# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Diego Cardenas' _publ_contact_author_email diego.cardenas@uam.es loop_ _publ_author_name 'Diego Cardenas' 'Elena Bunuel' 'Virtudes Pardo-Rodriguez' 'Daniel Collado-Sanz' # Attachment '- CIF 2i.cif' data_datos_0m _database_code_depnum_ccdc_archive 'CCDC 888322' #TrackingRef '- CIF 2i.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common WAP506 _chemical_formula_moiety ? _chemical_formula_sum 'C27 H35 B O6 S2' _chemical_melting_point ? _exptl_crystal_description ? _exptl_crystal_colour ? _diffrn_ambient_temperature 100(2) _chemical_formula_weight 530.48 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P n' _symmetry_int_tables_number 7 _chemical_absolute_configuration . loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y, z+1/2' _cell_length_a 8.0433(2) _cell_length_b 15.1139(3) _cell_length_c 11.0920(2) _cell_angle_alpha 90.00 _cell_angle_beta 95.4510(10) _cell_angle_gamma 90.00 _cell_volume 1342.31(5) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.312 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 564 _exptl_absorpt_coefficient_mu 0.238 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9584 _exptl_absorpt_correction_T_max 0.9720 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_radiation_probe ? _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 16483 _diffrn_reflns_av_R_equivalents 0.0359 _diffrn_reflns_av_sigmaI/netI 0.0467 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.35 _diffrn_reflns_theta_max 27.59 _reflns_number_total 6105 _reflns_number_gt 5494 _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^)+(0.1000P)^2^+0.3225P] 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 refxyz _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.04(7) _refine_ls_number_reflns 6105 _refine_ls_number_parameters 330 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0590 _refine_ls_R_factor_gt 0.0486 _refine_ls_wR_factor_ref 0.1421 _refine_ls_wR_factor_gt 0.1277 _refine_ls_goodness_of_fit_ref 1.014 _refine_ls_restrained_S_all 1.014 _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 B1 B -0.1080(4) 0.7178(2) 0.5286(3) 0.0231(7) Uani 1 1 d . . . O5 O -0.0394(3) 0.65015(15) 0.4680(2) 0.0302(5) Uani 1 1 d . . . O6 O -0.2219(3) 0.68974(15) 0.6030(3) 0.0363(6) Uani 1 1 d . . . O3 O 0.4174(3) 0.76243(16) 0.0902(2) 0.0265(5) Uani 1 1 d . . . O4 O 0.3062(3) 0.65092(15) 0.2259(2) 0.0296(5) Uani 1 1 d . . . O1 O 0.2399(3) 0.93646(15) 0.11949(19) 0.0223(5) Uani 1 1 d . . . O2 O 0.2664(3) 0.98793(14) 0.33173(19) 0.0214(4) Uani 1 1 d . . . S1 S 0.32193(8) 0.93047(4) 0.24018(6) 0.01732(16) Uani 1 1 d . . . S2 S 0.29246(9) 0.73665(5) 0.16829(7) 0.02065(17) Uani 1 1 d . . . C1 C 0.0929(4) 0.7399(2) 0.0852(3) 0.0223(6) Uani 1 1 d . . . C2 C -0.0356(4) 