# Electronic Supplementary Material (ESI) for Green Chemistry # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full 'Green Chemistry' _journal_coden_cambridge 1048 _journal_year ? _journal_volume ? _journal_page_first ? loop_ _publ_author_name 'Xuesen Fan' 'Yan He' 'Liangyan Cui' 'Xinying Zhang' 'Jianji Wang' _publ_contact_author_email xuesen.fan@yahoo.com _publ_contact_author_name 'Xuesen Fan' data_a _database_code_depnum_ccdc_archive 'CCDC 830432' #TrackingRef 'A.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H16 O3' _chemical_formula_weight 280.31 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 7.9077(10) _cell_length_b 10.7341(13) _cell_length_c 17.410(2) _cell_angle_alpha 90.00 _cell_angle_beta 93.7580(10) _cell_angle_gamma 90.00 _cell_volume 1474.7(3) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 4692 _cell_measurement_theta_min 2.76 _cell_measurement_theta_max 27.50 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.49 _exptl_crystal_size_mid 0.42 _exptl_crystal_size_min 0.40 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.263 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 592 _exptl_absorpt_coefficient_mu 0.085 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9594 _exptl_absorpt_correction_T_max 0.9667 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 10955 _diffrn_reflns_av_R_equivalents 0.0150 _diffrn_reflns_av_sigmaI/netI 0.0126 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.34 _diffrn_reflns_theta_max 25.50 _reflns_number_total 2746 _reflns_number_gt 2251 _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^)+(0.0624P)^2^+0.2563P] 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 2746 _refine_ls_number_parameters 191 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0471 _refine_ls_R_factor_gt 0.0379 _refine_ls_wR_factor_ref 0.1189 _refine_ls_wR_factor_gt 0.1090 _refine_ls_goodness_of_fit_ref 1.050 _refine_ls_restrained_S_all 1.050 _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 C1 C 1.07598(17) 0.36929(13) 0.13281(8) 0.0462(3) Uani 1 1 d . . . C2 C 1.18116(17) 0.40082(13) 0.19677(8) 0.0495(3) Uani 1 1 d . . . H2 H 1.1482 0.3830 0.2459 0.059 Uiso 1 1 calc R . . C3 C 1.33494(19) 0.45873(16) 0.18767(10) 0.0619(4) Uani 1 1 d . . . H3 H 1.4051 0.4795 0.2307 0.074 Uiso 1 1 calc R . . C4 C 1.3841(2) 0.4855(2) 0.11574(12) 0.0807(6) Uani 1 1 d . . . H4 H 1.4878 0.5240 0.1099 0.097 Uiso 1 1 calc R . . C5 C 1.2807(3) 0.4558(2) 0.05205(12) 0.0908(7) Uani 1 1 d . . . H5 H 1.3138 0.4749 0.0032 0.109 Uiso 1 1 calc R . . C6 C 1.1277(2) 0.39766(19) 0.06049(10) 0.0696(5) Uani 1 1 d . . . H6 H 1.0585 0.3773 0.0171 0.083 Uiso 1 1 calc R . . C7 C 0.90744(18) 0.30844(12) 0.13868(8) 0.0460(3) Uani 1 1 d . . . C8 C 0.85945(17) 0.26265(13) 0.21619(8) 0.0467(3) Uani 1 1 d . . . H8A H 0.8543 0.3329 0.2510 0.056 Uiso 1 1 calc R . . H8B H 0.9463 0.2062 0.2373 0.056 Uiso 1 1 calc R . . C9 C 0.68904(16) 0.19577(12) 0.21122(8) 0.0438(3) Uani 1 1 d . . . H9 H 0.6008 0.2521 0.1895 0.053 Uiso 1 1 calc R . . C10 C 0.69447(17) 0.07875(12) 0.16167(8) 0.0468(3) Uani 1 1 d . . . C11 C 0.53332(17) 0.02722(13) 0.12550(7) 