# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_EA1 _database_code_depnum_ccdc_archive 'CCDC 914468' #TrackingRef 'ea.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H21 B O4 S' _chemical_melting_point ? _exptl_crystal_description Prism _exptl_crystal_colour Colourless _diffrn_ambient_temperature 173(2) _chemical_formula_weight 308.19 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 21/c' _symmetry_int_tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.5821(19) _cell_length_b 14.345(3) _cell_length_c 12.465(3) _cell_angle_alpha 90.00 _cell_angle_beta 110.706(2) _cell_angle_gamma 90.00 _cell_volume 1602.7(6) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 9577 _cell_measurement_theta_min 2.2 _cell_measurement_theta_max 27.5 _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.277 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 656 _exptl_absorpt_coefficient_mu 0.213 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.89 _exptl_absorpt_correction_T_max 0.97 _exptl_absorpt_process_details ; Data were corrected for decay and absorption using the program SADABS (Sheldrick, G. M. (2003). SADABS. Version 2.10. University of G\"ottingen, Germany). ; _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 'Bruker APEXII CCD area detector' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0.0 _diffrn_reflns_number 18510 _diffrn_reflns_av_R_equivalents 0.0213 _diffrn_reflns_av_sigmaI/netI 0.0147 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.25 _diffrn_reflns_theta_max 27.51 _reflns_number_total 3682 _reflns_number_gt 3355 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker AXS, 2008)' _computing_cell_refinement 'APEX2 (Bruker AXS, 2008)' _computing_data_reduction 'APEX2 (Bruker AXS, 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-SEED, Barbour, 2001' _computing_publication_material 'CIFTAB (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0476P)^2^+0.6038P] 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 3682 _refine_ls_number_parameters 190 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0370 _refine_ls_R_factor_gt 0.0339 _refine_ls_wR_factor_ref 0.0931 _refine_ls_wR_factor_gt 0.0903 _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_restrained_S_all 1.044 _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 S1 S 0.96239(3) 0.12467(2) 0.37268(3) 0.02554(10) Uani 1 1 d . . . O1 O 1.09099(10) 0.11415(7) 0.33933(10) 0.0377(2) Uani 1 1 d . . . O2 O 0.98340(11) 0.11793(7) 0.49278(8) 0.0355(2) Uani 1 1 d . . . O3 O 0.56814(9) 0.14343(6) 0.12107(7) 0.02682(19) Uani 1 1 d . . . O4 O 0.40798(10) 0.10322(7) 0.21239(8) 0.0303(2) Uani 