# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Shengming Ma' _publ_contact_author_email masm@sioc.ac.cn _publ_author_name 'Shengming Ma' data_z_2j _database_code_depnum_ccdc_archive 'CCDC 886806' #TrackingRef '- Z-2j.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H20 B Br O2' _chemical_formula_weight 323.03 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 '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 10.0397(8) _cell_length_b 7.5575(6) _cell_length_c 20.5113(15) _cell_angle_alpha 90.00 _cell_angle_beta 97.104(2) _cell_angle_gamma 90.00 _cell_volume 1544.3(2) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.389 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 664 _exptl_absorpt_coefficient_mu 2.657 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4481 _exptl_absorpt_correction_T_max 0.5681 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 14022 _diffrn_reflns_av_R_equivalents 0.0305 _diffrn_reflns_av_sigmaI/netI 0.0231 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.00 _diffrn_reflns_theta_max 25.01 _reflns_number_total 2704 _reflns_number_gt 1988 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0441P)^2^+0.9561P] 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 2704 _refine_ls_number_parameters 172 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0563 _refine_ls_R_factor_gt 0.0369 _refine_ls_wR_factor_ref 0.0990 _refine_ls_wR_factor_gt 0.0892 _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_restrained_S_all 1.036 _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 Br1 Br 0.48730(4) 0.78503(6) 0.092434(17) 0.0819(2) Uani 1 1 d . . . B1 B 1.1302(3) 0.7308(4) -0.14542(15) 0.0401(7) Uani 1 1 d . . . O1 O 1.25911(18) 0.6748(3) -0.14601(9) 0.0506(5) Uani 1 1 d . . . O2 O 1.07195(18) 0.7848(3) -0.20580(9) 0.0478(5) Uani 1 1 d . . . C1 C 0.6249(3) 0.7776(4) 0.03683(14) 0.0525(7) Uani 1 1 d . . . C2 C 0.5928(3) 0.7339(5) -0.02801(15) 0.0642(9) Uani 1 1 d . . . H2A H 0.5049 0.7063 -0.0448 0.077 Uiso 1 1 calc R . . C3 C 0.6935(3) 0.7321(5) -0.06762(14) 0.0586(9) Uani 1 1 d . . . H3A H 0.6718 0.7037 -0.1118 0.070 Uiso 1 1 calc R . . C4 C 0.8263(3) 0.7706(4) -0.04469(13) 0.0402(6) Uani 1 1 d . . . C5 C 0.8540(3) 0.8160(4) 0.02082(14) 0.0543(8) Uani 1 1 d . . . H5A H 0.9414 0.8454 0.0378 0.065 Uiso 1 1 calc R . . C6 C 0.7541(3) 0.8185(5) 0.06173(15) 0.0615(9) Uani 1 1 d . . . H6A H 0.7747 0.8478 0.1059 0.074 Uiso 1 1 calc R . . C7 C 0.9257(3) 0.7651(4) -0.09136(13) 0.0430(7) Uani 1 1 d . . . H7A H 0.8908 0.7886 -0.1346 0.052 Uiso 1 1 calc R . . C8 C 1.0579(3) 0.7322(3) -0.08271(12) 0.0403(6) Uani 1 1 d . . . C9 C 1.1759(3) 0.7895(4) -0.24942(13) 0.0453(7) Uani 1 1 d . . . C10 C 1.2833(3) 0.6615(4) -0.21427(13) 0.0456(7) Uani 1 1 d . . . C11 C 