# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # 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_4ha _database_code_depnum_ccdc_archive 'CCDC 881214' #TrackingRef 'CBA05-4ha.cif' #============================================================================== # Compound 4ha #============================================================================== _audit_creation_date '20 December 2011' _audit_creation_method SHELXL-97 _chemical_name_systematic ; (Z)-Ethyl 2-(5-bromoisobenzofuran-1(3H)-ylidene)acetate ; _chemical_name_common ? _chemical_melting_point 123 _chemical_formula_moiety 'C12 H11 Br O3' _chemical_formula_sum 'C12 H11 Br O3' _chemical_formula_weight 283.12 _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_absolute_configuration . 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' 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' #============================================================================== # CRYSTAL DATA #============================================================================== _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 13.2003(10) _cell_length_b 11.6716(9) _cell_length_c 7.2810(6) _cell_angle_alpha 90.00 _cell_angle_beta 91.8430(10) _cell_angle_gamma 90.00 _cell_volume 1121.19(15) _cell_formula_units_Z 4 _cell_measurement_temperature 90 _cell_measurement_reflns_used 2632 _cell_measurement_theta_min 2.33 _cell_measurement_theta_max 27.46 _exptl_crystal_description bllock _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.677 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 568 _exptl_absorpt_coefficient_mu 3.654 _exptl_absorpt_correction_type analytical _exptl_absorpt_correction_T_min 0.5141 _exptl_absorpt_correction_T_max 0.8106 _exptl_absorpt_process_details ; Crystal Faces plugin in Bruker APEX2 software ; _exptl_special_details ; ? ; #============================================================================== # EXPERIMENTAL DATA #============================================================================== _diffrn_ambient_temperature 90 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker TXS fine-focus rotating anode' _diffrn_radiation_monochromator 'Bruker Helios multilayer confocal mirror' _diffrn_measurement_device_type 'Bruker APEXII CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 8.333 _diffrn_reflns_number 5250 _diffrn_reflns_av_R_equivalents 0.0210 _diffrn_reflns_av_sigmaI/netI 0.0245 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 2.33 _diffrn_reflns_theta_max 25.03 _reflns_number_total 1974 _reflns_number_gt 1766 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker AXS, 2006)' _computing_cell_refinement 'APEX2 (Bruker AXS, 2006)' _computing_data_reduction 'SAINT (Bruker AXS, 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XSHEL (Bruker AXS,2002)' _computing_publication_material 'XCIF (Bruker AXS, 2001)' _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^)+(0.0242P)^2^+0.5339P] 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 1974 _refine_ls_number_parameters 147 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0258 _refine_ls_R_factor_gt 0.0217 _refine_ls_wR_factor_ref 0.0520 _refine_ls_wR_factor_gt 0.0507 _refine_ls_goodness_of_fit_ref 1.042 _refine_ls_restrained_S_all 1.042 _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 Br1 Br 0.054146(16) 0.353451(18) 1.07147(3) 0.02312(9) Uani 1 1 d . . . C1 C 0.65947(16) 0.24472(18) 0.7514(3) 0.0162(4) Uani 1 1 d . . . C2 C 0.56462(15) 0.29323(18) 0.8098(3) 0.0161(4) Uani 1 1 d . . . H2 H 0.5599 0.3744 0.8132 0.019 Uiso 1 1 calc R . . C3 C 0.48264(16) 0.23374(17) 0.8596(3) 0.0154(4) Uani 1 1 d . . . C4 C 0.37820(15) 0.08092(17) 0.9276(3) 0.0167(4) Uani 1 1 d . . . H4A H 0.3851 0.0379 1.0446 0.020 Uiso 1 1 calc R . . H4B H 0.3433 0.0319 0.8344 0.020 Uiso 1 1 calc R . . C5 C 0.32144(15) 0.19070(17) 0.9537(3) 0.0145(4) Uani 1 1 d . . . C6 C 0.22222(15) 0.20951(17) 1.0026(3) 0.0165(4) Uani 1 1 d . . . H6 H 0.1781 0.1480 1.0300 0.020 Uiso 1 1 calc R . . C7 C 0.19055(15) 0.32288(18) 1.0097(3) 0.0165(4) Uani 1 1 d . . . C8 C 0.25341(16) 0.41500(17) 0.9705(3) 0.0172(4) Uani 1 1 d . . . H8 H 0.2285 0.4912 0.9766 0.021 Uiso 1 1 calc R . . C9 C 0.35213(16) 0.39472(17) 0.9228(3) 0.0160(4) Uani 1 1 d . . . H9 H 0.3964 0.4564 0.8967 0.019 Uiso 1 1 calc R . . C10 C 0.38543(15) 0.28143(17) 0.9138(3) 0.0148(4) Uani 1 1 d . . . C11 C 0.82239(15) 0.29592(18) 0.6414(3) 0.0185(7) Uani 0.999(7) 1 d P . . H11A H 0.8129 0.2356 0.5467 0.022 Uiso 0.999(7) 1 calc PR . . H11B H 0.8664 0.2652 0.7424 0.022 Uiso 0.999(7) 1 calc PR . . C12 C 0.86993(16) 0.40094(19) 0.5594(3) 0.0216(5) Uani 1 1 d . . . H12A H 0.8263 0.4296 0.4580 0.032 Uiso 1 1 calc R . . H12B H 0.9365 0.3811 0.5129 0.032 Uiso 1 1 calc R . . H12C H 0.8778 0.4604 0.6538 0.032 Uiso 1 1 calc R . . O1 O 0.47724(11) 0.11740(11) 0.86536(19) 0.0168(3) Uani 1 1 d . . . O2 O 0.68165(11) 0.14411(11) 0.7387(2) 0.0199(3) Uani 1 1 d . . . O3 O 0.72518(11) 0.33039(11) 0.7109(2) 0.0176(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 Br1 0.01538(13) 0.01863(13) 0.03550(15) -0.00433(9) 0.00319(9) 0.00180(9) C1 0.0181(11) 0.0166(12) 0.0136(11) -0.0006(8) -0.0014(8) -0.0001(9) C2 0.0185(11) 0.0120(10) 0.0179(11) -0.0008(8) 0.0005(8) 0.0013(8) C3 0.0199(11) 0.0134(11) 0.0128(10) -0.0014(8) -0.0015(8) 0.0008(8) C4 0.0147(11) 0.0140(11) 0.0216(11) 0.0006(9) 0.0019(9) -0.0014(8) C5 0.0174(11) 0.0137(10) 0.0123(10) -0.0007(8) -0.0034(8) -0.0006(8) C6 0.0193(11) 0.0134(11) 0.0167(11) 0.0004(8) -0.0001(9) -0.0027(9) C7 0.0142(11) 0.0181(11) 0.0173(11) -0.0015(8) 0.0009(8) 0.0034(8) C8 0.0206(11) 0.0120(11) 0.0188(11) -0.0018(8) 0.0001(9) 0.0016(9) C9 0.0189(11) 0.0121(10) 0.0172(11) 0.0004(8) 0.0004(8) -0.0015(8) C10 0.0176(11) 0.0157(11) 0.0111(10) 0.0010(8) -0.0019(8) 0.0008(8) C11 0.0150(12) 0.0189(12) 0.0218(12) 0.0006(9) 0.0041(9) 0.0038(9) C12 0.0177(11) 0.0201(11) 0.0270(12) -0.0027(9) 0.0019(9) -0.0005(9) O1 0.0161(8) 0.0111(7) 0.0232(8) 0.0001(6) 0.0022(6) 0.0012(6) O2 0.0207(8) 0.0132(8) 0.0258(8) -0.0010(6) 0.0015(7) 