -0.00304 0.00645 -0.00381 AFIX 43 H8 2 -0.306969 0.106655 -0.255032 11.00000 -1.20000 AFIX 0 C9 1 -0.219520 0.233310 -0.013515 11.00000 0.02063 0.03000 = 0.02269 0.00375 0.00814 0.00145 AFIX 43 H9 2 -0.225707 0.299180 0.014782 11.00000 -1.20000 AFIX 0 B3 3 -0.109725 0.135846 0.434300 11.00000 0.02404 0.02113 = 0.01932 0.00114 0.00439 0.00150 AFIX 153 H3 2 0.007115 0.135029 0.477114 11.00000 -1.20000 AFIX 0 B4 3 -0.196101 0.041753 0.331629 11.00000 0.02478 0.01880 = 0.02163 0.00138 0.00792 0.00123 AFIX 153 H4A 2 -0.136131 -0.022159 0.306920 11.00000 -1.20000 AFIX 0 B5 3 -0.341889 0.096821 0.223540 11.00000 0.01972 0.02069 = 0.01915 0.00195 0.00571 -0.00171 AFIX 153 H5 2 -0.378564 0.068724 0.127646 11.00000 -1.20000 AFIX 0 B6 3 -0.342869 0.225271 0.257604 11.00000 0.01975 0.02149 = 0.02084 0.00129 0.00624 0.00236 AFIX 153 H6A 2 -0.377865 0.282912 0.184735 11.00000 -1.20000 AFIX 0 B7 3 -0.230468 0.181742 0.512194 11.00000 0.02941 0.02345 = 0.01724 -0.00023 0.00878 -0.00185 AFIX 153 H7A 2 -0.193401 0.210544 0.607745 11.00000 -1.20000 AFIX 0 B8 3 -0.226851 0.052960 0.478435 11.00000 0.03202 0.02277 = 0.01934 0.00358 0.00688 -0.00053 AFIX 153 H8A 2 -0.188176 -0.004242 0.551251 11.00000 -1.20000 AFIX 0 B9 3 -0.370969 0.029194 0.347833 11.00000 0.02857 0.02349 = 0.02236 0.00023 0.01055 -0.00450 AFIX 153 H9A 2 -0.427383 -0.044039 0.334901 11.00000 -1.20000 AFIX 0 B10 3 -0.462426 0.143435 0.301205 11.00000 0.02173 0.02814 = 0.02327 0.00114 0.00909 -0.00085 AFIX 153 H10 2 -0.578978 0.146065 0.257295 11.00000 -1.20000 AFIX 0 B11 3 -0.374750 0.237657 0.403178 11.00000 0.02401 0.02441 = 0.02674 -0.00009 0.01297 0.00207 AFIX 153 H11 2 -0.432571 0.303373 0.426381 11.00000 -1.20000 AFIX 0 B12 3 -0.391997 0.116513 0.459207 11.00000 0.02779 0.02645 = 0.02297 -0.00022 0.01064 -0.00230 AFIX 153 H12 2 -0.462424 0.101268 0.519748 11.00000 -1.20000 HKLF 4 REM 2010acc0643 in P2(1)/n REM R1 = 0.0640 for 2576 Fo > 4sig(Fo) and 0.0880 for all 3301 data REM 195 parameters refined using 0 restraints END WGHT 0.0461 1.7124 REM Highest difference peak 0.315, deepest hole -0.245, 1-sigma level 0.055 Q1 1 0.0005 0.1563 0.4391 11.00000 0.05 0.32 Q2 1 -0.1279 0.1748 0.1356 11.00000 0.05 0.31 Q3 1 -0.3280 0.2810 0.2002 11.00000 0.05 0.28 Q4 1 -0.1459 0.1813 0.2438 11.00000 0.05 0.27 Q5 1 -0.1128 0.0144 0.3110 11.00000 0.05 0.27 Q6 1 -0.1561 0.2109 0.5789 11.00000 0.05 0.27 Q7 1 -0.3392 0.0811 0.1469 11.00000 0.05 0.27 Q8 1 -0.2044 0.2489 0.5818 11.00000 0.05 0.24 Q9 1 -0.4038 0.1729 0.2687 11.00000 0.05 0.23 Q10 1 -0.2706 0.0710 -0.1255 11.00000 0.05 0.22 Q11 1 -0.2330 0.0212 0.5340 11.00000 0.05 0.21 Q12 1 -0.2960 0.1154 0.4940 11.00000 0.05 0.21 Q13 1 -0.1820 0.1143 0.0582 11.00000 0.05 0.21 Q14 1 -0.3008 0.0569 0.2957 11.00000 0.05 0.20 Q15 1 -0.0738 0.3554 0.3572 11.00000 0.05 0.20 Q16 1 -0.1325 0.0631 -0.0446 11.00000 0.05 0.20 Q17 1 -0.1773 0.1423 0.4723 11.00000 0.05 0.20 Q18 1 -0.3989 0.3099 0.4011 11.00000 0.05 0.20 Q19 1 -0.3329 0.1775 0.4645 11.00000 0.05 0.20 Q20 1 -0.2773 0.0454 0.3577 11.00000 0.05 0.19 ; # Attachment '2010acc0644_1e.cif' data_2010acc0644 _database_code_depnum_ccdc_archive 'CCDC 816755' #TrackingRef '2010acc0644_1e.cif' _chemical_compound_source 'Jose Giner Planas' _database_code_CSD 10AC0644 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H21 B10 N O' _chemical_formula_weight 315.41 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/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 11.6364(16) _cell_length_b 11.4228(16) _cell_length_c 13.1428(14) _cell_angle_alpha 90.00 _cell_angle_beta 105.666(12) _cell_angle_gamma 90.00 _cell_volume 1682.0(4) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 2964 _cell_measurement_theta_min 3.22 _cell_measurement_theta_max 25.03 _exptl_crystal_description Fragment _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.245 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 656 _exptl_absorpt_coefficient_mu 0.067 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9802 _exptl_absorpt_correction_T_max 0.9934 _exptl_absorpt_process_details 'SADABS 2007/2 (Sheldrick, G.M., 2007)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker Nonius FR591 Rotating Anode' _diffrn_radiation_monochromator '10cm confocal mirrors' _diffrn_measurement_device_type 'Bruker-Nonius CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans to fill the asymmetric unit' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2964 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.1254 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.22 _diffrn_reflns_theta_max 25.03 _reflns_number_total 2964 _reflns_number_gt 1715 _reflns_threshold_expression >2\s(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement ; Duisenberg AJM, Hooft RWW, Schreurs AMM, Kroon J. Accurate cells from area-detector images. Journal of Applied Crystallography 2000; 33: 893-898. ; _computing_data_reduction ; Duisenberg AJM, Kroon-Batenburg LMJ, Schreurs AMM. An intensity evaluation method: EVAL-14. Journal of Applied Crystallography 2003; 36: 220-229. ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ; Images generated using CrystalMaker: a crystal and molecular structures program for Mac and Windows. CrystalMaker Software Ltd, Oxford, England (www.crystalmaker.com) ; _computing_publication_material 'WINGX (Farrugia, 1998)' _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^ > 2\s(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^)+(0.1460P)^2^+0.3717P] 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 2964 _refine_ls_number_parameters 231 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1483 _refine_ls_R_factor_gt 0.0989 _refine_ls_wR_factor_ref 0.2752 _refine_ls_wR_factor_gt 0.2428 _refine_ls_goodness_of_fit_ref 1.063 _refine_ls_restrained_S_all 1.063 _refine_ls_shift/su_max 0.018 _refine_ls_shift/su_mean 0.004 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.7505(3) 0.5679(2) -0.0223(2) 0.0271(8) Uani 1 1 d . . . N1 N 0.8407(3) 0.6925(3) 0.1488(2) 0.0196(8) Uani 1 1 d . . . C1 C 0.8524(4) 0.7155(3) -0.0992(3) 0.0172(9) Uani 1 1 d . . . C2 