1.2246(3) 0.9803(4) -0.25077(16) 0.0634(9) Uani 1 1 d . . . H11A H 1.1546 1.0531 -0.2728 0.095 Uiso 1 1 calc R . . H11B H 1.3021 0.9861 -0.2738 0.095 Uiso 1 1 calc R . . H11C H 1.2477 1.0219 -0.2066 0.095 Uiso 1 1 calc R . . C12 C 1.1138(3) 0.7310(5) -0.31736(14) 0.0611(9) Uani 1 1 d . . . H12A H 1.0490 0.8171 -0.3352 0.092 Uiso 1 1 calc R . . H12B H 1.0705 0.6187 -0.3142 0.092 Uiso 1 1 calc R . . H12C H 1.1829 0.7203 -0.3456 0.092 Uiso 1 1 calc R . . C13 C 1.2576(3) 0.4692(4) -0.23499(16) 0.0639(9) Uani 1 1 d . . . H13A H 1.3261 0.3952 -0.2123 0.096 Uiso 1 1 calc R . . H13B H 1.2593 0.4586 -0.2815 0.096 Uiso 1 1 calc R . . H13C H 1.1714 0.4329 -0.2242 0.096 Uiso 1 1 calc R . . C14 C 1.4275(3) 0.7126(5) -0.21827(16) 0.0610(9) Uani 1 1 d . . . H14A H 1.4861 0.6262 -0.1955 0.092 Uiso 1 1 calc R . . H14B H 1.4451 0.8265 -0.1984 0.092 Uiso 1 1 calc R . . H14C H 1.4430 0.7174 -0.2635 0.092 Uiso 1 1 calc R . . C15 C 1.1396(3) 0.6896(4) -0.01773(14) 0.0563(8) Uani 1 1 d . . . H15A H 1.0830 0.6953 0.0167 0.084 Uiso 1 1 calc R . . H15B H 1.2112 0.7737 -0.0091 0.084 Uiso 1 1 calc R . . H15C H 1.1764 0.5727 -0.0194 0.084 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.0604(2) 0.1321(4) 0.0587(2) 0.0017(2) 0.02909(17) 0.0080(2) B1 0.0392(16) 0.0414(18) 0.0400(17) 0.0001(14) 0.0058(13) -0.0014(14) O1 0.0404(10) 0.0743(15) 0.0373(10) 0.0042(9) 0.0054(8) 0.0090(10) O2 0.0372(10) 0.0698(13) 0.0377(10) 0.0071(9) 0.0097(8) 0.0069(9) C1 0.0502(17) 0.066(2) 0.0445(16) 0.0042(14) 0.0189(13) 0.0064(15) C2 0.0417(16) 0.104(3) 0.0470(18) -0.0009(17) 0.0060(13) 0.0036(16) C3 0.0451(16) 0.099(3) 0.0311(14) -0.0031(15) 0.0014(12) 0.0062(16) C4 0.0440(14) 0.0418(16) 0.0354(14) 0.0032(11) 0.0072(11) 0.0055(12) C5 0.0487(16) 0.071(2) 0.0446(16) -0.0132(15) 0.0112(13) -0.0085(15) C6 0.0593(19) 0.089(3) 0.0375(16) -0.0149(16) 0.0126(14) -0.0042(17) C7 0.0504(16) 0.0490(17) 0.0303(13) 0.0028(12) 0.0077(12) 0.0022(13) C8 0.0447(14) 0.0396(16) 0.0370(14) 0.0027(11) 0.0068(11) -0.0001(12) C9 0.0395(14) 0.0621(19) 0.0356(14) 0.0000(13) 0.0101(11) -0.0005(13) C10 0.0387(14) 0.0598(19) 0.0393(15) -0.0046(13) 0.0086(12) 0.0021(13) C11 0.074(2) 0.055(2) 0.064(2) 0.0078(16) 0.0199(17) -0.0053(17) C12 0.0539(18) 0.090(3) 0.0392(16) -0.0035(15) 0.0030(14) 0.0049(17) C13 0.064(2) 0.056(2) 0.071(2) -0.0084(17) 0.0076(17) 0.0090(17) C14 0.0372(15) 0.092(3) 0.0545(18) -0.0047(17) 0.0103(13) -0.0008(16) C15 0.0525(17) 0.072(2) 0.0447(16) 0.0116(15) 0.0069(13) 0.0075(16) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br1 C1 1.898(3) . ? B1 O1 1.363(4) . ? B1 O2 1.365(4) . ? B1 C8 1.553(4) . ? O1 C10 1.454(3) . ? O2 C9 1.457(3) . ? C1 C2 1.369(4) . ? C1 C6 1.370(4) . ? C2 C3 1.373(4) . ? C2 H2A 0.9300 . ? C3 C4 1.389(4) . ? C3 H3A 0.9300 . ? C4 C5 1.381(4) . ? C4 C7 1.466(4) . ? C5 C6 1.385(4) . ? C5 H5A 0.9300 . ? C6 H6A 0.9300 . ? C7 C8 1.341(4) . ? C7 H7A 0.9300 . ? C8 C15 1.510(4) . ? C9 C12 1.520(4) . ? C9 C11 1.524(4) . ? C9 C10 1.558(4) . ? C10 C14 1.511(4) . ? C10 C13 1.527(4) . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 B1 O2 112.7(2) . . ? O1 B1 C8 123.4(2) . . ? O2 B1 C8 123.9(2) . . ? B1 O1 C10 107.6(2) . . ? B1 O2 C9 107.8(2) . . ? C2 C1 C6 121.0(3) . . ? C2 C1 Br1 119.3(2) . . ? C6 C1 Br1 119.7(2) . . ? C1 C2 C3 118.4(3) . . ? C1 C2 H2A 120.8 . . ? C3 C2 H2A 120.8 . . ? C2 C3 C4 122.9(3) . . ? C2 C3 H3A 118.5 . . ? C4 C3 H3A 118.5 . . ? C5 C4 C3 116.8(3) . . ? C5 C4 C7 124.8(3) . . ? C3 C4 C7 118.4(2) . . ? C4 C5 C6 121.3(3) . . ? C4 C5 H5A 119.4 . . ? C6 C5 H5A 119.4 . . ? C1 C6 C5 119.6(3) . . ? C1 C6 H6A 120.2 . . ? C5 C6 H6A 120.2 . . ? C8 C7 C4 131.4(3) . . ? C8 C7 H7A 114.3 . . ? C4 C7 H7A 114.3 . . ? C7 C8 C15 125.2(2) . . ? C7 C8 B1 116.6(2) . . ? C15 C8 B1 118.1(2) . . ? O2 C9 C12 108.2(2) . . ? O2 C9 C11 106.8(2) . . ? C12 C9 C11 110.8(3) . . ? O2 C9 C10 102.0(2) . . ? C12 C9 C10 115.2(2) . . ? C11 C9 C10 113.0(2) . . ? O1 C10 C14 108.1(2) . . ? O1 C10 C13 107.0(2) . . ? C14 C10 C13 111.0(3) . . ? O1 C10 C9 102.4(2) . . ? C14 C10 C9 115.4(3) . . ? C13 C10 C9 112.3(2) . . ? C9 C11 H11A 109.5 . . ? C9 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C9 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C9 C12 H12A 109.5 . . ? C9 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C9 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C10 C13 H13A 109.5 . . ? C10 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C10 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C10 C14 H14A 109.5 . . ? C10 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C10 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C8 C15 H15A 109.5 . . ? C8 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C8 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2 B1 O1 C10 -10.3(3) . . . . ? C8 B1 O1 C10 169.6(3) . . . . ? O1 B1 O2 C9 -8.5(3) . . . . ? C8 B1 O2 C9 171.5(3) . . . . ? C6 C1 C2 C3 0.0(5) . . . . ? Br1 C1 C2 C3 179.0(3) . . . . ? C1 C2 C3 C4 0.7(5) . . . . ? C2 C3 C4 C5 -1.4(5) . . . . ? C2 C3 C4 C7 -179.9(3) . . . . ? C3 C4 C5 C6 1.5(5) . . . . ? C7 C4 C5 C6 179.8(3) . . . . ? C2 C1 C6 C5 0.1(5) . . . . ? Br1 C1 C6 C5 -178.9(3) . . . . ? C4 C5 C6 C1 -0.9(5) . . . . ? C5 C4 C7 C8 29.2(5) . . . . ? C3 C4 C7 C8 -152.4(3) . . . . ? C4 C7 C8 C15 0.3(5) . . . . ? C4 C7 C8 B1 177.6(3) . . . . ? O1 B1 C8 C7 -170.3(3) . . . . ? O2 B1 C8 C7 9.7(4) . . . . ? O1 B1 C8 C15 7.3(4) . . . . ? O2 B1 C8 C15 -172.8(3) . . . . ? B1 O2 C9 C12 143.8(3) . . . . ? B1 O2 C9 C11 -96.9(3) . . . . ? B1 O2 C9 C10 22.0(3) . . . . ? B1 O1 