1 1 d . . . C1 C 0.82895(13) 0.03916(8) 0.29574(11) 0.0274(3) Uani 1 1 d . . . H1A H 0.8154 0.0434 0.2134 0.033 Uiso 1 1 calc R . . H1B H 0.8692 -0.0235 0.3230 0.033 Uiso 1 1 calc R . . C2 C 0.67877(13) 0.04913(8) 0.30820(10) 0.0255(2) Uani 1 1 d . . . C3 C 0.42048(13) 0.17417(8) 0.04412(10) 0.0234(2) Uani 1 1 d . . . C4 C 0.32340(13) 0.16828(9) 0.12237(10) 0.0253(2) Uani 1 1 d . . . C5 C 0.65563(15) 0.01419(10) 0.39951(12) 0.0343(3) Uani 1 1 d . . . H5A H 0.7340 -0.0172 0.4572 0.041 Uiso 1 1 calc R . . H5B H 0.5608 0.0207 0.4069 0.041 Uiso 1 1 calc R . . C6 C 0.43714(16) 0.27158(9) 0.00215(12) 0.0325(3) Uani 1 1 d . . . H6A H 0.4690 0.3146 0.0674 0.049 Uiso 1 1 calc R . . H6B H 0.3412 0.2922 -0.0532 0.049 Uiso 1 1 calc R . . H6C H 0.5120 0.2707 -0.0348 0.049 Uiso 1 1 calc R . . C7 C 0.37157(16) 0.10568(9) -0.05550(11) 0.0317(3) Uani 1 1 d . . . H7A H 0.3612 0.0434 -0.0269 0.048 Uiso 1 1 calc R . . H7B H 0.4465 0.1040 -0.0924 0.048 Uiso 1 1 calc R . . H7C H 0.2755 0.1255 -0.1114 0.048 Uiso 1 1 calc R . . C8 C 0.31455(17) 0.25944(10) 0.18159(12) 0.0372(3) Uani 1 1 d . . . H8A H 0.4151 0.2850 0.2181 0.056 Uiso 1 1 calc R . . H8B H 0.2699 0.2482 0.2400 0.056 Uiso 1 1 calc R . . H8C H 0.2529 0.3039 0.1249 0.056 Uiso 1 1 calc R . . C9 C 0.16779(15) 0.12832(10) 0.06500(13) 0.0360(3) Uani 1 1 d . . . H9A H 0.1742 0.0694 0.0273 0.054 Uiso 1 1 calc R . . H9B H 0.1066 0.1726 0.0078 0.054 Uiso 1 1 calc R . . H9C H 0.1222 0.1172 0.1229 0.054 Uiso 1 1 calc R . . C10 C 0.88030(12) 0.23410(8) 0.32380(10) 0.0239(2) Uani 1 1 d . . . C11 C 0.79877(14) 0.27817(9) 0.38171(12) 0.0303(3) Uani 1 1 d . . . H11 H 0.7825 0.2486 0.4445 0.036 Uiso 1 1 calc R . . C12 C 0.74161(16) 0.36645(10) 0.34575(14) 0.0385(3) Uani 1 1 d . . . H12 H 0.6860 0.3978 0.3846 0.046 Uiso 1 1 calc R . . C13 C 0.76481(16) 0.40919(10) 0.25418(14) 0.0398(3) Uani 1 1 d . . . H13 H 0.7260 0.4698 0.2309 0.048 Uiso 1 1 calc R . . C14 C 0.84438(16) 0.36403(10) 0.19625(13) 0.0369(3) Uani 1 1 d . . . H14 H 0.8589 0.3933 0.1326 0.044 Uiso 1 1 calc R . . C15 C 0.90306(14) 0.27602(9) 0.23093(11) 0.0301(3) Uani 1 1 d . . . H15 H 0.9582 0.2448 0.1916 0.036 Uiso 1 1 calc R . . B1 B 0.54980(15) 0.10012(9) 0.21231(12) 0.0242(3) Uani 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 S1 0.01785(15) 0.02523(16) 0.02736(17) -0.00052(11) 0.00036(11) 0.00107(10) O1 0.0208(4) 0.0378(5) 0.0518(6) -0.0003(4) 0.0093(4) 0.0051(4) O2 0.0334(5) 0.0366(5) 0.0260(5) 0.0018(4) -0.0025(4) -0.0023(4) O3 0.0189(4) 0.0318(5) 0.0262(4) 0.0050(3) 0.0036(3) 0.0042(3) O4 0.0213(4) 0.0364(5) 0.0296(5) 0.0133(4) 0.0047(3) 0.0052(4) C1 0.0220(6) 0.0218(5) 0.0306(6) -0.0035(5) -0.0004(5) 