0.6901(2) 0.1275(3) 0.0288(7) Uani 1 1 d . . . H2 H -0.0164 0.6551 0.1987 0.035 Uiso 1 1 calc R . . C3 C -0.1912(4) 0.6929(3) 0.0635(4) 0.0348(8) Uani 1 1 d . . . H3 H -0.2816 0.6614 0.0924 0.042 Uiso 1 1 calc R . . C4 C -0.2166(4) 0.7414(3) -0.0429(4) 0.0372(9) Uani 1 1 d . . . H4 H -0.3239 0.7423 -0.0868 0.045 Uiso 1 1 calc R . . C5 C -0.0869(5) 0.7884(3) -0.0852(3) 0.0326(8) Uani 1 1 d . . . H5 H -0.1053 0.8210 -0.1585 0.039 Uiso 1 1 calc R . . C6 C 0.0709(4) 0.7885(2) -0.0211(3) 0.0243(6) Uani 1 1 d . . . H6 H 0.1606 0.8208 -0.0495 0.029 Uiso 1 1 calc R . . C7 C 0.5378(4) 0.9513(2) 0.2356(3) 0.0191(6) Uani 1 1 d . . . C8 C 0.6158(4) 0.9308(2) 0.1324(3) 0.0215(6) Uani 1 1 d . . . H8 H 0.5572 0.9007 0.0662 0.026 Uiso 1 1 calc R . . C9 C 0.7821(4) 0.9555(2) 0.1288(3) 0.0228(6) Uani 1 1 d . . . H9 H 0.8377 0.9427 0.0590 0.027 Uiso 1 1 calc R . . C10 C 0.8669(4) 0.9986(2) 0.2261(3) 0.0218(6) Uani 1 1 d . . . H10 H 0.9798 1.0158 0.2221 0.026 Uiso 1 1 calc R . . C11 C 0.7887(4) 1.0168(2) 0.3293(3) 0.0236(6) Uani 1 1 d . . . H11 H 0.8488 1.0450 0.3964 0.028 Uiso 1 1 calc R . . C12 C 0.6222(4) 0.9938(2) 0.3345(3) 0.0213(6) Uani 1 1 d . . . H12 H 0.5670 1.0070 0.4043 0.026 Uiso 1 1 calc R . . C13 C 0.2932(3) 0.81704(19) 0.2959(2) 0.0173(5) Uani 1 1 d . . . C14 C 0.1219(4) 0.80903(19) 0.3464(3) 0.0193(6) Uani 1 1 d . . . H14A H 0.0390 0.8416 0.2915 0.023 Uiso 1 1 calc R . . H14B H 0.0889 0.7459 0.3437 0.023 Uiso 1 1 calc R . . C15 C 0.1101(4) 0.8430(2) 0.4760(3) 0.0205(6) Uani 1 1 d . . . H15 H 0.1169 0.9091 0.4734 0.025 Uiso 1 1 calc R . . C16 C 0.2565(4) 0.8105(2) 0.5616(3) 0.0231(6) Uani 1 1 d . . . C17 C 0.4232(4) 0.8305(2) 0.5140(3) 0.0249(6) Uani 1 1 d . . . H17A H 0.5146 0.8079 0.5719 0.030 Uiso 1 1 calc R . . H17B H 0.4369 0.8954 0.5073 0.030 Uiso 1 1 calc R . . C18 C 0.4355(4) 0.7879(2) 0.3896(3) 0.0219(6) Uani 1 1 d . . . H18A H 0.4328 0.7228 0.3981 0.026 Uiso 1 1 calc R . . H18B H 0.5438 0.8042 0.3600 0.026 Uiso 1 1 calc R . . C19 C 0.2403(4) 0.7709(2) 0.6651(3) 0.0249(6) Uani 1 1 d . . . H19 H 0.1292 0.7604 0.6839 0.030 Uiso 1 1 calc R . . C20 C 0.3767(5) 0.7400(3) 0.7574(3) 0.0348(8) Uani 1 1 d . . . H20A H 0.4850 0.7464 0.7245 0.052 Uiso 1 1 calc R . . H20C H 0.3585 0.6777 0.7768 0.052 Uiso 1 1 calc R . . H20B H 0.3758 0.7757 0.8310 0.052 Uiso 1 1 calc R . . C21 C -0.0631(4) 0.8189(2) 0.5147(3) 0.0232(6) Uani 1 1 d . . . H21A H -0.1482 0.8452 0.4549 0.028 Uiso 1 1 calc R . . H21B H -0.0747 0.8481 0.5933 0.028 Uiso 1 1 calc R . . C22 C -0.1247(6) 0.5695(2) 0.4936(4) 0.0423(10) Uani 1 1 d . . . C23 C -0.2164(6) 0.5930(2) 0.6059(4) 0.0386(9) Uani 1 1 d . . . C24 C -0.2503(8) 0.5522(4) 0.3811(5) 0.0688(16) Uani 1 1 d . . . H24B H -0.3280 0.6021 0.3696 0.103 Uiso 1 1 calc R . . H24A H -0.3129 0.4978 0.3934 0.103 Uiso 1 1 