Supplementary Material (ESI) for Photochemical & Photobiological Sciences This journal is © The Royal Society of Chemistry and Owner Societies 2003 data_global _publ_contact_author_email bravic@icmcb.u-bordeaux.fr _publ_contact_author_name 'Georges Bravic' _journal_name_full Photochem.Photobiol.Sci. _journal_coden_Cambridge 0171 _journal_year ? _journal_volume ? _journal_page_first ? loop_ _publ_author_name 'Agus Sundaryono' 'Aziz Nourmamode' 'Christian Gardrat' 'Stephane Grelier' 'Georges Bravic' 'Daniel Chasseau' 'Alain Castellan' data_ccm _database_code_CSD 202736 _chemical_compound_source LCSV _chemical_name_systematic ? _chemical_name_common 'Flavanone 5' _chemical_formula_analytical ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_sum 'H14 C19 O2' _chemical_formula_weight 274.3 _chemical_melting_point ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source H H 0.000 0.000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.002 0.002 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.008 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _cell_length_a 26.9628(9) _cell_length_b 15.3036(4) _cell_length_c 6.9176(2) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 2854.4(3) _cell_formula_units_Z 8 _cell_measurement_temperature 295(1) _cell_measurement_reflns_used 6620 _cell_measurement_theta_min 1 _cell_measurement_theta_max 27.1 _cell_special_details ; ? ; _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+1/2, -z' ' -x, y+1/2, -z+1/2' ' -x+1/2, -y, z+1/2' ' -x, -y, -z' ' -x+1/2, y+1/2, z' ' x, -y+1/2, z+1/2' ' x+1/2, y, -z+1/2' _exptl_crystal_description platelet _exptl_crystal_colour colourless _exptl_crystal_size_max 0.418 _exptl_crystal_size_mid 0.231 _exptl_crystal_size_min 0.055 _exptl_crystal_density_diffrn 1.277 _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _exptl_crystal_F_000 1152 _exptl_absorpt_process_details ? _exptl_absorpt_coefficient_mu 0.089 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator 'horizonally mounted graphite crystal' _diffrn_radiation_detector CCD _diffrn_measurement_device_type KappaCCD _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean 9 _diffrn_reflns_number 16685 _diffrn_reflns_av_R_equivalents 0.034 _diffrn_reflns_av_sigmaI/netI 0.073 _diffrn_reflns_limit_h_min -34 _diffrn_reflns_limit_h_max 29 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 1.51 _diffrn_reflns_theta_max 27.16 _diffrn_reflns_reduction_process scalepack _reflns_number_total 3164 _reflns_number_observed 1700 _reflns_observed_criterion >3sigmaI _reflns_limit_h_min 0 _reflns_limit_h_max 34 _reflns_limit_k_min 0 _reflns_limit_k_max 19 _reflns_limit_l_min 0 _reflns_limit_l_max 8 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_B_iso_or_equiv _atom_site_thermal_displace_type O1 O 0.78729(5) 0.20910(8) -0.0496(2) 4.70(6) Bani C2 C 0.81132(7) 0.1287(1) 0.0057(3) 5.2(1) Bani C3 C 0.78570(8) 0.0542(1) -0.0923(4) 5.6(1) Bani C4 C 0.73109(8) 0.0524(1) -0.0614(3) 4.7(1) Bani O41 O 0.70811(6) -0.01588(9) -0.0854(2) 