C 0.8034(4) 0.7101(3) -0.2319(3) 0.0190(10) Uani 1 1 d . . . C3 C 0.6745(4) 0.6783(4) -0.2817(3) 0.0265(11) Uani 1 1 d . . . H3A H 0.6499 0.6174 -0.2394 0.040 Uiso 1 1 calc R . . H3B H 0.6656 0.6491 -0.3535 0.040 Uiso 1 1 calc R . . H3C H 0.6243 0.7477 -0.2844 0.040 Uiso 1 1 calc R . . C4 C 0.7583(4) 0.6885(3) -0.0382(3) 0.0184(9) Uani 1 1 d . . . H4 H 0.6789 0.7159 -0.0824 0.022 Uiso 1 1 calc R . . C5 C 0.7862(3) 0.7549(3) 0.0656(3) 0.0180(9) Uani 1 1 d . . . C6 C 0.7513(4) 0.8720(3) 0.0705(3) 0.0226(10) Uani 1 1 d . . . H6 H 0.7093 0.9126 0.0086 0.027 Uiso 1 1 calc R . . C7 C 0.7793(4) 0.9258(3) 0.1667(3) 0.0225(10) Uani 1 1 d . . . H7 H 0.7582 1.0054 0.1721 0.027 Uiso 1 1 calc R . . C8 C 0.8390(4) 0.8637(3) 0.2573(3) 0.0226(10) Uani 1 1 d . . . C9 C 0.8733(4) 0.9139(4) 0.3595(3) 0.0250(10) Uani 1 1 d . . . H9 H 0.8576 0.9944 0.3682 0.030 Uiso 1 1 calc R . . C10 C 0.9283(4) 0.8488(4) 0.4449(3) 0.0302(11) Uani 1 1 d . . . H10 H 0.9486 0.8831 0.5133 0.036 Uiso 1 1 calc R . . C11 C 0.9556(4) 0.7302(4) 0.4327(3) 0.0288(10) Uani 1 1 d . . . H11 H 0.9947 0.6851 0.4928 0.035 Uiso 1 1 calc R . . C12 C 0.9261(4) 0.6801(3) 0.3350(3) 0.0234(10) Uani 1 1 d . . . H12 H 0.9448 0.6002 0.3273 0.028 Uiso 1 1 calc R . . C13 C 0.8683(3) 0.7457(3) 0.2458(3) 0.0204(9) Uani 1 1 d . . . B3 B 0.8951(4) 0.6005(4) -0.1652(4) 0.0196(10) Uani 1 1 d . . . H3 H 0.8657 0.5078 -0.1603 0.024 Uiso 1 1 calc R . . B4 B 0.9967(4) 0.6698(4) -0.0581(4) 0.0195(11) Uani 1 1 d . . . H4A H 1.0356 0.6226 0.0181 0.023 Uiso 1 1 calc R . . B5 B 0.9594(4) 0.8211(4) -0.0610(4) 0.0200(10) Uani 1 1 d . . . H5 H 0.9743 0.8740 0.0131 0.024 Uiso 1 1 calc R . . B6 B 0.8339(4) 0.8438(4) -0.1688(4) 0.0194(10) Uani 1 1 d . . . H6A H 0.7644 0.9107 -0.1659 0.023 Uiso 1 1 calc R . . B7 B 0.9132(5) 0.6610(4) -0.2845(4) 0.0227(11) Uani 1 1 d . . . H7A H 0.8972 0.6081 -0.3588 0.027 Uiso 1 1 calc R . . B8 B 1.0388(4) 0.6369(4) -0.1744(4) 0.0216(11) Uani 1 1 d . . . H8 H 1.1068 0.5680 -0.1757 0.026 Uiso 1 1 calc R . . B9 B 1.0797(4) 0.7739(4) -0.1097(4) 0.0214(11) Uani 1 1 d . . . H9A H 1.1747 0.7958 -0.0684 0.026 Uiso 1 1 calc R . . B10 B 0.9763(4) 0.8817(4) -0.1798(4) 0.0226(11) Uani 1 1 d . . . H10A H 1.0028 0.9753 -0.1852 0.027 Uiso 1 1 calc R . . B11 B 0.8746(5) 0.8109(4) -0.2869(4) 0.0225(11) Uani 1 1 d . . . H11A H 0.8325 0.8571 -0.3630 0.027 Uiso 1 1 calc R . . B12 B 1.0271(4) 0.7684(4) -0.2500(4) 0.0236(11) Uani 1 1 d . . . H12B H 1.0877 0.7870 -0.3013 0.028 Uiso 1 1 calc R . . H901 H 0.795(5) 0.559(4) 0.039(4) 0.047(17) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.041(2) 0.0206(15) 0.0234(18) -0.0034(13) 0.0143(16) -0.0101(13) N1 0.019(2) 0.0236(17) 0.0174(18) 0.0002(14) 0.0079(15) -0.0022(14) C1 0.019(2) 0.0128(18) 0.018(2) -0.0038(16) 0.0018(17) -0.0035(15) C2 0.019(2) 0.020(2) 0.017(2) 0.0034(16) 0.0042(18) 0.0011(16) C3 0.019(2) 0.038(2) 0.021(2) -0.0035(19) 0.0027(19) -0.0031(18) C4 0.016(2) 0.0199(19) 0.021(2) -0.0010(16) 0.0082(18) -0.0058(16) C5 0.014(2) 0.0235(19) 0.017(2) 0.0025(17) 0.0059(16) -0.0061(17) C6 0.023(2) 0.020(2) 0.027(2) 0.0026(18) 0.011(2) 0.0015(17) C7 0.019(2) 0.019(2) 0.033(3) 0.0009(18) 0.014(2) -0.0010(16) C8 0.017(2) 0.027(2) 0.031(2) -0.0029(18) 0.017(2) -0.0056(17) C9 0.020(2) 0.029(2) 0.030(2) -0.0067(19) 0.013(2) -0.0033(18) C10 0.026(3) 0.044(3) 0.025(2) -0.011(2) 0.014(2) -0.010(2) C11 0.022(2) 0.045(3) 0.020(2) 0.004(2) 0.0060(18) -0.005(2) C12 0.019(2) 0.030(2) 0.024(2) -0.0008(18) 0.0098(19) 0.0001(17) C13 0.018(2) 0.025(2) 0.022(2) -0.0039(18) 0.0102(17) -0.0016(18) B3 0.020(2) 0.018(2) 0.022(3) -0.0004(19) 0.006(2) 0.0035(18) B4 0.018(3) 0.020(2) 0.019(2) 0.0037(19) 0.003(2) 0.0069(19) B5 0.020(3) 0.019(2) 0.020(2) -0.0004(19) 0.004(2) -0.0031(19) B6 0.019(3) 0.016(2) 0.023(3) 0.0039(19) 0.005(2) -0.0017(18) B7 0.025(3) 0.024(2) 0.021(3) -0.002(2) 0.010(2) 0.003(2) B8 0.022(3) 0.026(2) 0.016(2) 0.0028(19) 0.004(2) 0.003(2) B9 0.019(3) 0.020(2) 0.027(3) 0.003(2) 0.008(2) -0.0024(18) B10 0.021(3) 0.018(2) 0.031(3) 0.004(2) 0.011(2) -0.0008(19) B11 0.027(3) 0.024(2) 0.020(2) 0.007(2) 0.011(2) 0.000(2) B12 0.022(3) 0.025(2) 0.027(3) 0.007(2) 0.012(2) 0.001(2) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C4 1.400(4) . ? N1 C5 1.315(5) . ? N1 C13 1.371(5) . ? C1 C4 1.553(5) . ? C1 C2 1.684(5) . ? C1 B5 1.708(6) . ? C1 B4 1.701(6) . ? C1 B6 1.710(5) . ? C1 B3 1.721(5) . ? C2 C3 1.509(6) . ? C2 B11 1.690(6) . ? C2 B7 1.704(6) . ? C2 B6 1.729(6) . ? C2 B3 1.724(6) . ? C4 C5 1.517(5) . ? C5 C6 1.405(5) . ? C6 C7 1.362(5) . ? C7 C8 1.399(6) . ? C8 C13 1.408(5) . ? C8 C9 1.415(6) . ? C9 C10 1.355(6) . ? C10 C11 1.410(6) . ? C11 C12 1.363(5) . ? C12 C13 1.401(6) . ? B3 B8 1.758(7) . ? B3 B4 1.763(6) . ? B3 B7 1.777(6) . ? B4 B8 1.768(6) . ? B4 B9 1.778(6) . ? B4 B5 1.779(6) . ? B5 B6 1.758(7) . ? B5 B10 1.767(6) . ? B5 B9 1.773(7) . ? B6 B10 1.757(6) . ? B6 B11 1.781(6) . ? B7 B11 1.769(6) . ? B7 B12 1.773(7) . ? B7 B8 1.779(7) . ? B8 B9 1.783(6) . ? B8 B12 1.785(6) . ? B9 B12 1.780(7) . ? B9 B10 1.792(6) . ? B10 B11 1.771(7) . ? B10 B12 1.780(6) . ? B11 B12 1.776(7) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C5 N1 C13 118.2(3) . . ? C4 C1 C2 116.0(3) . . ? C4 C1 B5 123.3(3) . . ? C2 C1 B5 110.2(3) . . ? C4 C1 B4 123.2(3) . . ? C2 C1 B4 110.3(3) . . ? B5 C1 B4 62.9(3) . . ? C4 C1 B6 116.2(3) . . ? C2 C1 B6 61.2(2) . . ? B5 C1 B6 61.9(2) . . ? B4 C1 B6 113.8(3) . . ? C4 C1 B3 116.7(3) . . ? C2 C1 B3 60.8(2) . . ? B5 C1 B3 113.6(3) . . ? B4 C1 B3 62.0(3) . . ? B6 C1 B3 113.3(3) . . ? C3 C2 B11 121.5(3) . . ? C3 C2 C1 118.5(3) . . ? B11 C2 C1 110.5(3) . . ? C3 C2 B7 120.7(3) . . ? B11 C2 B7 62.8(2) . . ? C1 C2 B7 110.6(3) . . ? C3 C2 B6 118.2(3) . . ? B11 C2 B6 62.8(2) . . ? C1 C2 B6 60.1(2) . . ? B7 C2 B6 114.0(3) . . ? C3 C2 B3 116.9(3) . . ? B11 C2 B3 113.8(3) . . ? C1 C2 B3 60.6(2) . . ? B7 C2 B3 62.4(3) . . ? B6 C2 B3 112.3(3) . . ? O1 C4 C5 111.4(3) . . ? O1 C4 C1 110.8(3) . . ? C5 C4 C1 110.8(3) . . ? N1 C5 C6 124.0(4) . . ? N1 C5 C4 114.5(3) . . ? C6 C5 C4 121.5(3) . . ? C7 C6 C5 118.2(4) . . ? C6 C7 C8 120.0(4) . . ? C7 C8 C13 118.2(4) . . ? C7 C8 C9 