calc R . . H24C H -0.1893 0.5458 0.3092 0.103 Uiso 1 1 calc R . . C25 C -0.0053(8) 0.4945(3) 0.5017(6) 0.0653(15) Uani 1 1 d . . . H25B H 0.0413 0.4871 0.4239 0.098 Uiso 1 1 calc R . . H25A H -0.0636 0.4402 0.5216 0.098 Uiso 1 1 calc R . . H25C H 0.0851 0.5066 0.5651 0.098 Uiso 1 1 calc R . . C26 C -0.3851(9) 0.5553(4) 0.6069(10) 0.115(4) Uani 1 1 d . . . H26A H -0.4306 0.5710 0.6829 0.172 Uiso 1 1 calc R . . H26B H -0.3793 0.4908 0.5999 0.172 Uiso 1 1 calc R . . H26C H -0.4576 0.5791 0.5385 0.172 Uiso 1 1 calc R . . C27 C -0.1060(12) 0.5720(3) 0.7243(5) 0.085(2) Uani 1 1 d . . . H27A H 0.0093 0.5902 0.7158 0.128 Uiso 1 1 calc R . . H27B H -0.1091 0.5083 0.7403 0.128 Uiso 1 1 calc R . . H27C H -0.1482 0.6043 0.7917 0.128 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 B1 0.0225(16) 0.0207(17) 0.0264(17) 0.0049(13) 0.0029(14) 0.0044(13) O5 0.0367(13) 0.0198(11) 0.0360(13) -0.0008(10) 0.0124(10) -0.0009(10) O6 0.0442(14) 0.0147(11) 0.0545(16) 0.0061(10) 0.0279(12) 0.0047(10) O3 0.0211(11) 0.0300(12) 0.0289(12) -0.0071(9) 0.0046(9) 0.0023(9) O4 0.0338(13) 0.0184(11) 0.0356(13) 0.0000(9) -0.0014(10) 0.0053(10) O1 0.0190(10) 0.0242(11) 0.0228(11) 0.0009(9) -0.0029(8) 0.0004(8) O2 0.0182(10) 0.0214(11) 0.0246(10) -0.0045(9) 0.0017(8) 0.0013(8) S1 0.0143(3) 0.0181(3) 0.0193(3) -0.0017(3) 0.0002(2) 0.0013(3) S2 0.0184(3) 0.0200(3) 0.0233(4) -0.0033(3) 0.0007(3) 0.0023(3) C1 0.0186(14) 0.0229(15) 0.0248(15) -0.0112(12) -0.0012(11) -0.0010(11) C2 0.0278(17) 0.0281(17) 0.0310(17) -0.0068(14) 0.0049(13) -0.0063(13) C3 0.0240(16) 0.041(2) 0.040(2) -0.0177(16) 0.0067(14) -0.0111(14) C4 0.0236(17) 0.044(2) 0.042(2) -0.0210(17) -0.0075(15) 0.0019(15) C5 0.0345(18) 0.0354(19) 0.0260(17) -0.0097(14) -0.0070(14) 0.0045(15) C6 0.0252(15) 0.0247(15) 0.0224(15) -0.0094(12) -0.0009(12) -0.0018(12) C7 0.0147(13) 0.0195(14) 0.0229(14) 0.0014(11) 0.0014(11) -0.0004(10) C8 0.0228(15) 0.0208(15) 0.0207(14) 0.0002(11) 0.0020(11) 0.0012(11) C9 0.0231(14) 0.0207(15) 0.0255(15) 0.0031(12) 0.0072(12) 0.0043(12) C10 0.0153(13) 0.0191(14) 0.0305(16) 0.0054(12) -0.0002(11) 0.0011(11) C11 0.0193(14) 0.0231(15) 0.0269(15) 0.0024(12) -0.0052(12) -0.0001(12) C12 0.0216(14) 0.0215(14) 0.0208(14) -0.0002(11) 0.0011(11) 0.0012(12) C13 0.0170(13) 0.0170(13) 0.0179(13) -0.0010(11) 0.0009(11) 0.0012(10) C14 0.0158(13) 0.0195(14) 0.0223(14) 0.0012(11) 0.0009(11) 0.0005(11) C15 0.0209(13) 0.0175(13) 0.0232(14) -0.0003(11) 0.0031(11) 0.0005(11) C16 0.0231(15) 0.0205(14) 0.0253(15) -0.0026(12) -0.0009(12) 0.0024(12) C17 0.0213(15) 0.0259(16) 0.0267(15) 0.0004(12) -0.0017(12) -0.0012(12) C18 0.0161(13) 0.0273(15) 0.0219(14) 0.0008(12) -0.0008(11) 0.0045(12) C19 0.0245(15) 0.0279(16) 0.0225(15) 0.0014(12) 0.0041(12) 0.0045(12) C20 0.0380(19) 0.044(2) 0.0225(16) 0.0017(15) 