# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? loop_ _publ_author_name 'Eliska Matousova' 'Ales Ruzicka' 'Jiri Kunes' 'Jarmila Kralova' 'Milan Pour' _publ_contact_author_email ales.ruzicka@upce.cz _publ_contact_author_name 'Ales Ruzicka' data_shelxl _database_code_depnum_ccdc_archive 'CCDC 829174' #TrackingRef 'mp110105O1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H18 O4' _chemical_formula_sum 'C18 H18 O4' _chemical_formula_weight 298.32 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 orthorhombic _symmetry_space_group_name_H-M 'P b c a' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' _cell_length_a 12.9230(7) _cell_length_b 7.4390(12) _cell_length_c 30.766(2) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 2957.7(6) _cell_formula_units_Z 8 _cell_measurement_temperature 150(1) _cell_measurement_reflns_used 16499 _cell_measurement_theta_min 1 _cell_measurement_theta_max 27.5 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.37 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.340 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1264 _exptl_absorpt_coefficient_mu 0.094 # Absorption correction loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0 1 0 0.112 0 -1 0 0.178 0 0 -1 0.082 0 0 1 0.076 -1 0 0 0.073 1 0 0 0.120 1 1 0 0.110 -1 1 0 0.083 -1 -1 0 0.105 1 -1 0 0.143 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.977 _exptl_absorpt_correction_T_max 0.986 _exptl_absorpt_process_details ; Gaussian integration (Coppens, 1970) ; _diffrn_ambient_temperature 150(1) _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 'Bruker Nonius KappaCCD area detector' _diffrn_measurement_method '\f and \w scans to fill the Ewald sphere' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16377 _diffrn_reflns_av_R_equivalents 0.0567 _diffrn_reflns_av_sigmaI/netI 0.0388 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -39 _diffrn_reflns_limit_l_max 33 _diffrn_reflns_theta_min 2.65 _diffrn_reflns_theta_max 27.50 _reflns_number_total 3373 _reflns_number_gt 2474 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997)' _computing_cell_refinement 'COLLECT and DENZO' _computing_data_reduction 'COLLECT and DENZO' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material 'SHELXL-97 (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^)+(0.0353P)^2^+1.8542P] 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 3373 _refine_ls_number_parameters 199 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0853 _refine_ls_R_factor_gt 0.0548 _refine_ls_wR_factor_ref 0.1215 _refine_ls_wR_factor_gt 0.1065 _refine_ls_goodness_of_fit_ref 1.140 _refine_ls_restrained_S_all 1.140 _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 O4 O -0.12654(11) 0.12408(18) 0.06346(4) 0.0307(3) Uani 1 1 d . . . O1 O 0.05220(11) 0.07907(17) 0.07000(4) 0.0286(3) Uani 1 1 d . . . O3 O 0.10478(11) 0.61251(18) 0.07203(5) 0.0351(4) Uani 1 1 d . . . C6 C -0.04981(14) 0.5387(2) 0.14351(5) 0.0220(4) Uani 1 1 d . . . O2 O 0.11328(11) 0.42544(19) 0.01546(4) 0.0326(3) Uani 1 1 d . . . C16 C 0.07350(15) 0.4710(2) 0.04881(6) 0.0229(4) Uani 1 1 d . . . C15 C -0.14985(15) 0.5937(2) 