123.4(4) . . ? C13 C8 C9 118.4(4) . . ? C10 C9 C8 120.9(4) . . ? C9 C10 C11 120.2(4) . . ? C12 C11 C10 120.2(4) . . ? C11 C12 C13 120.3(4) . . ? N1 C13 C12 118.7(4) . . ? N1 C13 C8 121.5(4) . . ? C12 C13 C8 119.9(4) . . ? C1 B3 C2 58.5(2) . . ? C1 B3 B8 105.3(3) . . ? C2 B3 B8 105.3(3) . . ? C1 B3 B4 58.4(2) . . ? C2 B3 B4 105.6(3) . . ? B8 B3 B4 60.3(3) . . ? C1 B3 B7 105.5(3) . . ? C2 B3 B7 58.2(2) . . ? B8 B3 B7 60.4(3) . . ? B4 B3 B7 108.5(3) . . ? C1 B4 B3 59.5(2) . . ? C1 B4 B8 105.7(3) . . ? B3 B4 B8 59.7(3) . . ? C1 B4 B9 105.4(3) . . ? B3 B4 B9 108.1(3) . . ? B8 B4 B9 60.4(3) . . ? C1 B4 B5 58.7(2) . . ? B3 B4 B5 108.2(3) . . ? B8 B4 B5 108.1(3) . . ? B9 B4 B5 59.8(2) . . ? C1 B5 B6 59.1(2) . . ? C1 B5 B10 105.3(3) . . ? B6 B5 B10 59.8(3) . . ? C1 B5 B9 105.3(3) . . ? B6 B5 B9 108.6(3) . . ? B10 B5 B9 60.8(3) . . ? C1 B5 B4 58.3(2) . . ? B6 B5 B4 107.8(3) . . ? B10 B5 B4 108.4(3) . . ? B9 B5 B4 60.1(2) . . ? C1 B6 C2 58.6(2) . . ? C1 B6 B5 59.0(2) . . ? C2 B6 B5 105.9(3) . . ? C1 B6 B10 105.6(3) . . ? C2 B6 B10 104.7(3) . . ? B5 B6 B10 60.4(3) . . ? C1 B6 B11 105.1(3) . . ? C2 B6 B11 57.6(2) . . ? B5 B6 B11 108.2(3) . . ? B10 B6 B11 60.1(3) . . ? C2 B7 B11 58.2(2) . . ? C2 B7 B12 105.0(3) . . ? B11 B7 B12 60.2(3) . . ? C2 B7 B3 59.3(2) . . ? B11 B7 B3 107.6(3) . . ? B12 B7 B3 107.5(3) . . ? C2 B7 B8 105.2(3) . . ? B11 B7 B8 108.2(3) . . ? B12 B7 B8 60.4(3) . . ? B3 B7 B8 59.3(3) . . ? B3 B8 B4 60.0(3) . . ? B3 B8 B9 108.1(3) . . ? B4 B8 B9 60.1(2) . . ? B3 B8 B7 60.3(3) . . ? B4 B8 B7 108.2(3) . . ? B9 B8 B7 107.9(3) . . ? B3 B8 B12 107.8(3) . . ? B4 B8 B12 107.8(3) . . ? B9 B8 B12 59.9(2) . . ? B7 B8 B12 59.7(3) . . ? B5 B9 B4 60.1(2) . . ? B5 B9 B12 107.5(3) . . ? B4 B9 B12 107.5(3) . . ? B5 B9 B8 107.7(3) . . ? B4 B9 B8 59.5(2) . . ? B12 B9 B8 60.1(2) . . ? B5 B9 B10 59.4(3) . . ? B4 B9 B10 107.3(3) . . ? B12 B9 B10 59.8(3) . . ? B8 B9 B10 107.6(3) . . ? B6 B10 B5 59.9(3) . . ? B6 B10 B11 60.6(3) . . ? B5 B10 B11 108.3(3) . . ? B6 B10 B12 108.4(3) . . ? B5 B10 B12 107.8(3) . . ? B11 B10 B12 60.0(3) . . ? B6 B10 B9 107.8(3) . . ? B5 B10 B9 59.8(3) . . ? B11 B10 B9 107.9(3) . . ? B12 B10 B9 59.8(2) . . ? C2 B11 B10 105.7(3) . . ? C2 B11 B7 59.0(2) . . ? B10 B11 B7 108.4(3) . . ? C2 B11 B6 59.7(2) . . ? B10 B11 B6 59.3(3) . . ? B7 B11 B6 108.4(3) . . ? C2 B11 B12 105.4(3) . . ? B10 B11 B12 60.2(3) . . ? B7 B11 B12 60.0(3) . . ? B6 B11 B12 107.5(3) . . ? B7 B12 B9 108.3(3) . . ? B7 B12 B11 59.8(3) . . ? B9 B12 B11 108.2(3) . . ? B7 B12 B10 107.8(3) . . ? B9 B12 B10 60.4(2) . . ? B11 B12 B10 59.7(3) . . ? B7 B12 B8 60.0(3) . . ? B9 B12 B8 60.0(2) . . ? B11 B12 B8 107.6(3) . . ? B10 B12 B8 108.0(3) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.328 _refine_diff_density_min -0.746 _refine_diff_density_rms 0.098 # Attachment '2010acc0645_1f.cif' data_2010acc0645 _database_code_depnum_ccdc_archive 'CCDC 816756' #TrackingRef '2010acc0645_1f.cif' _chemical_compound_source ' Jose Giner Planas' _database_code_CSD 10AC0645 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common CQMec020 _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H21 B10 N O' _chemical_formula_weight 315.41 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbca 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' '-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 10.4622(2) _cell_length_b 10.4196(3) _cell_length_c 30.6975(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3346.39(15) _cell_formula_units_Z 8 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 22762 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description Fragment _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.252 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1312 _exptl_absorpt_coefficient_mu 0.067 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9788 _exptl_absorpt_correction_T_max 0.9953 _exptl_absorpt_process_details ; SADABS V2.10 (Sheldrick, G.M., 2003) ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker Nonius FR591 Rotating Anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans to fill the asymmetric unit' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 30061 _diffrn_reflns_av_R_equivalents 0.1179 _diffrn_reflns_av_sigmaI/netI 0.0825 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -39 _diffrn_reflns_limit_l_max 39 _diffrn_reflns_theta_min 3.06 _diffrn_reflns_theta_max 27.48 _reflns_number_total 3834 _reflns_number_gt 2490 _reflns_threshold_expression >2\s(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ; Images generated using CrystalMaker: a crystal and molecular structures program for Mac and Windows. CrystalMaker Software Ltd, Oxford, England (www.crystalmaker.com) ; _computing_publication_material 'WINGX (Farrugia, 1998)' _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^ > 2\s(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. Every hydrogen atom was clearly located in the difference map. All C-H and B-H hydrogens were placed in idealised positions and refined using a riding model, the CH3 torsion angle was initially allowed to refine but, but would not converge -- it was subsequently fixed in a staggered position. The OH hydrogen was freely refined. ; _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^)+(0.0930P)^2^+0.6578P] 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 3834 _refine_ls_number_parameters 230 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1111 _refine_ls_R_factor_gt 0.0660 _refine_ls_wR_factor_ref 0.1813 _refine_ls_wR_factor_gt 0.1585 _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_restrained_S_all 1.048 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.20731(14) 0.09896(15) 0.42323(5) 0.0241(4) Uani 1 1 d . . . N1 N -0.13305(17) 0.30973(17) 0.51317(6) 0.0215(4) Uani 1 1 d . . . C1 C 0.0437(2) 0.1237(2) 0.36976(7) 0.0192(5) Uani 1 1 d . . . C2 C 0.1281(2) 0.0942(2) 0.32423(7) 0.0221(5) Uani 1 1 d . . . C3 C 0.2686(2) 0.1307(2) 0.32337(8) 0.0276(6) Uani 1 1 d . . . H3A H 0.2769 0.2226 0.3171 0.041 Uiso 1 1 calc R . . H3B H 0.3125 0.0812 0.3007 0.041 Uiso 1 1 calc R . . H3C H 0.3072 