0.0024(14) 0.0116(16) C21 0.0207(14) 0.0198(14) 0.0296(15) 0.0042(12) 0.0056(12) 0.0020(11) C22 0.044(2) 0.0216(17) 0.064(3) -0.0024(17) 0.020(2) 0.0005(15) C23 0.056(2) 0.0178(16) 0.045(2) 0.0040(15) 0.0225(18) 0.0027(15) C24 0.089(4) 0.045(3) 0.069(3) 0.000(2) -0.012(3) -0.017(3) C25 0.081(4) 0.023(2) 0.099(4) 0.004(2) 0.042(3) 0.010(2) C26 0.087(5) 0.032(3) 0.243(10) -0.015(4) 0.105(6) -0.012(3) C27 0.180(8) 0.029(2) 0.045(3) 0.003(2) 0.006(4) -0.003(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag B1 O6 1.358(4) . ? B1 O5 1.368(4) . ? B1 C21 1.580(5) . ? O5 C22 1.440(4) . ? O6 C23 1.463(4) . ? O3 S2 1.441(2) . ? O4 S2 1.444(2) . ? O1 S1 1.438(2) . ? O2 S1 1.439(2) . ? S1 C7 1.770(3) . ? S1 C13 1.844(3) . ? S2 C1 1.774(3) . ? S2 C13 1.865(3) . ? C1 C6 1.387(5) . ? C1 C2 1.396(5) . ? C2 C3 1.380(5) . ? C3 C4 1.388(6) . ? C4 C5 1.381(6) . ? C5 C6 1.394(5) . ? C7 C12 1.391(4) . ? C7 C8 1.392(4) . ? C8 C9 1.393(4) . ? C9 C10 1.383(5) . ? C10 C11 1.385(5) . ? C11 C12 1.390(4) . ? C13 C18 1.536(4) . ? C13 C14 1.541(4) . ? C14 C15 1.538(4) . ? C15 C16 1.523(4) . ? C15 C21 1.540(4) . ? C16 C19 1.312(5) . ? C16 C17 1.518(5) . ? C17 C18 1.534(4) . ? C19 C20 1.502(5) . ? C22 C25 1.483(6) . ? C22 C23 1.547(6) . ? C22 C24 1.552(7) . ? C23 C26 1.473(7) . ? C23 C27 1.547(8) . ? 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 O6 B1 O5 113.0(3) . . ? O6 B1 C21 122.4(3) . . ? O5 B1 C21 124.6(3) . . ? B1 O5 C22 108.3(3) . . ? B1 O6 C23 107.8(3) . . ? O1 S1 O2 118.23(13) . . ? O1 S1 C7 109.07(14) . . ? O2 S1 C7 106.49(13) . . ? O1 S1 C13 108.01(13) . . ? O2 S1 C13 105.52(13) . . ? C7 S1 C13 109.25(13) . . ? O3 S2 O4 118.68(15) . . ? O3 S2 C1 109.18(15) . . ? O4 S2 C1 106.38(15) . . ? O3 S2 C13 109.13(13) . . ? O4 S2 C13 104.73(13) . . ? C1 S2 C13 108.29(13) . . ? C6 C1 C2 122.2(3) . . ? C6 C1 S2 119.5(3) . . ? C2 C1 S2 118.2(3) . . ? C3 C2 C1 118.4(3) . . ? C2 C3 C4 120.4(3) . . ? C5 C4 C3 120.4(3) . . ? C4 C5 C6 120.5(4) . . ? C1 C6 C5 118.1(3) . . ? C12 C7 C8 121.8(3) . . ? C12 C7 S1 117.8(2) . . ? C8 C7 S1 120.3(2) . . ? C7 C8 C9 118.2(3) . . ? C10 C9 C8 120.5(3) . . ? C9 C10 C11 120.6(3) . . ? C10 C11 C12 120.0(3) . . ? C11 C12 C7 118.9(3) . . ? C18 C13 C14 111.5(2) . . ? C18 C13 S1 112.6(2) . . ? C14 C13 S1 109.86(19) . . ? C18 C13 S2 106.0(2) . . ? C14 C13 S2 106.64(19) . . ? S1 C13 S2 110.07(14) . . ? C15 C14 C13 116.8(2) . . ? C16 C15 C14 111.2(2) . . ? C16 C15 C21 114.6(3) . . ? C14 C15 C21 108.6(2) . . ? C19 C16 C17 124.0(3) . . ? C19 C16 C15 123.9(3) . . ? C17 C16 C15 112.0(3) . . ? C16 C17 C18 111.4(3) . . ? C17 C18 C13 112.4(3) . . ? C16 C19 C20 127.7(3) . . ? C15 C21 B1 118.5(3) . . ? O5 C22 C25 109.9(4) . . ? O5 C22 C23 103.7(3) . . ? C25 C22 C23 118.8(4) . . ? O5 C22 C24 105.7(4) . . ? C25 C22 C24 106.7(4) . . ? C23 C22 C24 111.3(4) . . ? O6 C23 C26 111.1(4) . . ? O6 C23 C27 103.7(3) . . ? C26 C23 C27 111.7(6) . . ? O6 C23 C22 103.1(3) . . ? C26 C23 C22 115.3(5) . . ? C27 C23 C22 111.0(4) . