# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2003 data_global #============================================================================== # SUBMISSION DETAILS _journal_coden_Cambridge 440 _publ_contact_author ; Dr David Hibbs School of Chemistry University of Sydney Building F11 Science Road Sydney NSW 2006 AUSTRALIA ; _publ_contact_author_email hibbs_d@chem.usyd.edu.au _publ_contact_author_fax '+61 2 9036 9122' _publ_contact_author_phone '+61 2 9351 3329' _publ_requested_journal 'New Journal of Chemistry' #============================================================================== # TITLE AND AUTHOR LIST _publ_section_title ; The electron density in flavones. I. Baicalein ; loop_ _publ_author_name _publ_author_address 'Hibbs, David E.' ; School of Chemistry Building F11 University of Sydney NSW 2006 Australia ; 'Overgaard, Jacob' ; School of Chemistry Building F11 University of Sydney NSW 2006 Australia ; 'Gatti, Carlo' ; Centro CNR "Relazioni fra Struttura e Reattivita' Chimica" via Golgi 19 I-20133 Milano Italy ; #============================================================================== data_baicalein _database_code_CSD 207266 #============================================================================== # 5. CHEMICAL DATA _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common Baicalein _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H10 O5' _chemical_formula_weight 270.23 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' #============================================================================== # 6. CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 2(1)/c' loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +x,+y,+z 2 -x,1/2+y,1/2-z 3 -x,-y,-z 4 +x,-1/2-y,-1/2+z _cell_length_a 7.7707(5) _cell_length_b 13.2573(8) _cell_length_c 11.5427(7) _cell_angle_alpha 90.00 _cell_angle_beta 101.0270(10) _cell_angle_gamma 90.00 _cell_volume 1167.16(12) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 7393 _cell_measurement_theta_min 2.35 _cell_measurement_theta_max 31.65 _exptl_crystal_description block _exptl_crystal_colour brown _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.538 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 560 _exptl_absorpt_coefficient_mu 0.117 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.984 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details ; R. H. Blessing, Acta Cryst. (1995), A51, 33-38 ; #============================================================================== # 7. EXPERIMENTAL DATA _diffrn_ambient_temperature 100(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 'Bruker CCD area detector' _diffrn_measurement_method \w-scans _diffrn_detector_area_resol_mean ? _diffrn_standards_number none _diffrn_reflns_number 65595 _diffrn_reflns_av_R_equivalents 0.0456 _diffrn_reflns_av_sigmaI/netI 0.0193 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 32 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 2.36 _diffrn_reflns_theta_max 62.85 _diffrn_measured_fraction_theta_max 0.961 _diffrn_reflns_theta_full 62.85 _diffrn_measured_fraction_theta_full 0.961 _reflns_number_total 18451 _reflns_number_gt 8469 _reflns_threshold_expression >3sigma(I) _computing_data_collection 