# Electronic Supplementary Material (ESI) for Photochemical & Photobiological Science # This journal is © The Royal Society of Chemistry and Owner Societies 2011 data_global _journal_name_full Photochem.Photobiol.Sci. _journal_coden_cambridge 0171 _journal_year ? _journal_volume ? _journal_page_first ? loop_ _publ_author_name 'Azusa Kikuchi' 'Mikio Yagi' 'Haruo Saito' 'Masao Mori' _publ_contact_author_email akikuchi@ynu.ac.jp _publ_contact_author_name 'Azusa Kikuchi' data_p2(1)_c _database_code_depnum_ccdc_archive 'CCDC 828376' #TrackingRef '- MePMC.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H16 O3' _chemical_formula_weight 268.30 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)/c 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 11.979(13) _cell_length_b 7.958(8) _cell_length_c 15.235(16) _cell_angle_alpha 90.00 _cell_angle_beta 104.894(13) _cell_angle_gamma 90.00 _cell_volume 1403(3) _cell_formula_units_Z 4 _cell_measurement_temperature 90 _cell_measurement_reflns_used 3597 _cell_measurement_theta_min 2.56 _cell_measurement_theta_max 25.29 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.30 _exptl_crystal_density_diffrn 1.270 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 568 _exptl_absorpt_coefficient_mu 0.086 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9663 _exptl_absorpt_correction_T_max 0.9746 _exptl_absorpt_process_details 'SADABS Sheldrick 1996' _exptl_special_details ; ? ; _diffrn_ambient_temperature 90 _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 APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 8.333 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6437 _diffrn_reflns_av_R_equivalents 0.0211 _diffrn_reflns_av_sigmaI/netI 0.0265 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.76 _diffrn_reflns_theta_max 25.39 _reflns_number_total 2556 _reflns_number_gt 2188 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _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^)+(0.0438P)^2^+0.2862P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2556 _refine_ls_number_parameters 245 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0381 _refine_ls_R_factor_gt 0.0315 _refine_ls_wR_factor_ref 0.0856 _refine_ls_wR_factor_gt 0.0805 _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_restrained_S_all 1.029 _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 0.82362(7) 0.19379(10) 0.99686(5) 0.0263(2) Uani 1 1 d . . . O3 O 0.30758(7) 0.38389(9) 0.47017(5) 0.0277(2) Uani 1 1 d . . . O2 O 0.38133(7) 0.12534(10) 0.46388(5) 0.0296(2) Uani 1 1 d . . . C1 C 0.74539(10) 0.19456(13) 0.91324(7) 0.0226(3) Uani 1 1 d . . . C2 C 0.56869(10) 0.27623(13) 0.80583(8) 0.0229(3) Uani 1 1 d . . . C3 C 0.59755(9) 0.18295(13) 0.73624(7) 0.0217(2) Uani 1 1 d . . . C4 C 0.70161(10) 0.09118(13) 0.75855(8) 0.0233(3) Uani 1 1 d . . . C5 C 0.52402(10) 0.17667(13) 0.64262(7) 0.0219(3) Uani 1 