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 27.59 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.854 _refine_diff_density_min -0.446 _refine_diff_density_rms 0.132 # Attachment '- CIF 4g_.cif' data_datos _database_code_depnum_ccdc_archive 'CCDC 888323' #TrackingRef '- CIF 4g_.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C27 H35 B O6 S2' _chemical_formula_weight 530.48 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 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 12.4977(5) _cell_length_b 20.3568(8) _cell_length_c 10.5584(5) _cell_angle_alpha 90.00 _cell_angle_beta 96.757(2) _cell_angle_gamma 90.00 _cell_volume 2667.5(2) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 7002 _cell_measurement_theta_min 2.59 _cell_measurement_theta_max 26.54 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.47 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.321 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1128 _exptl_absorpt_coefficient_mu 0.240 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.8957 _exptl_absorpt_correction_T_max 0.9718 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 26845 _diffrn_reflns_av_R_equivalents 0.0385 _diffrn_reflns_av_sigmaI/netI 0.0394 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.64 _diffrn_reflns_theta_max 26.78 _reflns_number_total 5640 _reflns_number_gt 4114 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1523P)^2^+8.1432P] 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 5640 _refine_ls_number_parameters 330 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.1278 _refine_ls_R_factor_gt 0.0952 _refine_ls_wR_factor_ref 0.2907 _refine_ls_wR_factor_gt 0.2551 _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_restrained_S_all 1.047 _refine_ls_shift/su_max 3.409 _refine_ls_shift/su_mean 0.278 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group B1 B -0.1243(6) 0.2649(3) 0.0037(7) 0.0547(18) Uani 1 1 d . . . O1 O 0.3865(3) 0.25300(16) 0.1723(4) 0.0527(10) Uani 1 1 d . . . O2 O 0.4426(3) 0.16768(17) 0.3334(3) 0.0415(8) Uani 1 1 d . . . O3 O 0.3335(3) 0.03082(15) 0.2308(3) 0.0394(8) Uani 1 1 d . . . O4 O 0.1407(3) 0.0522(2) 0.2435(4) 0.0507(9) Uani 1 1 d . . . O5 O -0.2173(4) 0.2768(3) 0.0308(7) 0.099(2) Uani 1 1 d . . . O6 O -0.0676(3) 0.3243(2) -0.0341(5) 0.0741(14) Uani 1 1 d . . . S1 S 0.39667(10) 0.18473(5) 0.20674(11) 0.0358(3) Uani 1 1 d . . . S2 S 0.25057(9) 0.07273(6) 0.26909(11) 0.0358(3) Uani 1 1 d . . . C1 C 0.2589(4) 0.1508(2) 0.1830(4) 0.0366(10) Uani 1 1 d . . . C2 C 0.1853(4) 0.2050(3) 0.2315(5) 0.0463(12) Uani 1 1 d . . . H2A H 0.1937 0.2042 