'Bruker SMART (Bruker, 1998)' _computing_cell_refinement 'Bruker SMART (Bruker, 1998)' _computing_data_reduction 'SAINT+ V5.01 (Bruker, 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'XD (Koritsanszky et al, 1995)' #============================================================================== # REFINEMENT DATA _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^)+(0.1000P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 8469 _refine_ls_number_parameters 420 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.169 _refine_ls_R_factor_gt 0.043 _refine_ls_wR_factor_ref 0.035 _refine_ls_wR_factor_gt 0.033 _refine_ls_goodness_of_fit_ref 2.19 _refine_ls_restrained_S_all 2.19 _refine_ls_shift/su_max 0.00016 _refine_ls_shift/su_mean 0.00000004 _refine_diff_density_max 0.281 _refine_diff_density_min -0.233 #============================================================================== #ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv O(1) 0.75073(8) 1.05925(4) 0.51811(5) 1.0000 0.015 O(2) 0.6487(1) 0.7579(1) 0.5312(1) 1.0000 0.025 O(3) 0.5770(1) 0.7821(0) 0.7414(1) 1.0000 0.020 O(4) 0.5652(1) 0.9139(0) 0.9235(0) 1.0000 0.020 O(5) 0.6181(1) 1.1139(0) 0.8937(1) 1.0000 0.021 C(1) 0.68093(6) 0.85090(4) 0.52729(4) 1.0000 0.016 C(2) 0.73970(7) 0.89701(4) 0.42965(4) 1.0000 0.017 C(3) 0.77138(6) 0.99786(4) 0.42811(4) 1.0000 0.015 C(4) 0.69797(6) 1.01992(4) 0.61535(4) 1.0000 0.013 C(5) 0.66259(6) 0.91686(4) 0.62316(4) 1.0000 0.013 C(6) 0.61310(6) 0.88021(4) 0.72712(4) 1.0000 0.014 C(7) 0.60452(6) 0.94555(4) 0.81939(4) 1.0000 0.015 C(8) 0.63422(6) 1.04901(4) 0.80625(4) 1.0000 0.015 C(9) 0.68018(6) 1.08745(4) 0.70409(5) 1.0000 0.015 C(10) 0.83306(7) 1.05186(5) 0.33265(5) 1.0000 0.017 C(11) 0.88791(7) 1.15232(5) 0.34731(6) 1.0000 0.022 C(12) 0.95341(8) 1.20134(6) 0.25828(7) 1.0000 0.029 C(13) 0.96221(9) 1.15160(8) 0.15330(8) 1.0000 0.032 C(14) 0.90328(9) 1.05244(8) 0.13727(6) 1.0000 0.031 C(15) 0.83975(8) 1.00271(6) 0.22601(6) 1.0000 0.024 H(2) 0.75517 0.84978 0.35577 1.0000 0.020 H(3) 0.58569 0.74979 0.66730 1.0000 0.025 H(4) 0.60457 0.84517 0.94096 1.0000 0.025 H(5) 0.58308 1.07716 0.95808 1.0000 0.026 H(9) 0.70412 1.16718 0.69421 1.0000 0.018 H(11) 0.88702 1.19134 0.42963 1.0000 0.026 H(12) 1.00754 1.27622 0.27650 1.0000 0.035 H(13) 1.01111 1.19261 0.08517 1.0000 0.038 H(14) 0.90312 1.01135 0.05616 1.0000 0.037 H(15) 0.78806 0.92763 0.20523 1.0000 0.029 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 O(1) 0.0173(2) 0.0152(2) 0.0139(2) -0.0003(2) 0.0062(2) 0.0010(1) O(2) 0.0426(4) 0.0148(2) 0.0176(2) -0.0068(2) 0.0124(3) -0.0042(2) O(3) 0.0330(3) 0.0126(2) 0.0156(2) -0.0034(2) 0.0085(2) -0.0009(2) O(4) 0.0336(3) 0.0136(2) 0.0145(2) 0.0041(2) 0.0110(2) 0.0023(2) O(5) 0.0348(4) 0.0141(2) 0.0156(2) 0.0025(2) 0.0107(2) -0.0012(2) C(1) 0.0225(3) 0.0138(2) 0.0129(2) -0.0020(1) 0.0059(2) -0.0014(1) C(2) 0.0224(3) 0.0167(2) 0.0129(2) -0.0010(2) 0.0066(2) -0.0009(1) C(3) 0.0147(2) 0.0168(2) 0.0128(2) 0.0010(1) 0.0047(1) 0.0015(1) C(4) 0.0138(2) 0.0127(2) 0.0123(2) 0.0003(1) 0.0039(1) 0.0004(1) C(5) 0.0162(2) 0.0125(2) 0.0115(2) -0.0002(1) 0.0042(1) -0.0002(1) C(6) 0.0186(2) 0.0121(2) 0.0119(2) 0.0000(1) 0.0047(2) 0.0000(1) C(7) 0.0192(2) 0.0123(2) 0.0120(2) 0.0018(1) 0.0054(1) 