C10 C14 145.3(3) . . . . ? B1 O1 C10 C13 -95.1(3) . . . . ? B1 O1 C10 C9 23.1(3) . . . . ? O2 C9 C10 O1 -26.9(3) . . . . ? C12 C9 C10 O1 -143.8(2) . . . . ? C11 C9 C10 O1 87.5(3) . . . . ? O2 C9 C10 C14 -144.0(2) . . . . ? C12 C9 C10 C14 99.1(3) . . . . ? C11 C9 C10 C14 -29.6(3) . . . . ? O2 C9 C10 C13 87.5(3) . . . . ? C12 C9 C10 C13 -29.5(3) . . . . ? C11 C9 C10 C13 -158.2(3) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.326 _refine_diff_density_min -0.259 _refine_diff_density_rms 0.050 # Attachment '- z-2s.cif' data_z_2s _database_code_depnum_ccdc_archive 'CCDC 886807' #TrackingRef '- z-2s.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H29 B O2' _chemical_formula_weight 300.23 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 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 12.1475(11) _cell_length_b 6.0763(6) _cell_length_c 24.653(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.380(3) _cell_angle_gamma 90.00 _cell_volume 1819.6(3) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.39 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.096 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 656 _exptl_absorpt_coefficient_mu 0.068 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9741 _exptl_absorpt_correction_T_max 0.9953 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 19852 _diffrn_reflns_av_R_equivalents 0.0441 _diffrn_reflns_av_sigmaI/netI 0.0274 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 1.65 _diffrn_reflns_theta_max 25.01 _reflns_number_total 3210 _reflns_number_gt 2549 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0565P)^2^+0.9430P] 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 3210 _refine_ls_number_parameters 199 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0651 _refine_ls_R_factor_gt 0.0494 _refine_ls_wR_factor_ref 0.1302 _refine_ls_wR_factor_gt 0.1186 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.056 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.16605(10) 0.5106(2) 0.03541(5) 0.0331(3) Uani 1 1 d . . . O2 O 0.34078(10) 0.3999(2) 0.01617(5) 0.0334(3) Uani 1 1 d . . . B1 B 0.25395(15) 0.3856(3) 0.05113(8) 0.0268(4) Uani 1 1 d . . . C1 C 0.14847(13) 0.2039(3) 0.13124(7) 0.0261(4) Uani 1 1 d . . . C2 C 0.09549(15) 0.3691(3) 0.15977(8) 0.0330(4) Uani 1 1 d . . . H2A H 0.1286 0.5103 0.1625 0.040 Uiso 1 1 calc R . . C3 C -0.00524(15) 0.3315(3) 0.18452(8) 0.0360(5) Uani 1 1 d . . . H3A H -0.0388 0.4462 0.2047 0.043 Uiso 1 1 calc R . . C4 C -0.05737(15) 0.1299(3) 0.18024(8) 0.0357(5) Uani 1 1 d . . . C5 C -0.00499(15) -0.0342(3) 0.15152(8) 0.0353(5) Uani 1 1 d . . . H5A H -0.0390 -0.1744 0.1483 0.042 Uiso 1 1 calc R . . C6 C 0.09629(14) 0.0012(3) 0.12721(8) 0.0313(4) Uani 1 1 d . . . H6A H 0.1303 -0.1146 0.1076 