0.13736(6) 0.0264(4) Uani 1 1 d . . . H15 H -0.1897 0.5375 0.1162 0.032 Uiso 1 1 d R . . C1 C -0.01837(15) 0.3788(2) 0.07008(5) 0.0227(4) Uani 1 1 d . . . H1 H -0.0810 0.4447 0.0618 0.027 Uiso 1 1 d R . . C2 C -0.02800(15) 0.1876(2) 0.05282(6) 0.0249(4) Uani 1 1 d . . . H2 H -0.0213 0.1905 0.0211 0.030 Uiso 1 1 d R . . C7 C 0.01323(15) 0.6326(2) 0.17411(5) 0.0229(4) Uani 1 1 d . . . C12 C -0.03210(17) 0.7740(3) 0.19897(6) 0.0288(4) Uani 1 1 d . . . C5 C -0.01181(14) 0.3778(2) 0.11929(6) 0.0230(4) Uani 1 1 d . . . C3 C 0.04517(18) 0.0584(3) 0.11616(6) 0.0340(5) Uani 1 1 d . . . H3A H 0.1108 0.0143 0.1271 0.041 Uiso 1 1 d R . . H3B H -0.0070 -0.0314 0.1227 0.041 Uiso 1 1 d R . . C11 C 0.0286(2) 0.8679(3) 0.22956(7) 0.0404(6) Uani 1 1 d . . . H11 H -0.0013 0.9589 0.2460 0.048 Uiso 1 1 d R . . C8 C 0.12023(16) 0.5964(3) 0.18046(7) 0.0319(5) Uani 1 1 d . . . H8 H 0.1521 0.5063 0.1643 0.038 Uiso 1 1 d R . . C4 C 0.01826(15) 0.2288(3) 0.13927(6) 0.0284(4) Uani 1 1 d . . . H4 H 0.0229 0.2303 0.1694 0.034 Uiso 1 1 d R . . C18 C -0.14684(18) -0.0492(3) 0.04464(7) 0.0374(5) Uani 1 1 d . . . H18A H -0.1377 -0.0435 0.0137 0.045 Uiso 1 1 d R . . H18B H -0.2166 -0.0845 0.0511 0.045 Uiso 1 1 d R . . H18C H -0.0997 -0.1357 0.0567 0.045 Uiso 1 1 d R . . C17 C 0.19240(17) 0.7103(3) 0.05482(7) 0.0373(5) Uani 1 1 d . . . H17A H 0.2522 0.6338 0.0544 0.045 Uiso 1 1 d R . . H17B H 0.2059 0.8130 0.0729 0.045 Uiso 1 1 d R . . H17C H 0.1771 0.7495 0.0258 0.045 Uiso 1 1 d R . . C14 C -0.19401(16) 0.7324(3) 0.16210(6) 0.0321(5) Uani 1 1 d . . . H14 H -0.2628 0.7643 0.1577 0.039 Uiso 1 1 d R . . C9 C 0.17687(19) 0.6924(3) 0.21004(7) 0.0434(6) Uani 1 1 d . . . H9 H 0.2470 0.6683 0.2136 0.052 Uiso 1 1 d R . . C13 C -0.13729(17) 0.8199(3) 0.19223(7) 0.0344(5) Uani 1 1 d . . . H13 H -0.1674 0.9107 0.2087 0.041 Uiso 1 1 d R . . C10 C 0.1296(2) 0.8278(3) 0.23517(7) 0.0473(6) Uani 1 1 d . . . H10 H 0.1682 0.8898 0.2558 0.057 Uiso 1 1 d 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 O4 0.0284(7) 0.0300(7) 0.0336(7) -0.0085(6) 0.0079(6) -0.0061(6) O1 0.0323(8) 0.0250(7) 0.0285(7) 0.0009(6) 0.0064(6) 0.0060(6) O3 0.0371(8) 0.0277(7) 0.0406(8) -0.0064(6) 0.0154(7) -0.0094(6) C6 0.0262(10) 0.0204(8) 0.0194(9) 0.0035(7) 0.0013(7) 0.0010(7) O2 0.0354(8) 0.0360(8) 0.0266(7) -0.0004(6) 0.0079(6) -0.0034(6) C16 0.0256(10) 0.0199(8) 0.0233(9) 0.0041(7) -0.0001(7) 0.0040(7) C15 0.0265(10) 0.0258(9) 0.0269(9) 0.0003(8) -0.0003(8) -0.0007(8) C1 0.0253(9) 0.0221(9) 0.0208(9) 0.0007(7) 0.0015(7) 0.0039(7) C2 0.0279(10) 0.0240(9) 0.0229(9) -0.0014(7) 0.0052(8) 0.0007(8) C7 0.0277(10) 0.0215(8) 0.0194(8) 0.0049(7) -0.0001(7) -0.0014(8) C12 0.0429(12) 0.0234(9) 0.0201(9) 0.0025(7) 0.0033(8) -0.0026(9) C5 0.0241(9) 0.0225(9) 0.0224(9) 0.0008(7) 0.0017(7) -0.0020(8) C3 0.0457(13) 0.0256(10) 0.0307(11) 0.0049(8) 0.0022(9) 0.0091(9) C11 0.0624(16) 0.0296(11) 0.0291(11) -0.0029(9) -0.0019(10) -0.0073(11) C8 0.0306(11) 0.0312(11) 0.0338(10) 0.0073(8) -0.0047(9) -0.0017(9) C4 0.0366(11) 0.0275(10) 0.0213(9) 0.0018(7) -0.0009(8) 0.0015(9) C18 0.0391(12) 0.0351(11) 0.0382(11) -0.0107(9) 0.0074(9) -0.0123(10) C17 0.0328(12) 0.0259(10) 