0.0020(6) O3 0.0157(8) 0.0129(7) 0.0244(8) 0.0000(6) 0.0049(6) -0.0003(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br1 C7 1.904(2) . ? C1 O2 1.215(2) . ? C1 O3 1.362(2) . ? C1 C2 1.450(3) . ? C2 C3 1.345(3) . ? C2 H2 0.9500 . ? C3 O1 1.360(2) . ? C3 C10 1.464(3) . ? C4 O1 1.461(2) . ? C4 C5 1.499(3) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.386(3) . ? C5 C10 1.391(3) . ? C6 C7 1.389(3) . ? C6 H6 0.9500 . ? C7 C8 1.393(3) . ? C8 C9 1.380(3) . ? C8 H8 0.9500 . ? C9 C10 1.396(3) . ? C9 H9 0.9500 . ? C11 O3 1.451(2) . ? C11 C12 1.509(3) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 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 O2 C1 O3 122.44(19) . . ? O2 C1 C2 127.76(19) . . ? O3 C1 C2 109.80(17) . . ? C3 C2 C1 125.95(19) . . ? C3 C2 H2 117.0 . . ? C1 C2 H2 117.0 . . ? C2 C3 O1 124.53(18) . . ? C2 C3 C10 126.57(19) . . ? O1 C3 C10 108.90(17) . . ? O1 C4 C5 104.25(15) . . ? O1 C4 H4A 110.9 . . ? C5 C4 H4A 110.9 . . ? O1 C4 H4B 110.9 . . ? C5 C4 H4B 110.9 . . ? H4A C4 H4B 108.9 . . ? C6 C5 C10 121.23(19) . . ? C6 C5 C4 130.41(19) . . ? C10 C5 C4 108.34(18) . . ? C5 C6 C7 116.65(19) . . ? C5 C6 H6 121.7 . . ? C7 C6 H6 121.7 . . ? C6 C7 C8 123.06(19) . . ? C6 C7 Br1 118.39(16) . . ? C8 C7 Br1 118.54(15) . . ? C9 C8 C7 119.52(19) . . ? C9 C8 H8 120.2 . . ? C7 C8 H8 120.2 . . ? C8 C9 C10 118.41(19) . . ? C8 C9 H9 120.8 . . ? C10 C9 H9 120.8 . . ? C5 C10 C9 121.13(19) . . ? C5 C10 C3 108.07(17) . . ? C9 C10 C3 130.76(19) . . ? O3 C11 C12 107.24(16) . . ? O3 C11 H11A 110.3 . . ? C12 C11 H11A 110.3 . . ? O3 C11 H11B 110.3 . . ? C12 C11 H11B 110.3 . . ? H11A C11 H11B 108.5 . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C3 O1 C4 110.41(15) . . ? C1 O3 C11 116.64(15) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.368 _refine_diff_density_min -0.299 _refine_diff_density_rms 0.059 data_4ia _database_code_depnum_ccdc_archive 'CCDC 881215' #TrackingRef 'CBA05-4ia.cif' #============================================================================== # Compound 4ia #============================================================================== _audit_creation_date '04 February 2012' _audit_creation_method SHELXL-97 _chemical_name_systematic ; (Z)-Ethyl 2-(7-((trimethylsilyl)ethynyl)isochroman-1-ylidene)acetate ; _chemical_name_common ? _chemical_melting_point 91 _chemical_formula_moiety 'C18 H22 O3 Si' _chemical_formula_sum 'C18 H22 O3 Si' _chemical_formula_weight 314.45 _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_absolute_configuration . 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #============================================================================== # CRYSTAL DATA #============================================================================== _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 19.733(5) _cell_length_b 12.199(3) _cell_length_c 7.4044(17) _cell_angle_alpha 90.00 _cell_angle_beta 100.236(3) _cell_angle_gamma 90.00 _cell_volume 1754.0(7) _cell_formula_units_Z 4 _cell_measurement_temperature 90 _cell_measurement_reflns_used 4612 _cell_measurement_theta_min 2.68 _cell_measurement_theta_max 27.73 _exptl_crystal_description Block _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.27 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.191 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 672 _exptl_absorpt_coefficient_mu 0.143 _exptl_absorpt_correction_type analytical _exptl_absorpt_correction_T_min 0.9623 _exptl_absorpt_correction_T_max 0.9886 _exptl_absorpt_process_details ; Crystal Faces plugin in Bruker APEX2 software ; _exptl_special_details ; ? ; #============================================================================== # EXPERIMENTAL DATA #============================================================================== _diffrn_ambient_temperature 90 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker TXS fine-focus rotating anode' _diffrn_radiation_monochromator 'Bruker Helios multilayer confocal mirror' _diffrn_measurement_device_type 'Bruker APEXII CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 8.333 _diffrn_reflns_number 7915 _diffrn_reflns_av_R_equivalents 0.0248 _diffrn_reflns_av_sigmaI/netI 0.0272 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 2.10 _diffrn_reflns_theta_max 25.02 _reflns_number_total 3091 _reflns_number_gt 2735 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker AXS, 2006)' _computing_cell_refinement 'APEX2 (Bruker AXS, 2006)' _computing_data_reduction 'SAINT (Bruker AXS, 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XSHEL (Bruker AXS,2002)' _computing_publication_material 'XCIF (Bruker AXS, 2001)' _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^)+(0.0418P)^2^+1.2171P] 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 3091 _refine_ls_number_parameters 203 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0432 _refine_ls_R_factor_gt 0.0375 _refine_ls_wR_factor_ref 0.0959 _refine_ls_wR_factor_gt 0.0921 _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_restrained_S_all 1.025 _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 0.66175(8) 0.64747(14) 0.4120(2) 0.0182(3) Uani 1 1 d . . . C2 C 0.67062(8) 0.52820(13) 0.4180(2) 0.0181(3) Uani 1 1 d . . . H2 H 0.7161 0.5011 0.4548 0.022 Uiso 1 1 calc R . . C3 C 0.61953(8) 0.45299(13) 0.3755(2) 0.0169(3) Uani 1 1 d . . . C4 C 0.49885(8) 0.40442(13) 0.3017(2) 0.0184(3) Uani 1 1 d . . . H4A H 0.4939 0.3788 0.1732 0.022 Uiso 1 1 calc R . . H4B H 0.4546 0.4379 0.3178 0.022 Uiso 1 1 calc R . . C5 C 0.51422(8) 0.30766(13) 0.4295(2) 0.0177(3) Uani 1 1 d . . . H5A H 0.5160 0.3315 0.5581 0.021 Uiso 1 1 calc R . . H5B H 0.4776 0.2518 0.3999 0.021 Uiso 1 1 calc R . . C6 C 0.58247(8) 0.25993(13) 0.4068(2) 0.0168(3) Uani 1 1 d . . . C7 C 0.63405(8) 0.33351(13) 0.3757(2) 0.0166(3) Uani 1 1 d . . . C8 C 0.69700(8) 0.29352(13) 0.3414(2) 0.0173(3) Uani 1 1 d . . . H8 H 0.7316 0.3434 0.3191 0.021 Uiso 1 1 calc R . . C9 C 0.70946(8) 0.18072(13) 0.3396(2) 0.0181(3) Uani 1 1 d . . . C10 C 0.65801(8) 0.10785(13) 0.3739(2) 0.0191(4) Uani 1 1 d . . . H10 H 0.6661 0.0311 0.3747 0.023 Uiso 1 1 calc R . . C11 C 0.59556(8) 0.14785(13) 0.4065(2) 0.0178(3) Uani 1 1 d . . . H11 H 0.5611 0.0979 0.4290 0.021 Uiso 1 1 calc R . . C12 C 0.72033(9) 0.81701(13) 0.4789(2) 0.0226(4) Uani 1 1 d . . . H12A H 0.6830 0.8454 0.5395 0.027 Uiso 1 1 calc R . . H12B H 0.7117 0.8420 0.3496 0.027 Uiso 1 1 calc R . . C13 C 0.78920(10) 0.85837(15) 0.5764(3) 0.0292(4) Uani 1 1 d . . . H13A H 0.7959 0.8371 0.7060 0.044 Uiso 1 1 calc R . . H13B H 0.7906 0.9385 0.5670 0.044 Uiso 1 1 calc R . . H13C H 0.8259 0.8265 0.5197 0.044 Uiso 1 1 calc R . . C14 C 0.77261(8) 0.13980(13) 0.2931(2) 0.0197(4) Uani 1 1 d . . . C15 C 0.82444(9) 0.10570(14) 0.2461(2) 0.0229(4) Uani 1 1 d . . . C16 C 0.88964(10) 0.09803(17) -0.0894(3) 0.0362(5) Uani 1 1 d . . . H16A H 0.8504 0.0589 -0.1604 0.054 Uiso 1 1 calc R . . H16B H 0.9315 0.0798 -0.1370 0.054 Uiso 1 1 calc R . . H16C H 0.8814 0.1772 -0.0999 0.054 Uiso 1 1 calc R . . C17 C 0.97845(10) 0.12162(18) 0.2931(3) 0.0445(6) Uani 1 1 d . . . H17A H 0.9773 0.2007 0.2695 0.067 Uiso 1 1 calc R . . H17B H 1.0198 0.0900 0.2573 0.067 Uiso 1 1 calc R . . H17C H 0.9793 0.1085 0.4241 0.067 Uiso 1 1 calc R . . C18 C 0.90310(9) -0.09598(15) 0.1756(3) 0.0311(4) Uani 1 1 d . . . H18A H 0.9135 -0.1171 0.3053 0.047 Uiso 1 1 calc R . . H18B H 0.9389 -0.1246 0.1121 0.047 Uiso 1 1 calc R . . H18C H 0.8583 -0.1264 0.1193 0.047 Uiso 1 1 calc R . . O1 O 0.72201(6) 0.69765(9) 0.48664(15) 0.0206(3) Uani 1 1 d . . . O2 O 0.61037(6) 0.69885(9) 0.34910(16) 0.0234(3) Uani 1 1 d . . . O3 O 0.55312(6) 0.48690(9) 0.33633(15) 0.0199(3) Uani 1 1 d . . . Si1 Si 0.90035(2) 0.05648(4) 0.15692(7) 0.02415(15) 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 C1 0.0234(8) 0.0219(9) 0.0103(7) 0.0009(6) 0.0059(6) -0.0002(7) C2 0.0220(8) 0.0177(8) 0.0148(8) -0.0001(6) 0.0033(6) 0.0022(6) C3 0.0218(8) 0.0187(8) 0.0103(7) 0.0011(6) 0.0032(6) 0.0026(6) C4 0.0195(8) 0.0202(9) 0.0153(8) -0.0016(6) 0.0023(6) -0.0001(6) C5 0.0213(8) 0.0183(8) 0.0136(8) -0.0022(6) 0.0033(6) -0.0002(6) C6 0.0225(8) 0.0204(8) 0.0070(7) -0.0015(6) 0.0010(6) -0.0001(6) C7 0.0223(8) 0.0187(8) 0.0079(7) -0.0008(6) 0.0001(6) 0.0005(6) C8 0.0213(8) 0.0189(8) 0.0114(7) -0.0010(6) 0.0017(6) -0.0002(6) C9 0.0220(8) 0.0210(9) 0.0102(7) -0.0011(6) 0.0002(6) 0.0017(7) C10 0.0281(9) 0.0149(8) 0.0133(8) -0.0008(6) 0.0012(6) 0.0023(7) C11 0.0253(8) 0.0165(8) 0.0112(7) 0.0003(6) 0.0022(6) -0.0021(6) C12 0.0346(10) 0.0144(8) 0.0193(9) 0.0013(7) 0.0057(7) 0.0005(7) C13 0.0389(10) 0.0198(9) 0.0283(10) 0.0010(8) 0.0048(8) -0.0051(8) C14 0.0251(9) 0.0161(8) 0.0167(8) -0.0011(6) 0.0007(6) 0.0005(7) C15 0.0243(9) 0.0187(9) 0.0247(9) -0.0033(7) 0.0017(7) 0.0007(7) C16 0.0390(11) 0.0307(11) 0.0437(12) 0.0029(9) 0.0200(9) 0.0067(9) C17 0.0258(10) 0.0388(12) 0.0674(15) -0.0214(11) 0.0043(10) -0.0004(9) C18 0.0313(10) 0.0204(9) 0.0425(11) -0.0020(8) 0.0091(8) 0.0045(8) O1 0.0264(6) 0.0143(6) 0.0205(6) 0.0006(5) 0.0023(5) -0.0008(5) O2 0.0253(6) 0.0200(6) 0.0242(6) 0.0027(5) 0.0023(5) 0.0038(5) O3 