# Supplementary Material (ESI) for Green Chemistry # This journal is © The Royal Society of Chemistry 2010 data_global _journal_name_full 'Green Chemistry' _journal_coden_Cambridge 1048 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Liu Pei Nian' _publ_contact_author_email LIUPN@ECUST.EDU.CN _publ_section_title ; Triflic Acid Adsorbed on Silica Gel as an Efficient and Recyclable Catalyst for the Addition of ?-Dicarbonyl Compounds to Alcohols and Alkenes ; loop_ _publ_author_name 'Liu Pei Nian.' 'Jun Qin Chen.' 'Yu Jie Ren.' 'Qing Wei Wang.' 'Fei Xia.' # Attachment '3a.CIF' data_lpn8 _database_code_depnum_ccdc_archive 'CCDC 651081' #TrackingRef '3a.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H16 O2' _chemical_formula_weight 204.26 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 13.286(3) _cell_length_b 5.6083(12) _cell_length_c 15.808(3) _cell_angle_alpha 90.00 _cell_angle_beta 95.142(4) _cell_angle_gamma 90.00 _cell_volume 1173.2(4) _cell_formula_units_Z 4 _cell_measurement_temperature 294(2) _cell_measurement_reflns_used 691 _cell_measurement_theta_min 3.08 _cell_measurement_theta_max 23.41 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.156 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 440 _exptl_absorpt_coefficient_mu 0.077 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.610 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details 'SAIT v6.45, 2003; SADABS v5.10' _exptl_special_details ; ? ; _diffrn_ambient_temperature 294(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10563 _diffrn_reflns_av_R_equivalents 0.0982 _diffrn_reflns_av_sigmaI/netI 0.0984 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.92 _diffrn_reflns_theta_max 27.58 _reflns_number_total 2715 _reflns_number_gt 1114 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.1100P)^2^+1.4912P] 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 2715 _refine_ls_number_parameters 139 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1829 _refine_ls_R_factor_gt 0.0734 _refine_ls_wR_factor_ref 0.2822 _refine_ls_wR_factor_gt 0.2234 _refine_ls_goodness_of_fit_ref 1.017 _refine_ls_restrained_S_all 1.017 _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 0.8402(3) 0.5999(6) 0.5391(2) 0.0823(12) Uani 1 1 d . . . O2 O 0.8669(3) 0.0903(7) 0.3588(2) 0.0864(12) Uani 1 1 d . . . C1 C 0.6534(3) 0.2233(9) 0.5731(3) 0.0568(12) Uani 1 1 d . . . C2 C 0.6816(3) 0.0443(8) 0.6312(3) 0.0608(13) Uani 1 1 d . . . H2A H 0.7215 -0.0809 0.6148 0.073 Uiso 1 1 calc R . . C3 C 0.6521(4) 0.0479(9) 0.7122(3) 0.0669(14) Uani 1 1 d . . . H3A H 0.6726 -0.0722 0.7505 0.080 Uiso 1 1 calc R . . C4 C 0.5919(4) 0.2307(9) 0.7363(3) 0.0617(13) Uani 1 1 d . . . H4A H 0.5703 0.2336 0.7906 0.074 Uiso 1 1 calc R . . C5 C 0.5644(4) 0.4062(9) 0.6803(3) 0.0633(13) Uani 1 1 d . . . H5A H 0.5237 0.5301 0.6965 0.076 Uiso 1 1 calc R . . C6 C 0.5955(4) 0.4042(9) 0.5997(3) 0.0616(13) Uani 1 1 d . . . H6A H 0.5767 0.5286 0.5627 0.074 Uiso 1 1 calc R . . C7 C 0.6830(4) 0.2196(13) 0.4822(3) 0.093(2) Uani 1 1 d . . . H7A H 0.6597 0.3770 0.4619 0.111 Uiso 1 1 calc R . . C8 C 0.7863(4) 0.2339(12) 0.4719(3) 0.0859(19) Uani 1 1 d . . . H8A H 0.8097 0.0738 0.4890 0.103 Uiso 1 1 calc R . . C9 C 0.8537(3) 0.3903(8) 0.5310(2) 0.0443(10) Uani 1 1 d . . . C10 C 0.9381(4) 0.2634(11) 0.5779(3) 0.0834(17) Uani 1 1 d . . . H10A H 0.9734 0.3703 0.6176 0.125 Uiso 1 1 calc R . . H10B H 0.9837 0.2059 0.5387 0.125 Uiso 1 1 calc R . . H10C H 0.9123 0.1312 0.6079 0.125 Uiso 1 1 calc R . . C11 C 0.8202(3) 0.2527(9) 0.3832(3) 0.0520(11) Uani 1 1 d . . . C12 C 0.7968(5) 0.4657(10) 0.3308(4) 0.0887(18) Uani 1 1 d . . . H12A H 0.8365 0.4643 0.2830 0.133 Uiso 1 1 calc R . . H12B H 0.8122 0.6062 0.3641 0.133 Uiso 1 1 calc R . . H12C H 0.7263 0.4655 0.3110 0.133 Uiso 1 1 calc R . . C13 C 0.6178(3) 