1 d . . . C6 C 0.64109(10) 0.28211(13) 0.89383(8) 0.0236(3) Uani 1 1 d . . . C7 C 0.23771(10) 0.35786(13) 0.38030(8) 0.0246(3) Uani 1 1 d . . . C8 C 0.44100(10) 0.28484(14) 0.60199(8) 0.0235(3) Uani 1 1 d . . . C9 C 0.27920(11) 0.40962(14) 0.30744(8) 0.0277(3) Uani 1 1 d . . . C10 C 0.06115(11) 0.26837(16) 0.28026(8) 0.0301(3) Uani 1 1 d . . . C11 C 0.77527(10) 0.09851(14) 0.84519(8) 0.0242(3) Uani 1 1 d . . . C12 C 0.12892(10) 0.28704(14) 0.36987(8) 0.0264(3) Uani 1 1 d . . . C13 C 0.10058(11) 0.31959(16) 0.20574(8) 0.0306(3) Uani 1 1 d . . . C14 C 0.20941(11) 0.39075(15) 0.21899(8) 0.0294(3) Uani 1 1 d . . . C15 C 0.37692(9) 0.25211(13) 0.50699(8) 0.0226(3) Uani 1 1 d . . . C16 C 0.78814(11) 0.27077(16) 1.07073(8) 0.0279(3) Uani 1 1 d . . . C17 C 0.08650(12) 0.23482(19) 0.45127(9) 0.0346(3) Uani 1 1 d . . . H4 H 0.6194(11) 0.3472(15) 0.9403(9) 0.026(3) Uiso 1 1 d . . . H9 H 0.7146(12) 0.2223(15) 1.0763(9) 0.028(3) Uiso 1 1 d . . . H2 H 0.5393(10) 0.0876(15) 0.6056(8) 0.023(3) Uiso 1 1 d . . . H8 H 0.7790(11) 0.3937(18) 1.0620(9) 0.035(4) Uiso 1 1 d . . . H6 H 0.7195(11) 0.0225(16) 0.7117(8) 0.026(3) Uiso 1 1 d . . . H5 H 0.8479(11) 0.0345(15) 0.8608(8) 0.026(3) Uiso 1 1 d . . . H7 H 0.8488(12) 0.2459(17) 1.1252(10) 0.035(4) Uiso 1 1 d . . . H11 H 0.3570(12) 0.4571(16) 0.3187(9) 0.033(3) Uiso 1 1 d . . . H13 H -0.0168(13) 0.2185(17) 0.2712(9) 0.035(4) Uiso 1 1 d . . . H3 H 0.4953(11) 0.3365(16) 0.7920(8) 0.028(3) Uiso 1 1 d . . . H1 H 0.4210(11) 0.3853(16) 0.6305(8) 0.027(3) Uiso 1 1 d . . . H12 H 0.0509(13) 0.3054(18) 0.1445(11) 0.046(4) Uiso 1 1 d . . . H10 H 0.2375(12) 0.4279(17) 0.1666(10) 0.037(4) Uiso 1 1 d . . . H14 H 0.1381(13) 0.1543(19) 0.4908(10) 0.046(4) Uiso 1 1 d . . . H15 H 0.0792(14) 0.333(2) 0.4905(12) 0.058(5) Uiso 1 1 d . . . H16 H 0.0097(15) 0.188(2) 0.4318(11) 0.057(5) Uiso 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 O1 0.0226(4) 0.0335(4) 0.0218(4) 0.0002(3) 0.0042(3) -0.0007(3) O3 0.0311(5) 0.0245(4) 0.0232(4) -0.0038(3) -0.0010(3) 0.0066(3) O2 0.0350(5) 0.0257(4) 0.0255(4) -0.0049(3) 0.0029(4) 0.0061(3) C1 0.0229(6) 0.0225(5) 0.0218(6) 0.0033(4) 0.0047(5) -0.0051(4) C2 0.0233(6) 0.0208(5) 0.0248(6) 0.0014(4) 0.0065(5) 0.0009(5) C3 0.0245(6) 0.0190(5) 0.0223(6) 0.0014(4) 0.0075(5) -0.0023(4) C4 0.0275(6) 0.0217(5) 0.0229(6) 0.0007(4) 0.0106(5) -0.0001(4) C5 0.0246(6) 0.0203(5) 0.0230(6) -0.0019(4) 0.0099(5) -0.0025(4) C6 0.0270(6) 0.0222(5) 0.0228(6) -0.0019(4) 0.0088(5) -0.0015(5) C7 0.0278(6) 0.0215(5) 0.0222(6) -0.0023(4) 0.0022(5) 0.0065(5) C8 0.0266(6) 0.0222(5) 0.0224(6) -0.0031(4) 0.0077(5) -0.0001(4) C9 0.0277(6) 0.0238(6) 0.0314(7) -0.0007(5) 0.0071(5) 0.0007(5) C10 0.0241(6) 0.0382(7) 0.0271(7) 0.0001(5) 0.0053(5) 0.0009(5) C11 0.0221(6) 0.0251(5) 0.0262(6) 0.0038(4) 0.0078(5) 0.0011(5) C12 0.0279(6) 0.0280(6) 0.0240(6) -0.0001(5) 0.0077(5) 0.0064(5) C13 0.0294(7) 0.0386(7) 0.0220(6) -0.0005(5) 