0.1119 0.3517 0.041 Uiso 1 1 calc R . . C4 C 0.1181(2) 0.1884(2) 0.40762(7) 0.0207(5) Uani 1 1 d . . . H4 H 0.1658 0.2636 0.3956 0.025 Uiso 1 1 calc R . . C5 C 0.0298(2) 0.2363(2) 0.44383(7) 0.0194(5) Uani 1 1 d . . . C6 C 0.0101(2) 0.1599(2) 0.47961(7) 0.0211(5) Uani 1 1 d . . . H6 H 0.0519 0.0792 0.4816 0.025 Uiso 1 1 calc R . . C7 C -0.0713(2) 0.1998(2) 0.51337(7) 0.0223(5) Uani 1 1 d . . . H7 H -0.0824 0.1444 0.5377 0.027 Uiso 1 1 calc R . . C8 C -0.1115(2) 0.3919(2) 0.47881(7) 0.0206(5) Uani 1 1 d . . . C9 C -0.1724(2) 0.5130(2) 0.47983(7) 0.0234(5) Uani 1 1 d . . . H9 H -0.2277 0.5339 0.5033 0.028 Uiso 1 1 calc R . . C10 C -0.1525(2) 0.6002(2) 0.44736(7) 0.0256(5) Uani 1 1 d . . . H10 H -0.1945 0.6810 0.4481 0.031 Uiso 1 1 calc R . . C11 C -0.0695(2) 0.5700(2) 0.41273(7) 0.0265(5) Uani 1 1 d . . . H11 H -0.0549 0.6316 0.3905 0.032 Uiso 1 1 calc R . . C12 C -0.0098(2) 0.4543(2) 0.41054(7) 0.0241(5) Uani 1 1 d . . . H12 H 0.0457 0.4363 0.3868 0.029 Uiso 1 1 calc R . . C13 C -0.0296(2) 0.3601(2) 0.44337(7) 0.0195(5) Uani 1 1 d . . . B3 B 0.0849(2) -0.0336(2) 0.35647(8) 0.0224(6) Uani 1 1 d . . . H3 H 0.1542 -0.0937 0.3754 0.027 Uiso 1 1 calc R . . B4 B -0.0689(2) 0.0066(2) 0.37713(8) 0.0222(6) Uani 1 1 d . . . H4A H -0.1018 -0.0276 0.4099 0.027 Uiso 1 1 calc R . . B5 B 0.0177(3) 0.2171(2) 0.32411(8) 0.0233(6) Uani 1 1 d . . . H5 H 0.0434 0.3212 0.3219 0.028 Uiso 1 1 calc R . . B6 B -0.1110(2) 0.1616(3) 0.35683(9) 0.0246(6) Uani 1 1 d . . . H6A H -0.1720 0.2292 0.3761 0.029 Uiso 1 1 calc R . . B7 B 0.0753(3) -0.0413(3) 0.29903(8) 0.0237(6) Uani 1 1 d . . . H7A H 0.1381 -0.1075 0.2798 0.028 Uiso 1 1 calc R . . B8 B -0.0527(3) -0.0986(3) 0.33180(8) 0.0246(6) Uani 1 1 d . . . H8 H -0.0761 -0.2032 0.3344 0.029 Uiso 1 1 calc R . . B9 B 0.0343(3) 0.1130(3) 0.27882(8) 0.0266(6) Uani 1 1 d . . . H9A H 0.0698 0.1485 0.2466 0.032 Uiso 1 1 calc R . . B10 B -0.1204(3) 0.1529(3) 0.29937(9) 0.0269(6) Uani 1 1 d . . . H10A H -0.1886 0.2146 0.2806 0.032 Uiso 1 1 calc R . . B11 B -0.1744(3) 0.0213(3) 0.33167(9) 0.0263(6) Uani 1 1 d . . . H11A H -0.2780 -0.0045 0.3340 0.032 Uiso 1 1 calc R . . B12 B -0.0847(3) -0.0084(3) 0.28333(9) 0.0264(6) Uani 1 1 d . . . H12A H -0.1291 -0.0534 0.2538 0.032 Uiso 1 1 calc R . . H901 H 0.263(3) 0.138(3) 0.4441(11) 0.071(10) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0254(8) 0.0230(9) 0.0240(9) -0.0042(7) -0.0043(7) 0.0051(7) N1 0.0228(10) 0.0207(10) 0.0211(10) -0.0023(8) -0.0006(8) -0.0027(7) C1 0.0233(11) 0.0186(12) 0.0158(10) 0.0004(8) 0.0027(9) 0.0007(9) C2 0.0281(12) 0.0194(12) 0.0187(11) -0.0021(9) 0.0028(9) -0.0010(9) C3 0.0296(13) 0.0250(13) 0.0283(13) -0.0046(10) 0.0049(11) -0.0014(10) C4 0.0237(12) 0.0181(12) 0.0201(11) 0.0004(9) 0.0016(9) -0.0005(9) C5 0.0212(11) 0.0172(11) 0.0197(11) -0.0026(9) -0.0024(9) -0.0042(9) C6 0.0265(12) 0.0149(11) 0.0220(11) -0.0016(9) -0.0003(10) 0.0000(9) C7 0.0246(12) 0.0206(12) 0.0218(12) 0.0003(9) -0.0011(9) -0.0043(9) C8 0.0202(11) 0.0220(12) 0.0197(11) -0.0031(9) -0.0009(9) -0.0042(9) C9 0.0203(11) 0.0236(13) 0.0262(12) -0.0063(10) -0.0004(9) 0.0023(9) C10 0.0268(12) 0.0192(12) 0.0307(13) -0.0041(10) -0.0078(10) 0.0054(9) C11 0.0321(13) 0.0214(13) 0.0261(12) 0.0022(10) -0.0019(11) -0.0017(10) C12 0.0294(12) 0.0208(12) 0.0221(12) -0.0019(9) 0.0008(10) -0.0010(10) C13 0.0221(11) 0.0187(12) 0.0178(11) -0.0031(9) -0.0038(9) -0.0029(9) B3 0.0288(14) 0.0164(13) 0.0221(13) -0.0001(10) 0.0009(11) 0.0009(10) B4 0.0227(12) 0.0224(14) 0.0216(14) 0.0000(10) 0.0004(11) -0.0031(10) B5 0.0314(14) 0.0185(14) 0.0199(13) 0.0018(10) 0.0001(11) 0.0052(11) B6 0.0231(13) 0.0277(15) 0.0229(14) 0.0010(11) -0.0015(11) 0.0010(11) B7 0.0311(14) 0.0193(14) 0.0208(13) -0.0026(10) 0.0002(11) -0.0007(11) B8 0.0321(15) 0.0184(14) 0.0232(13) -0.0005(11) -0.0014(12) -0.0023(11) B9 0.0368(15) 0.0247(15) 0.0185(13) -0.0007(11) -0.0043(12) 0.0020(12) B10 0.0346(15) 0.0232(15) 0.0228(14) -0.0009(11) -0.0046(12) 0.0041(12) B11 0.0281(14) 0.0268(15) 0.0240(14) -0.0030(11) -0.0025(11) -0.0026(11) B12 0.0337(14) 0.0248(15) 0.0206(14) -0.0014(11) -0.0039(11) -0.0020(11) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C4 1.404(3) . ? N1 C7 1.315(3) . ? N1 C8 1.377(3) . ? C1 C4 1.552(3) . ? C1 C2 1.681(3) . ? C1 B4 1.711(3) . ? C1 B6 1.714(3) . ? C1 B5 1.728(3) . ? C1 B3 1.743(3) . ? C2 C3 1.519(3) . ? C2 B7 1.702(3) . ? C2 B9 1.716(3) . ? C2 B3 1.720(3) . ? C2 B5 1.725(3) . ? C4 C5 1.529(3) . ? C5 C6 1.372(3) . ? C5 C13 1.431(3) . ? C6 C7 1.404(3) . ? C8 C9 1.415(3) . ? C8 C13 1.423(3) . ? C9 C10 1.364(3) . ? C10 C11 1.408(3) . ? C11 C12 1.359(3) . ? C12 C13 1.422(3) . ? B3 B8 1.762(4) . ? B3 B7 1.768(4) . ? B3 B4 1.780(4) . ? B4 B8 1.779(4) . ? B4 B11 1.786(4) . ? B4 B6 1.787(4) . ? B5 B10 1.764(4) . ? B5 B9 1.772(4) . ? B5 B6 1.777(4) . ? B6 B10 1.769(4) . ? B6 B11 1.782(4) . ? B7 B12 1.776(4) . ? B7 B9 1.776(4) . ? B7 B8 1.779(4) . ? B8 B11 1.783(4) . ? B8 B12 1.792(4) . ? B9 B12 1.780(4) . ? B9 B10 1.787(4) . ? B10 B11 1.784(4) . ? B10 B12 1.791(4) . ? B11 B12 1.783(4) . ? 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 C7 N1 C8 117.67(19) . . ? C4 C1 C2 116.03(17) . . ? C4 C1 B4 123.76(17) . . ? C2 C1 B4 109.94(16) . . ? C4 C1 B6 123.12(18) . . ? C2 C1 B6 110.23(16) . . ? B4 C1 B6 62.89(14) . . ? C4 C1 B5 116.19(17) . . ? C2 C1 B5 60.78(13) . . ? B4 C1 B5 113.59(17) . . ? B6 C1 B5 62.16(14) . . ? C4 C1 B3 117.39(17) . . ? C2 C1 B3 60.25(13) . . ? B4 C1 B3 62.01(14) . . ? B6 C1 B3 113.34(17) . . ? B5 C1 B3 112.27(17) . . ? C3 C2 C1 118.48(17) . . ? C3 C2 B7 120.94(19) . . ? C1 C2 B7 111.05(17) . . ? C3 C2 B9 120.69(19) . . ? C1 C2 B9 110.74(17) . . ? B7 C2 B9 62.62(15) . . ? C3 C2 B3 117.31(19) . . ? C1 C2 B3 61.65(13) . . ? B7 C2 B3 62.23(14) . . ? B9 C2 B3 113.95(18) . . ? C3 C2 B5 117.52(18) . . ? C1 C2 B5 60.95(13) . . ? B7 C2 B5 113.43(18) . . ? B9 C2 B5 61.98(14) . . ? B3 C2 B5 113.58(17) . . ? O1 C4 C5 111.74(17) . . ? O1 C4 C1 107.48(17) . . ? C5 C4 C1 112.55(17) . . ? C6 C5 C13 117.7(2) . . ? C6 C5 C4 118.89(19) . . ? C13 C5 C4 123.31(19) . . ? C5 C6 C7 120.7(2) . . ? N1 C7 C6 123.5(2) . . ? N1 C8 C9 