6.50(8) Bani C5 C 0.70784(7) 0.1363(1) -0.0151(3) 4.15(9) Bani C6 C 0.73735(7) 0.2108(1) -0.0247(2) 4.08(9) Bani C7 C 0.71716(8) 0.2954(1) -0.0147(3) 4.7(1) Bani C8 C 0.66813(9) 0.3052(1) 0.0130(3) 5.1(1) Bani C11 C 0.58526(9) 0.2451(2) 0.0717(3) 6.2(1) Bani C12 C 0.5542(1) 0.1763(2) 0.0970(4) 7.2(2) Bani C13 C 0.5729(1) 0.0918(2) 0.0845(4) 7.2(2) Bani C14 C 0.62237(8) 0.0767(2) 0.0469(3) 5.9(1) Bani C15 C 0.65556(7) 0.1469(1) 0.0207(3) 4.6(1) Bani C16 C 0.63600(8) 0.2331(1) 0.0355(3) 4.8(1) Bani C21 C 0.86516(8) 0.1334(1) -0.0486(4) 5.7(1) Bani C22 C 0.8807(1) 0.1696(2) -0.2208(5) 7.4(2) Bani C23 C 0.9291(1) 0.1678(2) -0.2746(7) 9.5(2) Bani C24 C 0.9628(1) 0.1307(2) -0.1596(8) 9.6(2) Bani C25 C 0.9500(1) 0.0945(3) 0.0133(8) 9.7(2) Bani C26 C 0.8993(1) 0.0954(2) 0.0717(5) 7.7(2) Bani H20 H 0.8062(5) 0.123(1) 0.158(2) 6.2(3) Biso H31 H 0.7929(6) 0.063(1) -0.230(3) 8.1(3) Biso H32 H 0.7989(6) 0.002(1) -0.058(2) 5.8(3) Biso H71 H 0.7404(6) 0.344(1) -0.033(2) 5.3(3) Biso H81 H 0.6544(6) 0.363(1) 0.019(2) 6.2(3) Biso H111 H 0.5744(6) 0.303(1) 0.084(2) 6.4(3) Biso H121 H 0.5182(6) 0.188(1) 0.119(2) 7.5(3) Biso H131 H 0.5528(7) 0.039(1) 0.108(3) 8.1(3) Biso H141 H 0.6335(6) 0.014(1) 0.033(2) 6.6(3) Biso H221 H 0.8567(7) 0.192(1) -0.303(3) 8.8(4) Biso H231 H 0.9397(9) 0.190(2) -0.409(4) 11.6(5) Biso H241 H 0.9971(8) 0.128(1) -0.200(3) 9.2(4) Biso H251 H 0.9669(8) 0.065(2) 0.114(3) 10.9(5) Biso H261 H 0.8879(8) 0.063(2) 0.180(3) 11.1(5) Biso loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O1 0.0631(9) 0.0466(7) 0.0691(9) -0.0008(6) 0.0012(7) 0.0007(6) C2 0.070(1) 0.052(1) 0.077(1) 0.0022(9) -0.001(1) 0.004(1) C3 0.073(2) 0.047(1) 0.094(2) 0.001(1) 0.007(1) -0.008(1) C4 0.074(1) 0.050(1) 0.055(1) -0.006(1) 0.001(1) -0.0029(9) O41 0.085(1) 0.0551(9) 0.107(1) -0.0128(8) 0.0042(9) -0.0165(8) C5 0.063(1) 0.052(1) 0.043(1) -0.0014(9) -0.0041(9) -0.0008(8) C6 0.064(1) 0.051(1) 0.041(1) 0.0004(9) -0.0023(9) -0.0021(8) C7 0.074(1) 0.051(1) 0.053(1) 0.001(1) -0.002(1) -0.0014(9) C8 0.080(2) 0.059(1) 0.057(1) 0.013(1) -0.002(1) -0.001(1) C11 0.076(2) 0.092(2) 0.067(1) 0.018(1) -0.001(1) 0.005(1) C12 0.065(2) 0.121(3) 0.086(2) 0.009(2) 0.003(1) 0.009(2) C13 0.071(2) 0.106(2) 0.097(2) -0.015(2) 0.000(1) 0.014(2) C14 0.067(2) 0.081(2) 0.077(1) -0.007(1) -0.000(1) 0.005(1) C15 0.065(1) 0.065(1) 0.043(1) -0.004(1) -0.0056(9) 0.0035(9) C16 0.066(1) 0.073(2) 0.045(1) 0.008(1) -0.0030(9) 0.0022(9) C21 0.063(1) 0.052(1) 0.100(2) -0.001(1) -0.005(1) -0.002(1) C22 0.077(2) 0.083(2) 0.120(2) -0.001(1) 0.014(2) 0.020(2) C23 0.086(2) 0.096(2) 0.179(4) -0.001(2) 0.036(2) 0.013(2) C24 0.072(2) 0.094(2) 0.201(4) -0.014(2) 0.017(3) -0.031(3) C25 0.086(2) 0.111(3) 0.170(4) 0.022(2) -0.042(2) -0.029(3) C26 0.083(2) 0.091(2) 0.118(2) 0.012(1) -0.018(2) -0.007(2) _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type userblock _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.050P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method 'Becker-Coppens