0.0033(5) 0.0040(5) C14 0.0336(7) 0.0311(6) 0.0252(6) 0.0027(5) 0.0104(5) 0.0032(5) C15 0.0229(6) 0.0212(5) 0.0247(6) 0.0000(4) 0.0082(5) 0.0011(4) C16 0.0291(7) 0.0315(6) 0.0221(6) -0.0010(5) 0.0047(5) -0.0029(5) C17 0.0317(7) 0.0468(8) 0.0267(7) 0.0030(6) 0.0102(6) 0.0048(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 O1 C1 1.3739(17) . ? O1 C16 1.4382(18) . ? O3 C15 1.3656(16) . ? O3 C7 1.4244(18) . ? O2 C15 1.2123(16) . ? C1 C6 1.394(2) . ? C1 C11 1.4064(19) . ? C2 C6 1.398(2) . ? C2 C3 1.4082(19) . ? C2 H3 0.976(13) . ? C3 C4 1.4088(19) . ? C3 C5 1.472(2) . ? C4 C11 1.388(2) . ? C4 H6 0.967(13) . ? C5 C8 1.3404(18) . ? C5 H2 0.952(12) . ? C6 H4 0.965(13) . ? C7 C9 1.390(2) . ? C7 C12 1.391(2) . ? C8 C15 1.477(2) . ? C8 H1 0.969(13) . ? C9 C14 1.399(2) . ? C9 H11 0.980(14) . ? C10 C13 1.398(2) . ? C10 C12 1.405(2) . ? C10 H13 0.991(15) . ? C11 H5 0.983(13) . ? C12 C17 1.514(2) . ? C13 C14 1.388(2) . ? C13 H12 0.976(16) . ? C14 H10 0.988(14) . ? C16 H9 0.985(14) . ? C16 H8 0.990(14) . ? C16 H7 0.972(15) . ? C17 H14 0.981(16) . ? C17 H15 0.999(18) . ? C17 H16 0.967(18) . ? 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 C1 O1 C16 117.09(11) . . ? C15 O3 C7 115.35(9) . . ? O1 C1 C6 124.01(11) . . ? O1 C1 C11 116.03(12) . . ? C6 C1 C11 119.95(11) . . ? C6 C2 C3 121.86(12) . . ? C6 C2 H3 119.6(7) . . ? C3 C2 H3 118.6(7) . . ? C2 C3 C4 117.69(11) . . ? C2 C3 C5 123.08(12) . . ? C4 C3 C5 119.22(10) . . ? C11 C4 C3 120.97(11) . . ? C11 C4 H6 121.3(7) . . ? C3 C4 H6 117.7(7) . . ? C8 C5 C3 127.86(11) . . ? C8 C5 H2 115.9(7) . . ? C3 C5 H2 116.2(7) . . ? C1 C6 C2 119.21(11) . . ? C1 C6 H4 120.5(7) . . ? C2 C6 H4 120.2(7) . . ? C9 C7 C12 123.07(11) . . ? C9 C7 O3 118.82(12) . . ? C12 C7 O3 118.07(11) . . ? C5 C8 C15 118.45(11) . . ? C5 C8 H1 124.2(7) . . ? C15 C8 H1 117.3(7) . . ? C7 C9 C14 119.30(13) . . ? C7 C9 H11 119.6(8) . . ? C14 C9 H11 121.1(8) . . ? C13 C10 C12 121.78(13) . . ? C13 C10 H13 120.4(8) . . ? C12 C10 H13 117.8(8) . . ? C4 C11 C1 120.26(12) . . ? C4 C11 H5 121.0(7) . . ? C1 C11 H5 118.7(7) . . ? C7 C12 C10 116.37(11) . . ? C7 C12 C17 121.29(11) . . ? C10 C12 C17 122.34(13) . . ? C14 C13 C10 120.12(12) . . ? C14 C13 H12 120.3(9) . . ? C10 C13 H12 119.5(9) . . ? C13 C14 C9 119.36(12) . . ? C13 C14 H10 120.4(8) . . ? C9 C14 H10 120.2(8) . . ? O2 C15 O3 121.54(12) . . ? O2 C15 C8 126.42(11) . . ? O3 C15 C8 112.03(10) . . ? O1 C16 H9 110.6(7) . . ? O1 C16 H8 111.1(8) . . ? H9 C16 H8 109.2(11) . . ? O1 C16 H7 105.9(8) . . ? H9 C16 H7 109.6(11) . . ? H8 C16 H7 110.4(11) . . ? C12 C17 H14 113.0(9) . . ? C12 C17 H15 112.1(10) . . ? H14 C17 H15 106.2(13) . . ? C12 C17 H16 110.4(10) . . ? H14 C17 H16 109.5(13) . . ? H15 C17 H16 105.3(14) . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 25.39 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.160 _refine_diff_density_min -0.218 _refine_diff_density_rms 0.034