0.0610(9) 0.4262(3) 0.0625(13) Uani 1 1 d . . . H13A H 0.6330 0.0820 0.3684 0.094 Uiso 1 1 calc R . . H13B H 0.5481 0.0998 0.4309 0.094 Uiso 1 1 calc R . . H13C H 0.6299 -0.1019 0.4428 0.094 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 0.117(3) 0.053(2) 0.078(3) -0.0037(19) 0.019(2) 0.003(2) O2 0.091(3) 0.087(3) 0.082(3) -0.008(2) 0.014(2) 0.024(2) C1 0.052(2) 0.079(3) 0.041(2) -0.008(2) 0.0083(19) -0.025(2) C2 0.055(3) 0.054(3) 0.076(3) -0.010(3) 0.020(2) -0.006(2) C3 0.075(3) 0.063(3) 0.065(3) 0.012(3) 0.017(3) -0.002(3) C4 0.071(3) 0.070(3) 0.046(3) -0.001(3) 0.020(2) -0.008(3) C5 0.068(3) 0.060(3) 0.063(3) -0.009(3) 0.013(2) 0.002(2) C6 0.069(3) 0.064(3) 0.051(3) 0.006(2) 0.003(2) -0.004(3) C7 0.074(3) 0.156(6) 0.050(3) -0.030(3) 0.021(2) -0.059(4) C8 0.065(3) 0.147(5) 0.048(3) -0.021(3) 0.014(2) -0.048(3) C9 0.046(2) 0.052(3) 0.036(2) -0.002(2) 0.0095(17) -0.0065(19) C10 0.069(3) 0.107(5) 0.073(4) 0.000(3) 0.002(3) 0.022(3) C11 0.047(2) 0.070(3) 0.039(2) 0.000(2) 0.0086(18) -0.006(2) C12 0.119(5) 0.074(4) 0.070(4) 0.017(3) -0.010(3) -0.005(3) C13 0.058(3) 0.074(3) 0.055(3) -0.017(3) 0.003(2) -0.009(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 O1 C9 1.198(5) . ? O2 C11 1.185(5) . ? C1 C6 1.362(6) . ? C1 C2 1.389(7) . ? C1 C7 1.524(6) . ? C2 C3 1.373(6) . ? C2 H2A 0.9300 . ? C3 C4 1.374(7) . ? C3 H3A 0.9300 . ? C4 C5 1.352(7) . ? C4 H4A 0.9300 . ? C5 C6 1.373(6) . ? C5 H5A 0.9300 . ? C6 H6A 0.9300 . ? C7 C8 1.399(7) . ? C7 C13 1.479(6) . ? C7 H7A 0.9800 . ? C8 C9 1.514(6) . ? C8 C11 1.515(6) . ? C8 H8A 0.9800 . ? C9 C10 1.471(6) . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 C12 1.471(7) . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 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 C6 C1 C2 117.5(4) . . ? C6 C1 C7 120.1(5) . . ? C2 C1 C7 122.4(5) . . ? C3 C2 C1 121.5(4) . . ? C3 C2 H2A 119.2 . . ? C1 C2 H2A 119.2 . . ? C2 C3 C4 119.4(5) . . ? C2 C3 H3A 120.3 . . ? C4 C3 H3A 120.3 . . ? C5 C4 C3 119.5(4) . . ? C5 C4 H4A 120.3 . . ? C3 C4 H4A 120.3 . . ? C4 C5 C6 121.0(5) . . ? C4 C5 H5A 119.5 . . ? C6 C5 H5A 119.5 . . ? C1 C6 C5 121.1(5) . . ? C1 C6 H6A 119.4 . . ? C5 C6 H6A 119.4 . . ? C8 C7 C13 119.5(5) . . ? C8 C7 C1 116.6(4) . . ? C13 C7 C1 112.7(4) . . ? C8 C7 H7A 101.3 . . ? C13 C7 H7A 101.3 . . ? C1 C7 H7A 101.3 . . ? C7 C8 C9 119.6(5) . . ? C7 C8 C11 119.2(4) . . ? C9 C8 C11 108.8(4) . . ? C7 C8 H8A 101.9 . . ? C9 C8 H8A 101.9 . . ? C11 C8 H8A 101.9 . . ? O1 C9 C10 122.4(4) . . ? O1 C9 C8 123.3(5) . . ? C10 C9 C8 114.4(5) . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? O2 C11 C12 122.1(4) . . ? O2 C11 C8 117.1(5) . . ? C12 C11 C8 120.8(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 . . ? C7 C13 H13A 109.5 . . ? C7 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C7 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 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 C6 C1 C2 C3 0.4(6) . . . . ? C7 C1 C2 C3 -178.4(4) . . . . ? C1 C2 C3 C4 1.0(7) . . . . ? C2 C3 C4 C5 -1.2(7) . . . . ? C3 C4 C5 C6 0.1(7) . . . . ? C2 C1 C6 C5 -1.5(7) . . . . ? C7 C1 C6 C5 177.3(4) . . . . ? C4 C5 C6 C1 1.3(7) . . . . ? C6 C1 C7 C8 117.4(7) . . . . ? C2 C1 C7 C8 -63.9(7) . . . . ? C6 C1 C7 C13 -98.8(6) . . . . ? C2 C1 C7 C13 79.9(6) . . . . ? C13 C7 C8 C9 -178.1(5) . . . . ? C1 C7 C8 C9 -36.9(9) . . . . ? C13 C7 C8 C11 44.0(9) . . . . ? C1 C7 C8 C11 -174.7(5) . . . . ? C7 C8 C9 O1 -58.0(8) . . . . ? C11 C8 C9 O1 83.8(6) . . . . ? C7 C8 C9 C10 122.1(6) . . . . ? C11 C8 C9 C10 -96.1(6) . . . . ? C7 C8 C11 O2 -114.2(7) . . . . ? C9 C8 C11 O2 103.8(6) . . . . ? C7 C8 C11 C12 66.5(8) . . . . ? C9 C8 C11 C12 -75.4(6) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.58 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.435 _refine_diff_density_min -0.373 _refine_diff_density_rms 0.054