Supplementary Material (ESI) for Green Chemistry This journal is © The Royal Society of Chemistry 2003 data_global _journal_name_full 'Green Chemistry' _journal_coden_Cambridge 1048 loop_ _publ_author_name 'Ingeborg Csoregh' 'Fumio Toda' 'Shinji Toyota' 'Kazuhiro Yoshizawa' _publ_contact_author_name 'Prof Ingeborg Csoregh' _publ_contact_author_address ; Department of Structural Chemistry Institute of Physical, Inorganic and Structural Chemistry Arrhenius Laboratory, Stockholm Uni Stockholm S-106 91 SWEDEN ; _publ_contact_author_email ICS@STRUC.SU.SE _publ_section_title ; Preparative and mechanistic studies of solvent-free Rap-Stoermer reactions ; data_8a _database_code_CSD 200218 _audit_creation_method SHELXL _chemical_name_systematic ; cis-2-benzoyl-3-hydroxy-2,3-dihydrobenzofuran (8a) ; _chemical_name_common 'cis-2-benzoyl-3-hydroxy-2,3-dihydrobenzofuran (8a)' _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C15 H12 O3' _chemical_formula_weight 240.25 _chemical_melting_point ? _chemical_compound_source ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O .0106 .0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pbc21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x, y+1/2, z' 'x, -y+1/2, z+1/2' _cell_length_a 5.9120(10) _cell_length_b 8.0430(10) _cell_length_c 25.070(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1192.1(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description rhombic _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.339 _exptl_crystal_density_method ? _exptl_crystal_F_000 504 _exptl_absorpt_coefficient_mu 0.093 _exptl_absorpt_correction_type 'no abs. correction' _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoKa _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'STOE IPDS' _diffrn_measurement_method ? _diffrn_standards_number 'data collection without standards' _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7807 _diffrn_reflns_av_R_equivalents 0.0848 _diffrn_reflns_av_sigmaI/netI 0.0556 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 3.25 _diffrn_reflns_theta_max 25.85 _reflns_number_total 2204 _reflns_number_observed 1994 _reflns_observed_criterion >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-92 (Sheldrick, 1993)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 8 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[s^2^(Fo^2^)+( 0.0730P)^2^+0.0000P] 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 ? _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 -0.1(10) _refine_ls_number_reflns 2196 _refine_ls_number_parameters 172 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0532 _refine_ls_R_factor_obs 0.0411 _refine_ls_wR_factor_all 0.1043 _refine_ls_wR_factor_obs 0.1020 _refine_ls_goodness_of_fit_all 1.060 _refine_ls_goodness_of_fit_obs 1.092 _refine_ls_restrained_S_all 1.274 _refine_ls_restrained_S_obs 1.092 _refine_ls_shift/esd_max 0.025 _refine_ls_shift/esd_mean 0.002 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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group O1 O 0.5299 0.0145 0.4852 0.0487(4) Uani 1 d . . C2 C 0.6863(3) 0.0374(2) 0.52885(9) 0.0380(4) Uani 1 d . . H2 H 0.7573(3) -0.0693(2) 0.53756(9) 0.038(5) Uiso 1 