117.62(19) . . ? N1 C8 C13 122.7(2) . . ? C9 C8 C13 119.7(2) . . ? C10 C9 C8 120.6(2) . . ? C9 C10 C11 119.8(2) . . ? C12 C11 C10 121.3(2) . . ? C11 C12 C13 120.7(2) . . ? C12 C13 C8 117.9(2) . . ? C12 C13 C5 124.5(2) . . ? C8 C13 C5 117.58(19) . . ? C2 B3 C1 58.10(13) . . ? C2 B3 B8 105.37(18) . . ? C1 B3 B8 105.08(17) . . ? C2 B3 B7 58.38(14) . . ? C1 B3 B7 105.18(17) . . ? B8 B3 B7 60.52(15) . . ? C2 B3 B4 105.11(17) . . ? C1 B3 B4 58.13(13) . . ? B8 B3 B4 60.32(14) . . ? B7 B3 B4 108.36(18) . . ? C1 B4 B8 105.68(17) . . ? C1 B4 B3 59.87(13) . . ? B8 B4 B3 59.36(14) . . ? C1 B4 B11 105.13(17) . . ? B8 B4 B11 60.02(15) . . ? B3 B4 B11 107.47(18) . . ? C1 B4 B6 58.61(14) . . ? B8 B4 B6 107.92(18) . . ? B3 B4 B6 108.15(18) . . ? B11 B4 B6 59.83(14) . . ? C2 B5 C1 58.28(13) . . ? C2 B5 B10 105.55(18) . . ? C1 B5 B10 105.35(18) . . ? C2 B5 B9 58.76(14) . . ? C1 B5 B9 106.03(17) . . ? B10 B5 B9 60.70(15) . . ? C2 B5 B6 105.36(17) . . ? C1 B5 B6 58.52(13) . . ? B10 B5 B6 59.94(15) . . ? B9 B5 B6 108.60(19) . . ? C1 B6 B10 105.76(18) . . ? C1 B6 B5 59.32(14) . . ? B10 B6 B5 59.68(15) . . ? C1 B6 B11 105.21(18) . . ? B10 B6 B11 60.33(15) . . ? B5 B6 B11 107.69(19) . . ? C1 B6 B4 58.49(13) . . ? B10 B6 B4 108.37(18) . . ? B5 B6 B4 107.72(18) . . ? B11 B6 B4 60.05(15) . . ? C2 B7 B3 59.38(14) . . ? C2 B7 B12 105.62(18) . . ? B3 B7 B12 108.38(19) . . ? C2 B7 B9 59.09(14) . . ? B3 B7 B9 108.74(18) . . ? B12 B7 B9 60.17(15) . . ? C2 B7 B8 105.42(18) . . ? B3 B7 B8 59.58(15) . . ? B12 B7 B8 60.54(15) . . ? B9 B7 B8 108.64(19) . . ? B3 B8 B7 59.90(15) . . ? B3 B8 B4 60.32(14) . . ? B7 B8 B4 107.88(18) . . ? B3 B8 B11 108.35(18) . . ? B7 B8 B11 107.51(18) . . ? B4 B8 B11 60.16(14) . . ? B3 B8 B12 107.92(18) . . ? B7 B8 B12 59.64(15) . . ? B4 B8 B12 107.97(18) . . ? B11 B8 B12 59.82(15) . . ? C2 B9 B5 59.26(14) . . ? C2 B9 B7 58.29(14) . . ? B5 B9 B7 107.67(18) . . ? C2 B9 B12 104.79(18) . . ? B5 B9 B12 107.77(19) . . ? B7 B9 B12 59.90(15) . . ? C2 B9 B10 104.94(18) . . ? B5 B9 B10 59.43(15) . . ? B7 B9 B10 107.83(19) . . ? B12 B9 B10 60.27(16) . . ? B5 B10 B6 60.38(15) . . ? B5 B10 B11 108.14(19) . . ? B6 B10 B11 60.19(15) . . ? B5 B10 B9 59.86(15) . . ? B6 B10 B9 108.28(19) . . ? B11 B10 B9 107.69(19) . . ? B5 B10 B12 107.64(19) . . ? B6 B10 B12 108.10(19) . . ? B11 B10 B12 59.82(15) . . ? B9 B10 B12 59.69(15) . . ? B6 B11 B12 107.91(19) . . ? B6 B11 B8 107.98(18) . . ? B12 B11 B8 60.33(15) . . ? B6 B11 B10 59.48(15) . . ? B12 B11 B10 60.28(15) . . ? B8 B11 B10 108.32(19) . . ? B6 B11 B4 60.12(14) . . ? B12 B11 B4 108.10(19) . . ? B8 B11 B4 59.82(14) . . ? B10 B11 B4 107.75(18) . . ? B7 B12 B9 59.93(15) . . ? B7 B12 B11 107.68(18) . . ? B9 B12 B11 108.03(18) . . ? B7 B12 B10 107.66(19) . . ? B9 B12 B10 60.04(15) . . ? B11 B12 B10 59.90(15) . . ? B7 B12 B8 59.82(15) . . ? B9 B12 B8 107.88(18) . . ? B11 B12 B8 59.85(15) . . ? B10 B12 B8 107.64(18) . . ? 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 H901 N1 0.96(4) 1.79(4) 2.740(2) 172(3) 4_556 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.376 _refine_diff_density_min -0.411 _refine_diff_density_rms 0.083 _iucr_refine_instruction_details ; TITL 2010ACC0645 in Pbca CELL 0.71073 10.4622 10.4196 30.6975 90.000 90.000 90.000 ZERR 8.00 0.0002 0.0003 0.0009 0.000 0.000 0.000 LATT 1 SYMM 1/2 - X, - Y, 1/2 + Z SYMM - X, 1/2 + Y, 1/2 - Z SYMM 1/2 + X, 1/2 - Y, - Z SFAC C H B N O UNIT 104 168 80 8 8 MERG 2 SHEL 7 0.77 FMAP 2 HTAB O1 N1_$1 EQIV $1 [ x+1/2, -y+1/2, -z+1 ] PLAN 20 SIZE 0.07 0.22 0.32 ACTA 55.00 BOND L.S. 4 TEMP -153.00 WGHT 0.093000 0.657800 FVAR 0.13404 O1 5 0.207313 0.098956 0.423234 11.00000 0.02538 0.02304 = 0.02395 -0.00424 -0.00435 0.00513 N1 4 -0.133046 0.309727 0.513170 11.00000 0.02281 0.02065 = 0.02110 -0.00233 -0.00062 -0.00268 C1 1 0.043742 0.123664 0.369760 11.00000 0.02330 0.01858 = 0.01584 0.00038 0.00265 0.00074 C2 1 0.128112 0.094162 0.324233 11.00000 0.02810 0.01941 = 0.01869 -0.00214 0.00276 -0.00104 C3 1 0.268633 0.130714 0.323367 11.00000 0.02959 0.02496 = 0.02834 -0.00459 0.00490 -0.00140 AFIX 33 H3A 2 0.276862 0.222569 0.317104 11.00000 -1.50000 H3B 2 0.312456 0.081236 0.300694 11.00000 -1.50000 H3C 2 0.307246 0.111919 0.351745 11.00000 -1.50000 AFIX 0 C4 1 0.118058 0.188402 0.407619 11.00000 0.02375 0.01812 = 0.02013 0.00044 0.00155 -0.00053 AFIX 13 H4 2 0.165796 0.263616 0.395589 11.00000 -1.20000 AFIX 0 C5 1 0.029766 0.236328 0.443830 11.00000 0.02125 0.01723 = 0.01971 -0.00259 -0.00238 -0.00419 C6 1 0.010067 0.159928 0.479607 11.00000 0.02649 0.01492 = 0.02199 -0.00158 -0.00031 0.00004 AFIX 43 H6 2 0.051917 0.079219 0.481556 11.00000 -1.20000 AFIX 0 C7 1 -0.071309 0.199788 0.513374 11.00000 0.02459 0.02056 = 0.02179 0.00025 -0.00105 -0.00427 AFIX 43 H7 2 -0.082354 0.144381 0.537661 11.00000 -1.20000 AFIX 0 C8 1 -0.111455 0.391855 0.478808 11.00000 0.02015 0.02196 = 0.01974 -0.00306 -0.00094 -0.00417 C9 1 -0.172400 0.513041 0.479833 11.00000 0.02034 0.02363 = 0.02615 -0.00627 -0.00043 0.00228 AFIX 43 H9 2 -0.227681 0.533918 0.503339 11.00000 -1.20000 AFIX 0 C10 1 -0.152478 0.600168 0.447364 11.00000 0.02675 0.01924 = 0.03067 -0.00409 -0.00777 0.00541 AFIX 43 H10 2 -0.194479 0.680972 0.448112 11.00000 -1.20000 AFIX 0 C11 1 -0.069463 0.569978 0.412729 11.00000 0.03210 0.02142 = 0.02606 0.00217 -0.00188 -0.00166 AFIX 43 H11 2 -0.054920 0.631635 0.390477 11.00000 -1.20000 AFIX 0 C12 1 -0.009785 0.454348 0.410540 11.00000 0.02940 0.02085 = 0.02206 -0.00188 0.00079 -0.00103 AFIX 43 H12 2 0.045746 0.436259 0.386837 11.00000 -1.20000 AFIX 0 C13 1 -0.029598 0.360094 0.443375 11.00000 0.02205 0.01875 = 0.01778 -0.00314 -0.00382 -0.00288 B3 3 0.084893 -0.033625 0.356471 11.00000 0.02875 0.01644 = 0.02208 -0.00006 0.00093 0.00094 AFIX 153 H3 2 0.154178 -0.093665 0.375399 11.00000 -1.20000 AFIX 0 B4 3 -0.068906 0.006568 0.377131 11.00000 0.02271 0.02238 = 0.02158 -0.00003 0.00037 -0.00313 AFIX 153 H4A 2 -0.101831 -0.027619 0.409851 11.00000 -1.20000 AFIX 0 B5 3 0.017684 0.217099 0.324113 11.00000 0.03142 0.01849 = 0.01987 0.00182 0.00009 0.00519 AFIX 153 H5 2 0.043443 0.321229 0.321916 11.00000 -1.20000 