0.0023(4) C2 0.0204(5) 0.0200(5) 0.0280(6) 0.0003(4) -0.0014(4) -0.0003(4) C3 0.0207(5) 0.0242(6) 0.0215(5) 0.0018(4) 0.0027(4) 0.0036(4) C4 0.0221(5) 0.0275(6) 0.0226(5) 0.0049(4) 0.0033(4) 0.0057(5) C5 0.0279(6) 0.0315(7) 0.0345(7) 0.0088(5) -0.0001(5) -0.0011(5) C6 0.0352(7) 0.0278(6) 0.0308(6) 0.0059(5) 0.0073(5) -0.0002(5) C7 0.0357(7) 0.0312(6) 0.0250(6) -0.0034(5) 0.0068(5) 0.0034(5) C8 0.0402(7) 0.0400(8) 0.0300(7) -0.0047(6) 0.0105(6) 0.0097(6) C9 0.0206(6) 0.0439(8) 0.0383(7) 0.0056(6) 0.0040(5) 0.0033(5) C10 0.0186(5) 0.0220(5) 0.0276(6) -0.0029(4) 0.0037(4) -0.0014(4) C11 0.0256(6) 0.0311(6) 0.0353(7) -0.0054(5) 0.0121(5) -0.0036(5) C12 0.0289(7) 0.0317(7) 0.0569(9) -0.0116(6) 0.0174(6) 0.0014(5) C13 0.0315(7) 0.0236(6) 0.0581(9) 0.0005(6) 0.0082(6) 0.0020(5) C14 0.0365(7) 0.0310(7) 0.0406(8) 0.0064(6) 0.0105(6) -0.0022(6) C15 0.0277(6) 0.0310(6) 0.0313(6) -0.0014(5) 0.0102(5) 0.0005(5) B1 0.0210(6) 0.0210(6) 0.0254(6) 0.0005(5) 0.0017(5) 0.0001(5) _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 S1 O1 1.4410(11) . ? S1 O2 1.4415(11) . ? S1 C10 1.7650(12) . ? S1 C1 1.7867(12) . ? O3 B1 1.3608(16) . ? O3 C3 1.4685(13) . ? O4 B1 1.3600(16) . ? O4 C4 1.4642(14) . ? C1 C2 1.5078(17) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 C5 1.3321(19) . ? C2 B1 1.5641(17) . ? C3 C6 1.5202(17) . ? C3 C7 1.5216(17) . ? C3 C4 1.5702(17) . ? C4 C8 1.5187(18) . ? C4 C9 1.5196(18) . ? C5 H5A 0.9500 . ? C5 H5B 0.9500 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 C15 1.3884(18) . ? C10 C11 1.3892(17) . ? C11 C12 1.390(2) . ? C11 H11 0.9500 . ? C12 C13 1.381(2) . ? C12 H12 0.9500 . ? C13 C14 1.383(2) . ? C13 H13 0.9500 . ? C14 C15 1.3874(19) . ? C14 H14 0.9500 . ? C15 H15 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 S1 O2 118.23(6) . . ? O1 S1 C10 108.40(6) . . ? O2 S1 C10 107.45(6) . . ? O1 S1 C1 107.21(6) . . ? O2 S1 C1 108.79(6) . . ? C10 S1 C1 106.16(6) . . ? B1 O3 C3 107.68(9) . . ? B1 O4 C4 107.62(9) . . ? C2 C1 S1 114.05(9) . . ? C2 C1 H1A 108.7 . . ? S1 C1 H1A 108.7 . . ? C2 C1 H1B 108.7 . . ? S1 C1 H1B 108.7 . . ? H1A C1 H1B 107.6 . . ? C5 C2 C1 120.37(11) . . ? C5 C2 B1 120.25(12) . . ? C1 C2 B1 119.38(11) . . ? O3 C3 C6 107.86(10) . . ? O3 C3 C7 106.67(9) . . ? C6 C3 C7 110.62(10) . . ? O3 C3 C4 102.92(9) . . ? C6 C3 C4 114.87(10) . . ? C7 C3 C4 113.14(10) . . ? O4 C4 C8 106.69(10) . . ? O4 C4 C9 107.78(10) . . ? C8 C4 C9 109.84(11) . . ? O4 C4 C3 102.79(9) . . ? C8 C4 C3 113.75(11) . . ? C9 C4 C3 115.23(11) . . ? C2 C5 H5A 120.0 . . ? C2 C5 H5B 120.0 . . ? H5A C5 H5B 120.0 . . ? C3 C6 H6A 109.5 . . ? C3 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C3 