type 1 Gaussian isotropic' _refine_ls_extinction_coef 1.18 _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 2560 _refine_ls_number_parameters 248 _refine_ls_number_restraints 56 _refine_ls_number_constraints 0 _refine_ls_R_factor_all ? _refine_ls_R_factor_obs 0.049 _refine_ls_wR_factor_all 0.123 _refine_ls_wR_factor_obs ? _refine_ls_goodness_of_fit_all 0.999 _refine_ls_goodness_of_fit_obs ? _refine_ls_shift/esd_max 0.34 _refine_ls_shift/esd_mean 0.09 _refine_diff_density_min -0.132 _refine_diff_density_max 0.161 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 C2 1.442(2) . ? O1 C6 1.358(2) . ? C2 C3 1.496(3) . ? C2 C21 1.501(3) . ? C3 C4 1.488(3) . ? C4 O41 1.226(3) . ? C4 C5 1.464(3) . ? C5 C6 1.392(3) . ? C5 C15 1.440(3) . ? C6 C7 1.406(3) . ? C7 C8 1.344(3) . ? C8 C16 1.411(3) . ? C11 C12 1.357(4) . ? C11 C16 1.403(3) . ? C12 C13 1.391(4) . ? C13 C14 1.378(4) . ? C14 C15 1.410(3) . ? C15 C16 1.424(3) . ? C21 C22 1.379(4) . ? C21 C26 1.370(4) . ? C22 C23 1.357(5) . ? C23 C24 1.334(6) . ? C24 C25 1.363(6) . ? C25 C26 1.426(5) . ? C2 H20 1.07(2) . ? C3 H31 0.98(2) . ? C7 H71 0.98(2) . ? C8 H81 0.96(2) . ? C11 H111 0.94(2) . ? C12 H121 1.00(2) . ? C13 H131 0.99(2) . ? C14 H141 1.01(2) . ? C22 H221 0.93(2) . ? C23 H231 1.03(3) . ? C24 H241 0.97(2) . ? C25 H251 0.95(2) . ? C26 H261 0.95(2) . ? 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 O1 C6 115.4(1) . . ? O1 C2 C3 108.8(2) . . ? O1 C2 C21 109.1(2) . . ? C3 C2 C21 111.7(2) . . ? C2 C3 C4 114.0(2) . . ? C3 C4 O41 119.8(2) . . ? C3 C4 C5 116.0(2) . . ? O41 C4 C5 124.1(2) . . ? C4 C5 C6 117.6(2) . . ? C4 C5 C15 123.7(2) . . ? C6 C5 C15 118.4(2) . . ? O1 C6 C5 123.9(2) . . ? O1 C6 C7 114.1(2) . . ? C5 C6 C7 122.0(2) . . ? C6 C7 C8 119.4(2) . . ? C7 C8 C16 122.1(2) . . ? C12 C11 C16 121.6(2) . . ? C11 C12 C13 119.3(3) . . ? C12 C13 C14 121.2(3) . . ? C13 C14 C15 120.7(2) . . ? C5 C15 C14 123.9(2) . . ? C5 C15 C16 118.6(2) . . ? C14 C15 C16 117.5(2) . . ? C8 C16 C11 121.1(2) . . ? C8 C16 C15 119.3(2) . . ? C11 C16 C15 119.7(2) . . ? C2 C21 C22 122.0(2) . . ? C2 C21 C26 118.5(2) . . ? C22 C21 C26 119.4(2) . . ? C21 C22 C23 121.4(3) . . ? C22 C23 C24 120.0(4) . . ? C23 C24 C25 121.6(4) . . ? C24 C25 C26 119.2(4) . . ? C21 C26 C25 118.4(3) . . ? O1 C2 H20 105.9(8) . . ? C3 C2 H20 109.0(8) . . ? C21 C2 H20 112.1(8) . . ? C2 C3 H31 104(1) . . ? C4 C3 H31 110(1) . . ? C6 C7 H71 116.4(9) . . ? C8 C7 H71 124.2(9) . . ? C7 C8 H81 119(1) . . ? C16 C8 H81 119(1) . . ? C12 C11 H111 122(1) . . ? C16 C11 H111 116(1) . . ? C11 C12 H121 119(1) . . ? C13 C12 H121 122(1) . . ? C12 C13 H131 124(1) . . ? C14 C13 H131 115(1) . . ? C13 C14 H141 118(1) . . ? C15 C14 H141 122(1) . . ? C21 C22 H221 118(1) . . ? C23 C22 H221 121(1) . . ? C22 C23 H231 120(1) . . ? C24 C23 H231 119(1) . . ? C23 C24 H241 120(1) . . ? C25 C24 H241 119(1) . . ? C24 C25 H251 136(2) . . ? C26 C25 H251 105(1) . . ? C21 C26 H261 119(1) . . ? C25 C26 H261 122(1) . . ? 