AFIX 0 B6 3 -0.111037 0.161619 0.356828 11.00000 0.02309 0.02766 = 0.02292 0.00104 -0.00148 0.00104 AFIX 153 H6A 2 -0.171989 0.229224 0.376144 11.00000 -1.20000 AFIX 0 B7 3 0.075338 -0.041283 0.299029 11.00000 0.03107 0.01926 = 0.02080 -0.00258 0.00019 -0.00065 AFIX 153 H7A 2 0.138082 -0.107537 0.279842 11.00000 -1.20000 AFIX 0 B8 3 -0.052734 -0.098623 0.331801 11.00000 0.03213 0.01838 = 0.02322 -0.00053 -0.00137 -0.00227 AFIX 153 H8 2 -0.076127 -0.203238 0.334387 11.00000 -1.20000 AFIX 0 B9 3 0.034328 0.113039 0.278818 11.00000 0.03675 0.02469 = 0.01850 -0.00072 -0.00428 0.00197 AFIX 153 H9A 2 0.069778 0.148458 0.246559 11.00000 -1.20000 AFIX 0 B10 3 -0.120430 0.152925 0.299374 11.00000 0.03464 0.02322 = 0.02281 -0.00092 -0.00462 0.00410 AFIX 153 H10A 2 -0.188552 0.214633 0.280575 11.00000 -1.20000 AFIX 0 B11 3 -0.174352 0.021266 0.331667 11.00000 0.02815 0.02684 = 0.02402 -0.00297 -0.00246 -0.00256 AFIX 153 H11A 2 -0.278048 -0.004506 0.334037 11.00000 -1.20000 AFIX 0 B12 3 -0.084678 -0.008387 0.283326 11.00000 0.03368 0.02482 = 0.02061 -0.00141 -0.00390 -0.00204 AFIX 153 H12A 2 -0.129051 -0.053390 0.253845 11.00000 -1.20000 AFIX 0 H901 2 0.263193 0.138281 0.444058 11.00000 0.07100 HKLF 4 REM 2010ACC0645 in Pbca REM R1 = 0.0660 for 2490 Fo > 4sig(Fo) and 0.1111 for all 3834 data REM 230 parameters refined using 0 restraints END WGHT 0.0929 0.6607 REM Highest difference peak 0.376, deepest hole -0.411, 1-sigma level 0.083 Q1 1 0.0756 0.3032 0.3255 11.00000 0.05 0.38 Q2 1 0.3227 0.0257 0.3214 11.00000 0.05 0.38 Q3 1 0.2942 0.1534 0.2923 11.00000 0.05 0.32 Q4 1 -0.0474 0.5879 0.3261 11.00000 0.05 0.29 Q5 1 0.1046 0.0886 0.1991 11.00000 0.05 0.28 Q6 1 0.3066 0.2047 0.3411 11.00000 0.05 0.28 Q7 1 0.0826 0.4808 0.3332 11.00000 0.05 0.27 Q8 1 0.1690 -0.0793 0.2901 11.00000 0.05 0.26 Q9 1 -0.0261 0.5021 0.3423 11.00000 0.05 0.25 Q10 1 0.0772 0.1625 0.3911 11.00000 0.05 0.24 Q11 1 0.1096 0.0599 0.5224 11.00000 0.05 0.24 Q12 1 0.3480 -0.0135 0.3498 11.00000 0.05 0.24 Q13 1 0.1490 0.0828 0.4913 11.00000 0.05 0.24 Q14 1 -0.3832 0.0599 0.3170 11.00000 0.05 0.23 Q15 1 0.0870 0.0071 0.4912 11.00000 0.05 0.23 Q16 1 0.0135 0.6004 0.3489 11.00000 0.05 0.23 Q17 1 0.4645 0.0543 0.3220 11.00000 0.05 0.23 Q18 1 -0.0272 0.4153 0.3188 11.00000 0.05 0.23 Q19 1 0.2598 0.3792 0.3222 11.00000 0.05 0.23 Q20 1 -0.1358 0.2441 0.3804 11.00000 0.05 0.23 ; # Attachment '2010acc0646_2b.cif' data_2010acc0646 _database_code_depnum_ccdc_archive 'CCDC 816757' #TrackingRef '2010acc0646_2b.cif' _chemical_compound_source 'Jose Giner Planas' _database_code_CSD 10AC0646 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common SPCB022 _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C9 H19 B10 N O' _chemical_formula_weight 265.35 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 C2/c 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 21.1947(7) _cell_length_b 7.1376(2) _cell_length_c 19.7547(6) _cell_angle_alpha 90.00 _cell_angle_beta 92.129(2) _cell_angle_gamma 90.00 _cell_volume 2986.41(16) _cell_formula_units_Z 8 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 16500 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description Fragment _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.180 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1104 _exptl_absorpt_coefficient_mu 0.063 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9784 _exptl_absorpt_correction_T_max 0.9938 _exptl_absorpt_process_details ; SADABS V2.10 (Sheldrick, G.M., 2003) ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker Nonius FR591 Rotating Anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans to fill the asymmetric unit' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 23120 _diffrn_reflns_av_R_equivalents 0.0679 _diffrn_reflns_av_sigmaI/netI 0.0487 _diffrn_reflns_limit_h_min -27 _diffrn_reflns_limit_h_max 27 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 3.01 _diffrn_reflns_theta_max 27.48 _reflns_number_total 3424 _reflns_number_gt 2642 _reflns_threshold_expression >2\s(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ; Images generated using CrystalMaker: a crystal and molecular structures program for Mac and Windows. CrystalMaker Software Ltd, Oxford, England (www.crystalmaker.com) ; _computing_publication_material 'WINGX (Farrugia, 1998)' _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^ > 2\s(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. Every hydrogen atom was clearly located in the difference map. All C-H and B-H hydrogens were placed in idealised positions and refined using a riding model, the CH3 torsion angle was allowed to refine. The OH hydrogen was freely refined. ; _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^)+(0.0973P)^2^+1.6592P] 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 3424 _refine_ls_number_parameters 195 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0774 _refine_ls_R_factor_gt 0.0583 _refine_ls_wR_factor_ref 0.1715 _refine_ls_wR_factor_gt 0.1584 _refine_ls_goodness_of_fit_ref 1.062 _refine_ls_restrained_S_all 1.062 _refine_ls_shift/su_max 0.011 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.31008(6) -0.23767(16) 0.20092(7) 0.0284(3) Uani 1 1 d . . . N1 N 0.17849(6) 0.07652(18) 0.17946(7) 0.0197(3) Uani 1 1 d . . . C1 C 0.32574(7) 0.0595(2) 0.14903(8) 0.0176(3) Uani 1 1 d . . . C2 C 0.39809(8) -0.0171(2) 0.14148(9) 0.0245(4) Uani 1 1 d . . . H2 H 0.4141 -0.1492 0.1675 0.029 Uiso 1 1 calc R . . C3 C 0.28312(8) -0.0592(2) 0.19504(8) 0.0203(4) Uani 1 1 d . . . H3 H 0.2825 -0.0002 0.2409 0.024 Uiso 1 1 calc R . . C4 C 0.21607(7) -0.0690(2) 0.16516(8) 0.0191(3) Uani 1 1 d . . . C5 C 0.19601(8) -0.2179(2) 0.12458(9) 0.0247(4) Uani 1 1 d . . . H5 H 0.2233 -0.3202 0.1161 0.030 Uiso 1 1 calc R . . C6 C 0.13500(9) -0.2127(3) 0.09680(9) 0.0301(4) Uani 1 1 d . . . H6 H 0.1197 -0.3123 0.0689 0.036 Uiso 1 1 calc R . . C7 C 0.09669(8) -0.0618(3) 0.10999(9) 0.0285(4) Uani 1 1 d . . . H7 H 0.0551 -0.0553 0.0904 0.034 Uiso 1 1 calc R . . C8 C 0.11945(8) 0.0806(2) 0.15226(8) 0.0235(4) Uani 1 1 d . . . C9 C 0.07861(9) 