0.0440(3) Uani 1 1 d . . . C12 C 0.37980(18) 0.08917(17) 0.12534(9) 0.0588(4) Uani 1 1 d . . . H12 H 0.3745 0.1672 0.1483 0.071 Uiso 1 1 calc R . . C13 C 0.2343(2) 0.0361(2) 0.09138(10) 0.0735(5) Uani 1 1 d . . . H13 H 0.1316 0.0783 0.0917 0.088 Uiso 1 1 calc R . . C14 C 0.2408(2) -0.07842(19) 0.05734(9) 0.0718(5) Uani 1 1 d . . . H14 H 0.1426 -0.1137 0.0345 0.086 Uiso 1 1 calc R . . C15 C 0.3919(3) -0.14154(17) 0.05679(9) 0.0672(5) Uani 1 1 d . . . H15 H 0.3958 -0.2195 0.0337 0.081 Uiso 1 1 calc R . . C16 C 0.5378(2) -0.08913(14) 0.09052(8) 0.0536(4) Uani 1 1 d . . . H16 H 0.6399 -0.1319 0.0899 0.064 Uiso 1 1 calc R . . C17 C 0.64713(18) 0.15608(14) 0.29242(9) 0.0522(4) Uani 1 1 d . . . C18 C 0.5082(3) 0.22077(18) 0.32893(10) 0.0748(5) Uani 1 1 d . . . H18A H 0.4972 0.1873 0.3795 0.112 Uiso 1 1 calc R . . H18B H 0.4040 0.2089 0.2983 0.112 Uiso 1 1 calc R . . H18C H 0.5332 0.3082 0.3327 0.112 Uiso 1 1 calc R . . O1 O 0.81176(14) 0.29475(12) 0.08202(6) 0.0687(4) Uani 1 1 d . . . O2 O 0.82776(14) 0.02527(11) 0.15588(8) 0.0750(4) Uani 1 1 d . . . O3 O 0.72747(17) 0.07370(15) 0.32437(9) 0.0933(5) 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 0.0464(7) 0.0441(7) 0.0479(7) 0.0000(6) 0.0027(6) -0.0010(6) C2 0.0462(7) 0.0481(8) 0.0537(8) 0.0002(6) -0.0003(6) -0.0029(6) C3 0.0472(8) 0.0609(10) 0.0761(11) 0.0044(8) -0.0067(7) -0.0064(7) C4 0.0503(10) 0.0955(14) 0.0968(14) 0.0225(11) 0.0080(9) -0.0152(9) C5 0.0711(12) 0.1324(19) 0.0709(12) 0.0242(12) 0.0195(10) -0.0175(12) C6 0.0638(10) 0.0932(13) 0.0517(9) 0.0058(9) 0.0037(7) -0.0110(9) C7 0.0502(8) 0.0416(7) 0.0455(7) -0.0056(6) -0.0022(6) -0.0055(6) C8 0.0483(8) 0.0440(7) 0.0468(7) -0.0009(6) -0.0039(6) -0.0098(6) C9 0.0400(7) 0.0407(7) 0.0498(8) 0.0018(6) -0.0024(5) -0.0017(5) C10 0.0412(7) 0.0395(7) 0.0591(8) 0.0020(6) 0.0002(6) -0.0022(6) C11 0.0462(7) 0.0469(7) 0.0388(7) 0.0023(6) 0.0022(5) -0.0092(6) C12 0.0442(8) 0.0734(10) 0.0588(9) -0.0150(8) 0.0025(6) -0.0049(7) C13 0.0441(9) 0.1096(15) 0.0664(10) -0.0183(10) 0.0012(7) -0.0095(9) C14 0.0629(11) 0.0961(14) 0.0552(9) -0.0031(9) -0.0047(8) -0.0359(10) C15 0.0918(13) 0.0571(9) 0.0509(9) -0.0023(7) -0.0094(8) -0.0245(9) C16 0.0654(9) 0.0468(8) 0.0478(8) 0.0025(6) -0.0028(7) -0.0058(7) C17 0.0475(8) 0.0500(8) 0.0579(9) 0.0080(7) -0.0044(6) -0.0102(7) C18 0.0964(14) 0.0689(11) 0.0615(10) 0.0041(9) 0.0223(9) 0.0066(10) O1 0.0688(7) 0.0863(8) 0.0489(6) -0.0014(5) -0.0112(5) -0.0254(6) O2 0.0465(6) 0.0572(7) 0.1198(10) -0.0237(7) -0.0069(6) 0.0066(5) O3 0.0748(8) 0.1126(11) 0.0932(10) 0.0525(9) 0.0098(7) 0.0201(8) _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 C6 1.383(2) . ? C1 C2 1.3875(19) . ? C1 C7 1.4937(19) . ? C2 C3 1.384(2) . ? C2 H2 0.9300 . ? C3 C4 1.366(3) . ? C3 H3 0.9300 . ? C4 C5 1.372(3) . ? C4 H4 0.9300 . ? C5 C6 1.377(3) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 O1 1.2122(16) . ? C7 C8 1.5078(19) . ? C8 C9 1.5243(18) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.5260(19) . ? C9 C17 1.533(2) . ? C9 H9 0.9800 . ? C10 O2 1.2103(17) . ? C10 C11 1.4903(18) . ? C11 C12 1.384(2) . ? C11 C16 1.391(2) . ? C12 C13 1.382(2) . ? C12 H12 0.9300 . ? C13 C14 1.367(3) . ? C13 H13 0.9300 . ? C14 C15 1.374(3) . ? C14 H14 0.9300 . ? C15 C16 1.380(2) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? C17 O3 1.2036(19) . ? C17 C18 1.478(2) . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 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 118.65(14) . . ? C6 C1 C7 118.50(13) . . ? C2 C1 C7 122.84(12) . . ? C3 C2 C1 120.18(14) . . ? C3 C2 H2 119.9 . . ? C1 C2 H2 119.9 . . ? C4 C3 C2 120.29(15) . . ? C4 C3 H3 119.9 . . ? C2 C3 H3 119.9 . . ? C3 C4 C5 120.13(16) . . ? C3 C4 H4 119.9 . . ? C5 C4 H4 119.9 . . ? C4 C5 C6 120.03(17) . . ? C4 C5 H5 120.0 . . ? C6 C5 H5 120.0 . . ? C5 C6 C1 120.73(16) . . ? C5 C6 H6 119.6 . . ? C1 C6 H6 119.6 . . ? O1 C7 C1 120.62(13) . . ? O1 C7 C8 120.56(12) . . ? C1 C7 C8 118.81(11) . . ? C7 C8 C9 112.10(11) . . ? C7 C8 H8A 109.2 . . ? C9 C8 H8A 109.2 . . ? C7 C8 H8B 109.2 . . ? C9 C8 H8B 109.2 . . ? H8A C8 H8B 107.9 . . ? C8 C9 C10 111.23(11) . . ? C8 C9 C17 108.80(11) . . ? C10 C9 C17 107.96(11) . . ? C8 C9 H9 109.6 . . ? C10 C9 H9 109.6 . . ? C17 C9 H9 109.6 . . ? O2 C10 C11 120.93(13) . . ? O2 C10 C9 119.64(12) . . ? C11 C10 C9 119.30(11) . . ? C12 C11 C16 118.55(13) . . ? C12 C11 C10 123.24(13) . . ? C16 C11 C10 118.22(13) . . ? C11 C12 C13 120.56(16) . . ? C11 C12 H12 119.7 . . ? C13 C12 H12 119.7 . . ? C14 C13 C12 120.15(17) . . ? C14 C13 H13 119.9 . . ? C12 C13 H13 119.9 . . ? C15 C14 C13 120.26(15) . . ? C15 C14 H14 119.9 . . ? C13 C14 H14 119.9 . . ? C14 C15 C16 119.95(16) . . ? C14 C15 H15 120.0 . . ? C16 C15 H15 120.0 . . ? C15 C16 C11 120.53(16) . . ? C15 C16 H16 119.7 . . ? C11 C16 H16 119.7 . . ? O3 C17 C18 122.08(15) . . ? O3 C17 C9 119.39(15) . . ? C18 C17 C9 118.53(13) . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 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(2) . . . . ? C7 C1 C2 C3 -179.06(14) . . . . ? C1 C2 C3 C4 0.2(3) . . . . ? C2 C3 C4 C5 0.4(3) . . . . ? C3 C4 C5 C6 -0.7(4) . . . . ? C4 C5 C6 C1 0.4(3) . . . . ? C2 C1 C6 C5 0.1(3) . . . . ? C7 C1 C6 C5 178.84(18) . . . . ? C6 C1 C7 O1 -6.7(2) . . . . ? C2 C1 C7 O1 171.95(14) . . . . ? C6 C1 C7 C8 172.43(14) . . . . ? C2 C1 C7 C8 -8.9(2) . . . . ? O1 C7 C8 C9 2.79(19) . . . . ? C1 C7 C8 C9 -176.34(11) . . . . ? C7 C8 C9 C10 63.01(15) . . . . ? C7 C8 C9 C17 -178.20(12) . . . . ? C8 C9 C10 O2 26.90(18) . . . . ? C17 C9 C10 O2 -92.40(16) . . . . ? C8 C9 C10 C11 -157.27(12) . . . . ? C17 C9 C10 C11 83.43(14) . . . . ? O2 C10 C11 C12 -174.90(15) . . . . ? C9 C10 C11 C12 9.3(2) . . . . ? O2 C10 C11 C16 5.4(2) . . . . ? C9 C10 C11 C16 -170.40(12) . . . . ? C16 C11 C12 C13 0.3(2) . . . . ? C10 C11 C12 C13 -179.46(15) . . . . ? C11 C12 C13 C14 -0.2(3) . . . . ? C12 C13 C14 C15 0.1(3) . . . . ? C13 C14 C15 C16 -0.2(3) . . . . ? C14 C15 C16 C11 0.3(2) . . . . ? C12 C11 C16 C15 -0.3(2) . . . . ? C10 C11 C16 C15 179.42(13) . . . . ? C8 C9 C17 O3 -70.43(18) . . . . ? C10 C9 C17 O3 50.40(18) . . . . ? C8 C9 C17 C18 109.65(15) . . . . ? C10 C9 C17 C18 -129.52(15) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.282 _refine_diff_density_min -0.194 _refine_diff_density_rms 0.027