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C3 C7 H7A 109.5 . . ? C3 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C3 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C4 C8 H8A 109.5 . . ? C4 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C4 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C4 C9 H9A 109.5 . . ? C4 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C4 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C15 C10 C11 121.27(12) . . ? C15 C10 S1 119.40(9) . . ? C11 C10 S1 119.29(10) . . ? C10 C11 C12 118.49(13) . . ? C10 C11 H11 120.8 . . ? C12 C11 H11 120.8 . . ? C13 C12 C11 120.72(13) . . ? C13 C12 H12 119.6 . . ? C11 C12 H12 119.6 . . ? C12 C13 C14 120.22(13) . . ? C12 C13 H13 119.9 . . ? C14 C13 H13 119.9 . . ? C13 C14 C15 120.08(14) . . ? C13 C14 H14 120.0 . . ? C15 C14 H14 120.0 . . ? C14 C15 C10 119.21(12) . . ? C14 C15 H15 120.4 . . ? C10 C15 H15 120.4 . . ? O4 B1 O3 114.21(10) . . ? O4 B1 C2 122.30(11) . . ? O3 B1 C2 123.48(11) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 S1 C1 C2 -171.97(9) . . . . ? O2 S1 C1 C2 59.11(10) . . . . ? C10 S1 C1 C2 -56.25(10) . . . . ? S1 C1 C2 C5 -82.51(14) . . . . ? S1 C1 C2 B1 98.04(12) . . . . ? B1 O3 C3 C6 138.05(11) . . . . ? B1 O3 C3 C7 -103.08(11) . . . . ? B1 O3 C3 C4 16.23(12) . . . . ? B1 O4 C4 C8 -100.68(12) . . . . ? B1 O4 C4 C9 141.41(11) . . . . ? B1 O4 C4 C3 19.27(12) . . . . ? O3 C3 C4 O4 -21.25(11) . . . . ? C6 C3 C4 O4 -138.19(10) . . . . ? C7 C3 C4 O4 93.47(11) . . . . ? O3 C3 C4 C8 93.69(11) . . . . ? C6 C3 C4 C8 -23.26(14) . . . . ? C7 C3 C4 C8 -151.60(11) . . . . ? O3 C3 C4 C9 -138.20(10) . . . . ? C6 C3 C4 C9 104.86(13) . . . . ? C7 C3 C4 C9 -23.48(14) . . . . ? O1 S1 C10 C15 24.44(12) . . . . ? O2 S1 C10 C15 153.28(10) . . . . ? C1 S1 C10 C15 -90.46(11) . . . . ? O1 S1 C10 C11 -153.18(10) . . . . ? O2 S1 C10 C11 -24.35(11) . . . . ? C1 S1 C10 C11 91.92(11) . . . . ? C15 C10 C11 C12 -0.94(19) . . . . ? S1 C10 C11 C12 176.64(10) . . . . ? C10 C11 C12 C13 0.3(2) . . . . ? C11 C12 C13 C14 0.6(2) . . . . ? C12 C13 C14 C15 -0.9(2) . . . . ? C13 C14 C15 C10 0.3(2) . . . . ? C11 C10 C15 C14 0.67(19) . . . . ? S1 C10 C15 C14 -176.91(10) . . . . ? C4 O4 B1 O3 -10.16(14) . . . . ? C4 O4 B1 C2 171.00(11) . . . . ? C3 O3 B1 O4 -4.74(14) . . . . ? C3 O3 B1 C2 174.08(11) . . . . ? C5 C2 B1 O4 -6.29(19) . . . . ? C1 C2 B1 O4 173.16(11) . . . . ? C5 C2 B1 O3 174.98(12) . . . . ? C1 C2 B1 O3 -5.56(18) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.51 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.377 _refine_diff_density_min -0.367 _refine_diff_density_rms 0.045