0.3259 0.056 Uiso 1 1 calc R . . H2B H 0.2099 0.2484 0.2046 0.056 Uiso 1 1 calc R . . C3 C 0.0672(5) 0.1971(4) 0.1832(6) 0.0632(18) Uani 1 1 d . . . H3A H 0.0267 0.2348 0.2128 0.076 Uiso 1 1 calc R . . H3B H 0.0396 0.1567 0.2201 0.076 Uiso 1 1 calc R . . C4 C 0.0463(5) 0.1930(5) 0.0326(7) 0.087(3) Uani 1 1 d . . . H4 H 0.0823 0.2318 -0.0022 0.104 Uiso 1 1 calc R . . C5 C 0.1097(4) 0.1298(3) -0.0017(5) 0.0516(14) Uani 1 1 d . . . C6 C 0.2771(4) 0.0856(2) 0.4357(4) 0.0344(10) Uani 1 1 d . . . C7 C 0.1942(4) 0.1082(2) 0.5024(5) 0.0402(11) Uani 1 1 d . . . H7 H 0.1260 0.1197 0.4586 0.048 Uiso 1 1 calc R . . C8 C 0.2139(5) 0.1134(2) 0.6341(5) 0.0451(12) Uani 1 1 d . . . H8 H 0.1590 0.1292 0.6812 0.054 Uiso 1 1 calc R . . C9 C 0.3128(5) 0.0956(2) 0.6971(5) 0.0459(12) Uani 1 1 d . . . H9 H 0.3255 0.0996 0.7873 0.055 Uiso 1 1 calc R . . C10 C 0.3940(4) 0.0721(2) 0.6303(5) 0.0428(11) Uani 1 1 d . . . H10 H 0.4615 0.0597 0.6747 0.051 Uiso 1 1 calc R . . C11 C 0.3762(4) 0.0668(2) 0.4986(5) 0.0369(10) Uani 1 1 d . . . H11 H 0.4312 0.0506 0.4519 0.044 Uiso 1 1 calc R . . C12 C 0.4735(4) 0.1484(2) 0.0949(4) 0.0334(10) Uani 1 1 d . . . C13 C 0.5255(4) 0.0887(2) 0.1230(5) 0.0418(11) Uani 1 1 d . . . H13 H 0.5166 0.0654 0.1990 0.050 Uiso 1 1 calc R . . C14 C 0.5904(4) 0.0647(2) 0.0369(6) 0.0508(14) Uani 1 1 d . . . H14 H 0.6264 0.0240 0.0539 0.061 Uiso 1 1 calc R . . C15 C 0.6042(4) 0.0982(3) -0.0729(5) 0.0489(13) Uani 1 1 d . . . H15 H 0.6497 0.0808 -0.1307 0.059 Uiso 1 1 calc R . . C16 C 0.5522(5) 0.1567(3) -0.0987(5) 0.0498(13) Uani 1 1 d . . . H16 H 0.5610 0.1796 -0.1751 0.060 Uiso 1 1 calc R . . C17 C 0.4864(4) 0.1827(3) -0.0137(5) 0.0432(11) Uani 1 1 d . . . H17 H 0.4510 0.2236 -0.0308 0.052 Uiso 1 1 calc R . . C18 C 0.0654(4) 0.0785(3) -0.0653(5) 0.0524(14) Uani 1 1 d . . . H18 H -0.0098 0.0812 -0.0917 0.063 Uiso 1 1 calc R . . C19 C 0.1204(4) 0.0170(3) -0.1004(6) 0.0509(13) Uani 1 1 d . . . H19A H 0.1547 0.0246 -0.1779 0.076 Uiso 1 1 calc R . . H19B H 0.0672 -0.0184 -0.1155 0.076 Uiso 1 1 calc R . . H19C H 0.1753 0.0045 -0.0305 0.076 Uiso 1 1 calc R . . C20 C -0.0687(6) 0.1969(4) -0.0140(7) 0.0668(18) Uani 1 1 d . . . H20A H -0.1070 0.1629 0.0305 0.080 Uiso 1 1 calc R . . H20B H -0.0780 0.1858 -0.1059 0.080 Uiso 1 1 calc R . . C21 C 0.2288(4) 0.1356(3) 0.0395(5) 0.0401(11) Uani 1 1 d . . . H21A H 0.2582 0.1709 -0.0110 0.048 Uiso 1 1 calc R . . H21B H 0.2639 0.0940 0.0193 0.048 Uiso 1 1 calc R . . C22 C -0.2253(7) 0.3448(5) 0.0427(16) 0.184(8) Uani 1 1 d D . . C23 C -0.1512(5) 0.3732(3) -0.0275(8) 0.070(2) Uani 1 1 d D . . C24 C -0.1532(18) 0.3800(9) 0.1692(18) 0.308(18) Uani 1 1 d D . . H24A H -0.0841 0.3952 0.1449 0.463 Uiso 1 1 calc R . . H24B H -0.1403 0.3478 0.2384 0.463 Uiso 1 1 calc R . . H24C H -0.1932 0.4174 0.1981 0.463 Uiso 1 