0.038 Uiso 1 1 calc R . . C7 C -0.16979(17) 0.0921(4) 0.20483(10) 0.0542(6) Uani 1 1 d . . . H7A H -0.1931 -0.0597 0.1979 0.081 Uiso 1 1 calc R . . H7B H -0.2230 0.1940 0.1885 0.081 Uiso 1 1 calc R . . H7C H -0.1659 0.1175 0.2440 0.081 Uiso 1 1 calc R . . C8 C 0.25595(13) 0.2436(3) 0.10356(7) 0.0267(4) Uani 1 1 d . . . C9 C 0.35353(14) 0.1649(3) 0.12050(7) 0.0278(4) Uani 1 1 d . . . H9A H 0.4126 0.1958 0.0966 0.033 Uiso 1 1 calc R . . C10 C 0.38715(14) 0.0360(3) 0.17053(8) 0.0313(4) Uani 1 1 d . . . C11 C 0.50930(16) 0.0832(4) 0.18125(9) 0.0488(6) Uani 1 1 d . . . H11A H 0.5522 0.0425 0.1493 0.073 Uiso 1 1 calc R . . H11B H 0.5345 -0.0030 0.2126 0.073 Uiso 1 1 calc R . . H11C H 0.5193 0.2403 0.1888 0.073 Uiso 1 1 calc R . . C12 C 0.37389(19) -0.2106(3) 0.15986(9) 0.0470(6) Uani 1 1 d . . . H12A H 0.2961 -0.2441 0.1531 0.071 Uiso 1 1 calc R . . H12B H 0.3997 -0.2934 0.1916 0.071 Uiso 1 1 calc R . . H12C H 0.4173 -0.2522 0.1281 0.071 Uiso 1 1 calc R . . C13 C 0.32272(17) 0.1010(4) 0.22096(8) 0.0451(5) Uani 1 1 d . . . H13A H 0.2443 0.0707 0.2150 0.068 Uiso 1 1 calc R . . H13B H 0.3330 0.2583 0.2281 0.068 Uiso 1 1 calc R . . H13C H 0.3494 0.0157 0.2521 0.068 Uiso 1 1 calc R . . C14 C 0.18735(14) 0.5884(3) -0.01948(7) 0.0309(4) Uani 1 1 d . . . C15 C 0.31570(14) 0.5714(3) -0.02323(7) 0.0303(4) Uani 1 1 d . . . C16 C 0.14184(18) 0.8187(4) -0.02536(9) 0.0449(5) Uani 1 1 d . . . H16A H 0.0614 0.8146 -0.0226 0.067 Uiso 1 1 calc R . . H16B H 0.1625 0.8786 -0.0608 0.067 Uiso 1 1 calc R . . H16C H 0.1721 0.9125 0.0034 0.067 Uiso 1 1 calc R . . C17 C 0.12761(17) 0.4334(4) -0.05775(9) 0.0445(5) Uani 1 1 d . . . H17A H 0.0480 0.4515 -0.0535 0.067 Uiso 1 1 calc R . . H17B H 0.1482 0.2813 -0.0493 0.067 Uiso 1 1 calc R . . H17C H 0.1480 0.4673 -0.0952 0.067 Uiso 1 1 calc R . . C18 C 0.37482(17) 0.7778(4) -0.00462(9) 0.0444(5) Uani 1 1 d . . . H18A H 0.4545 0.7568 -0.0080 0.067 Uiso 1 1 calc R . . H18B H 0.3567 0.8076 0.0333 0.067 Uiso 1 1 calc R . . H18C H 0.3516 0.9024 -0.0272 0.067 Uiso 1 1 calc R . . C19 C 0.35878(18) 0.4988(4) -0.07765(8) 0.0448(5) Uani 1 1 d . . . H19A H 0.4394 0.4933 -0.0764 0.067 Uiso 1 1 calc R . . H19B H 0.3351 0.6036 -0.1056 0.067 Uiso 1 1 calc R . . H19C H 0.3298 0.3524 -0.0863 0.067 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 0.0262(6) 0.0384(8) 0.0347(7) 0.0095(6) 0.0027(5) 0.0054(5) O2 0.0255(6) 0.0371(7) 0.0375(7) 0.0124(6) 0.0046(5) 0.0056(5) B1 0.0231(9) 0.0247(10) 0.0324(11) -0.0007(9) -0.0004(8) -0.0015(8) C1 0.0234(8) 0.0292(10) 0.0257(9) 0.0053(8) -0.0013(7) 0.0005(7) C2 0.0313(9) 0.0299(10) 0.0377(11) 0.0015(8) 0.0013(8) -0.0009(8) C3 0.0316(10) 0.0394(11) 0.0370(11) 0.0030(9) 0.0062(8) 0.0081(9) C4 0.0253(9) 0.0474(12) 0.0344(11) 0.0109(9) 0.0005(8) 0.0011(8) C5 