0.0531(13) -0.0020(9) 0.0129(10) -0.0056(9) C14 0.0253(10) 0.0306(10) 0.0404(11) 0.0030(9) 0.0059(9) 0.0066(9) C9 0.0378(13) 0.0446(13) 0.0478(13) 0.0121(11) -0.0199(11) -0.0103(11) C13 0.0414(13) 0.0272(10) 0.0347(11) -0.0018(8) 0.0121(9) 0.0042(9) C10 0.0650(18) 0.0389(13) 0.0381(12) 0.0017(10) -0.0202(12) -0.0152(12) _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 O4 C2 1.397(2) . ? O4 C18 1.437(2) . ? O1 C2 1.416(2) . ? O1 C3 1.431(2) . ? O3 C16 1.335(2) . ? O3 C17 1.446(2) . ? C6 C15 1.369(3) . ? C6 C7 1.427(3) . ? C6 C5 1.493(2) . ? O2 C16 1.197(2) . ? C16 C1 1.519(3) . ? C15 C14 1.404(3) . ? C15 H15 0.9301 . ? C1 C5 1.517(2) . ? C1 C2 1.524(2) . ? C1 H1 0.9800 . ? C2 H2 0.9799 . ? C7 C8 1.422(3) . ? C7 C12 1.427(3) . ? C12 C11 1.410(3) . ? C12 C13 1.417(3) . ? C5 C4 1.326(3) . ? C3 C4 1.495(3) . ? C3 H3A 0.9699 . ? C3 H3B 0.9700 . ? C11 C10 1.351(3) . ? C11 H11 0.9300 . ? C8 C9 1.369(3) . ? C8 H8 0.9300 . ? C4 H4 0.9299 . ? C18 H18A 0.9602 . ? C18 H18B 0.9599 . ? C18 H18C 0.9599 . ? C17 H17A 0.9600 . ? C17 H17B 0.9599 . ? C17 H17C 0.9601 . ? C14 C13 1.349(3) . ? C14 H14 0.9300 . ? C9 C10 1.409(4) . ? C9 H9 0.9301 . ? C13 H13 0.9299 . ? C10 H10 0.9300 . ? 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 C2 O4 C18 112.04(15) . . ? C2 O1 C3 112.66(14) . . ? C16 O3 C17 115.95(15) . . ? C15 C6 C7 118.95(17) . . ? C15 C6 C5 118.76(17) . . ? C7 C6 C5 122.24(16) . . ? O2 C16 O3 123.53(17) . . ? O2 C16 C1 125.24(17) . . ? O3 C16 C1 111.23(15) . . ? C6 C15 C14 121.92(18) . . ? C6 C15 H15 119.0 . . ? C14 C15 H15 119.0 . . ? C5 C1 C16 112.87(15) . . ? C5 C1 C2 110.35(15) . . ? C16 C1 C2 109.59(15) . . ? C5 C1 H1 107.9 . . ? C16 C1 H1 107.9 . . ? C2 C1 H1 108.0 . . ? O4 C2 O1 112.76(15) . . ? O4 C2 C1 107.97(15) . . ? O1 C2 C1 110.03(15) . . ? O4 C2 H2 108.7 . . ? O1 C2 H2 108.7 . . ? C1 C2 H2 108.6 . . ? C8 C7 C12 117.71(18) . . ? C8 C7 C6 123.59(17) . . ? C12 C7 C6 118.68(17) . . ? C11 C12 C13 120.77(19) . . ? C11 C12 C7 119.7(2) . . ? C13 C12 C7 119.56(18) . . ? C4 C5 C6 122.38(16) . . ? C4 C5 C1 118.92(17) . . ? C6 C5 C1 118.40(15) . . ? O1 C3 C4 113.30(15) . . ? O1 C3 H3A 109.0 . . ? C4 C3 H3A 109.0 . . ? O1 C3 H3B 108.8 . . ? C4 C3 H3B 108.9 . . ? H3A C3 H3B 107.7 . . ? C10 C11 C12 120.9(2) . . ? C10 C11 H11 119.6 . . ? C12 C11 H11 119.5 . . ? C9 C8 C7 120.8(2) . . ? C9 C8 H8 119.6 . . ? C7 C8 H8 119.6 . . ? C5 C4 C3 123.83(17) . . ? C5 C4 H4 118.1 . . ? C3 C4 H4 118.0 . . ? O4 C18 H18A 109.7 . . ? O4 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? O4 C18 H18C 109.3 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? O3 C17 H17A 109.7 . . ? O3 C17 H17B 109.3 . . ? H17A C17 H17B 109.5 . . ? O3 C17 H17C 109.4 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C13 C14 C15 120.42(19) . . ? C13 C14 H14 119.8 . . ? C15 C14 H14 119.8 . . ? C8 C9 C10 120.4(2) . . ? C8 C9 H9 119.9 . . ? C10 C9 H9 119.7 . . ? C14 C13 C12 120.36(19) . . ? C14 C13 H13 119.9 . . ? C12 C13 H13 119.8 . . ? C11 C10 C9 120.5(2) . . ? C11 C10 H10 119.7 . . ? C9 C10 H10 119.9 . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.356 _refine_diff_density_min -0.239 _refine_diff_density_rms 0.048