1 calc R . . C25 C -0.3404(6) 0.3658(5) 0.0454(10) 0.094(3) Uani 1 1 d D . . H25A H -0.3431 0.4134 0.0582 0.141 Uiso 1 1 calc R . . H25B H -0.3704 0.3434 0.1154 0.141 Uiso 1 1 calc R . . H25C H -0.3826 0.3543 -0.0357 0.141 Uiso 1 1 calc R . . C26 C -0.1051(9) 0.4373(4) -0.0284(17) 0.144(6) Uani 1 1 d D . . H26A H -0.1627 0.4701 -0.0403 0.215 Uiso 1 1 calc R . . H26B H -0.0604 0.4405 -0.0984 0.215 Uiso 1 1 calc R . . H26C H -0.0605 0.4452 0.0529 0.215 Uiso 1 1 calc R . . C27 C -0.2318(15) 0.3739(10) -0.1676(10) 0.259(14) Uani 1 1 d D . . H27A H -0.2986 0.3501 -0.1580 0.389 Uiso 1 1 calc R . . H27B H -0.1948 0.3526 -0.2333 0.389 Uiso 1 1 calc R . . H27C H -0.2489 0.4194 -0.1926 0.389 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 B1 0.070(4) 0.030(3) 0.058(4) 0.002(3) -0.019(3) 0.018(3) O1 0.078(3) 0.0213(16) 0.062(2) -0.0023(15) 0.021(2) 0.0063(17) O2 0.051(2) 0.0391(18) 0.0336(17) -0.0046(14) 0.0004(15) -0.0103(15) O3 0.049(2) 0.0253(16) 0.0448(19) -0.0041(13) 0.0111(15) 0.0024(14) O4 0.0364(19) 0.062(2) 0.053(2) -0.0070(18) 0.0037(16) -0.0139(17) O5 0.066(3) 0.072(4) 0.166(6) 0.004(4) 0.039(4) -0.006(3) O6 0.037(2) 0.071(3) 0.118(4) -0.007(3) 0.024(2) 0.014(2) S1 0.0493(7) 0.0206(5) 0.0382(6) -0.0033(4) 0.0078(5) 0.0031(5) S2 0.0356(6) 0.0324(6) 0.0397(6) -0.0042(4) 0.0059(5) -0.0008(5) C1 0.037(2) 0.036(2) 0.036(2) -0.0030(19) 0.0020(19) 0.0115(19) C2 0.051(3) 0.047(3) 0.041(3) -0.005(2) 0.006(2) 0.022(2) C3 0.051(3) 0.082(5) 0.055(3) -0.020(3) 0.002(3) 0.035(3) C4 0.036(3) 0.150(8) 0.074(4) -0.062(5) 0.001(3) 0.026(4) C5 0.037(3) 0.075(4) 0.042(3) -0.010(3) 0.001(2) 0.019(3) C6 0.040(2) 0.024(2) 0.041(2) 0.0009(17) 0.0101(19) -0.0031(18) C7 0.044(3) 0.031(2) 0.048(3) -0.001(2) 0.015(2) -0.002(2) C8 0.059(3) 0.030(2) 0.051(3) -0.007(2) 0.024(2) -0.011(2) C9 0.064(3) 0.033(2) 0.041(3) -0.006(2) 0.006(2) -0.018(2) C10 0.048(3) 0.034(2) 0.046(3) 0.003(2) 0.000(2) -0.011(2) C11 0.040(3) 0.027(2) 0.044(3) 0.0016(18) 0.006(2) -0.0050(19) C12 0.038(2) 0.023(2) 0.040(2) -0.0054(17) 0.0039(19) 0.0000(17) C13 0.039(3) 0.028(2) 0.059(3) 0.004(2) 0.007(2) 0.004(2) C14 0.040(3) 0.030(3) 0.084(4) -0.008(2) 0.014(3) 0.004(2) C15 0.042(3) 0.051(3) 0.056(3) -0.023(3) 0.014(2) -0.004(2) C16 0.055(3) 0.058(3) 0.038(3) 0.000(2) 0.011(2) 0.003(3) C17 0.051(3) 0.039(3) 0.041(3) 0.001(2) 0.009(2) 0.005(2) C18 0.035(3) 0.075(4) 0.048(3) -0.004(3) 0.007(2) 0.010(3) C19 0.041(3) 0.056(3) 0.057(3) -0.003(3) 0.011(2) -0.010(2) C20 0.059(4) 0.062(4) 0.080(5) -0.004(3) 0.012(3) 0.001(3) C21 0.040(3) 0.044(3) 0.036(2) -0.007(2) 0.004(2) 0.013(2) C22 0.068(5) 0.072(6) 0.43(3) 0.067(10) 0.114(10) 0.003(4) C23 0.050(3) 0.040(3) 0.128(6) 0.018(3) 0.037(4) 0.018(3) C24 0.37(3) 0.25(2) 0.248(19) -0.213(18) -0.20(2) 0.21(2) C25 0.065(5) 0.101(7) 0.119(7) -0.022(5) 