0.0006(1) C(8) 0.0190(2) 0.0121(2) 0.0130(2) 0.0023(1) 0.0052(2) 0.0000(1) C(9) 0.0184(2) 0.0123(2) 0.0145(2) 0.0009(1) 0.0057(2) 0.0003(1) C(10) 0.0157(2) 0.0218(2) 0.0150(2) 0.0026(2) 0.0061(2) 0.0045(2) C(11) 0.0211(3) 0.0227(3) 0.0228(2) -0.0004(2) 0.0074(2) 0.0072(2) C(12) 0.0239(3) 0.0312(3) 0.0310(3) 0.0006(2) 0.0099(2) 0.0149(3) C(13) 0.0252(3) 0.0436(4) 0.0269(3) 0.0063(3) 0.0124(2) 0.0175(3) C(14) 0.0300(4) 0.0431(4) 0.0199(2) 0.0077(3) 0.0135(2) 0.0096(3) C(15) 0.0269(3) 0.0301(3) 0.0164(2) 0.0043(2) 0.0107(2) 0.0033(2) #============================================================================== #MOLECULAR GEOMETRY loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag O(1) C(3) 1.3532(7) 1_555 1_555 yes O(1) C(4) 1.3695(7) 1_555 1_555 yes O(2) C(1) 1.2604(8) 1_555 1_555 yes O(3) C(6) 1.3478(7) 1_555 1_555 yes O(4) C(7) 1.3618(7) 1_555 1_555 yes O(5) C(8) 1.3498(7) 1_555 1_555 yes C(1) C(2) 1.4316(7) 1_555 1_555 yes C(1) C(5) 1.4387(7) 1_555 1_555 yes C(2) C(3) 1.3602(7) 1_555 1_555 yes C(3) C(10) 1.4691(7) 1_555 1_555 yes C(4) C(5) 1.4001(7) 1_555 1_555 yes C(4) C(9) 1.3871(7) 1_555 1_555 yes C(5) C(6) 1.4143(6) 1_555 1_555 yes C(6) C(7) 1.3843(7) 1_555 1_555 yes C(7) C(8) 1.4039(7) 1_555 1_555 yes C(8) C(9) 1.3925(7) 1_555 1_555 yes C(10) C(11) 1.3987(8) 1_555 1_555 yes C(10) C(15) 1.4024(8) 1_555 1_555 yes C(11) C(12) 1.3920(8) 1_555 1_555 yes C(12) C(13) 1.3926(14) 1_555 1_555 yes C(13) C(14) 1.3927(14) 1_555 1_555 yes C(14) C(15) 1.3860(9) 1_555 1_555 yes 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C(3) O(1) C(4) 119.88(5) 1_555 1_555 1_555 yes O(2) C(1) C(2) 122.76(5) 1_555 1_555 1_555 yes O(2) C(1) C(5) 121.17(5) 1_555 1_555 1_555 yes C(2) C(1) C(5) 116.07(5) 1_555 1_555 1_555 yes C(1) C(2) C(3) 121.05(5) 1_555 1_555 1_555 yes O(1) C(3) C(2) 122.19(5) 1_555 1_555 1_555 yes O(1) C(3) C(10) 112.73(5) 1_555 1_555 1_555 yes C(2) C(3) C(10) 125.07(5) 1_555 1_555 1_555 yes O(1) C(4) C(5) 121.17(5) 1_555 1_555 1_555 yes O(1) C(4) C(9) 116.56(5) 1_555 1_555 1_555 yes C(5) C(4) C(9) 122.26(5) 1_555 1_555 1_555 yes C(1) C(5) C(4) 119.61(5) 1_555 1_555 1_555 yes C(1) C(5) C(6) 121.79(5) 1_555 1_555 1_555 yes C(4) C(5) C(6) 118.58(5) 1_555 1_555 1_555 yes O(3) C(6) C(5) 122.13(5) 1_555 1_555 1_555 yes O(3) C(6) C(7) 117.93(5) 1_555 1_555 1_555 yes C(5) C(6) C(7) 119.92(5) 1_555 1_555 1_555 yes O(4) C(7) C(6) 122.56(5) 1_555 1_555 1_555 yes O(4) C(7) C(8) 117.76(5) 1_555 1_555 1_555 yes C(6) C(7) C(8) 119.67(4) 1_555 1_555 1_555 yes O(5) C(8) C(7) 120.07(5) 1_555 1_555 1_555 yes O(5) C(8) C(9) 118.39(5) 1_555 1_555 1_555 yes C(7) C(8) C(9) 121.55(4) 1_555 1_555 1_555 yes C(4) C(9) C(8) 117.84(4) 1_555 1_555 1_555 yes C(3) C(10) C(11) 120.58(6) 1_555 1_555 1_555 yes C(3) C(10) C(15) 120.27(6) 1_555 1_555 1_555 yes C(11) C(10) C(15) 119.14(6) 1_555 1_555 1_555 yes C(10) C(11) C(12) 120.08(7) 1_555 1_555 1_555 yes C(11) C(12) C(13) 120.47(7) 1_555 1_555 1_555 yes C(12) C(13) C(14) 119.53(6) 1_555 1_555 1_555 yes C(13) C(14) C(15) 120.36(8) 1_555 1_555 1_555 yes C(10) C(15) C(14) 120.39(7) 1_555 1_555 1_555 yes #========================================================================= # END of CIF #=========================================================================