0.2450(3) 0.16932(10) 0.0336(4) Uani 1 1 d . . . H9A H 0.0593 0.2227 0.2129 0.050 Uiso 1 1 calc R . . H9B H 0.0454 0.2609 0.1339 0.050 Uiso 1 1 calc R . . H9C H 0.1045 0.3586 0.1723 0.050 Uiso 1 1 calc R . . B3 B 0.38673(9) 0.1752(3) 0.19138(10) 0.0236(4) Uani 1 1 d . . . H3A H 0.3940 0.1790 0.2478 0.028 Uiso 1 1 calc R . . B4 B 0.32423(9) 0.2980(2) 0.14912(10) 0.0218(4) Uani 1 1 d . . . H4 H 0.2901 0.3846 0.1777 0.026 Uiso 1 1 calc R . . B5 B 0.29954(9) 0.1680(2) 0.07605(9) 0.0200(4) Uani 1 1 d . . . H5A H 0.2493 0.1701 0.0565 0.024 Uiso 1 1 calc R . . B6 B 0.34575(9) -0.0384(3) 0.07340(9) 0.0223(4) Uani 1 1 d . . . H6A H 0.3262 -0.1737 0.0530 0.027 Uiso 1 1 calc R . . B7 B 0.45107(9) 0.1604(3) 0.13650(11) 0.0287(5) Uani 1 1 d . . . H7A H 0.5011 0.1555 0.1566 0.034 Uiso 1 1 calc R . . B8 B 0.40453(10) 0.3673(3) 0.13943(10) 0.0272(4) Uani 1 1 d . . . H8 H 0.4239 0.5014 0.1611 0.033 Uiso 1 1 calc R . . B9 B 0.35004(9) 0.3629(3) 0.06793(10) 0.0229(4) Uani 1 1 d . . . H9 H 0.3334 0.4952 0.0425 0.027 Uiso 1 1 calc R . . B10 B 0.36373(9) 0.1534(3) 0.02101(10) 0.0227(4) Uani 1 1 d . . . H10 H 0.3564 0.1466 -0.0354 0.027 Uiso 1 1 calc R . . B11 B 0.42582(9) 0.0282(3) 0.06379(11) 0.0275(4) Uani 1 1 d . . . H11 H 0.4594 -0.0635 0.0364 0.033 Uiso 1 1 calc R . . B12 B 0.42867(9) 0.2776(3) 0.05976(10) 0.0266(4) Uani 1 1 d . . . H12 H 0.4639 0.3530 0.0288 0.032 Uiso 1 1 calc R . . H901 H 0.3069(13) -0.282(4) 0.2485(15) 0.067(8) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0373(7) 0.0214(6) 0.0267(7) 0.0066(5) 0.0055(5) 0.0068(5) N1 0.0193(7) 0.0231(7) 0.0168(7) -0.0005(5) 0.0021(5) -0.0034(5) C1 0.0186(8) 0.0179(7) 0.0164(8) -0.0001(6) 0.0010(6) 0.0023(6) C2 0.0213(8) 0.0256(9) 0.0268(9) 0.0049(7) 0.0045(7) 0.0045(6) C3 0.0231(8) 0.0206(8) 0.0172(8) 0.0034(6) 0.0028(6) 0.0001(6) C4 0.0237(8) 0.0206(8) 0.0133(7) 0.0015(6) 0.0047(6) -0.0039(6) C5 0.0321(9) 0.0220(8) 0.0204(8) -0.0008(7) 0.0053(7) -0.0042(7) C6 0.0377(10) 0.0325(10) 0.0201(9) -0.0039(7) 0.0012(7) -0.0154(8) C7 0.0256(9) 0.0379(10) 0.0220(9) 0.0017(7) -0.0016(7) -0.0104(7) C8 0.0222(8) 0.0307(9) 0.0175(8) 0.0027(7) 0.0015(6) -0.0033(6) C9 0.0245(9) 0.0427(11) 0.0335(10) -0.0036(8) -0.0013(7) 0.0063(8) B3 0.0226(9) 0.0261(10) 0.0219(10) 0.0003(7) -0.0013(7) -0.0031(7) B4 0.0273(9) 0.0177(8) 0.0205(9) -0.0013(7) 0.0017(7) 0.0017(7) B5 0.0231(9) 0.0198(9) 0.0171(9) 0.0014(7) 0.0010(7) -0.0005(7) B6 0.0279(10) 0.0209(9) 0.0186(9) -0.0019(7) 0.0058(7) 0.0009(7) B7 0.0185(9) 0.0375(11) 0.0301(11) 0.0083(8) 0.0004(8) -0.0031(8) B8 0.0316(10) 0.0247(10) 0.0253(10) -0.0002(8) -0.0008(8) -0.0076(8) B9 0.0270(10) 0.0184(9) 0.0232(10) 0.0025(7) 0.0001(7) -0.0006(7) B10 0.0267(10) 0.0223(9) 0.0193(9) 0.0020(7) 0.0044(7) -0.0005(7) B11 0.0252(10) 0.0307(10) 0.0274(10) 0.0046(8) 0.0104(8) 0.0041(8) B12 0.0238(10) 0.0285(10) 0.0276(10) 0.0057(8) 0.0027(8) -0.0031(8) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C3 1.3990(19) . ? N1 C8 1.344(2) . ? N1 C4 1.345(2) . ? C1 C3 1.556(2) . ? C1 C2 1.640(2) . ? C1 B4 1.703(2) . ? C1 B5 1.711(2) . ? C1 B6 1.717(2) . ? C1 B3 1.724(2) . ? C2 B11 1.695(3) . ? C2 B7 1.698(3) . ? C2 B3 1.712(3) . ? C2 B6 1.718(3) . ? C3 C4 1.520(2) . ? C4 C5 1.389(2) . ? C5 C6 1.386(3) . ? C6 C7 1.379(3) . ? C7 C8 1.390(2) . ? C8 C9 1.504(2) . ? B3 B8 1.762(3) . ? B3 B4 1.772(3) . ? B3 B7 1.777(3) . ? B4 B9 1.775(3) . ? B4 B5 1.778(3) . ? B4 B8 1.789(3) . ? B5 B9 1.766(3) . ? B5 B6 1.771(3) . ? B5 B10 1.776(3) . ? B6 B10 1.766(3) . ? B6 B11 1.779(3) . ? B7 B8 1.778(3) . ? B7 B12 1.780(3) . ? B7 B11 1.784(3) . ? B8 B9 1.791(3) . ? B8 B12 1.791(3) . ? B9 B12 1.788(3) . ? B9 B10 1.789(3) . ? B10 B11 1.778(3) . ? B10 B12 1.786(3) . ? B11 B12 1.783(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 C8 N1 C4 118.85(14) . . ? C3 C1 C2 115.90(12) . . ? C3 C1 B4 122.16(13) . . ? C2 C1 B4 110.55(12) . . ? C3 C1 B5 124.16(13) . . ? C2 C1 B5 110.47(12) . . ? B4 C1 B5 62.77(10) . . ? C3 C1 B6 117.03(12) . . ? C2 C1 B6 61.52(10) . . ? B4 C1 B6 114.39(12) . . ? B5 C1 B6 62.23(10) . . ? C3 C1 B3 114.73(13) . . ? C2 C1 B3 61.12(10) . . ? B4 C1 B3 62.25(10) . . ? B5 C1 B3 113.95(12) . . ? B6 C1 B3 114.34(13) . . ? C1 C2 B11 112.06(13) . . ? C1 C2 B7 112.28(13) . . ? B11 C2 B7 63.44(12) . . ? C1 C2 B3 61.87(10) . . ? B11 C2 B3 115.42(14) . . ? B7 C2 B3 62.79(11) . . ? C1 C2 B6 61.44(10) . . ? B11 C2 B6 62.84(11) . . ? B7 C2 B6 115.45(13) . . ? B3 C2 B6 114.91(12) . . ? O1 C3 C4 111.32(13) . . ? O1 C3 C1 107.46(13) . . ? C4 C3 C1 110.66(12) . . ? N1 C4 C5 122.76(15) . . ? N1 C4 C3 115.82(13) . . ? C5 C4 C3 121.41(15) . . ? C6 C5 C4 117.98(16) . . ? C7 C6 C5 119.54(16) . . ? C6 C7 C8 119.38(16) . . ? N1 C8 C7 121.44(16) . . ? N1 C8 C9 117.53(15) . . ? C7 C8 C9 121.03(16) . . ? C2 B3 C1 57.01(9) . . ? C2 B3 B8 104.52(13) . . ? C1 B3 B8 105.25(13) . . ? C2 B3 B4 104.13(13) . . ? C1 B3 B4 58.29(10) . . ? B8 B3 B4 60.84(11) . . ? C2 B3 B7 58.24(11) . . ? C1 B3 B7 104.72(13) . . ? B8 B3 B7 60.31(11) . . ? B4 B3 B7 108.61(14) . . ? C1 B4 B3 59.45(10) . . ? C1 B4 B9 104.68(13) . . ? B3 B4 B9 107.75(13) . . ? C1 B4 B5 58.83(9) . . ? B3 B4 B5 108.46(13) . . ? B9 B4 B5 59.61(10) . . ? C1 B4 B8 104.95(13) . . ? B3 B4 B8 59.31(11) . . ? B9 B4 B8 60.34(11) . . ? B5 B4 B8 108.04(13) . . ? C1 B5 B9 104.74(12) . . ? C1 B5 B6 59.04(10) . . ? B9 B5 B6 108.35(13) . . ? C1 B5 B10 104.89(12) . . ? B9 B5 B10 60.67(11) . . ? B6 B5 B10 59.72(10) . . ? C1 B5 B4 58.40(10) . . ? B9 B5 B4 60.11(10) . . ? B6 B5 B4 108.16(13) . . ? B10 B5 B4 108.58(13) . . ? C1 B6 C2 57.04(10) . . ? C1 B6 B10 105.09(12) . . ? C2 B6 B10 104.07(13) . . ? C1 B6 B5 58.74(10) . . ? C2 B6 B5 104.18(13) . . ? B10 B6 B5 60.27(10) . . ? C1 B6 B11 104.57(13) . . ? C2 B6 B11 57.95(10) . . ? B10 B6 B11 60.20(11) . . ? B5 B6 B11 108.15(13) . . ? C2 B7 B3 58.98(10) . . ? C2 B7 B8 104.41(13) . . ? B3 B7 B8 59.44(11) . . ? C2 B7 B12 104.11(14) . . ? B3 B7 B12 107.79(14) . . ? B8 B7 B12 60.46(11) . . ? C2 B7 B11 58.19(11) . . ? B3 B7 B11 107.97(13) . . ? B8 B7 B11 108.37(14) . . ? B12 B7 B11 60.01(12) . . ? B3 B8 B7 60.25(11) . . ? B3 B8 B4 59.85(11) . . ? B7 B8 B4 