calc R . C3 C 0.8700(3) 0.1605(2) 0.50889(10) 0.0375(4) Uani 1 d . . H3 H 1.0204(3) 0.1208(2) 0.51925(10) 0.041(5) Uiso 1 calc R . O3 O 0.8370(2) 0.32543(14) 0.52760(8) 0.0430(3) Uani 1 d . . H3O H 0.7139(2) 0.36286(14) 0.51092(8) 0.084(9) Uiso 1 d R . C3A C 0.8394(3) 0.1430(2) 0.45004(10) 0.0393(4) Uani 1 d . . C4 C 0.9692(4) 0.1998(3) 0.40800(10) 0.0549(5) Uani 1 d . . H4 H 1.1042(4) 0.2559(3) 0.41416(10) 0.081(8) Uiso 1 calc R . C5 C 0.8940(5) 0.1713(3) 0.35651(12) 0.0683(7) Uani 1 d . . H5 H 0.9796(5) 0.2082(3) 0.32774(12) 0.068(7) Uiso 1 calc R . C6 C 0.6946(5) 0.0892(3) 0.34754(11) 0.0655(6) Uani 1 d . . H6 H 0.6482(5) 0.0711(3) 0.31257(11) 0.066(7) Uiso 1 calc R . C7 C 0.5599(4) 0.0324(3) 0.38890(9) 0.0548(5) Uani 1 d . . H7 H 0.4239(4) -0.0225(3) 0.38270(9) 0.061(7) Uiso 1 calc R . C7A C 0.6389(3) 0.0617(2) 0.43991(10) 0.0405(4) Uani 1 d . . C8 C 0.5572(3) 0.0997(2) 0.57666(9) 0.0386(4) Uani 1 d . . O8 O 0.3724(2) 0.1625(2) 0.57150(9) 0.0542(4) Uani 1 d . . C9 C 0.6637(3) 0.0828(2) 0.63030(10) 0.0404(4) Uani 1 d . . C10 C 0.8697(3) 0.0040(3) 0.63823(10) 0.0498(5) Uani 1 d . . H10 H 0.9513(3) -0.0362(3) 0.60926(10) 0.041(5) Uiso 1 calc R . C11 C 0.9528(4) -0.0144(3) 0.68929(12) 0.0656(6) Uani 1 d . . H11 H 1.0905(4) -0.0678(3) 0.69465(12) 0.061(7) Uiso 1 calc R . C12 C 0.8347(5) 0.0450(4) 0.73205(13) 0.0745(8) Uani 1 d . . H12 H 0.8919(5) 0.0320(4) 0.76636(13) 0.092(10) Uiso 1 calc R . C13 C 0.6288(5) 0.1252(4) 0.72422(12) 0.0698(7) Uani 1 d . . H13 H 0.5487(5) 0.1663(4) 0.75330(12) 0.067(7) Uiso 1 calc R . C14 C 0.5445(4) 0.1437(3) 0.67403(10) 0.0540(5) Uani 1 d . . H14 H 0.4067(4) 0.1972(3) 0.66894(10) 0.092(10) Uiso 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 0.0430(7) 0.0576(8) 0.0454(8) -0.0011(6) -0.0052(6) -0.0208(5) C2 0.0371(8) 0.0321(8) 0.0448(10) 0.0000(7) -0.0052(7) -0.0033(6) C3 0.0281(7) 0.0292(8) 0.0553(11) -0.0013(7) -0.0062(7) 0.0000(6) O3 0.0394(6) 0.0298(6) 0.0597(9) -0.0059(5) -0.0080(5) -0.0021(4) C3A 0.0367(8) 0.0316(8) 0.0495(11) -0.0024(7) 0.0023(8) 0.0020(6) C4 0.0553(12) 0.0470(11) 0.0625(14) -0.0060(9) 0.0161(10) -0.0051(9) C5 0.092(2) 0.0623(14) 0.0511(14) -0.0028(11) 0.0257(13) -0.0042(13) C6 0.093(2) 0.0635(15) 0.0405(13) -0.0050(10) -0.0011(11) 0.0075(13) C7 0.0570(12) 0.0566(12) 0.0507(13) -0.0073(10) -0.0098(10) 0.0015(9) C7A 0.0371(8) 0.0369(8) 0.0476(10) -0.0021(8) -0.0015(9) 0.0009(7) C8 0.0343(7) 0.0305(8) 0.0512(10) 0.0009(7) -0.0028(8) -0.0031(7) O8 0.0397(7) 0.0571(9) 0.0658(10) -0.0012(7) -0.0096(6) 0.0090(5) C9 0.0413(9) 0.0343(9) 0.0457(11) 0.0027(7) -0.0021(7) -0.0035(6) C10 0.0447(10) 0.0519(11) 0.0529(13) 0.0030(9) -0.0079(9) 0.0036(8) C11 0.062(2) 0.0660(15) 0.0688(14) 0.0146(11) -0.0204(12) 0.0006(11) C12 0.102(2) 0.073(2) 0.0487(14) 0.0137(12) -0.0252(14) -0.0087(14) C13 0.096(2) 0.071(2) 0.0431(14) 0.0019(10) 0.0081(12) -0.0069(13) C14 0.0556(12) 0.0512(12) 0.0551(13) 0.0014(9) 0.0056(10) -0.0021(9) _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 C7A 1.360(2) . ? O1 C2 1.444(2) . ? C2 C8 1.507(3) . ? C2 C3 1.552(2) . ? C2 H2 0.98 . ? C3 O3 1.421(2) . ? C3 C3A 1.493(3) . ? C3 H3 0.98 . ? O3 H3O 0.89 . ? C3A C4 1.381(3) . ? C3A C7A 1.377(2) . ? C4 C5 1.384(4) . ? C4 H4 0.93 . ? C5 C6 1.370(4) . ? C5 H5 0.93 . ? C6 C7 1.385(3) . ? C6 H6 0.93 . ? C7 C7A 1.382(3) . ? C7 H7 0.93 . ? C8 O8 1.210(2) . ? C8 C9 1.491(3) . ? C9 C10 1.387(3) . ? C9 C14 1.392(3) . ? C10 C11 1.379(3) . ? C10 H10 0.93 . ? C11 C12 1.366(5) . ? C11 H11 0.93 . ? C12 C13 1.391(4) . ? C12 H12 0.93 . ? C13 C14 1.362(3) . ? C13 H13 0.93 . ? C14 H14 0.93 . ? 