0.0303(9) 0.0360(11) 0.0396(11) 0.0066(9) -0.0034(8) -0.0093(8) C6 0.0289(9) 0.0308(10) 0.0343(10) 0.0007(8) 0.0003(8) 0.0009(8) C7 0.0306(11) 0.0733(17) 0.0589(14) 0.0176(13) 0.0087(10) -0.0025(11) C8 0.0248(9) 0.0237(9) 0.0316(10) -0.0001(8) 0.0012(7) -0.0006(7) C9 0.0250(8) 0.0266(9) 0.0318(10) 0.0011(8) 0.0025(7) -0.0020(7) C10 0.0264(9) 0.0328(10) 0.0346(10) 0.0047(8) -0.0019(8) 0.0003(8) C11 0.0329(11) 0.0609(15) 0.0523(13) 0.0135(12) -0.0107(10) -0.0027(10) C12 0.0544(13) 0.0364(12) 0.0502(13) 0.0080(10) -0.0091(11) 0.0053(10) C13 0.0446(12) 0.0573(14) 0.0335(11) 0.0080(10) -0.0015(9) 0.0087(10) C14 0.0274(9) 0.0332(10) 0.0322(10) 0.0070(8) -0.0002(8) 0.0023(8) C15 0.0280(9) 0.0302(10) 0.0327(10) 0.0089(8) 0.0022(8) 0.0003(8) C16 0.0455(12) 0.0418(12) 0.0476(13) 0.0113(10) 0.0022(10) 0.0137(10) C17 0.0413(11) 0.0468(13) 0.0452(13) 0.0079(10) -0.0097(10) -0.0087(10) C18 0.0411(11) 0.0427(12) 0.0493(13) 0.0082(10) -0.0042(10) -0.0098(10) C19 0.0453(12) 0.0491(13) 0.0401(12) 0.0080(10) 0.0100(9) 0.0049(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 B1 1.364(2) . ? O1 C14 1.458(2) . ? O2 B1 1.369(2) . ? O2 C15 1.456(2) . ? B1 C8 1.554(3) . ? C1 C2 1.387(3) . ? C1 C6 1.388(3) . ? C1 C8 1.497(2) . ? C2 C3 1.390(3) . ? C2 H2A 0.9500 . ? C3 C4 1.382(3) . ? C3 H3A 0.9500 . ? C4 C5 1.381(3) . ? C4 C7 1.515(3) . ? C5 C6 1.389(3) . ? C5 H5A 0.9500 . ? C6 H6A 0.9500 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 C9 1.342(2) . ? C9 C10 1.515(3) . ? C9 H9A 0.9500 . ? C10 C13 1.525(3) . ? C10 C12 1.529(3) . ? C10 C11 1.533(3) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 C16 1.511(3) . ? C14 C17 1.515(3) . ? C14 C15 1.566(2) . ? C15 C19 1.509(3) . ? C15 C18 1.514(3) . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag B1 O1 C14 107.51(14) . . ? B1 O2 C15 107.86(13) . . ? O1 B1 O2 112.99(16) . . ? O1 B1 C8 123.58(16) . . ? O2 B1 C8 123.42(16) . . ? C2 C1 C6 117.72(16) . . ? C2 C1 C8 121.58(16) . . ? C6 C1 C8 120.64(16) . . ? C1 C2 C3 121.11(18) . . ? C1 C2 H2A 119.4 . . ? C3 C2 H2A 119.4 . . ? C4 C3 C2 121.08(18) . . ? C4 C3 H3A 119.5 . . ? C2 C3 H3A 119.5 . . ? C5 C4 C3 117.81(17) . . ? C5 C4 C7 121.00(19) . . ? C3 C4 C7 121.16(19) . . ? C4 C5 C6 121.47(18) . . ? C4 C5 H5A 119.3 . . ? C6 C5 H5A 119.3 . . ? C1 C6 C5 120.78(18) . . ? C1 C6 H6A 119.6 . . ? C5 C6 H6A 119.6 . . ? C4 C7 H7A 109.5 . . ? C4 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C4 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C9 C8 C1 124.88(16) . . ? C9 C8 B1 117.74(16) . . ? C1 C8 B1 117.37(14) . . ? C8 C9 C10 132.09(16) . . ? C8 C9 H9A 114.0 . . ? C10 C9 H9A 114.0 . . ? C9 C10 C13 113.12(16) . . ? C9 C10 C12 109.81(16) . . ? C13 C10 C12 109.86(17) . . ? C9 C10 C11 107.41(15) . . ? C13 C10 C11 108.20(17) . . ? C12 C10 C11 108.29(17) . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C10 C12 H12A 109.5 . . ? C10 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C10 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C10 C13 H13A 109.5 . . ? C10 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C10 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? O1 C14 C16 108.81(16) . . ? O1 C14 C17 106.80(15) . . ? C16 C14 C17 110.03(16) . . ? O1 C14 C15 102.49(13) . . ? C16 C14 C15 114.78(16) . . ? C17 C14 C15 113.29(16) . . ? O2 C15 C19 108.15(15) . . ? O2 C15 C18 107.10(15) . . ? C19 C15 C18 110.16(16) . . ? O2 C15 C14 102.24(13) . . ? C19 C15 C14 115.02(16) . . ? C18 C15 C14 113.45(16) . . ? C14 C16 H16A 109.5 . . ? C14 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C14 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C14 C17 H17A 109.5 . . ? C14 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C14 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C15 C18 H18A 109.5 . . ? C15 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C15 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C15 C19 H19A 109.5 . . ? C15 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C15 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C14 O1 B1 O2 10.1(2) . . . . ? C14 O1 B1 C8 -170.50(17) . . . . ? C15 O2 B1 O1 7.9(2) . . . . ? C15 O2 B1 C8 -171.47(16) . . . . ? C6 C1 C2 C3 1.4(3) . . . . ? C8 C1 C2 C3 178.85(17) . . . . ? C1 C2 C3 C4 -1.8(3) . . . . ? C2 C3 C4 C5 1.3(3) . . . . ? C2 C3 C4 C7 -176.94(19) . . . . ? C3 C4 C5 C6 -0.5(3) . . . . ? C7 C4 C5 C6 177.71(18) . . . . ? C2 C1 C6 C5 -0.6(3) . . . . ? C8 C1 C6 C5 -178.11(17) . . . . ? C4 C5 C6 C1 0.2(3) . . . . ? C2 C1 C8 C9 107.7(2) . . . . ? C6 C1 C8 C9 -74.9(2) . . . . ? C2 C1 C8 B1 -72.7(2) . . . . ? C6 C1 C8 B1 104.7(2) . . . . ? O1 B1 C8 C9 -166.54(17) . . . . ? O2 B1 C8 C9 12.8(3) . . . . ? O1 B1 C8 C1 13.8(3) . . . . ? O2 B1 C8 C1 -166.87(17) . . . . ? C1 C8 C9 C10 -4.8(3) . . . . ? B1 C8 C9 C10 175.58(18) . . . . ? C8 C9 C10 C13 -35.0(3) . . . . ? C8 C9 C10 C12 88.1(2) . . . . ? C8 C9 C10 C11 -154.4(2) . . . . ? B1 O1 C14 C16 -144.04(16) . . . . ? B1 O1 C14 C17 97.22(17) . . . . ? B1 O1 C14 C15 -22.11(18) . . . . ? B1 O2 C15 C19 -142.60(16) . . . . ? B1 O2 C15 C18 98.68(17) . . . . ? B1 O2 C15 C14 -20.83(18) . . . . ? O1 C14 C15 O2 25.72(17) . . . . ? C16 C14 C15 O2 143.48(16) . . . . ? C17 C14 C15 O2 -88.97(18) . . . . ? O1 C14 C15 C19 142.65(16) . . . . ? C16 C14 C15 C19 -99.6(2) . . . . ? C17 C14 C15 C19 28.0(2) . . . . ? O1 C14 C15 C18 -89.25(18) . . . . ? C16 C14 C15 C18 28.5(2) . . . . ? C17 C14 C15 C18 156.07(17) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.323 _refine_diff_density_min -0.194 _refine_diff_density_rms 0.042