107.77(13) . . ? B3 B8 B9 107.46(13) . . ? B7 B8 B9 107.59(14) . . ? B4 B8 B9 59.44(11) . . ? B3 B8 B12 107.93(14) . . ? B7 B8 B12 59.84(11) . . ? B4 B8 B12 107.40(13) . . ? B9 B8 B12 59.86(11) . . ? B5 B9 B4 60.29(10) . . ? B5 B9 B12 108.06(13) . . ? B4 B9 B12 108.20(13) . . ? B5 B9 B10 59.94(10) . . ? B4 B9 B10 108.14(13) . . ? B12 B9 B10 59.90(11) . . ? B5 B9 B8 108.50(13) . . ? B4 B9 B8 60.23(11) . . ? B12 B9 B8 60.07(11) . . ? B10 B9 B8 108.11(13) . . ? B6 B10 B5 60.01(10) . . ? B6 B10 B11 60.27(11) . . ? B5 B10 B11 108.00(13) . . ? B6 B10 B12 108.25(13) . . ? B5 B10 B12 107.72(13) . . ? B11 B10 B12 60.03(11) . . ? B6 B10 B9 107.56(13) . . ? B5 B10 B9 59.39(10) . . ? B11 B10 B9 107.77(14) . . ? B12 B10 B9 60.01(11) . . ? C2 B11 B10 104.53(13) . . ? C2 B11 B6 59.21(11) . . ? B10 B11 B6 59.53(11) . . ? C2 B11 B12 104.16(14) . . ? B10 B11 B12 60.20(11) . . ? B6 B11 B12 107.80(14) . . ? C2 B11 B7 58.38(11) . . ? B10 B11 B7 108.15(14) . . ? B6 B11 B7 108.31(14) . . ? B12 B11 B7 59.89(11) . . ? B7 B12 B11 60.10(11) . . ? B7 B12 B10 107.99(13) . . ? B11 B12 B10 59.78(11) . . ? B7 B12 B9 107.65(14) . . ? B11 B12 B9 107.63(13) . . ? B10 B12 B9 60.09(11) . . ? B7 B12 B8 59.70(12) . . ? B11 B12 B8 107.84(14) . . ? B10 B12 B8 108.25(14) . . ? B9 B12 B8 60.07(11) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.582 _refine_diff_density_min -0.400 _refine_diff_density_rms 0.107 _iucr_refine_instruction_details ; TITL 2010acc0646 in C2/c CELL 0.71073 21.1947 7.1376 19.7547 90.000 92.129 90.000 ZERR 8.00 0.0007 0.0002 0.0006 0.000 0.002 0.000 LATT 7 SYMM - X, Y, 1/2 - Z SFAC C H B N O UNIT 72 152 80 8 8 MERG 2 SHEL 7 0.77 FMAP 2 PLAN 20 SIZE 0.10 0.30 0.35 ACTA 55.00 BOND L.S. 4 TEMP -153.00 WGHT 0.097300 1.659200 FVAR 0.13017 O1 5 0.310079 -0.237670 0.200922 11.00000 0.03731 0.02142 = 0.02672 0.00658 0.00553 0.00685 N1 4 0.178492 0.076522 0.179457 11.00000 0.01929 0.02305 = 0.01678 -0.00050 0.00207 -0.00342 C1 1 0.325742 0.059459 0.149025 11.00000 0.01856 0.01791 = 0.01640 -0.00008 0.00104 0.00227 C2 1 0.398091 -0.017103 0.141482 11.00000 0.02134 0.02563 = 0.02676 0.00485 0.00445 0.00450 AFIX 153 H2 2 0.414095 -0.149198 0.167459 11.00000 -1.20000 AFIX 0 C3 1 0.283124 -0.059219 0.195039 11.00000 0.02315 0.02060 = 0.01715 0.00340 0.00275 0.00014 AFIX 13 H3 2 0.282500 -0.000172 0.240915 11.00000 -1.20000 AFIX 0 C4 1 0.216072 -0.068970 0.165162 11.00000 0.02374 0.02056 = 0.01331 0.00150 0.00475 -0.00391 C5 1 0.196007 -0.217884 0.124579 11.00000 0.03207 0.02204 = 0.02039 -0.00078 0.00529 -0.00423 AFIX 43 H5 2 0.223262 -0.320229 0.116106 11.00000 -1.20000 AFIX 0 C6 1 0.134998 -0.212686 0.096799 11.00000 0.03768 0.03254 = 0.02011 -0.00392 0.00117 -0.01537 AFIX 43 H6 2 0.119681 -0.312349 0.068870 11.00000 -1.20000 AFIX 0 C7 1 0.096688 -0.061824 0.109989 11.00000 0.02556 0.03791 = 0.02197 0.00172 -0.00163 -0.01035 AFIX 43 H7 2 0.055138 -0.055271 0.090375 11.00000 -1.20000 AFIX 0 C8 1 0.119449 0.080566 0.152258 11.00000 0.02223 0.03072 = 0.01750 0.00268 0.00147 -0.00325 C9 1 0.078614 0.245031 0.169323 11.00000 0.02445 0.04273 = 0.03346 -0.00355 -0.00134 0.00630 AFIX 137 H9A 2 0.059253 0.222748 0.212883 11.00000 -1.50000 H9B 2 0.045449 0.260867 0.133885 11.00000 -1.50000 H9C 2 0.104535 0.358634 0.172320 11.00000 -1.50000 AFIX 0 B3 3 0.386729 0.175152 0.191383 11.00000 0.02264 0.02613 = 0.02185 0.00030 -0.00132 -0.00315 AFIX 153 H3A 2 0.393966 0.178958 0.247817 11.00000 -1.20000 AFIX 0 B4 3 0.324227 0.298036 0.149115 11.00000 0.02731 0.01766 = 0.02050 -0.00128 0.00170 0.00167 AFIX 153 H4 2 0.290100 0.384625 0.177701 11.00000 -1.20000 AFIX 0 B5 3 0.299537 0.168039 0.076050 11.00000 0.02307 0.01979 = 0.01705 0.00140 0.00096 -0.00050 AFIX 153 H5A 2 0.249256 0.170051 0.056505 11.00000 -1.20000 AFIX 0 B6 3 0.345754 -0.038392 0.073404 11.00000 0.02788 0.02089 = 0.01855 -0.00188 0.00578 0.00089 AFIX 153 H6A 2 0.326236 -0.173711 0.052979 11.00000 -1.20000 AFIX 0 B7 3 0.451073 0.160438 0.136503 11.00000 0.01848 0.03747 = 0.03012 0.00830 0.00044 -0.00313 AFIX 153 H7A 2 0.501145 0.155525 0.156641 11.00000 -1.20000 AFIX 0 B8 3 0.404532 0.367276 0.139431 11.00000 0.03162 0.02467 = 0.02525 -0.00023 -0.00083 -0.00760 AFIX 153 H8 2 0.423905 0.501350 0.161089 11.00000 -1.20000 AFIX 0 B9 3 0.350035 0.362924 0.067935 11.00000 0.02702 0.01840 = 0.02320 0.00252 0.00014 -0.00062 AFIX 153 H9 2 0.333390 0.495179 0.042523 11.00000 -1.20000 AFIX 0 B10 3 0.363726 0.153386 0.021015 11.00000 0.02667 0.02233 = 0.01932 0.00198 0.00443 -0.00047 AFIX 153 H10 2 0.356362 0.146600 -0.035368 11.00000 -1.20000 AFIX 0 B11 3 0.425822 0.028244 0.063788 11.00000 0.02517 0.03071 = 0.02743 0.00456 0.01036 0.00407 AFIX 153 H11 2 0.459364 -0.063453 0.036430 11.00000 -1.20000 AFIX 0 B12 3 0.428675 0.277574 0.059757 11.00000 0.02380 0.02846 = 0.02760 0.00570 0.00266 -0.00306 AFIX 153 H12 2 0.463907 0.352998 0.028838 11.00000 -1.20000 AFIX 0 H901 2 0.306916 -0.281841 0.248474 11.00000 0.06708 HKLF 4 REM 2010acc0646 in C2/c REM R1 = 0.0583 for 2642 Fo > 4sig(Fo) and 0.0774 for all 3424 data REM 195 parameters refined using 0 restraints END WGHT 0.0878 1.8879 REM Highest difference peak 0.582, deepest hole -0.400, 1-sigma level 0.107 Q1 1 0.2953 -0.0513 0.2613 11.00000 0.05 0.58 Q2 1 0.2217 -0.5453 0.0972 11.00000 0.05 0.32 Q3 1 0.3899 0.1109 0.2356 11.00000 0.05 0.32 Q4 1 0.2579 0.5024 0.0640 11.00000 0.05 0.31 Q5 1 0.3004 0.5545 0.0724 11.00000 0.05 0.29 Q6 1 0.3461 0.4345 0.0590 11.00000 0.05 0.29 Q7 1 0.2580 -0.4677 0.1061 11.00000 0.05 0.28 Q8 1 0.4245 0.6098 0.0578 11.00000 0.05 0.27 Q9 1 0.3381 0.5175 0.0744 11.00000 0.05 0.27 Q10 1 0.2415 0.4550 0.1404 11.00000 0.05 0.27 Q11 1 0.1841 -0.4658 0.1091 11.00000 0.05 0.27 Q12 1 0.3927 0.3681 0.0907 11.00000 0.05 0.27 Q13 1 0.4479 0.5638 0.0232 11.00000 0.05 0.27 Q14 1 0.3002 0.4595 0.0706 11.00000 0.05 0.26 Q15 1 0.2769 0.3225 0.1804 11.00000 0.05 0.26 Q16 1 0.4187 0.3508 0.0901 11.00000 0.05 0.26 Q17 1 0.2607 -0.4210 0.1572 11.00000 0.05 0.26 Q18 1 0.2995 0.3465 0.1988 11.00000 0.05 0.25 Q19 1 0.3819 0.5586 0.0646 11.00000 0.05 0.25 Q20 1 0.4788 0.0261 0.2308 11.00000 0.05 0.25 ;