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 C7A O1 C2 107.09(10) . . ? O1 C2 C8 108.69(12) . . ? O1 C2 C3 106.55(14) . . ? C8 C2 C3 113.50(14) . . ? O1 C2 H2 109.34(7) . . ? C8 C2 H2 109.34(10) . . ? C3 C2 H2 109.34(9) . . ? O3 C3 C3A 113.43(14) . . ? O3 C3 C2 113.16(14) . . ? C3A C3 C2 100.02(13) . . ? O3 C3 H3 109.95(8) . . ? C3A C3 H3 109.95(9) . . ? C2 C3 H3 109.95(9) . . ? C3 O3 H3O 105.80(8) . . ? C4 C3A C7A 119.6(2) . . ? C4 C3A C3 131.0(2) . . ? C7A C3A C3 109.3(2) . . ? C5 C4 C3A 118.6(2) . . ? C5 C4 H4 120.71(14) . . ? C3A C4 H4 120.71(12) . . ? C4 C5 C6 120.6(2) . . ? C4 C5 H5 119.69(14) . . ? C6 C5 H5 119.69(14) . . ? C5 C6 C7 122.1(2) . . ? C5 C6 H6 118.97(14) . . ? C7 C6 H6 118.97(14) . . ? C7A C7 C6 116.2(2) . . ? C7A C7 H7 121.88(12) . . ? C6 C7 H7 121.88(14) . . ? O1 C7A C7 124.4(2) . . ? O1 C7A C3A 112.7(2) . . ? C7 C7A C3A 122.9(2) . . ? O8 C8 C9 121.0(2) . . ? O8 C8 C2 120.7(2) . . ? C9 C8 C2 118.23(15) . . ? C10 C9 C14 119.5(2) . . ? C10 C9 C8 122.8(2) . . ? C14 C9 C8 117.7(2) . . ? C9 C10 C11 119.7(2) . . ? C9 C10 H10 120.17(12) . . ? C11 C10 H10 120.2(2) . . ? C12 C11 C10 120.6(2) . . ? C12 C11 H11 119.7(2) . . ? C10 C11 H11 119.7(2) . . ? C11 C12 C13 119.9(2) . . ? C11 C12 H12 120.0(2) . . ? C13 C12 H12 120.0(2) . . ? C14 C13 C12 120.1(2) . . ? C14 C13 H13 120.0(2) . . ? C12 C13 H13 120.0(2) . . ? C13 C14 C9 120.2(2) . . ? C13 C14 H14 119.9(2) . . ? C9 C14 H14 119.88(13) . . ? 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 C7A O1 C2 C8 142.42(13) . . . . ? C7A O1 C2 C3 19.76(14) . . . . ? O1 C2 C3 O3 101.07(15) . . . . ? C8 C2 C3 O3 -18.5(2) . . . . ? O1 C2 C3 C3A -19.90(15) . . . . ? C8 C2 C3 C3A -139.5(2) . . . . ? O3 C3 C3A C4 69.6(2) . . . . ? C2 C3 C3A C4 -169.6(2) . . . . ? O3 C3 C3A C7A -107.1(2) . . . . ? C2 C3 C3A C7A 13.7(2) . . . . ? C7A C3A C4 C5 -0.7(3) . . . . ? C3 C3A C4 C5 -177.1(2) . . . . ? C3A C4 C5 C6 0.3(4) . . . . ? C4 C5 C6 C7 0.4(4) . . . . ? C5 C6 C7 C7A -0.6(3) . . . . ? C2 O1 C7A C7 168.7(2) . . . . ? C2 O1 C7A C3A -11.3(2) . . . . ? C6 C7 C7A O1 -179.8(2) . . . . ? C6 C7 C7A C3A 0.2(3) . . . . ? C4 C3A C7A O1 -179.6(2) . . . . ? C3 C3A C7A O1 -2.4(2) . . . . ? C4 C3A C7A C7 0.4(3) . . . . ? C3 C3A C7A C7 177.6(2) . . . . ? O1 C2 C8 O8 -19.1(2) . . . . ? C3 C2 C8 O8 99.3(2) . . . . ? O1 C2 C8 C9 161.26(13) . . . . ? C3 C2 C8 C9 -80.4(2) . . . . ? O8 C8 C9 C10 176.6(2) . . . . ? C2 C8 C9 C10 -3.8(2) . . . . ? O8 C8 C9 C14 -0.8(3) . . . . ? C2 C8 C9 C14 178.8(2) . . . . ? C14 C9 C10 C11 0.6(3) . . . . ? C8 C9 C10 C11 -176.8(2) . . . . ? C9 C10 C11 C12 -0.4(4) . . . . ? C10 C11 C12 C13 -0.1(4) . . . . ? C11 C12 C13 C14 0.3(4) . . . . ? C12 C13 C14 C9 -0.1(4) . . . . ? C10 C9 C14 C13 -0.3(3) . . . . ? C8 C9 C14 C13 177.1(2) . . . . ? _refine_diff_density_max .186 _refine_diff_density_min -.178 _refine_diff_density_rms .038