0.0208(6) 0.0171(6) 0.0213(6) -0.0002(5) 0.0025(5) 0.0013(5) Si1 0.0209(3) 0.0187(3) 0.0334(3) -0.0057(2) 0.0063(2) 0.00134(18) _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 C1 O2 1.212(2) . ? C1 O1 1.364(2) . ? C1 C2 1.465(2) . ? C2 C3 1.358(2) . ? C2 H2 0.9500 . ? C3 O3 1.3554(19) . ? C3 C7 1.485(2) . ? C4 O3 1.4585(19) . ? C4 C5 1.510(2) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.504(2) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C11 1.391(2) . ? C6 C7 1.407(2) . ? C7 C8 1.399(2) . ? C8 C9 1.398(2) . ? C8 H8 0.9500 . ? C9 C10 1.406(2) . ? C9 C14 1.440(2) . ? C10 C11 1.386(2) . ? C10 H10 0.9500 . ? C11 H11 0.9500 . ? C12 O1 1.457(2) . ? C12 C13 1.508(2) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 C15 1.211(2) . ? C15 Si1 1.8417(18) . ? C16 Si1 1.868(2) . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 Si1 1.863(2) . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 Si1 1.8650(19) . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 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 O2 C1 O1 122.20(15) . . ? O2 C1 C2 127.75(15) . . ? O1 C1 C2 110.04(13) . . ? C3 C2 C1 125.74(15) . . ? C3 C2 H2 117.1 . . ? C1 C2 H2 117.1 . . ? C2 C3 O3 119.55(14) . . ? C2 C3 C7 121.84(14) . . ? O3 C3 C7 118.59(14) . . ? O3 C4 C5 111.70(12) . . ? O3 C4 H4A 109.3 . . ? C5 C4 H4A 109.3 . . ? O3 C4 H4B 109.3 . . ? C5 C4 H4B 109.3 . . ? H4A C4 H4B 107.9 . . ? C6 C5 C4 108.46(13) . . ? C6 C5 H5A 110.0 . . ? C4 C5 H5A 110.0 . . ? C6 C5 H5B 110.0 . . ? C4 C5 H5B 110.0 . . ? H5A C5 H5B 108.4 . . ? C11 C6 C7 119.12(15) . . ? C11 C6 C5 123.43(14) . . ? C7 C6 C5 117.38(14) . . ? C8 C7 C6 119.93(15) . . ? C8 C7 C3 121.29(14) . . ? C6 C7 C3 118.76(14) . . ? C9 C8 C7 120.54(15) . . ? C9 C8 H8 119.7 . . ? C7 C8 H8 119.7 . . ? C8 C9 C10 119.11(15) . . ? C8 C9 C14 120.31(15) . . ? C10 C9 C14 120.49(15) . . ? C11 C10 C9 120.12(15) . . ? C11 C10 H10 119.9 . . ? C9 C10 H10 119.9 . . ? C10 C11 C6 121.16(15) . . ? C10 C11 H11 119.4 . . ? C6 C11 H11 119.4 . . ? O1 C12 C13 107.65(14) . . ? O1 C12 H12A 110.2 . . ? C13 C12 H12A 110.2 . . ? O1 C12 H12B 110.2 . . ? C13 C12 H12B 110.2 . . ? H12A C12 H12B 108.5 . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C15 C14 C9 177.21(17) . . ? C14 C15 Si1 175.70(15) . . ? Si1 C16 H16A 109.5 . . ? Si1 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? Si1 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? Si1 C17 H17A 109.5 . . ? Si1 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? Si1 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? Si1 C18 H18A 109.5 . . ? Si1 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? Si1 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C1 O1 C12 114.85(12) . . ? C3 O3 C4 118.61(12) . . ? C15 Si1 C17 108.31(9) . . ? C15 Si1 C18 108.26(8) . . ? C17 Si1 C18 112.01(10) . . ? C15 Si1 C16 107.67(8) . . ? C17 Si1 C16 110.59(11) . . ? C18 Si1 C16 109.86(9) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.419 _refine_diff_density_min -0.322 _refine_diff_density_rms 0.045