0.026(5) 0.004(5) C26 0.101(7) 0.051(5) 0.295(19) 0.030(7) 0.090(10) 0.016(5) C27 0.34(3) 0.37(3) 0.072(7) 0.086(11) 0.041(11) 0.26(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag B1 O5 1.252(9) . ? B1 O6 1.479(9) . ? B1 C20 1.571(9) . ? O1 S1 1.438(4) . ? O2 S1 1.434(3) . ? O3 S2 1.437(3) . ? O4 S2 1.431(4) . ? O5 C22 1.395(11) . ? O6 C23 1.451(7) . ? S1 C12 1.769(5) . ? S1 C1 1.845(5) . ? S2 C6 1.771(5) . ? S2 C1 1.840(5) . ? C1 C21 1.549(6) . ? C1 C2 1.561(6) . ? C2 C3 1.512(8) . ? C3 C4 1.583(9) . ? C4 C20 1.466(9) . ? C4 C5 1.576(9) . ? C5 C18 1.327(8) . ? C5 C21 1.505(7) . ? C6 C11 1.388(7) . ? C6 C7 1.398(7) . ? C7 C8 1.387(7) . ? C8 C9 1.382(8) . ? C9 C10 1.386(8) . ? C10 C11 1.387(7) . ? C12 C17 1.369(7) . ? C12 C13 1.393(6) . ? C13 C14 1.377(7) . ? C14 C15 1.372(8) . ? C15 C16 1.369(8) . ? C16 C17 1.392(7) . ? C18 C19 1.496(8) . ? C22 C23 1.380(11) . ? C22 C25 1.504(10) . ? C22 C24 1.681(15) . ? C23 C26 1.427(10) . ? C23 C27 1.689(13) . ? 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 O5 B1 O6 113.0(5) . . ? O5 B1 C20 129.2(7) . . ? O6 B1 C20 117.1(6) . . ? B1 O5 C22 106.9(6) . . ? C23 O6 B1 100.2(4) . . ? O2 S1 O1 118.9(2) . . ? O2 S1 C12 109.4(2) . . ? O1 S1 C12 105.9(2) . . ? O2 S1 C1 107.5(2) . . ? O1 S1 C1 105.9(2) . . ? C12 S1 C1 108.9(2) . . ? O4 S2 O3 118.8(2) . . ? O4 S2 C6 107.1(2) . . ? O3 S2 C6 108.1(2) . . ? O4 S2 C1 105.5(2) . . ? O3 S2 C1 106.8(2) . . ? C6 S2 C1 110.4(2) . . ? C21 C1 C2 112.2(4) . . ? C21 C1 S2 106.8(3) . . ? C2 C1 S2 112.2(4) . . ? C21 C1 S1 108.8(3) . . ? C2 C1 S1 105.5(3) . . ? S2 C1 S1 111.2(2) . . ? C3 C2 C1 113.8(5) . . ? C2 C3 C4 112.5(5) . . ? C20 C4 C5 117.8(6) . . ? C20 C4 C3 111.9(5) . . ? C5 C4 C3 104.2(6) . . ? C18 C5 C21 123.2(5) . . ? C18 C5 C4 124.6(5) . . ? C21 C5 C4 112.1(5) . . ? C11 C6 C7 121.5(5) . . ? C11 C6 S2 119.1(4) . . ? C7 C6 S2 119.0(4) . . ? C8 C7 C6 118.4(5) . . ? C7 C8 C9 120.4(5) . . ? C10 C9 C8 120.8(5) . . ? C9 C10 C11 119.8(5) . . ? C6 C11 C10 119.1(5) . . ? C17 C12 C13 121.7(5) . . ? C17 C12 S1 118.2(4) . . ? C13 C12 S1 119.9(4) . . ? C14 C13 C12 117.7(5) . . ? C15 C14 C13 121.6(5) . . ? C14 C15 C16 119.7(5) . . ? C15 C16 C17 120.4(5) . . ? C12 C17 C16 118.8(5) . . ? C5 C18 C19 127.4(5) . . ? C4 C20 B1 115.9(6) . . ? C5 C21 C1 114.6(4) . . ? C23 C22 O5 107.9(8) . . ? C23 C22 C25 126.5(9) . . ? O5 C22 C25 111.3(7) . . ? C23 C22 C24 85.3(12) . . ? O5 C22 C24 117.2(11) . . ? C25 C22 C24 106.7(12) . . ? C22 C23 C26 133.1(9) . . ? C22 C23 O6 105.7(6) . . ? C26 C23 O6 109.5(6) . . ? C22 C23 C27 96.0(10) . . ? C26 C23 C27 100.7(11) . . ? O6 C23 C27 108.8(7) . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 26.78 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 1.266 _refine_diff_density_min -0.784 _refine_diff_density_rms 0.133