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 O1 C2 C3 52.2(2) . . . . ? C6 O1 C2 C21 174.3(2) . . . . ? C2 O1 C6 C5 -22.5(2) . . . . ? C2 O1 C6 C7 159.3(2) . . . . ? O1 C2 C3 C4 -52.9(2) . . . . ? C21 C2 C3 C4 -173.4(2) . . . . ? O1 C2 C21 C22 -40.6(2) . . . . ? O1 C2 C21 C26 143.6(2) . . . . ? C3 C2 C21 C22 79.7(2) . . . . ? C3 C2 C21 C26 -96.0(2) . . . . ? C2 C3 C4 O41 -159.5(2) . . . . ? C2 C3 C4 C5 24.4(2) . . . . ? C3 C4 C5 C6 6.8(2) . . . . ? C3 C4 C5 C15 -179.6(2) . . . . ? O41 C4 C5 C6 -169.2(2) . . . . ? O41 C4 C5 C15 4.5(2) . . . . ? C4 C5 C6 O1 -8.8(2) . . . . ? C4 C5 C6 C7 169.3(2) . . . . ? C15 C5 C6 O1 177.2(2) . . . . ? C15 C5 C6 C7 -4.7(2) . . . . ? C4 C5 C15 C14 10.9(2) . . . . ? C4 C5 C15 C16 -170.7(2) . . . . ? C6 C5 C15 C14 -175.5(2) . . . . ? C6 C5 C15 C16 2.9(2) . . . . ? O1 C6 C7 C8 -178.9(2) . . . . ? C5 C6 C7 C8 2.8(2) . . . . ? C7 C8 C16 C11 177.5(2) . . . . ? C7 C8 C16 C15 -2.6(2) . . . . ? C16 C11 C12 C13 -0.8(2) . . . . ? C11 C12 C13 C14 0.0(3) . . . . ? C12 C13 C14 C15 0.2(2) . . . . ? C13 C14 C15 C5 178.7(2) . . . . ? C13 C14 C15 C16 0.3(2) . . . . ? C2 C21 C22 C23 -175.2(3) . . . . ? C26 C21 C22 C23 0.5(3) . . . . ? C2 C21 C26 C25 175.6(3) . . . . ? C22 C21 C26 C25 -0.2(3) . . . . ? C21 C22 C23 C24 -0.2(3) . . . . ? C22 C23 C24 C25 -0.4(4) . . . . ? C23 C24 C25 C26 0.7(4) . . . . ? C24 C25 C26 C21 -0.4(3) . . . . ? C6 O1 C2 H20 -64.8(9) . . . . ? O1 C2 C3 H31 67(1) . . . . ? C21 C2 C3 H31 -54(1) . . . . ? H20 C2 C3 C4 62.1(9) . . . . ? H20 C2 C3 H31 -178(1) . . . . ? H20 C2 C21 C22 -157.6(9) . . . . ? H20 C2 C21 C26 26.7(9) . . . . ? H31 C3 C4 O41 84(1) . . . . ? H31 C3 C4 C5 -92(1) . . . . ? O1 C6 C7 H71 3(1) . . . . ? C5 C6 C7 H71 -175(1) . . . . ? H81 C8 C16 C11 -2(1) . . . . ? H81 C8 C16 C15 178(1) . . . . ? C16 C11 C12 H121 -178(1) . . . . ? H111 C11 C12 C13 -177(1) . . . . ? H111 C11 C12 H121 5(2) . . . . ? C11 C12 C13 H131 177(1) . . . . ? H121 C12 C13 C14 178(1) . . . . ? H121 C12 C13 H131 -6(2) . . . . ? C12 C13 C14 H141 -177(1) . . . . ? H131 C13 C14 C15 -177(1) . . . . ? H131 C13 C14 H141 6(2) . . . . ? H141 C14 C15 C5 -4(1) . . . . ? H141 C14 C15 C16 177(1) . . . . ? C2 C21 C22 H221 1(1) . . . . ? C26 C21 C22 H221 176(1) . . . . ? C2 C21 C26 H261 5(2) . . . . ? C22 C21 C26 H261 -171(2) . . . . ? C21 C22 C23 H231 174(2) . . . . ? H221 C22 C23 C24 -176(1) . . . . ? H221 C22 C23 H231 -1(2) . . . . ? C22 C23 C24 H241 178(1) . . . . ? H231 C23 C24 C25 -175(2) . . . . ? H231 C23 C24 H241 4(2) . . . . ? C23 C24 C25 H251 179(2) . . . . ? H241 C24 C25 C26 -178(1) . . . . ? H241 C24 C25 H251 0(3) . . . . ? C24 C25 C26 H261 170(2) . . . . ? H251 C25 C26 C21 -179(2) . . . . ? H251 C25 C26 H261 -9(2) . . . . ? _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_data_reduction 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_cell_refinement 'HKL Denzo (Otwinowski & Minor 1997)' _computing_structure_solution 'SIR-97 (Altomare et al. 1994)' _computing_structure_refinement ? _computing_molecular_graphics 'CrystalMaker (Palmer 2002)' _computing_publication_material ?